Sulfadimidine: Difference between revisions

Sulfamethazine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01EB03 (WHO) QJ01EQ03 (WHO) QP51AG01 (WHO) QP51AG51 (WHO);
Identifiers
	IUPAC name 4-amino-N-(4,6-dimethylpyrimidin-2-yl); benzene-1-sulfonamide;
CAS Number	57-68-1 ;
PubChem CID	5327;
DrugBank	DB01582 ;
ChemSpider	5136 ;
UNII	48U51W007F;
KEGG	D02436 ;
ChEBI	CHEBI:102265 ;
ChEMBL	ChEMBL446 ;
NIAID ChemDB	027749;
CompTox Dashboard (EPA)	DTXSID6021290 ;
ECHA InfoCard	100.000.315
Chemical and physical data
Formula	C12H14N4O2S
Molar mass	278.33 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	176 °C (349 °F)
	SMILES O=S(=O)(Nc1nc(cc(n1)C)C)c2ccc(N)cc2;
	InChI InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16) ; Key:ASWVTGNCAZCNNR-UHFFFAOYSA-N ;
	(verify)

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Latest revision as of 15:33, 8 October 2024

Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.

There are non-standardized^a abbreviations for it as "sulfadimidine" (abbreviated SDI^[1]^[2] and more commonly but less reliably^b SDD^[3]^[4]) and as "sulfamethazine" (abbreviated SMT^[5]^[6] and more commonly but less reliably^c SMZ^[7]^[8]). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.^{[citation needed]}

References

^ Romváry A, Simon F (1992). "Sulfonamide residues in eggs". Acta Veterinaria Hungarica. 40 (1–2): 99–106. PMID 1476095.
^ Reddy KS, Jain SK, Uppal RP (1988). "Pharmacokinetic studies of sulphonamides in poultry". Indian Journal of Animal Sciences.
^ Kamakura K, Hasegawa M, Koiguchi S, Miyata M, Okamoto K, Narita M, et al. (1993). "[Studies on the identification of sulfadimidine in pork by high performance liquid chromatography with photodiode array detector and gas chromatograph-mass spectrometry]". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (111): 61–5. PMID 7920569.
^ Garg SK, Ghosh SS, Mathur VS (January 1986). "Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (1): 23–5. PMID 3485584.
^ Peña MS, Salinas F, Mahedero MC, Aaron JJ (February 1994). "Solvent effect on the determination of sulfamethazine by room-temperature photochemically induced fluorescence". Talanta. 41 (2): 233–6. doi:10.1016/0039-9140(94)80113-4. PMID 18965913.
^ Kaniou S, Pitarakis K, Barlagianni I, Poulios I (July 2005). "Photocatalytic oxidation of sulfamethazine". Chemosphere. 60 (3): 372–80. Bibcode:2005Chmsp..60..372K. doi:10.1016/j.chemosphere.2004.11.069. PMID 15924956.
^ Calvo R, Sarabia S, Carlos R, Du Souich P (Mar 1987). "Sulfamethazine absorption and disposition: effect of surgical procedures for gastroduodenal ulcers". Biopharmaceutics & Drug Disposition. 8 (2): 115–24. doi:10.1002/bdd.2510080203. PMID 3593892.
^ De Liguoro M, Fioretto B, Poltronieri C, Gallina G (June 2009). "The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim". Chemosphere. 75 (11): 1519–24. Bibcode:2009Chmsp..75.1519D. doi:10.1016/j.chemosphere.2009.02.002. PMID 19269673.

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{Drugbox
 | verifiedrevid = 470472902
-| IUPAC_name = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzenesulfonamide
+| IUPAC_name = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzene-1-sulfonamide
 | image = Sulfadimidine.svg
 | drug_name = Sulfamethazine
 <!--Clinical data-->
 | tradename =
 | Drugs.com = {{drugs.com|international|sulfamethazine}}
 | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
 | pregnancy_US = <!-- A / B            / C / D / X -->
 | pregnancy_category =
 | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
 | legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
 | legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
 | legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
 | bioavailability =
 | protein_bound =
 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
-| CASNo_Ref = {{cascite|correct|CAS}}
 | CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 57-68-1
 | ATC_prefix = J01
 | ATC_suffix = EB03
-| ATC_supplemental =   {{ATCvet|J01|EQ03}} {{ATCvet|P51|AG01}}
+| ATC_supplemental =   {{ATCvet|J01|EQ03}} {{ATCvet|P51|AG01}} {{ATCvet|P51|AG51}}
 | PubChem = 5327
 | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
@@ Line 46: / Line 43: @@
 | ChEMBL = 446
 | NIAID_ChemDB = 027749
 <!--Chemical data-->
 | C=12 | H=14 | N=4 | O=2 | S=1
-| molecular_weight = 278.33 g/mol
 | smiles = O=S(=O)(Nc1nc(cc(n1)C)C)c2ccc(N)cc2
-| InChI = 1/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
-| InChIKey = ASWVTGNCAZCNNR-UHFFFAOYAK
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = ASWVTGNCAZCNNR-UHFFFAOYSA-N
+| melting_point     = 176
-}}
+|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}
 '''Sulfadimidine''' or '''sulfamethazine''' is a [[sulfonamide (medicine)|sulfonamide]] [[antibacterial]].
-There are non-standardized{{Ref|reference_name_A|a}} abbreviations for it as "sulfadimidine" (abbreviated '''SDI'''<ref>{{cite journal |pmid=1476095 |year=1992 |last1=Romváry |first1=A |last2=Simon |title=Sulfonamide residues in eggs |volume=40 |issue=1–2 |pages=99–106 |issn=0236-6290 |journal=Acta veterinaria Hungarica |first2=F}}</ref><ref>{{cite journal |last1=Reddy |first2=S. K. |last2=Jain |last3=Uppal |first3=R. P. |year=1988 |title=Pharmacokinetic studies of sulphonamides in poultry |journal=Indian Journal of Animal Sciences}}</ref> and more commonly but less reliably{{Ref|reference_name_B|b}} '''SDD'''<ref>{{cite journal |pmid=7920569 |year=1993 |last1=Kamakura |first1=K |last2=Hasegawa |last3=Koiguchi |last4=Miyata |last5=Okamoto |last6=Narita |last7=Hirahara |last8=Yamana |last9=Tonogai |title=Studies on the identification of sulfadimidine in pork by high performance liquid chromatography with photodiode array detector and gas chromatograph-mass spectrometry |issue=111 |pages=61–5 |issn=0077-4715 |journal=Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences |first2=M |first3=S |first4=M |first5=K |first6=M |first7=Y |first8=T |first9=Y|last10=Ito |first10=Y |display-authors=8 }}</ref><ref>{{cite journal |pmid=3485584 |date=Jan 1986 |last1=Garg |first1=SK |last2=Ghosh |last3=Mathur |title=Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers |volume=24 |issue=1 |pages=23–5 |issn=0174-4879 |journal=International journal of clinical pharmacology, therapy, and toxicology |first2=SS |first3=VS}}</ref>) and as "sulfamethazine" (abbreviated '''SMT'''<ref>{{cite journal |pmid=18965913 |date=Feb 1994 |last1=Peña |first1=MS |last2=Salinas |last3=Mahedero |last4=Aaron |title=Solvent effect on the determination of sulfamethazine by room-temperature photochemically induced fluorescence |volume=41 |issue=2 |pages=233–6 |issn=0039-9140 |journal=Talanta |doi=10.1016/0039-9140(94)80113-4 |first2=F |first3=MC |first4=JJ}}</ref><ref>{{cite journal |pmid=15924956 |date=Jul 2005 |last1=Kaniou |first1=S |last2=Pitarakis |last3=Barlagianni |last4=Poulios |title=Photocatalytic oxidation of sulfamethazine |volume=60 |issue=3 |pages=372–80 |issn=0045-6535 |doi=10.1016/j.chemosphere.2004.11.069 |journal=Chemosphere |first2=K |first3=I |first4=I}}</ref> and more commonly but less reliably{{Ref|reference_name_C|c}} '''SMZ'''<ref>{{cite journal |pmid=3593892 |date=Mar 1987 |last1=Calvo |first1=R |last2=Sarabia |last3=Carlos |last4=Du Souich |title=Sulfamethazine absorption and disposition: effect of surgical procedures for gastroduodenal ulcers |volume=8 |issue=2 |pages=115–24 |issn=0142-2782 |journal=Biopharmaceutics & drug disposition |doi=10.1002/bdd.2510080203 |first2=S |first3=R |first4=P}}</ref><ref>{{cite journal |pmid=19269673 |date=Jun 2009 |last1=De Liguoro |first1=M |last2=Fioretto |last3=Poltronieri |last4=Gallina |title=The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim |volume=75 |issue=11 |pages=1519–24 |issn=0045-6535 |doi=10.1016/j.chemosphere.2009.02.002 |journal=Chemosphere |first2=B |first3=C |first4=G}}</ref>). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.
+There are non-standardized{{Ref|reference_name_A|a}} abbreviations for it as "sulfadimidine" (abbreviated '''SDI'''<ref>{{cite journal | vauthors = Romváry A, Simon F | title = Sulfonamide residues in eggs | journal = Acta Veterinaria Hungarica | volume = 40 | issue = 1–2 | pages = 99–106 | year = 1992 | pmid = 1476095 }}</ref><ref>{{cite journal | vauthors = Reddy KS, Jain SK, Uppal RP |year=1988 |title=Pharmacokinetic studies of sulphonamides in poultry |journal=Indian Journal of Animal Sciences}}</ref> and more commonly but less reliably{{Ref|reference_name_B|b}} '''SDD'''<ref>{{cite journal | vauthors = Kamakura K, Hasegawa M, Koiguchi S, Miyata M, Okamoto K, Narita M, Hirahara Y, Yamana T, Tonogai Y, Ito Y | display-authors = 6 | title = [Studies on the identification of sulfadimidine in pork by high performance liquid chromatography with photodiode array detector and gas chromatograph-mass spectrometry] | journal = Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences | issue = 111 | pages = 61–5 | year = 1993 | pmid = 7920569 }}</ref><ref>{{cite journal | vauthors = Garg SK, Ghosh SS, Mathur VS | title = Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 24 | issue = 1 | pages = 23–5 | date = January 1986 | pmid = 3485584 }}</ref>) and as "sulfamethazine" (abbreviated '''SMT'''<ref>{{cite journal | vauthors = Peña MS, Salinas F, Mahedero MC, Aaron JJ | title = Solvent effect on the determination of sulfamethazine by room-temperature photochemically induced fluorescence | journal = Talanta | volume = 41 | issue = 2 | pages = 233–6 | date = February 1994 | pmid = 18965913 | doi = 10.1016/0039-9140(94)80113-4 }}</ref><ref>{{cite journal | vauthors = Kaniou S, Pitarakis K, Barlagianni I, Poulios I | title = Photocatalytic oxidation of sulfamethazine | journal = Chemosphere | volume = 60 | issue = 3 | pages = 372–80 | date = July 2005 | pmid = 15924956 | doi = 10.1016/j.chemosphere.2004.11.069 | bibcode = 2005Chmsp..60..372K }}</ref> and more commonly but less reliably{{Ref|reference_name_C|c}} '''SMZ'''<ref>{{cite journal | vauthors = Calvo R, Sarabia S, Carlos R, Du Souich P | title = Sulfamethazine absorption and disposition: effect of surgical procedures for gastroduodenal ulcers | journal = Biopharmaceutics & Drug Disposition | volume = 8 | issue = 2 | pages = 115–24 | date = Mar 1987 | pmid = 3593892 | doi = 10.1002/bdd.2510080203 }}</ref><ref>{{cite journal | vauthors = De Liguoro M, Fioretto B, Poltronieri C, Gallina G | title = The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim | journal = Chemosphere | volume = 75 | issue = 11 | pages = 1519–24 | date = June 2009 | pmid = 19269673 | doi = 10.1016/j.chemosphere.2009.02.002 | bibcode = 2009Chmsp..75.1519D }}</ref>). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.{{cn|date=January 2023}}
-==Notes==
+== References ==
-*{{note|reference_name_A|a}} Abbreviations are not found in the databases (such as ChemDB, ChemIDplus, PubChem), but often seen in the published literature.{{Citation needed|date=September 2009}}
-*{{note|reference_name_B|b}} "SDD" is not found in databases, but often seen in the published literature; it could however be confused with [[Tiferron]]/[[Sodium catechol sulfate]] (1,2-Dihydroxybenzene-3,5-disulfonic acid disodium Salt), uncommon but found officially abbreviated SDD in the ChemIDplus database.<ref><nowiki>http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHandle=Search&actionHandle=getAll3DMViewFiles&nextPage=jsp%2Fcommon%2FChemFull.jsp%3FcalledFrom%3Dlite&chemid=000149451&formatType=_3D</nowiki>{{Dead link|date=September 2009}}</ref>
-*{{note|reference_name_C|c}} "SMZ" is not found in databases, but often seen in the published literature; it could however be confused with [[sulfamethoxazole]], also seen abbreviated SMZ.{{Citation needed|date=September 2009}}
-==References==
 {{Reflist}}
-==Further reading==
+== Further reading ==
-* ChemDB. [http://chemdb.niaid.nih.gov/struct_search/all/url_search.asp?aids_no=027749 "Sulfamethazine"], ''ChemDB'', [[National Institute of Allergy and Infectious Diseases]] (NIAID), [[National Institutes of Health]] (NIH)
+* ChemDB. [https://archive.today/20121215074008/http://chemdb.niaid.nih.gov/struct_search/all/url_search.asp?aids_no=027749 "Sulfamethazine"], ''ChemDB'', [[National Institute of Allergy and Infectious Diseases]] (NIAID), [[National Institutes of Health]] (NIH)
-* {{ChemID|57-68-1}}
-* PubChem. [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=611470 "Sulfamethazine - Substance Summary"], ''[[PubChem]]'', [[National Center for Biotechnology Information]] (NCBI), [[National Library of Medicine]] (NLM), [[National Institutes of Health]] (NIH)
 {{Sulfonamides and trimethoprim}}
@@ Line 79: / Line 66: @@
 [[Category:Sulfonamide antibiotics]]
 [[Category:Pyrimidines]]
+[[Category:4-Aminophenyl compounds]]
 {{antibiotic-stub}}