跳转到内容

氨苄西林:修订间差异

维基百科,自由的百科全书
删除的内容 添加的内容
InternetArchiveBot留言 | 贡献
补救8个来源,并将0个来源标记为失效。) #IABot (v2.0.9.5
 
(未显示10个用户的18个中间版本)
第1行: 第1行:

{{Drugbox | verifiedrevid = 443387440
{{Drugbox
| IUPAC_name = (2''S'',5''R'',6''R'')-6-([(2''R'')-2-amino-2-phenylacetyl]amino)<br />-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-<br />carboxylic acid
| Watchedfields = changed
| image = Ampicillin Structural Formulae V.1.svg
| verifiedrevid = 443387440
| width = 256
| image2 = Ampicillin 3d structure pdb.gif
| image = Ampicillin structure.svg
| caption =氨苄西林的[[鍵線式]](骨架式)結構
<!--Clinical data-->
| width = 200
| tradename = Principen,及其他<ref name=drugs.comINT>Drugs.com [http://www.drugs.com/international/ampicillin.html International trade names for Ampicillin] Retrieved 14 January 2015</ref>
| alt =
| pregnancy_category = A <small>([[澳大利亚]])</small>、B <small>(美國)</small>
| image2 = Ampicillin-from-xtal-3D-bs-17.png
| legal_UK = POM
| caption2 = 三水合物晶體結構中[[兩性離子]]型態的氨苄西林[[球棍模型]]。<ref>{{ cite journal | url = https://dx.doi.org/10.5517/ccb0nkj | title = CSD Entry: AMPCIH01 | website = [[Cambridge Structural Database]]: Access Structures | year = 2006 | publisher = [[Cambridge Crystallographic Data Centre]] | doi = 10.5517/ccb0nkj | access-date = 2022-06-28 | vauthors = Burley JC, Van De Streek J, Stephens PW }}</ref><ref>{{ cite journal | title = Ampicillin trihydrate from synchrotron powder diffraction data | vauthors = Burley JC, van de Streek J, Stephens PW | journal = [[Acta Crystallographica|Acta Crystallogr. E]] | volume = 62 | pages = o797–o799 | year = 2006 | issue = 2 | doi = 10.1107/S1600536806001371 | bibcode = 2006AcCrE..62O.797B | doi-access = free }}</ref>
| licence_US = Ampicillin
| width2 = 180
| routes_of_administration = 口服、[[靜脈注射]]
| alt2 =
| Drugs.com = {{drugs.com|monograph|ampicillin}}

| MedlinePlus = a685002
<!--Pharmacokinetic data-->
<!-- Clinical data -->
| pronounce =
| bioavailability = 口服:40%
| tradename = Principen及其他<ref name="drugs.comINT">{{cite web | title=Ampicillin - international drug names | website=Drugs.com | date=2019-11-30 | url=https://www.drugs.com/international/ampicillin.html | archive-url=https://web.archive.org/web/20191130211432/https://www.drugs.com/international/ampicillin.html | archive-date=2019-11-30 | url-status=live | access-date= 2020-01-26 }}</ref>
| protein_bound = 15 至 25%
| Drugs.com = {{drugs.com|monograph|ampicillin}}
| metabolism = 12 至 50%
| MedlinePlus = a685002
| elimination_half-life = 約1小時
| DailyMedID = Ampicillin
| excretion = 75-85% 經[[腎]]排除
| pregnancy_AU = A
<!--Identifiers-->
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Ampicillin Use During Pregnancy | website=Drugs.com | date=2019-05-02 | url=https://www.drugs.com/pregnancy/ampicillin.html | access-date=2020-01-26 | archive-url=https://web.archive.org/web/20190822052019/https://www.drugs.com/pregnancy/ampicillin.html | archive-date=2019-08-22 | url-status=live }}</ref>
| CAS_number_Ref = {{cascite|correct|??}}
| pregnancy_category =
| CAS_number = 69-53-4
| routes_of_administration = [[口服給藥]], 靜脈輸注, [[肌肉注射]]
| ATC_prefix = J01
| class = [[氨基青黴素]]
| ATC_suffix = CA01
| ATC_prefix = J01
| ATC_supplemental = {{ATC|S01|AA19}} {{ATCvet|J51|CA01}}
| ATC_suffix = CA01
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ATC_supplemental = {{ATC|S01|AA19}} {{ATCvet|J51|CA01}} {{ATC|J01|CR50}} {{ATC|J01|CA51}}
| ChEBI = 28971

| PubChem = 6249
<!-- Legal status -->
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| legal_AU = S4
| DrugBank = DB00415
| legal_AU_comment =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| ChemSpiderID = 6013
| legal_BR_comment =
| UNII_Ref = {{fdacite|correct|FDA}}
| legal_CA = Rx-only
| UNII = 7C782967RD
| legal_CA_comment =
| KEGG_Ref = {{keggcite|correct|kegg}}
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| KEGG = D00204
| legal_DE_comment =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| legal_NZ = <!-- Class A, B, C -->
| ChEMBL = 174
| legal_NZ_comment =
<!--Chemical data-->
| C=16 | H=19 | N=3 | O=4 | S=1
| legal_UK = POM
| legal_UK_comment =
| molecular_weight = 349.41 g/mol
| legal_US = Rx-only
| SMILES = O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
| legal_US_comment = <ref name=AHFS2015 />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| StdInChI = 1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
| legal_UN_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| legal_status = <!--For countries not listed above-->
| StdInChIKey = AVKUERGKIZMTKX-NJBDSQKTSA-N

<!-- Pharmacokinetic data -->
| bioavailability = 62% ±17% (非消化道給藥)<br /><!--<ref name=eghianruwa/>-->< 30–55% (口服)<!--<ref name=AHFS2015 />-->
| protein_bound = 15到25%<!--<ref name=eghianruwa/>-->
| metabolism = 12到50%
| metabolites = {{le|青黴烯酸|Penicilloic acid}}<!--<ref name=eghianruwa/>-->
| onset =
| elimination_half-life = 約1小時<!--<ref name=eghianruwa/>-->
| duration_of_action =
| excretion = 75到85%([[腎]]臟)

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 69-53-4
| CAS_supplemental =
| PubChem = 6249
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00415
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6013
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7C782967RD
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00204
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = C06574
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28971
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 174
| NIAID_ChemDB =
| PDB_ligand = AIC
| synonyms = AM/AMP<ref>{{cite web |title=Antibiotic abbreviations list |url=https://microbiologie-clinique.com/antibiotic-family-abbreviation.html |access-date=2023-06-22 |archive-date=2023-06-22 |archive-url=https://web.archive.org/web/20230622223700/https://microbiologie-clinique.com/antibiotic-family-abbreviation.html |dead-url=no }}</ref>

<!-- Chemical and physical data -->
| IUPAC_name = (2''S'',5''R'',6''R'')-6-([(2''R'')-2-Amino-2-phenylacetyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
| C = 16
| H = 19
| N = 3
| O = 4
| S = 1
| SMILES = CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AVKUERGKIZMTKX-NJBDSQKTSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}
}}
<!-- Definition and uses -->
'''氨苄青黴素'''<ref group="注">「苄」在普通話/國語中音同「便」</ref>({{lang|en|Ampicillin}}),又稱'''安比西林'''、'''氨苄西林''',是一種[[β-內酰胺類抗生素]],可治療多種細菌感染<ref name=AHFS2015/>。適應症包含[[respiratory tract infection|呼吸道感染]]、[[泌尿道感染]]、[[脑膜炎]]、[[沙門氏菌感染症]],以及[[Endocarditis|心內膜炎]]<!-- <ref name=AHFS2015/> -->。本品也能用於預防新生兒的{{tsl|en|group B streptococcal infection||B群鏈球菌感染}}<!-- <ref name=AHFS2015/> -->,可經由口服、[[intramuscular injection|肌肉注射]],以及靜脈注射給藥<ref name=AHFS2015>{{cite web|title=Ampicillin|url=http://www.drugs.com/monograph/ampicillin.html|publisher=The American Society of Health-System Pharmacists|accessdate=1 August 2015}}</ref>。


'''氨苄西林'''({{lang-en|Ampicillin}})是一種[[抗生素]],屬於[[青黴素]]家族的[[氨基青黴素]]類,用於預防和治療多種[[病原細菌|細菌]]感染,如[[呼吸道感染]]、[[泌尿道感染]]、[[腦膜炎]]、[[沙門氏菌感染症]]和[[心內膜炎]]。<ref name=AHFS2015/>它也用於預防新生兒[[B型鏈球菌感染]]。<ref name=AHFS2015/>給藥方式有[[口服給藥|口服]]、[[肌肉注射]]或是靜脈輸注。<ref name=AHFS2015>{{cite web|title=Ampicillin|url=https://www.drugs.com/monograph/ampicillin.html|publisher=The American Society of Health-System Pharmacists|access-date=2015-08-01|url-status=live|archive-url=https://web.archive.org/web/20150712001731/http://www.drugs.com/monograph/ampicillin.html|archive-date=2015-07-12}}</ref>
氨苄青霉素屬於氨基青霉素類。氨基青霉素也包含了[[阿莫西林]](Amoxicillin),他們比[[青黴素]]或[[耐青霉素酶青霉素]](penicillinase-resistant penicillins)更易穿透[[革蘭氏陰性菌]],不過易被細菌[[β-内酰胺酶]](Beta-lactamase)分解,因此常搭配[[舒巴坦]](一種β-内酰胺酶抑制劑)一起使用以加強對可产生β-内酰胺酶细菌的治療效果。氨苄青霉素主要使用於治療細菌感染如中耳炎、鼻竇炎及急性細菌性膀胱炎等。和阿莫西林相比,口服氨苄青霉素生物利用度較低,且易產生[[腸道]]副作用。

使用後常見的副作有皮[[疹]]、[[噁心]]和[[腹瀉]]。<ref name=AHFS2015/>對青黴素過敏的人不宜使用。<ref name=AHFS2015/>嚴重的副作用有[[艱難擬梭菌感染|艱難你梭菌]]結腸炎或[[過敏性休克]]。<ref name=AHFS2015/>雖然有腎臟問題的個體可使用,但可能需要減少劑量。<ref name=AHFS2015/>個體在[[妊娠|懷孕]]期間使用對於胎兒,和在[[母乳哺育]]期間對於嬰兒似乎無安全的問題。<ref name=AHFS2015/><ref>{{cite web|title=Ampicillin use while Breastfeeding|url=https://www.drugs.com/breastfeeding/ampicillin.html|access-date=2010-8-01|date=March 2015|url-status=live|archive-url=https://web.archive.org/web/20150923220701/http://www.drugs.com/breastfeeding/ampicillin.html|archive-date=2015-09-23}}</ref>

氨芐西林於1958年被發現,並於1961年進入醫療用途。<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons|isbn=9783527607495|page=490|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA490|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220081307/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA490|archive-date=2016-12-20}}</ref><ref>{{cite book| vauthors = Ravina E |title=The evolution of drug discovery : from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=9783527326693|page=262|edition=1|url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA262|url-status=live|archive-url=https://web.archive.org/web/20160809201757/https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA262|archive-date=2016-08-09}}</ref>它已被列入[[世界衛生組織基本藥物標準清單]]之中。<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref>][[世界衛生組織]](WHO)將此藥物列為對人類醫學非常重要的一種。<ref>{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | isbn=9789241515528 | hdl-access=free }}</ref>市面上已有其[[通用名藥物]]流通。<ref name=AHFS2015/>

==醫療用途==
===適用疾病===
*細菌性腦膜炎;可添加[[氨基糖苷類抗生素]]以提高治療革蘭氏陰性腦膜炎細菌的功效<ref name="dailymed">{{cite web | title=Ampicillin- ampicillin sodium injection, powder, for solution | website=DailyMed | date=2019-09-11 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0642ef5e-7eff-4117-a0df-4bd15d7b7d63 | access-date=2020-01-25 | archive-url=https://web.archive.org/web/20180222104913/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0642ef5e-7eff-4117-a0df-4bd15d7b7d63 | archive-date=2018-02-22 | url-status=live }}</ref>
*[[腸球菌]]菌株引起的心內膜炎([[仿單標示外使用]]),通常與氨基糖苷類抗生素一起使用<ref name="medscape">{{cite web|url=http://reference.medscape.com/drug/ampi-omnipen-ampicillin-342475|title=ampicillin (Rx)|last=WebMD|work=Medscape|access-date=2017-08-22|archive-url=https://web.archive.org/web/20170815211547/http://reference.medscape.com/drug/ampi-omnipen-ampicillin-342475|archive-date=2017-08-15|url-status=live}}</ref>
*由受污染(如[[沙門氏菌屬]])的水或食物引起的[[消化道]]感染<ref name="dailymed" />
*[[泌尿生殖系統]]感染<ref name="dailymed" />
*與使用導尿[[醫用導管|導管]]有關,且對其他藥物無反應的[[醫療照顧相關感染|相關感染]]<ref name="Harrison">{{cite book|title=Harrison's Principles of Internal Medicine | volume = 1 | vauthors = Finberg R, Fingeroth J | name-list-style = vanc |publisher=McGraw-Hill Medical|year=2012|isbn=978-0-07-174887-2| veditors = Longo D, Fauci A, Kasper D, Hauser S, Jameson J, Loscalzo J |edition = 18th|chapter=Chapter 132: Infections in Transplant Recipients }}</ref>
*[[中耳炎]]
*對先前患有[[風濕性心臟病]],或正在接受牙科手術、陰道子宮切除術或[[剖腹產]]的個體進行預防感染。<ref name="AHFS2015" />它也用於B型鏈球菌攜帶者的孕婦,以預防早發性新生兒感染。<ref name="AHFS2015" />
*呼吸道感染,包括[[支氣管炎]]、[[咽炎]]<ref name="AHFS2015" />
*[[鼻竇炎]]
*[[敗血症]]<ref name=dailymed-vet>{{cite web | title=Ampicillin injection, powder, for suspension | website=DailyMed | date=2017-10-26 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=af6eb56d-698f-43aa-bb3b-a0a69732a7ae | access-date=2020-01-26 | archive-url=https://web.archive.org/web/20180222165046/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=af6eb56d-698f-43aa-bb3b-a0a69732a7ae | archive-date=2018-02-22 | url-status=live }}</ref>
*對[[百日咳]]作預防,及治療其繼發性感染<ref name="AHFS2015" />

氨苄西林曾在過去用於治療[[淋病]],但現在因存在太多對青黴素具抗藥性的菌株,而必須改用別的藥物治療。<ref name="AHFS2015" />

===針對的細菌類===
氨芐西林用於治療許多[[革蘭氏陽性菌]]和[[革蘭氏陰性菌]]的感染。它是第一種對革蘭氏陽性菌具有治療活性的"廣譜"青黴素,包括[[肺炎鏈球菌]]、[[化膿性鏈球菌]]、[[金黃色葡萄球菌]]的一些分離株(但不包括青黴素抗藥性或[[耐甲氧西林金黃色葡萄球菌]]菌株)、[[釀膿特呂佩爾氏菌]]和一些腸球菌。它是少數能對多重抗藥性{{le|糞腸球菌|Enterococcus faecalis}}和{{le|屎腸球菌|Enterococcus faecium}}具活性的抗生素之一。<ref name="magdesian">{{cite book|url=https://books.google.com/books?id=AiV4DgAAQBAJ&pg=PT59|title=Equine Pharmacology, an Issue of Veterinary Clinics of North America: Equine Practice, E-Book| vauthors = Magdesian KG |publisher=Elsevier Health Sciences|year=2017|isbn=978-0-323-52438-4|pages=59}}</ref>此藥物對革蘭氏陰性菌(如[[腦膜炎雙球菌]]、一些[[流感嗜血桿菌]]和一些[[腸桿菌科]]細菌(雖然大多數腸桿菌科細菌和[[假單胞菌屬]]具有抗藥性))具治療活性。<ref name="magdesian" /><ref name=papich>{{cite book|url=https://books.google.com/books?id=ip8_CwAAQBAJ&pg=PA43|title=Saunders Handbook of Veterinary Drugs: Small and Large Animal|vauthors=Papich MG|publisher=Elsevier Health Sciences|year=2015|isbn=978-0-323-24485-5|pages=43–47|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010324/https://books.google.com/books?id=ip8_CwAAQBAJ&pg=PA43|dead-url=no}}</ref>氨苄西林可與{{le|舒巴坦|Sulbactam}}聯合使用,舒巴坦是一種抑制[[β-內醯胺酶]](此種酶由細菌產生,可滅活氨芐西林和相關抗生素<ref name="Hauser">{{cite book|url=https://books.google.com/books?id=17pMk0v3_bYC&pg=PA25|title=Antibiotic Basics for Clinicians: The ABCs of Choosing the Right Antibacterial Agent|vauthors=Hauser AR|publisher=Lippincott Williams & Wilkins|year=2012|isbn=978-1-4511-1221-4|pages=25–28|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010331/https://books.google.com/books?id=17pMk0v3_bYC&pg=PA25|dead-url=no}}</ref><ref>{{cite journal | vauthors = Akova M | title = Sulbactam-containing beta-lactamase inhibitor combinations | journal = Clinical Microbiology and Infection | volume = 14 | pages = 185–188 | date = January 2008 | issue = Suppl 1 | pmid = 18154545 | doi = 10.1111/j.1469-0691.2007.01847.x | doi-access = free }}</ref>)藥物,氨苄西林的活性譜因此得以增強。氨苄西林有時也與其他具有不同作用機制的抗生素(如[[萬古黴素]]、[[利奈唑胺]]、[[達托黴素]]和[[替加環素]])合併使用,。<ref name="Suleyman2016rev">{{cite journal | vauthors = Suleyman G, Zervos MJ | title = Safety and efficacy of commonly used antimicrobial agents in the treatment of enterococcal infections: a review | journal = Expert Opinion on Drug Safety | volume = 15 | issue = 2 | pages = 153–167 | date = 2016 | pmid = 26629598 | doi = 10.1517/14740338.2016.1127349 | s2cid = 25488987 }}</ref><ref>{{cite book| vauthors = Torok ME, Moran E, Cooke F |title=Oxford Handbook of Infectious Diseases and Microbiology|publisher=Oxford University Press|isbn=9780191503108|page=721|url=https://books.google.com/books?id=G4KuDQAAQBAJ&pg=PA721|language=en|url-status=live|archive-url=https://web.archive.org/web/20170323064830/https://books.google.com/books?id=G4KuDQAAQBAJ&pg=PA721|archive-date= 2017-03-23|date=December 2016}}</ref>

===配方形式===
氨芐西林的攝取方式有口服、肌肉注射或靜脈輸注。<ref name=AHFS2015/>口服形式為[[膠囊劑|膠囊]]或懸浮液,並非用作嚴重感染的初始治療,而是作為肌肉注射或靜脈輸注的後續治療之用。<ref name=AHFS2015/>對於靜脈輸注和肌肉注射,氨苄西林是以粉末形式存在,須加上溶劑配製後使用。<ref name="wanamaker">{{cite book|url=https://books.google.com/books?id=7s3sAwAAQBAJ&pg=PA243|title=Applied Pharmacology for Veterinary Technicians - E-Book|vauthors=Wanamaker BP, Massey K|publisher=Elsevier Health Sciences|year=2014|isbn=978-0-323-29170-5|pages=244|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010325/https://books.google.com/books?id=7s3sAwAAQBAJ&pg=PA243|dead-url=no}}</ref>

靜脈輸注必須緩慢執行,進行太快可能會導致[[癲癇發作]]。<ref name="AHFS2015" /><ref>{{cite web | last=WebMD | title=Ampicillin Intravenous: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing | work=WebMD | access-date=2018-02-23 | url=https://www.webmd.com/drugs/2/drug-18412/ampicillin-intravenous/details | archive-url=https://web.archive.org/web/20180223171300/https://www.webmd.com/drugs/2/drug-18412/ampicillin-intravenous/details | archive-date=2018-02-23 | url-status=live }}</ref>

===特定群體===
氨芐西林是個體於懷孕期間最常使用的藥物之一,<ref name="weiner">{{cite book|url=https://archive.org/details/completeguidetom0000wein_t9k5|url-access=registration|quote=ampicillin pregnancy.|title=The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby| vauthors = Weiner CP, Rope K |publisher=St. Martin's Press|year=2013|isbn=978-1-250-03720-6|pages=[https://archive.org/details/completeguidetom0000wein_t9k5/page/47 47]–49}}</ref>[[美國食品藥物管理局]](FDA)將其歸為B類,{{le|澳洲治療用品管理局|Therapeutic Goods Administration}}將其歸為A類,表示兩者認為此藥物通常對於胎兒無害。<ref name="AHFS2015" /><ref>{{cite web|url=https://www.tga.gov.au/prescribing-medicines-pregnancy-database|title=Prescribing medicines in pregnancy database | author = Australian Government Department of Health Therapeutic Goods Administration|date=2017-10-25|work=Therapeutic Goods Administration (TGA)|publisher=Australian Government Department of Health|access-date=2018-02-23|archive-url=https://web.archive.org/web/20161220210434/https://www.tga.gov.au/prescribing-medicines-pregnancy-database|archive-date=2016-12-20|url-status=live}} {{Small|Note: scroll down to "Search by name" and type "ampicillin" into the search bar. Requires JavaScript to be enabled.}} <!-- If you can find a way to link directly to the "ampicillin" entry, please replace the URL (and title, if needed) and remove the appended note. --></ref>它是治療孕婦[[李斯特菌]]感染的首選藥物,可單獨使用或與氨基糖苷類抗生素合併使用。<ref name="AHFS2015" />懷孕會讓人體對芐西林的清除率增加高達50%,因此需要用到更高的劑量才能達到治療目的。<ref name="weiner" /><ref name="rello">{{cite book|url=https://books.google.com/books?id=wysQmU5bYAAC&pg=PA172|title=Infectious Diseases in Critical Care| vauthors = Rello J, Kollef MH, Díaz E, Rodríguez A |publisher=Springer Science & Business Media|year=2010|isbn=978-3-540-34406-3|pages=172}}</ref>

氨芐西林會穿過[[胎盤]]並以母體血漿濃度的50-100%保留在[[羊水]]中,可能會導致新生兒體內的氨芐西林濃度較高。<ref name="rello" />

雖然哺乳母親會分泌一些氨芐西林進入乳汁中,但份量很少。<ref name="AHFS2015" /><ref name="weiner" />

新生兒體內的氨芐西林[[生物半衰期]]較長,[[血漿蛋白]]結合較低。<ref name=eghianruwa>{{cite book|url=https://books.google.com/books?id=CtfIAgAAQBAJ&pg=PA26|title=Essential Drug Data for Rational Therapy in Veterinary Practice|vauthors=Eghianruwa K|publisher=AuthorHouse|year=2014|isbn=978-1-4918-0010-2|pages=26|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010325/https://books.google.com/books?id=CtfIAgAAQBAJ&pg=PA26|dead-url=no}}</ref>由於新生兒的腎功能尚未完全發育,腎臟的清除率也較低。<ref name="AHFS2015" />

==禁忌症==
氨苄西林對青黴素過敏的人會引發致命的過敏性休克,因此禁用。過敏反應包含有頻繁的皮[[疹]]和[[蕁麻疹]]、{{le|剝脫性皮膚炎|Erythroderma}}、{{le|多形紅斑|erythema multiforme}}以及[[紅血球]]和[[白血球]]暫時減少。<ref name="dailymed" />

不建議對併發[[傳染性單核白血球增多症]]的患者使用氨芐西林,因為超過40%的使用者會出現皮疹。<ref name="dailymed" />

==副作用==
氨芐西林的毒性較其他抗生素相對較少,對青黴素敏感以及有[[氣喘]]或[[過敏]]史的人更易出現副作用。<ref name="dailymed" />它在極少數情況下也會引起嚴重的副作用,例如[[血管性水腫]]、過敏反應和艱難擬梭菌感染(範圍從輕度腹瀉到嚴重的假膜性結腸炎)。<ref name="dailymed" />有些人會發展出黑色"毛茸狀"舌頭。嚴重的不良反應還有癲癇發作和[[血清病]]。在約10%使用者身上最常出現的副作用是腹瀉和皮疹。較不常見的有噁心、嘔吐、搔癢和血液病。口服氨苄西林後較常見的消化道反應有毛茸狀舌頭、噁心、嘔吐、腹瀉和結腸炎。<ref name="dailymed" />另有其他病症可能會在治療結束後幾週才出現。<ref name=AHFS2015/>

===過量===
攝入過量氨芐西林可導致行為改變、{{le|意識混亂|Confusion}}、昏厥和抽搐,以及神經肌肉過敏、[[電解質不平衡]]和[[腎衰竭]]。<ref name="dailymed" />

==與其他藥物交互作用==
氨芐西林會與[[丙磺舒]]和[[氨甲蝶呤|胺甲蝶呤]]發生反應,降低腎臟的排泄。高劑量氨芐西林與[[華法林]]和其他口服[[抗凝劑]]同時使用可能會增加出血風險(可能是透過抑制[[血小板]]凝結的緣故)。<ref>{{cite web|url=https://www.drugs.com/drug-interactions/ampicillin-with-anisindione-196-0-210-0.html?professional=1|title=Drug interactions between ampicillin and anisindione|work=Drugs.com|access-date=2018-02-22|archive-url=https://web.archive.org/web/20180223171235/https://www.drugs.com/drug-interactions/ampicillin-with-anisindione-196-0-210-0.html?professional=1|archive-date=2018-02-23|url-status=live}}</ref>據說氨芐西林會降低口服[[避孕藥]]的效果,<ref name=AHFS2015/>但此點一直存在爭議。<ref>{{cite book|url=https://books.google.com/books?id=94x8C5pbhqoC&pg=PA213|title=Drug Interactions in Infectious Diseases|vauthors=Piscitelli SC, Rodvold KA, Pai MP|publisher=Springer Science & Business Media|year=2011|isbn=978-1-61779-213-7|pages=213–214|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010332/https://books.google.com/books?id=94x8C5pbhqoC&pg=PA213|dead-url=no}}</ref>其他抗生素如[[氯黴素]]、[[紅黴素]]、[[頭孢菌素]]和[[四環素類抗生素]]可能會降低氨苄西林療效。<ref name="wanamaker" />例如四環素類抗生素會抑制細菌中蛋白質合成,導致氨芐西林的作用標靶減少。<ref>{{cite web|url=https://www.drugs.com/drug-interactions/ampicillin-with-bismuth-subcitrate-potassium-metronidazole-tetracycline-196-0-388-0.html?professional=1|title=Drug interactions between ampicillin and bismuth subcitrate potassium / metronidazole / tetracycline|work=Drugs.com|access-date=2018-02-22|archive-url=https://web.archive.org/web/20180223171253/https://www.drugs.com/drug-interactions/ampicillin-with-bismuth-subcitrate-potassium-metronidazole-tetracycline-196-0-388-0.html?professional=1|archive-date= 2018-02-23|url-status=live}}</ref>如果它與氨基糖苷類抗生素同時服用,會發生兩者結合,讓氨苄西林失去活性。分開給藥時,氨基糖苷類抗生素和氨芐西林反可發生相互增強的作用。<ref name="AHFS2015" /><ref>{{cite web|url=https://www.drugs.com/drug-interactions/amikacin-with-ampicillin-153-0-196-0.html?professional=1|title=Drug interactions between amikacin and ampicillin|work=Drugs.com|access-date=2018-02-22|archive-url=https://web.archive.org/web/20180223171312/https://www.drugs.com/drug-interactions/amikacin-with-ampicillin-153-0-196-0.html?professional=1|archive-date=2018-02-23|url-status=live}}</ref>

氨芐西林與別嘌呤醇一起服用時更易引起皮疹。<ref name="dailymed" />

[[霍亂]]活疫苗和[[傷寒]]活疫苗與氨苄西林一起使用均會失效。氨芐西林通常用於治療霍亂和傷寒,但會抑制身體產生免疫反應的能力。<ref>{{cite web|url=https://www.drugs.com/drug-interactions/ampicillin-with-cholera-vaccine-live-196-0-3772-0.html?professional=1|title=Drug interactions between ampicillin and cholera vaccine, live|work=Drugs.com|access-date=2018-02-22|archive-url=https://web.archive.org/web/20180223171311/https://www.drugs.com/drug-interactions/ampicillin-with-cholera-vaccine-live-196-0-3772-0.html?professional=1|archive-date=2018-02-23|url-status=live}}</ref><ref>{{cite web|url=https://www.drugs.com/drug-interactions/ampicillin-with-typhoid-vaccine-live-196-0-2271-0.html?professional=1|title=Drug interactions between ampicillin and typhoid vaccine, live|work=Drugs.com|access-date=2018-02-22|archive-url=https://web.archive.org/web/20180223110946/https://www.drugs.com/drug-interactions/ampicillin-with-typhoid-vaccine-live-196-0-2271-0.html?professional=1|archive-date=2018-02-23|url-status=live}}</ref><ref>{{cite web|url=https://emedicine.medscape.com/article/962643-medication|title=Cholera Medication| vauthors = Handa S |date=2017-06-22|work=Medscape|access-date= 2018-02-23|archive-url=https://web.archive.org/web/20180223110950/https://emedicine.medscape.com/article/962643-medication|archive-date=2018-02-23|url-status=live}}</ref>

==藥理學==
===作用機制===
氨芐西林屬於青黴素類中的[[Β-內醯胺抗生素]],是氨基青黴素類家族的一份子。其活性大致相當於[[阿莫西林]]。氨苄西林能夠穿透革蘭氏陽性菌和一些革蘭氏陰性菌的外膜。它與[[苄青黴素]]的不同之處僅在擁有氨基。氨芐西林和阿莫西林上都有此氨基,有助此類抗生素能穿過革蘭氏陰性菌(例如[[大腸桿菌]]、{{le|奇異變形桿菌|Proteus mirabilis}}、[[腸道沙門氏菌]]和[[志賀氏菌屬]])的外膜孔。<ref name="Hauser" /><ref>{{cite journal | vauthors = Delcour AH | title = Outer membrane permeability and antibiotic resistance | journal = Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics | volume = 1794 | issue = 5 | pages = 808–816 | date = May 2009 | pmid = 19100346 | pmc = 2696358 | doi = 10.1016/j.bbapap.2008.11.005 }}</ref>

氨苄西林是{{le|轉肽酶|DD-transpeptidase }}的不可逆抑制劑,而細菌需要轉肽酶來製造細胞壁。<ref name="AHFS2015" />它會抑制二元[[分裂 (生物學)|分裂]]中細菌細胞壁合成的第三階段和最後階段,最終導致細胞{{le|裂解|lysis}},氨芐西林因而具有溶菌的效力。<ref name="AHFS2015" /><ref name="Goodman">{{cite book | veditors = Brunton L, Chabner B, Knollman B | vauthors = Petri WA | title=Goodman and Gilman's the Pharmacological Basis of Therapeutics | edition = Twelfth | chapter=Penicillins, Cephalosporins, and Other Beta-Lactam Antibiotics | location=New York | year=2011 | pages=1477–1504 | publisher=McGraw Hill Professional | isbn=978-0-07-176939-6 }}</ref>

===藥物動力學===
氨芐西林在個體的消化道中吸收良好(但有食物時會降低其吸收),並在一到兩個小時內達到[[最大血藥濃度]]。經由胃腸外途徑攝取的[[生物利用度]]約為62%。氨芐西林的血漿蛋白結合度僅有15-20%,與其他青黴素通常的60-90%血漿蛋白結合度不同。<ref name="AHFS2015" /><ref name="eghianruwa" />

氨芐西林會擴散到大多數組織中,但主要是集中在[[肝臟]]和腎臟。當腦膜發炎(例如腦膜炎)時,也會在[[腦脊液]]中出現。<ref name="eghianruwa" />有些氨芐西林會被β-內醯胺環水解為{{le|青黴烯酸|Penicilloic acid}},而後代謝,<ref name="AHFS2015" />但大部分會以原形排出體外。<ref name="dailymed" />在腎臟中,它主要透過腎小管過濾,有的還經[[腎絲球]]濾過,其餘隨糞便和膽汁排出。

[[海他西林]]和[[匹氨西林]]是開發用於提高生物利用率的氨苄西林酯類 。<ref name=giguere>{{cite book|url=https://books.google.com/books?id=ybA2AAAAQBAJ&pg=RA2-PT166|title=Antimicrobial Therapy in Veterinary Medicine|vauthors=Giguère S, Prescott JF, Dowling PM|publisher=John Wiley & Sons|year=2013|isbn=978-1-118-67507-6|pages=167–170|access-date=2024-07-21|archive-date=2023-01-12|archive-url=https://web.archive.org/web/20230112010325/https://books.google.com/books?id=ybA2AAAAQBAJ&pg=RA2-PT166|dead-url=no}}</ref>

==歷史==
氨芐西林自1961年起已被廣泛用於治療細菌感染。<ref name = acred>{{cite journal | vauthors = Acred P, Brown DM, Turner DH, Wilson MJ | title = Pharmacology and chemotherapy of ampicillin--a new broad-spectrum penicillin | journal = British Journal of Pharmacology and Chemotherapy | volume = 18 | issue = 2 | pages = 356–369 | date = April 1962 | pmid = 13859205 | pmc = 1482127 | doi = 10.1111/j.1476-5381.1962.tb01416.x }}</ref>在英國藥業{{le|Beecham Group|Beecham Group}}推出氨芐西林之前,青黴素療法僅對葡萄球菌和鏈球菌等革蘭氏陽性菌有效。<ref name=Goodman/>氨芐西林(最初品牌為"Penbritin")也展現對革蘭氏陰性菌(例如流感嗜血桿菌、大腸桿菌群和變形桿菌屬)的活性。<ref name = acred/>

==社會與文化==
===經濟學===
氨芐西林的售價相對便宜。<ref>{{cite book |vauthors=Hanno PM, Guzzo TJ, Malkowicz SB, Wein AJ |title=Penn Clinical Manual of Urology E-Book |date=2014 |publisher=Elsevier Health Sciences |isbn=978-0-323-24466-4 |page=122 |url=https://books.google.com/books?id=OQTbAgAAQBAJ&pg=PA122 |language=en |access-date=2024-07-21 |archive-date=2023-04-14 |archive-url=https://web.archive.org/web/20230414211301/https://books.google.com/books?id=OQTbAgAAQBAJ&pg=PA122 |dead-url=no }}</ref>在美國有其通用名藥物流通。<ref name=AHFS2015/>


==獸醫用途==
<!-- Adverse effects -->
在獸醫學中,氨芐西林可用於貓、狗和農場動物,治療下列感染:<ref name="dailymed-vet" />
常見副作用包含紅疹、惡心,以及腹瀉<!-- <ref name=AHFS2015/> -->。本品不適用於對[[青黴素]]過敏的患者<!-- <ref name=AHFS2015/> -->。嚴重副作用包含[[偽膜性結腸炎]]及[[全身型過敏性反應]]<!-- <ref name=AHFS2015/> -->。[[腎功能衰竭]]患者用藥必須減低劑量<ref name=AHFS2015/>。[[妊娠]]及[[母乳餵養|哺乳]]期間遇藥目前顯示安全<ref name=AHFS2015/><ref>{{cite web|title=Ampicillin use while Breastfeeding|url=http://www.drugs.com/breastfeeding/ampicillin.html|accessdate=1 August 2015|date=March 2015}}</ref>。


*[[肛門腺]]感染
<!-- Society and culture -->
*皮膚感染,如[[膿瘍]]、[[蜂窩性組織炎]]和膿皰性[[皮膚炎]]
氨苄青霉素于1961年首次發現<ref>{{cite book|last1=Ravina|first1=Enrique|title=The evolution of drug discovery : from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=9783527326693|page=262|edition=1|url=https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA262}}</ref>,該藥列名於[[世界卫生组织基本药物标准清单]],為基礎公衛體系必備藥物之一<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>。在2014年,每劑靜脈注射針劑批發價約於 0.13 到 1.20 美金之間<ref name=Erc2015>{{cite web|title=Ampicillin|url=http://erc.msh.org/dmpguide/resultsdetail.cfm?language=english&code=AMP1A&s_year=2014&year=2014&str=1%20g&desc=Ampicillin&pack=new&frm=VIAL&rte=INJ&class_code2=06%2E2%2E1%2E&supplement=&class_name=%2806%2E2%2E1%2E%29Beta%20lactam%20medicines%3Cbr%3E|website=International Drug Price Indicator Guide|accessdate=1 August 2015}}</ref>。該藥屬於[[通用名药物|學名藥]],十天療程約會花費 13 美金左右<ref name=AHFS2015/>。
*[[家牛]]、[[綿羊]]和[[山羊]]的大腸桿菌和沙門氏菌感染(口服形式)。因細菌抗藥性增加,用於此目的的氨芐西林數量已有減少。<ref name="giguere" />
*母豬的[[乳腺炎]]<ref>{{cite web|url=http://www.merckvetmanual.com/reproductive-system/mastitis-in-large-animals/mastitis-in-sows|title=Mastitis in Sows| vauthors = Erskine R |work=Merck Veterinary Manual|access-date=2017-08-22|archive-url=https://web.archive.org/web/20170704115129/http://www.merckvetmanual.com/reproductive-system/mastitis-in-large-animals/mastitis-in-sows|archive-date=2017-07-04|url-status=live}}</ref>
*需氧-厭氧菌類混合感染,例如貓咬傷<ref name="giguere" />
*多重抗藥性糞腸球菌和屎腸球菌感染<ref name="magdesian" />
*預防[[家禽]]的沙門氏菌、大腸桿菌或金黃色葡萄球菌導致的敗血症<ref name="giguere" />
*呼吸道感染,包括[[扁桃體炎|扁桃腺炎]]、{{le|牛呼吸道疾病|Bovine respiratory disease}}、{{le|運輸熱|Shipping fever}}、{{le|支氣管肺炎|bronchopneumonia}}、小牛及牛肺炎
*狗的泌尿道感染


通常不會使用口服氨芐西林治療馬的疾病,因為其β-內酰胺的生物利用度較低。<ref name="magdesian" />
== 作用机制 ==
氨苄青霉素是殺菌性的抗生素。能滲透[[革蘭氏陽性菌]]及部份[[革蘭氏陰性菌]]。經由結合在[[細菌]][[細胞壁]]上的青霉素結合蛋白(penicillin-binding proteins,PBPs),阻礙細菌合成細胞壁的第三及最後階段,最終引致[[細胞裂解]]。


藥物在動物體內的生物半衰期與人類的大致相同(僅一個多小時)。貓和狗的口服劑生物利用度低於50%,馬的口服劑生物利用度低於4%。<ref name="papich" />
== 用途 ==
=== 治療 ===
氨苄青黴素與另一種青黴素的阿莫西林非常相關,兩者都是用來治療[[泌尿道感染]]、[[中耳炎]]、普遍的[[肺炎]],及由[[流感嗜血桿菌]]、[[沙門氏桿菌]]及[[李氏桿菌]]引起的[[腦膜炎]]。它與[[氟氯西林]](Flucloxacillin)組合作為[[蜂窩組織炎]]的[[經驗治療]],及抵抗[[金黃色葡萄球菌]]協助治療[[一型鏈球菌感染]]。由於對氨苄青黴素的抗藥性,一般都會與其他抗生素組合使用,或轉用另一種抗生素。


=== 基因轉殖的用途 ===
== 參考文獻 ==
{{Reflist|2}}
氨苄青黴素時常被用於[[分子生物學]]上,作為[[基因轉殖]]成功與否的指標。通常基因轉殖所用的基因載體皆帶有抗氨苄青黴素的基因,細胞(如[[大腸桿菌]])在被人工轉殖基因的[[質粒|基因載體]][[轉化 (生物)|轉型]]進入後,其載體上的基因表現能使其在充滿氨苄青黴素的培養皿中存活,因此可推斷所需基因有成功插入基因載體內。


== 注釋 ==
== 外部連結 ==
* {{cite patent |country=GB |number=902703 |status=patent |title=Penicillins |pubdate=1962-08-09 |fdate=1960-08-25 |pridate=1960-08-25 |inventor=Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith |assign1=Beecham Research Laboratories Ltd |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=GB&NR=902703&KC=&FT=E&locale=en_EP}}
{{reflist|group="注"}}
* {{cite patent |country=US |number=2985648 |status=patent |title=Alpha-aminobenzylpenicillins |pubdate=1961-05-23 |gdate=1961-05-23 |fdate=1961-02-02 |pridate=1958-10-06 |inventor=Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=2985648&KC=&FT=E&locale=en_EP}}
==外部連結==
* {{cite patent |country=US |number=3157640 |status=patent |title=D-(-)-alpha-aminobenzylpenicillin trihydrate |pubdate=1964-11-17 |gdate=1964-11-17 |fdate=1963-03-21 |pridate=1963-03-21 |invent1=David A Johnson |invent2=Glenn A Hardcastle Jr |assign1=Bristol Myers Co |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=3157640&KC=&FT=E&locale=en_EP}}
* [[蛋白質資料庫]]上有關[http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=AIC 氨苄青黴素結合蛋白的資料]


{{模板:細胞壁破壞性抗生素}}
{{PenicillinAntiBiotics}}
{{Portal bar | Medicine}}
{{Authority control}}


[[分類:對映純藥物]]
[[Category:Β-内酰胺类抗生素]]
[[分類:青黴素]]
[[Category:对映纯药物]]
[[Category:世界卫生组织本药物]]
[[分類:化合物]]
[[分類:世界衛生組織基本藥物]]
[[Category:芳香化合物]]
[[分類:RTT]]
[[Category:含硫杂环]]

2024年9月20日 (五) 15:21的最新版本

氨苄西林
氨苄西林的鍵線式(骨架式)結構
三水合物晶體結構中兩性離子型態的氨苄西林球棍模型[1][2]
臨床資料
商品名英语Drug nomenclaturePrincipen及其他[3]
其他名稱AM/AMP[4]
AHFS/Drugs.comMonograph
MedlinePlusa685002
核准狀況
懷孕分級
给药途径口服給藥, 靜脈輸注, 肌肉注射
藥物類別英语Drug class氨基青黴素
ATC碼
法律規範狀態
法律規範
藥物動力學數據
生物利用度62% ±17% (非消化道給藥)
< 30–55% (口服)
血漿蛋白結合率15到25%
药物代谢12到50%
代謝產物青黴烯酸英语Penicilloic acid
生物半衰期約1小時
排泄途徑75到85%(臟)
识别信息
  • (2S,5R,6R)-6-([(2R)-2-Amino-2-phenylacetyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS号69-53-4  checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB配體ID
CompTox Dashboard英语CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.000.645 編輯維基數據鏈接
化学信息
化学式C16H19N3O4S
摩尔质量349.41 g·mol−1
3D模型(JSmol英语JSmol
  • CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
  • InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1 checkY
  • Key:AVKUERGKIZMTKX-NJBDSQKTSA-N checkY

氨苄西林(英語:Ampicillin)是一種抗生素,屬於青黴素家族的氨基青黴素類,用於預防和治療多種細菌感染,如呼吸道感染泌尿道感染腦膜炎沙門氏菌感染症心內膜炎[6]它也用於預防新生兒B型鏈球菌感染[6]給藥方式有口服肌肉注射或是靜脈輸注。[6]

使用後常見的副作有皮噁心腹瀉[6]對青黴素過敏的人不宜使用。[6]嚴重的副作用有艱難你梭菌結腸炎或過敏性休克[6]雖然有腎臟問題的個體可使用,但可能需要減少劑量。[6]個體在懷孕期間使用對於胎兒,和在母乳哺育期間對於嬰兒似乎無安全的問題。[6][7]

氨芐西林於1958年被發現,並於1961年進入醫療用途。[8][9]它已被列入世界衛生組織基本藥物標準清單之中。[10]]世界衛生組織(WHO)將此藥物列為對人類醫學非常重要的一種。[11]市面上已有其通用名藥物流通。[6]

醫療用途

[编辑]

適用疾病

[编辑]

氨苄西林曾在過去用於治療淋病,但現在因存在太多對青黴素具抗藥性的菌株,而必須改用別的藥物治療。[6]

針對的細菌類

[编辑]

氨芐西林用於治療許多革蘭氏陽性菌革蘭氏陰性菌的感染。它是第一種對革蘭氏陽性菌具有治療活性的"廣譜"青黴素,包括肺炎鏈球菌化膿性鏈球菌金黃色葡萄球菌的一些分離株(但不包括青黴素抗藥性或耐甲氧西林金黃色葡萄球菌菌株)、釀膿特呂佩爾氏菌和一些腸球菌。它是少數能對多重抗藥性糞腸球菌英语Enterococcus faecalis屎腸球菌英语Enterococcus faecium具活性的抗生素之一。[16]此藥物對革蘭氏陰性菌(如腦膜炎雙球菌、一些流感嗜血桿菌和一些腸桿菌科細菌(雖然大多數腸桿菌科細菌和假單胞菌屬具有抗藥性))具治療活性。[16][17]氨苄西林可與舒巴坦英语Sulbactam聯合使用,舒巴坦是一種抑制β-內醯胺酶(此種酶由細菌產生,可滅活氨芐西林和相關抗生素[18][19])藥物,氨苄西林的活性譜因此得以增強。氨苄西林有時也與其他具有不同作用機制的抗生素(如萬古黴素利奈唑胺達托黴素替加環素)合併使用,。[20][21]

配方形式

[编辑]

氨芐西林的攝取方式有口服、肌肉注射或靜脈輸注。[6]口服形式為膠囊或懸浮液,並非用作嚴重感染的初始治療,而是作為肌肉注射或靜脈輸注的後續治療之用。[6]對於靜脈輸注和肌肉注射,氨苄西林是以粉末形式存在,須加上溶劑配製後使用。[22]

靜脈輸注必須緩慢執行,進行太快可能會導致癲癇發作[6][23]

特定群體

[编辑]

氨芐西林是個體於懷孕期間最常使用的藥物之一,[24]美國食品藥物管理局(FDA)將其歸為B類,澳洲治療用品管理局英语Therapeutic Goods Administration將其歸為A類,表示兩者認為此藥物通常對於胎兒無害。[6][25]它是治療孕婦李斯特菌感染的首選藥物,可單獨使用或與氨基糖苷類抗生素合併使用。[6]懷孕會讓人體對芐西林的清除率增加高達50%,因此需要用到更高的劑量才能達到治療目的。[24][26]

氨芐西林會穿過胎盤並以母體血漿濃度的50-100%保留在羊水中,可能會導致新生兒體內的氨芐西林濃度較高。[26]

雖然哺乳母親會分泌一些氨芐西林進入乳汁中,但份量很少。[6][24]

新生兒體內的氨芐西林生物半衰期較長,血漿蛋白結合較低。[27]由於新生兒的腎功能尚未完全發育,腎臟的清除率也較低。[6]

禁忌症

[编辑]

氨苄西林對青黴素過敏的人會引發致命的過敏性休克,因此禁用。過敏反應包含有頻繁的皮蕁麻疹剝脫性皮膚炎英语Erythroderma多形紅斑英语erythema multiforme以及紅血球白血球暫時減少。[12]

不建議對併發傳染性單核白血球增多症的患者使用氨芐西林,因為超過40%的使用者會出現皮疹。[12]

副作用

[编辑]

氨芐西林的毒性較其他抗生素相對較少,對青黴素敏感以及有氣喘過敏史的人更易出現副作用。[12]它在極少數情況下也會引起嚴重的副作用,例如血管性水腫、過敏反應和艱難擬梭菌感染(範圍從輕度腹瀉到嚴重的假膜性結腸炎)。[12]有些人會發展出黑色"毛茸狀"舌頭。嚴重的不良反應還有癲癇發作和血清病。在約10%使用者身上最常出現的副作用是腹瀉和皮疹。較不常見的有噁心、嘔吐、搔癢和血液病。口服氨苄西林後較常見的消化道反應有毛茸狀舌頭、噁心、嘔吐、腹瀉和結腸炎。[12]另有其他病症可能會在治療結束後幾週才出現。[6]

過量

[编辑]

攝入過量氨芐西林可導致行為改變、意識混亂英语Confusion、昏厥和抽搐,以及神經肌肉過敏、電解質不平衡腎衰竭[12]

與其他藥物交互作用

[编辑]

氨芐西林會與丙磺舒胺甲蝶呤發生反應,降低腎臟的排泄。高劑量氨芐西林與華法林和其他口服抗凝劑同時使用可能會增加出血風險(可能是透過抑制血小板凝結的緣故)。[28]據說氨芐西林會降低口服避孕藥的效果,[6]但此點一直存在爭議。[29]其他抗生素如氯黴素紅黴素頭孢菌素四環素類抗生素可能會降低氨苄西林療效。[22]例如四環素類抗生素會抑制細菌中蛋白質合成,導致氨芐西林的作用標靶減少。[30]如果它與氨基糖苷類抗生素同時服用,會發生兩者結合,讓氨苄西林失去活性。分開給藥時,氨基糖苷類抗生素和氨芐西林反可發生相互增強的作用。[6][31]

氨芐西林與別嘌呤醇一起服用時更易引起皮疹。[12]

霍亂活疫苗和傷寒活疫苗與氨苄西林一起使用均會失效。氨芐西林通常用於治療霍亂和傷寒,但會抑制身體產生免疫反應的能力。[32][33][34]

藥理學

[编辑]

作用機制

[编辑]

氨芐西林屬於青黴素類中的Β-內醯胺抗生素,是氨基青黴素類家族的一份子。其活性大致相當於阿莫西林。氨苄西林能夠穿透革蘭氏陽性菌和一些革蘭氏陰性菌的外膜。它與苄青黴素的不同之處僅在擁有氨基。氨芐西林和阿莫西林上都有此氨基,有助此類抗生素能穿過革蘭氏陰性菌(例如大腸桿菌奇異變形桿菌英语Proteus mirabilis腸道沙門氏菌志賀氏菌屬)的外膜孔。[18][35]

氨苄西林是轉肽酶英语DD-transpeptidase的不可逆抑制劑,而細菌需要轉肽酶來製造細胞壁。[6]它會抑制二元分裂中細菌細胞壁合成的第三階段和最後階段,最終導致細胞裂解,氨芐西林因而具有溶菌的效力。[6][36]

藥物動力學

[编辑]

氨芐西林在個體的消化道中吸收良好(但有食物時會降低其吸收),並在一到兩個小時內達到最大血藥濃度。經由胃腸外途徑攝取的生物利用度約為62%。氨芐西林的血漿蛋白結合度僅有15-20%,與其他青黴素通常的60-90%血漿蛋白結合度不同。[6][27]

氨芐西林會擴散到大多數組織中,但主要是集中在肝臟和腎臟。當腦膜發炎(例如腦膜炎)時,也會在腦脊液中出現。[27]有些氨芐西林會被β-內醯胺環水解為青黴烯酸英语Penicilloic acid,而後代謝,[6]但大部分會以原形排出體外。[12]在腎臟中,它主要透過腎小管過濾,有的還經腎絲球濾過,其餘隨糞便和膽汁排出。

海他西林匹氨西林是開發用於提高生物利用率的氨苄西林酯類 。[37]

歷史

[编辑]

氨芐西林自1961年起已被廣泛用於治療細菌感染。[38]在英國藥業Beecham Group英语Beecham Group推出氨芐西林之前,青黴素療法僅對葡萄球菌和鏈球菌等革蘭氏陽性菌有效。[36]氨芐西林(最初品牌為"Penbritin")也展現對革蘭氏陰性菌(例如流感嗜血桿菌、大腸桿菌群和變形桿菌屬)的活性。[38]

社會與文化

[编辑]

經濟學

[编辑]

氨芐西林的售價相對便宜。[39]在美國有其通用名藥物流通。[6]

獸醫用途

[编辑]

在獸醫學中,氨芐西林可用於貓、狗和農場動物,治療下列感染:[15]

通常不會使用口服氨芐西林治療馬的疾病,因為其β-內酰胺的生物利用度較低。[16]

藥物在動物體內的生物半衰期與人類的大致相同(僅一個多小時)。貓和狗的口服劑生物利用度低於50%,馬的口服劑生物利用度低於4%。[17]

參考文獻

[编辑]
  1. ^ Burley JC, Van De Streek J, Stephens PW. CSD Entry: AMPCIH01. Cambridge Structural Database: Access Structures (Cambridge Crystallographic Data Centre). 2006 [2022-06-28]. doi:10.5517/ccb0nkj. 
  2. ^ Burley JC, van de Streek J, Stephens PW. Ampicillin trihydrate from synchrotron powder diffraction data. Acta Crystallogr. E. 2006, 62 (2): o797–o799. Bibcode:2006AcCrE..62O.797B. doi:10.1107/S1600536806001371可免费查阅. 
  3. ^ Ampicillin - international drug names. Drugs.com. 2019-11-30 [2020-01-26]. (原始内容存档于2019-11-30). 
  4. ^ Antibiotic abbreviations list. [2023-06-22]. (原始内容存档于2023-06-22). 
  5. ^ Ampicillin Use During Pregnancy. Drugs.com. 2019-05-02 [2020-01-26]. (原始内容存档于2019-08-22). 
  6. ^ 6.00 6.01 6.02 6.03 6.04 6.05 6.06 6.07 6.08 6.09 6.10 6.11 6.12 6.13 6.14 6.15 6.16 6.17 6.18 6.19 6.20 6.21 6.22 6.23 6.24 6.25 6.26 6.27 6.28 6.29 Ampicillin. The American Society of Health-System Pharmacists. [2015-08-01]. (原始内容存档于2015-07-12). 
  7. ^ Ampicillin use while Breastfeeding. March 2015 [2010-8-01]. (原始内容存档于2015-09-23). 
  8. ^ Fischer J, Ganellin CR. Analogue-based Drug Discovery. John Wiley & Sons. 2006: 490. ISBN 9783527607495. (原始内容存档于2016-12-20) (英语). 
  9. ^ Ravina E. The evolution of drug discovery : from traditional medicines to modern drugs 1. Weinheim: Wiley-VCH. 2011: 262. ISBN 9783527326693. (原始内容存档于2016-08-09). 
  10. ^ World Health Organization. The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. 2023. hdl:10665/371090可免费查阅. WHO/MHP/HPS/EML/2023.02. 
  11. ^ World Health Organization. Critically important antimicrobials for human medicine 6th revision. Geneva: World Health Organization. 2019. ISBN 9789241515528. hdl:10665/312266可免费查阅. 
  12. ^ 12.00 12.01 12.02 12.03 12.04 12.05 12.06 12.07 12.08 12.09 12.10 Ampicillin- ampicillin sodium injection, powder, for solution. DailyMed. 2019-09-11 [2020-01-25]. (原始内容存档于2018-02-22). 
  13. ^ WebMD. ampicillin (Rx). Medscape. [2017-08-22]. (原始内容存档于2017-08-15). 
  14. ^ Finberg R, Fingeroth J. Chapter 132: Infections in Transplant Recipients. Longo D, Fauci A, Kasper D, Hauser S, Jameson J, Loscalzo J (编). Harrison's Principles of Internal Medicine 1 18th. McGraw-Hill Medical. 2012. ISBN 978-0-07-174887-2. 
  15. ^ 15.0 15.1 Ampicillin injection, powder, for suspension. DailyMed. 2017-10-26 [2020-01-26]. (原始内容存档于2018-02-22). 
  16. ^ 16.0 16.1 16.2 16.3 Magdesian KG. Equine Pharmacology, an Issue of Veterinary Clinics of North America: Equine Practice, E-Book. Elsevier Health Sciences. 2017: 59. ISBN 978-0-323-52438-4. 
  17. ^ 17.0 17.1 Papich MG. Saunders Handbook of Veterinary Drugs: Small and Large Animal. Elsevier Health Sciences. 2015: 43–47 [2024-07-21]. ISBN 978-0-323-24485-5. (原始内容存档于2023-01-12). 
  18. ^ 18.0 18.1 Hauser AR. Antibiotic Basics for Clinicians: The ABCs of Choosing the Right Antibacterial Agent. Lippincott Williams & Wilkins. 2012: 25–28 [2024-07-21]. ISBN 978-1-4511-1221-4. (原始内容存档于2023-01-12). 
  19. ^ Akova M. Sulbactam-containing beta-lactamase inhibitor combinations. Clinical Microbiology and Infection. January 2008, 14 (Suppl 1): 185–188. PMID 18154545. doi:10.1111/j.1469-0691.2007.01847.x可免费查阅. 
  20. ^ Suleyman G, Zervos MJ. Safety and efficacy of commonly used antimicrobial agents in the treatment of enterococcal infections: a review. Expert Opinion on Drug Safety. 2016, 15 (2): 153–167. PMID 26629598. S2CID 25488987. doi:10.1517/14740338.2016.1127349. 
  21. ^ Torok ME, Moran E, Cooke F. Oxford Handbook of Infectious Diseases and Microbiology. Oxford University Press. December 2016: 721. ISBN 9780191503108. (原始内容存档于2017-03-23) (英语). 
  22. ^ 22.0 22.1 Wanamaker BP, Massey K. Applied Pharmacology for Veterinary Technicians - E-Book. Elsevier Health Sciences. 2014: 244 [2024-07-21]. ISBN 978-0-323-29170-5. (原始内容存档于2023-01-12). 
  23. ^ WebMD. Ampicillin Intravenous: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing. WebMD. [2018-02-23]. (原始内容存档于2018-02-23). 
  24. ^ 24.0 24.1 24.2 Weiner CP, Rope K. The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby需要免费注册. St. Martin's Press. 2013: 47–49. ISBN 978-1-250-03720-6. ampicillin pregnancy. 
  25. ^ Australian Government Department of Health Therapeutic Goods Administration. Prescribing medicines in pregnancy database. Therapeutic Goods Administration (TGA). Australian Government Department of Health. 2017-10-25 [2018-02-23]. (原始内容存档于2016-12-20).  Note: scroll down to "Search by name" and type "ampicillin" into the search bar. Requires JavaScript to be enabled.
  26. ^ 26.0 26.1 Rello J, Kollef MH, Díaz E, Rodríguez A. Infectious Diseases in Critical Care. Springer Science & Business Media. 2010: 172. ISBN 978-3-540-34406-3. 
  27. ^ 27.0 27.1 27.2 Eghianruwa K. Essential Drug Data for Rational Therapy in Veterinary Practice. AuthorHouse. 2014: 26 [2024-07-21]. ISBN 978-1-4918-0010-2. (原始内容存档于2023-01-12). 
  28. ^ Drug interactions between ampicillin and anisindione. Drugs.com. [2018-02-22]. (原始内容存档于2018-02-23). 
  29. ^ Piscitelli SC, Rodvold KA, Pai MP. Drug Interactions in Infectious Diseases. Springer Science & Business Media. 2011: 213–214 [2024-07-21]. ISBN 978-1-61779-213-7. (原始内容存档于2023-01-12). 
  30. ^ Drug interactions between ampicillin and bismuth subcitrate potassium / metronidazole / tetracycline. Drugs.com. [2018-02-22]. (原始内容存档于2018-02-23). 
  31. ^ Drug interactions between amikacin and ampicillin. Drugs.com. [2018-02-22]. (原始内容存档于2018-02-23). 
  32. ^ Drug interactions between ampicillin and cholera vaccine, live. Drugs.com. [2018-02-22]. (原始内容存档于2018-02-23). 
  33. ^ Drug interactions between ampicillin and typhoid vaccine, live. Drugs.com. [2018-02-22]. (原始内容存档于2018-02-23). 
  34. ^ Handa S. Cholera Medication. Medscape. 2017-06-22 [2018-02-23]. (原始内容存档于2018-02-23). 
  35. ^ Delcour AH. Outer membrane permeability and antibiotic resistance. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. May 2009, 1794 (5): 808–816. PMC 2696358可免费查阅. PMID 19100346. doi:10.1016/j.bbapap.2008.11.005. 
  36. ^ 36.0 36.1 Petri WA. Penicillins, Cephalosporins, and Other Beta-Lactam Antibiotics. Brunton L, Chabner B, Knollman B (编). Goodman and Gilman's the Pharmacological Basis of Therapeutics Twelfth. New York: McGraw Hill Professional. 2011: 1477–1504. ISBN 978-0-07-176939-6. 
  37. ^ 37.0 37.1 37.2 37.3 Giguère S, Prescott JF, Dowling PM. Antimicrobial Therapy in Veterinary Medicine. John Wiley & Sons. 2013: 167–170 [2024-07-21]. ISBN 978-1-118-67507-6. (原始内容存档于2023-01-12). 
  38. ^ 38.0 38.1 Acred P, Brown DM, Turner DH, Wilson MJ. Pharmacology and chemotherapy of ampicillin--a new broad-spectrum penicillin. British Journal of Pharmacology and Chemotherapy. April 1962, 18 (2): 356–369. PMC 1482127可免费查阅. PMID 13859205. doi:10.1111/j.1476-5381.1962.tb01416.x. 
  39. ^ Hanno PM, Guzzo TJ, Malkowicz SB, Wein AJ. Penn Clinical Manual of Urology E-Book. Elsevier Health Sciences. 2014: 122 [2024-07-21]. ISBN 978-0-323-24466-4. (原始内容存档于2023-04-14) (英语). 
  40. ^ Erskine R. Mastitis in Sows. Merck Veterinary Manual. [2017-08-22]. (原始内容存档于2017-07-04). 

外部連結

[编辑]
  • GB patent 902703,Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith,「Penicillins」,发表于1962-08-09,指定于Beecham Research Laboratories Ltd 
  • US patent 2985648,Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith,「Alpha-aminobenzylpenicillins」,发表于1961-05-23,发行于1961-05-23 
  • US patent 3157640,David A Johnson & Glenn A Hardcastle Jr,「D-(-)-alpha-aminobenzylpenicillin trihydrate」,发表于1964-11-17,发行于1964-11-17,指定于Bristol Myers Co