4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide

• ChemBase ID: 4460
• Molecular Formular: C15H14N4O2S
• Molecular Mass: 314.36226
• Monoisotopic Mass: 314.08374671
• SMILES: S(=O)(=O)(Nc1n(ncc1)c1ccccc1)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1ccnn1c1ccccc1
• InChI: 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
• InChIKey: QWCJHSGMANYXCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
• IUPAC Traditional name: merian
• Synonyms: Sulfabid; Sulphenazole; Raziosulfa; 1-Phenyl-5-sulfanilamidopyrazole; 3-(p-Aminobenzenesulfonamido)-2-pheny-2H-lpyrazole; 3-(p-Aminobenzenesulfonamido)-2-phenylpyrazole; 4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)-benzenesulfonamide; 4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide; 4-Amino-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide; 5-Sulfanilamido-1-phenylpyrazole; Benzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-; Depocid; Depotsulfonamide; Eftolon; Firmazolo; Inamil; Isarol; Isarol v; Lopac-S-0758; Merian; Microtan pirazolo; N'-(1-Phenylpyrazol-5-yl)sulfanilamide; N(sup 1)-(1-Phenylpyrazol-5-yl)sulfanilamide; N1-(1-Phenylpyrazol-5-yl)sulfanilamide; Orisul; Orisulf; Paidazolo; Phenylsulfapyrazole; Plisulfan; Prestwick_454; S0758_SIGMA; SP; SPP; Solfafenazolo; Solfafenazolo [dcit]; Sulfafenazol; Sulfafenazol [inn-spanish]; Sulfafenazolo; Sulfafenazolo [italian]; Sulfanilamide, N(sup 1)-(1-phenylpyrazol-5-yl)-; Sulfanilamide, N(sup 1)-(1-phenylpyrazol-5-yl)- (8CI); Sulfanilamide, N1-(1-phenylpyrazol-5-yl)-; Sulfaphenazol [inn-french]; Sulfaphenazole (jan/inn); Sulfaphenazole [inn:jan]; Sulfaphenazolum; Sulfaphenazolum [inn-latin]; Sulfaphenazon; Sulfaphenylpipazol; Sulfaphenylpyrazol; Sulfaphenylpyrazole; Sulphaphenazole; Sulfaphenazol; UC166_SIGMA; UNII-0J8L4V3F81; Sulfaphenazole; Sulfaphenazole

Database IDs

• CAS Number: 526-08-9
• EC Number: 208-384-3
• MDL Number: MFCD00057226
• PubChem SID: 24724643; 160967892; 99443275; 24278198
• PubChem CID: 5335

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8978763
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.7916471
• LogD (pH = 7.4): 1.3204253
• Log P: 1.8070947
• Molar Refractivity: 85.2056 cm^3
• Polarizability: 33.401253 Å^3
• Polar Surface Area: 90.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.59
• LOG S: -3.05
• Solubility (Water): 2.78e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.5 mg/mL at 25 oC [MERCK INDEX (1989)]
• Apperance: white to light yellow
• Melting Point: 179-183 °C
• Hydrophobicity(logP): 1.52 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: DA9520000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP2C18(1562), CYP2C19(1557), CYP2C9(1559)

Product Information

• Purity: ≥98%; ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H14N4O2S

DETAILS

DrugBank - DB06729

• Drug Groups: experimental
• Description: Sulfaphenazole is a sulfonamide antibacterial.
• Indication: For the treatment bacterial infections.
• Affected Organisms: Gram negative and gram positive bacteria
• Biotransformation: Hepatic.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - S0758

Biochem/physiol Actions
Antibacterial. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Inhibits bradykinin-induced tPA release.

Sigma Aldrich - UC166

Biochem/physiol Actions
Antibacterial. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Specific inhibitor of CYP2C9. Blocks pro-inflammatory and atherogenic effects of linoleic acid (increase in oxidative stress and activation of AP-1) mediated by CYP2C9. Inhibits bradykinin-induced tPA release.