Sulfafurazole

Not to be confused with sulfadiazine.

Sulfafurazole
Systematic (IUPAC) name

4-amino-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601049
Pregnancy category	To be avoided within two months of term
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Excretion	Excreted unchanged in urine
Identifiers
CAS Number	127-69-5^Y
ATC code	J01EB05 S01AB02 QJ01EQ05
PubChem	CID 5344
DrugBank	DB00263^N
UNII	740T4C525W^N
KEGG	D00450^Y
ChEMBL	CHEMBL453^N
Chemical data
Formula	C₁₁H₁₃N₃O₃S
Molar mass	267.30 g/mol
SMILES CC1=C(ON=C1C)NS(=O)(=O)C2=CC=C(C=C2)N
Physical data
Melting point	194 °C (381 °F)
^NY (what is this?) (verify)

Sulfafurazole (INN, also known as sulfisoxazole) is a sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of Gram-negative and Gram-positive organisms. It is sometimes given in combination with erythromycin (see erythromycin/Sulfafurazole) or phenazopyridine. It is used locally in a 4% solution or ointment.

Synthesis

Sulfisoxazole synthesis: U.S. Patent 2,430,094 GB 595775

External links

Sulfisoxazole at the US National Library of Medicine Medical Subject Headings (MeSH)
MedlinePlus DrugInfo medmaster-a601049
MedlinePlus DrugInfo medmaster-a601115
DDB 30455

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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Sulfafurazole

Synthesis

See also

External links