Sulfamerazine

Sulfamerazine
Systematic (IUPAC) name

4-amino-N-(4-methylpyrimidin-2-yl) benzenesulfonamide
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	127-79-7^Y
ATC code	D06BA06 (WHO) J01ED07 QJ01EQ17
PubChem	CID 5325
DrugBank	DB01581^Y
ChemSpider	5134^Y
UNII	UR1SAB295F^Y
KEGG	D02435^Y
ChEBI	CHEBI:102130^Y
ChEMBL	CHEMBL438^Y
Chemical data
Formula	C₁₁H₁₂N₄O₂S
Molar mass	264.305 g/mol
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

References

↑ 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.

External links

Media related to Sulfonamide antibiotics at Wikimedia Commons

Sulfamerazine (DrugBank)
Sulfamerazine (NIST)

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics

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

Chemotherapeutics

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

Antibacterials: nucleic acid inhibitors (J01E, J01M)

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

DHFR inhibitor

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

Sulfonamides
(DHPS inhibitor)

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

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

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

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

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

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Sulfamerazine

Synthesis

See also

References

External links