Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 References 2 Further reading

Sulfadimidine

●العربية ●Deutsch ●فارسی ●Italiano ●Română ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Suomi ●ไทย ●Українська ●粵語 ●中文 Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version In other projects ●Wikimedia Commons Appearance From Wikipedia, the free encyclopedia

Sulfamethazine
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	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 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)^Y Key:ASWVTGNCAZCNNR-UHFFFAOYSA-N^Y
(verify)

Sulfadimidineorsulfamethazine 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[edit]

^ 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.

Further reading[edit]

ChemDB. "Sulfamethazine", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

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

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^‡/Levonadifloxacin/Alalevonadifloxacin 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^‡