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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 470472902
| 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
| image = Sulfadimidine.svg
| drug_name = Sulfamethazine
| drug_name = Sulfamethazine

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| Drugs.com = {{drugs.com|international|sulfamethazine}}
| Drugs.com = {{drugs.com|international|sulfamethazine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 57-68-1
| CAS_number = 57-68-1
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = EB03
| ATC_suffix = EB03
| ATC_supplemental = {{ATCvet|J01|EQ03}} {{ATCvet|P51|AG01}}
| ATC_supplemental = {{ATCvet|J01|EQ03}} {{ATCvet|P51|AG01}} {{ATCvet|P51|AG51}}
| PubChem = 5327
| PubChem = 5327
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
Line 46: Line 43:
| ChEMBL = 446
| ChEMBL = 446
| NIAID_ChemDB = 027749
| NIAID_ChemDB = 027749

<!--Chemical data-->
<!--Chemical data-->
| C=12 | H=14 | N=4 | O=2 | S=1
| 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
| 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_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)
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ASWVTGNCAZCNNR-UHFFFAOYSA-N
| StdInChIKey = ASWVTGNCAZCNNR-UHFFFAOYSA-N
| melting_point = 176
}}
|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}
'''Sulfadimidine''' or '''sulfamethazine''' is a [[sulfonamide (medicine)|sulfonamide]] [[antibacterial]].
'''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}}
==Synthesis==
[[File:Sulfamethazine synthesis.svg|thumb|center|500px|Sulfamethazine synthesis: {{Cite patent|GB|546158}} {{Cite patent|GB|552887}} {{US patent|3119818}} <ref>{{Cite doi|10.1021/ja01853a045}}</ref>]]
Sulfamethazine is syntheized by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4,6-dimethyl[[pyrimidine]], which in turn is synthesized by condensing [[acetylacetone]] with [[guanidine]] followed by hydrolysis of the acetylamino group with a base.


==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}}
==See also==
*[[Sulfadiazine]]
*[[Sulfamerazine]]
==References==
{{Reflist}}
{{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}}
{{Sulfonamides and trimethoprim}}
Line 84: Line 66:
[[Category:Sulfonamide antibiotics]]
[[Category:Sulfonamide antibiotics]]
[[Category:Pyrimidines]]
[[Category:Pyrimidines]]
[[Category:4-Aminophenyl compounds]]



{{antibiotic-stub}}
{{antibiotic-stub}}

Latest revision as of 15:33, 8 October 2024

Sulfamethazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 4-amino-N-(4,6-dimethylpyrimidin-2-yl)
    benzene-1-sulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.315 Edit this at Wikidata
Chemical and physical data
FormulaC12H14N4O2S
Molar mass278.33 g·mol−1
3D model (JSmol)
Melting point176 °C (349 °F)
  • O=S(=O)(Nc1nc(cc(n1)C)C)c2ccc(N)cc2
  • 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) checkY
  • Key:ASWVTGNCAZCNNR-UHFFFAOYSA-N checkY
  (verify)

Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.

There are non-standardizeda abbreviations for it as "sulfadimidine" (abbreviated SDI[1][2] and more commonly but less reliablyb SDD[3][4]) and as "sulfamethazine" (abbreviated SMT[5][6] and more commonly but less reliablyc SMZ[7][8]). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.[citation needed]

References

[edit]
  1. ^ Romváry A, Simon F (1992). "Sulfonamide residues in eggs". Acta Veterinaria Hungarica. 40 (1–2): 99–106. PMID 1476095.
  2. ^ Reddy KS, Jain SK, Uppal RP (1988). "Pharmacokinetic studies of sulphonamides in poultry". Indian Journal of Animal Sciences.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.

Further reading

[edit]
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