U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H14N4O2S
Molecular Weight 314.362
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAPHENAZOLE

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=CC=NN2C3=CC=CC=C3

InChI

InChIKey=QWCJHSGMANYXCW-UHFFFAOYSA-N
InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2

HIDE SMILES / InChI

Molecular Formula C15H14N4O2S
Molecular Weight 314.362
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sulfaphenazole is an oral antibiotic, which was used for the treatment of bacterial infections under the name Sulfabid. The drug was found to block folate synthesis in bacterias by inhibiting the enzyme dihydropteroate synthase. Sulfaphenazole is also known to inhibit CYP2C9 with high potency and specificity. Sulfabid is no longer marketed in the USA.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.94 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SULFABID

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
439 mg single, oral
SULFAPHENAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
731 μg × h/mL
439 mg single, oral
SULFAPHENAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
439 mg single, oral
SULFAPHENAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
439 mg single, oral
SULFAPHENAZOLE plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
1 g suspension given orally.
Route of Administration: Oral
In Vitro Use Guide
The minimal inhibitory concentrations of sulfaphenazole were 64 ug/ml for A. fumigatus and 4-8 ug/ml for C. neoformans var grubii.
Substance Class Chemical
Record UNII
0J8L4V3F81
Record Status Validated (UNII)
Record Version