Sulfamerazine

Sulfamerazine
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	D06BA06 (WHO) J01ED07 (WHO) QJ01EQ17 (WHO)
Identifiers
IUPAC name 4-amino-N-(4-methylpyrimidin-2-yl) benzenesulfonamide
CAS Number	127-79-7^Y
PubChem (CID)	5325
DrugBank	DB01581^Y
ChemSpider	5134^Y
UNII	UR1SAB295F^Y
KEGG	D02435^Y
ChEBI	CHEBI:102130^Y
ChEMBL	CHEMBL438^Y
ECHA InfoCard	100.004.425
Chemical and physical data
Formula	C₁₁H₁₂N₄O₂S
Molar mass	264.305 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(Nc1nc(ccn1)C)c2ccc(N)cc2
InChI InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)^Y Key:QPPBRPIAZZHUNT-UHFFFAOYSA-N^Y
(verify)

Sulfamerazine is a sulfonamide antibacterial.

Synthesis

Sulfamerazine synthesis:^[1]^[2] U.S. Patent 2,378,813

↑ Roblin, R. O.; Williams, J. H.; Winnek, P. S.; English, J. P. (1940). "Chemotherapy. II. Some Sulfanilamido Heterocycles1". Journal of the American Chemical Society. 62 (8): 2002. doi:10.1021/ja01865a027.
↑ Sprague, J. M.; Kissinger, L. W.; Lincoln, R. M. (1941). "Sulfonamido Derivatives of Pyrimidines". Journal of the American Chemical Society. 63 (11): 3028. doi:10.1021/ja01856a046.

Media related to Sulfonamide antibiotics at Wikimedia Commons

Tetracycline and derivatives	Demeclocycline Chlortetracycline Oxytetracycline Tetracycline

Others	Amphenicol: Chloramphenicol Aminoglycosides: Neomycin Gentamicin Amikacin Quinolone: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Fusidic acid Bacitracin Tyrothricin Mupirocin

Sulfonamides	Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine

Antivirals	Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine

Other	Ingenol mebutate Metronidazole

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

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Related (DG)

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

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