CAS 526-08-9|Sulfafenazol [inn-spanish]|Sulfabid|UC166_SIGMA|S0758_SIGMA|Benzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-|3-(p-Aminobenzenesulfonamido)-2-pheny-2H-lpyrazole|Solfafenazolo|De...

General Information

Structure

Molecular Formula

C₁₅H₁₄N₄O₂S

Molecular Mass

314.36226

Exact Mass

314.08374671

Charge

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

Canonic Smiles

Nc1ccc(cc1)S(=O)(=O)Nc1ccnn1c1ccccc1

Isomeric Smiles

S(=O)(=O)(Nc1n(ncc1)c1ccccc1)c1ccc(N)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

1.19

LogD (pH = 5.5)

1.78

Log P

1.81

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

6.62

Polar Surface Area

90.01

Polarizability

31.19

Molar Refractivity

85.21

LOG S

-3.77

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Sulfafenazol [inn-spanish]SulfabidUC166_SIGMAS0758_SIGMABenzenesulfonamide, 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)-3-(p-Aminobenzenesulfonamido)-2-pheny-2H-lpyrazoleSolfafenazoloDepocidSulfaphenazoleSulfafenazolo [italian]Sulfaphenazolum [inn-latin]N1-(1-Phenylpyrazol-5-yl)sulfanilamideLopac-S-0758PlisulfanSolfafenazolo [dcit]SulphaphenazoleN'-(1-Phenylpyrazol-5-yl)sulfanilamideMicrotan pirazoloSulfanilamide, N(sup 1)-(1-phenylpyrazol-5-yl)-Sulfaphenylpipazol1-Phenyl-5-sulfanilamidopyrazoleIsarolSulfaphenazole (jan/inn)3-(p-Aminobenzenesulfonamido)-2-phenylpyrazoleSulphenazoleSulfaphenazonFirmazoloSulfaphenazolumInamilOrisulfPhenylsulfapyrazoleMerianSPOrisulSulfaphenylpyrazolSulfaphenylpyrazole4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide5-Sulfanilamido-1-phenylpyrazole4-Amino-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamidePaidazoloSulfafenazolRaziosulfaIsarol v4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)-benzenesulfonamideN(sup 1)-(1-Phenylpyrazol-5-yl)sulfanilamidePrestwick_454SPPSulfafenazoloDepotsulfonamideSulfanilamide, N1-(1-phenylpyrazol-5-yl)-EftolonSulfaphenazol [inn-french]Sulfaphenazole [inn:jan]Sulfanilamide, N(sup 1)-(1-phenylpyrazol-5-yl)- (8CI)SulfaphenazolUNII-0J8L4V3F81Sulfaphenazole1-phenyl-5-sulfanilamidopyrazoleN(1)-(1-phenylpyrazol-5-yl)sulfanilamide3-(p-aminobenzenesulfonamido)-2-phenylpyrazolesulfaphenazole5-sulfanilamido-1-phenylpyrazolesulphaphenazoleN'-(1-phenylpyrazol-5-yl)sulfanilamide

IUPAC Traditional name

merian sulfaphenazole

IUPAC name

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

International Nonproprietary Name (INN)

sulfaphenazolumsulfaphenazolesulfafenazolsulfaphenazol

Brand Name

Sulfabid

Names and Identifiers

Registration numbers

CAS Number

526-08-9

PubChem SID

242781989944327516096789224724643223443207

MDL Number

EC Number

PubChem CID

Patent number

BRENDA Database

1.14.14.11.14.13.291.14.14.551.14.13.181

LINCS Database

LSM-5279

SureChEMBL Database

SCHEMBL122040

HMDB Database

HMDB0015667

PubMed Citation Links

986434324519941138737712278502118845175

MetaboLights Database

MTBLS1918MTBLS1071MTBLS1642MTBLS2145MTBLS3750

BindingDB Database

ACToR Database

CompTox Database

KEGG DRUG Database

BKMS React Database

CHEMBL

Wikipedia Title

Reaxys Registry

DrugBank ID

BRENDA Ligand Database

16724

Drug Central Database

2,523

CHEBI ID

CHEBI:77780

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

1.52 [HANSCH,C ET AL. (1995)]

Solubility

1.5 mg/mL at 25 oC [MERCK INDEX (1989)]

Melting Point

179-183 °C

Apperance

white to light yellow

Safety Information

German water hazard class

RTECS

DA9520000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

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

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

UC166

ChEBI

CHEBI:77780

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.

Molecule Details

References

PubChem Literature

No Data Available

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References

Bioactivity

PubChem BioAssay

Bioactivity