Sulfadimidine

Chemical compound

J01EB03 (WHO) QJ01EQ03 (WHO) QP51AG01 (WHO) QP51AG51 (WHO)

Identifiers

IUPAC name

4-amino-N-(4,6-dimethylpyrimidin-2-yl)
benzene-1-sulfonamide

CAS Number

57-68-1^Y

PubChem CID

5327

DrugBank

DB01582^Y

ChemSpider

5136^Y

UNII

48U51W007F

KEGG

D02436^Y

ChEBI

CHEBI:102265^Y

ChEMBL

ChEMBL446^Y

NIAID ChemDB

027749

CompTox Dashboard (EPA)

DTXSID6021290

ECHA InfoCard100.000.315

Chemical and physical dataFormulaC₁₂H₁₄N₄O₂SMolar mass278.33 g·mol⁻¹3D model (JSmol)

Interactive image

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)^Y
Key:ASWVTGNCAZCNNR-UHFFFAOYSA-N^Y

(verify)

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.^{[citation needed]}

References

^ Romváry A, Simon F (1992). "Sulfonamide residues in eggs". Acta Veterinaria Hungarica. 40 (1–2): 99–106. PMID 1476095.
^ Reddy KS, Jain SK, Uppal RP (1988). "Pharmacokinetic studies of sulphonamides in poultry". Indian Journal of Animal Sciences.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone