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Sulfadimidine: Difference between revisions

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{{Short description|Chemical compound}}
{{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''',<ref name=biam>{{cite web |url=http://www.biam2.org/www/Sub3321.html |title=Sulfadimidine |language=French |publisher=] |date=15 November 1999 |accessdate=14 September 2009}}</ref> is a ] ].
'''Sulfadimidine''' or '''sulfamethazine''' is a ] ].


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 |url=http://www.cababstractsplus.org/abstracts/Abstract.aspx?AcNo=19892292426 |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}}</ref><ref>{{cite journal |pmid=3485584 |year=1986 |month=Jan |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 |year=1994 |month=Feb |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 |year=2005 |month=Jul |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 |year=1987 |month=Mar |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 |year=2009 |month=Jun |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.<ref name=biam/> 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}}


==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 ]/] (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 ], also seen abbreviated SMZ.{{Citation needed|date=September 2009}}

==References==
{{Reflist}} {{Reflist}}


==Further reading== == Further reading ==
* ChemDB. , ''ChemDB'', ] (NIAID), ] (NIH) * ChemDB. , ''ChemDB'', ] (NIAID), ] (NIH)
* {{ChemID|57-68-1}}
* PubChem. , '']'', ] (NCBI), ] (NLM), ] (NIH)


{{Sulfonamides and trimethoprim}} {{Sulfonamides and trimethoprim}}
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] ]
] ]
]



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

]

Latest revision as of 15:33, 8 October 2024

Chemical compound Pharmaceutical compound
Sulfamethazine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 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
3D model (JSmol)
Melting point176 °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)

Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.

There are non-standardized abbreviations for it as "sulfadimidine" (abbreviated SDI and more commonly but less reliably SDD) and as "sulfamethazine" (abbreviated SMT and more commonly but less reliably SMZ). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.

References

  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). "". 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

Antibacterials that inhibit nucleic acid (J01E, J01M)
Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor
Sulfonamides
(DHPS inhibitor)
Short-acting
Intermediate-acting
Long-acting
Other/ungrouped
Combinations
Other DHPS inhibitors
Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
1st generation
Fluoroquinolones
2nd generation
3rd generation
4th generation
Veterinary
Newer non-fluorinated
Related (DG)
Anaerobic DNA
inhibitors
Nitroimidazole derivatives
RNA synthesis
Rifamycins/
RNA polymerase
Lipiarmycins
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