Basic information
- CAS
526-08-9- Standard SMILES
Nc1ccc(S(=O)(=O)Nc2ccnn2-c2ccccc2)cc1- InChIKey
QWCJHSGMANYXCW-UHFFFAOYSA-N- Molecular formula
- C15H14N4O2S
- Average molar mass
- 314.4 g/mol
- Monoisotopic mass
- 314.08374688
Overview
Sulfaphenazole is a sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent. It has a role as an antibacterial drug, a P450 inhibitor, an EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor and an EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor. It is a member of pyrazoles, a sulfonamide, a substituted aniline, a primary amino compound and a sulfonamide antibiotic.
Names & identifiers
- Preferred name
- Sulfaphenazole
- IUPAC
- 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
- English name
- SULFAPHENAZOLE
- Molecular formula
- C15H14N4O2S
- Molecular weight
- 314.36
Names & synonyms
sulfaphenazole526-08-9SulphaphenazoleSulfabid4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamideSulfafenazolSulfaphenazolSulfaphenazolumSulfafenazoloSulfaphenylpyrazol1-Phenyl-5-sulfanilamidopyrazole5-Sulfanilamido-1-phenylpyrazole
Show more names
SPTFF2Trefoil factor 2SulfaphenylpyrazoleSML1OrisulInamil
N'-(1-Phenylpyrazol-5-yl)sulfanilamide4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamidePhenylsulfapyrazoleOrisulf3-(p-Aminobenzenesulfonamido)-2-phenylpyrazoleBenzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-DTXSID20441314-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
Database identifiers
- CAS
526-08-9- PubChem CID
- 5335
- DTXSID
DTXSID2044131- ChEMBL
CHEMBL1109- ChEBI
CHEBI:77780
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 98.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 451
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
1.52
1.35
Solubility0.6 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point101 °C
Physical DescriptionSolid
Collision Cross Section
157.93 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- DA9520000
- hs_code
- 29339900
- Toxicity
- LD50 orally in mice: 5800 mg/kg (Seki)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QS - Sensory organs
Mechanism of Action
Sulfaphenazole is a sulfonamide antibacterial. In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be "starved" of folate and die.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Cellular LocationsMembrane
Uses & manufacturing
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionCYP2C9 is a major cytochrome P450 enzyme that is involved in the metabolic clearance of various therapeutic agents. Disruption of this enzyme’s activity can lead to adverse drug reactions. Sulfaphenazole is an inhibitor of CYP2C9 (Ki = 0.3 μM) that demonstrates at least 100-fold selectivity over other CYP450 isoforms (Kis = 63 and 29 μM for CYP2C8 and CYP2C18, respectively, and no activity at CYP1A1, CYP1A2, CYP3A4, CYP2C19). At 10 μM, sulfaphenazole has been shown to inhibit endothelium-derived hyperpolarizing factor synthase, a CYP450 isozyme in the porcine coronary artery homologous to CYP2C8/9 that generates reactive oxygen species in coronary endothelial cells and modulates vascular tone and homeostasis.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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