Sulfadimidine

Sulfamethazine

Systematic (IUPAC) name
4-amino-N-(4,6-dimethylpyrimidin-2-yl) benzenesulfonamide
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	57-68-1
ATC code	J01EB03 (WHO) QJ01EQ03 QP51AG01
PubChem	CID 5327
DrugBank	DB01582
ChemSpider	5136
UNII	48U51W007F
KEGG	D02436
ChEBI	CHEBI:102265
ChEMBL	CHEMBL446
NIAID ChemDB	027749
Chemical data
Formula	C12H14N4O2S
Molar mass	278.33 g/mol
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
Physical data
Melting point	176 °C (349 °F)
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Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.

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.

Availability

In Pakistan, it is available with the brand name of "Sanadine-33.3 %" as potential treatment of E-coli enteritis in veterinary medicine. ^[9]

Notes

• ^a Abbreviations are not found in the databases (such as ChemDB, ChemIDplus, PubChem), but often seen in the published literature.
• ^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.
• ^[9] http://www.sannalabs.com/productslist.htm

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

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)