Sulfamerazine

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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
KEGG	D02435^Y
ChEBI	CHEBI:102130^Y
ChEMBL	ChEMBL438^Y
CompTox Dashboard (EPA)	DTXSID0023612
ECHA InfoCard	100.004.425
Chemical and physical data
Formula	C₁₁H₁₂N₄O₂S
Molar mass	264.30 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	234 to 238 °C (453 to 460 °F)
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

Sulfamerazine is a sulfonamide antibacterial.

Synthesis[]

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

References[]

^ Roblin RO, Williams JH, Winnek PS, English JP (1940). "Chemotherapy. II. Some Sulfanilamido Heterocycles1". Journal of the American Chemical Society. 62 (8): 2002. doi:10.1021/ja01865a027.
^ Sprague JM, Kissinger LW, Lincoln RM (1941). "Sulfonamido Derivatives of Pyrimidines". Journal of the American Chemical Society. 63 (11): 3028. doi:10.1021/ja01856a046.

External links[]

Media related to Sulfamerazine 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 Quinolones: 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 Tirbanibulin

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^†
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole () 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	Sulfacetamide Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine

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

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

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

RNA synthesis

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

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^‡Withdrawn from market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

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Sulfamerazine

Contents

Synthesis[]

See also[]

References[]

External links[]