Sulfadimidine

Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.

Sulfamethazine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01EB03 (WHO) QJ01EQ03 (WHO) QP51AG01 (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
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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.

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). "[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. 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. doi:10.1016/j.chemosphere.2009.02.002. PMID 19269673.

Further reading

• ChemDB. "Sulfamethazine", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)
• Sulfadimidine in the ChemIDplus database
• PubChem. "Sulfamethazine - Substance Summary", PubChem, National Center for Biotechnology Information (NCBI), National Library of Medicine (NLM), National Institutes of Health (NIH)