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Revision as of 18:11, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 467819867 of page Sulfadimidine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 15:33, 8 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:4-Aminophenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 470472902
| Verifiedfields = changed
⚫ | IUPAC_name = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzene-1-sulfonamide
| Watchedfields = changed
⚫ | verifiedrevid = 409962958
⚫ | IUPAC_name = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzenesulfonamide
| 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|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01582 | DrugBank = DB01582
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02436 | KEGG = D02436
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 102265 | ChEBI = 102265
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 446 | ChEMBL = 446
| 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 ] ].

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 = | 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}}

== References ==
{{Reflist}}

== Further reading ==
* ChemDB. , ''ChemDB'', ] (NIAID), ] (NIH)

{{Sulfonamides and trimethoprim}}

]
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{{antibiotic-stub}}