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{{Drugbox
{{Drugbox
| IUPAC_name       = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzenesulfonamide
| verifiedrevid = 470472902
| image             = Sulfadimidine.svg
| IUPAC_name = 4-amino-''N''-(4,6-dimethylpyrimidin-2-yl)<br>benzenesulfonamide
| CAS_number        = 57-68-1
| image = Sulfadimidine Wiki Str.png
| ATC_prefix        = J01
 
| ATC_suffix        = EB03
| drug_name = Sulfamethazine
| PubChem          = 5327
 
| DrugBank          =  
<!--Clinical data-->
| C=12|H=14|N=4|O=2|S=1
| tradename =
| molecular_weight  = 278.331 g/mol
| Drugs.com = {{drugs.com|international|sulfamethazine}}
| bioavailability  =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound    =
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism        =
| pregnancy_category =   
| elimination_half-life =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| excretion        =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_category=   
| legal_status =
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| routes_of_administration =
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
<!--Pharmacokinetic data-->
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| bioavailability = 
| legal_status     =  
| protein_bound = 
| routes_of_administration =  
| 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}}
| PubChem = 5327
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01582
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5136
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 48U51W007F
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02436
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 102265
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| 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
}}
}}
__NOTOC__
{{SI}}
{{SI}}
{{CMG}}
== Overview ==
'''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.


'''Sulfadimidine''' (or '''sulfamethazine''') is a [[sulfonamide]] [[antibacterial]].
==Notes==
*{{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|2}}
==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)
* {{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}}


[[Category:Drug]]
[[Category:Sulfonamide antibiotics]]
[[Category:Sulfonamide antibiotics]]
[[Category:Pyrimidines]]


{{WH}}
{{antibiotic-stub}}
{{WS}}

Latest revision as of 12:36, 13 April 2015

Sulfamethazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC12H14N4O2S
Molar mass278.33 g/mol
3D model (JSmol)
Melting point176 °C (348.8 °F)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

Notes

  • ^a Abbreviations are not found in the databases (such as ChemDB, ChemIDplus, PubChem), but often seen in the published literature.[citation needed]
  • ^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.[9]
  • ^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]

References

  1. ↑ Romváry, A; Simon, F (1992). "Sulfonamide residues in eggs". Acta veterinaria Hungarica. 40 (1–2): 99–106. ISSN 0236-6290. PMID 1476095.
  2. ↑ Reddy; Jain, S. K.; Uppal, R. P. (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; Hirahara, Y; Yamana, T; 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. ISSN 0077-4715. PMID 7920569.
  4. ↑ Garg, SK; Ghosh, SS; Mathur, VS (Jan 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. ISSN 0174-4879. PMID 3485584.
  5. ↑ Peña, MS; Salinas, F; Mahedero, MC; Aaron, JJ (Feb 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. ISSN 0039-9140. PMID 18965913.
  6. ↑ Kaniou, S; Pitarakis, K; Barlagianni, I; Poulios, I (Jul 2005). "Photocatalytic oxidation of sulfamethazine". Chemosphere. 60 (3): 372–80. doi:10.1016/j.chemosphere.2004.11.069. ISSN 0045-6535. 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. ISSN 0142-2782. PMID 3593892.
  8. ↑ De Liguoro, M; Fioretto, B; Poltronieri, C; Gallina, G (Jun 2009). "The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim". Chemosphere. 75 (11): 1519–24. doi:10.1016/j.chemosphere.2009.02.002. ISSN 0045-6535. PMID 19269673.
  9. ↑ http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHandle=Search&actionHandle=getAll3DMViewFiles&nextPage=jsp%2Fcommon%2FChemFull.jsp%3FcalledFrom%3Dlite&chemid=000149451&formatType=_3D[dead link]

Further reading

Template:Sulfonamides and trimethoprim


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