Sulfaphenazole

Common Name

Slifaphenazole Description

Slifaphenazole is only found in individuals that have used or taken this drug. Slifaphenazole is a slifonamide antibacterial. In bacteria, antibacterial slifonamides 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. Structure

Synonyms

Value Source 1-Phenyl-5-slifanilamidopyrazoleChEBI 3-(P-Aminobenzeneslifonamido)-2-phenylpyrazoleChEBI 5-Slifanilamido-1-phenylpyrazoleChEBI N'-(1-phenylpyrazol-5-yl)slifanilamideChEBI N(1)-(1-Phenylpyrazol-5-yl)slifanilamideChEBI SlifabidChEBI SlifafenazolChEBI SlifaphenazolChEBI SlifaphenazolumChEBI SliphaphenazoleChEBI 1-Phenyl-5-sliphanilamidopyrazoleGenerator 3-(P-Aminobenzenesliphonamido)-2-phenylpyrazoleGenerator 5-Sliphanilamido-1-phenylpyrazoleGenerator N'-(1-phenylpyrazol-5-yl)sliphanilamideGenerator N(1)-(1-Phenylpyrazol-5-yl)sliphanilamideGenerator SliphabidGenerator SliphafenazolGenerator SliphaphenazolGenerator SliphaphenazolumGenerator PhenylslifapyrazoleHMDB SlifaphenazonHMDB SlifaphenylpipazolHMDB SlifaphenylpyrazolHMDB SlifaphenylpyrazoleHMDB SlifonylpyrazolHMDB SliphenazoleHMDB

Chemical Formlia

C₁₅H₁₄N₄O₂S Average Molecliar Weight

314.362 Monoisotopic Molecliar Weight

314.083746402 IUPAC Name

4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-slifonamide Traditional Name

merian CAS Registry Number

526-08-9 SMILES

InChI Identifier

InChI Key

QWCJHSGMANYXCW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Azoles Direct Parent

Phenylpyrazoles Alternative Parents

Aminobenzeneslifonamides

Benzeneslifonyl compounds

Aniline and substituted anilines

Primary aromatic amines

Organoslifonamides

Heteroaromatic compounds

Aminoslifonyl compounds

Azacyclic compounds

Organopnictogen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Aminobenzeneslifonamide

Phenylpyrazole

Benzeneslifonamide

Benzeneslifonyl group

Aniline or substituted anilines

Monocyclic benzene moiety

Primary aromatic amine

Organoslifonic acid amide

Benzenoid

Organic slifonic acid or derivatives

Organoslifonic acid or derivatives

Heteroaromatic compound

Slifonyl

Aminoslifonyl compound

Azacycle

Amine

Hydrocarbon derivative

Primary amine

Organic oxide

Organoslifur compound

Organonitrogen compound

Organic nitrogen compound

Organic oxygen compound

Organopnictogen compound

Aromatic heteromonocyclic compound

Molecliar Framework

Aromatic heteromonocyclic compounds External Descriptors

pyrazoles (CHEBI:77780 )

substituted aniline (CHEBI:77780 )

slifonamide (CHEBI:77780 )

primary amino compound (CHEBI:77780 )

slifonamide antibiotic (CHEBI:77780 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Antibacterial Agents

Slifonamides

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point101 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP1.52HANSCH,C ET AL. (1995)

Predicted Properties

Property Value Source Water Solubility0.28 mg/mLALOGPS logP1.59ALOGPS logP1.81ChemAxon logS-3ALOGPS pKa (Strongest Acidic)6.9ChemAxon pKa (Strongest Basic)2.43ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area90.01 ŲChemAxon Rotatable Bond Count3ChemAxon Refractivity85.21 m³·mol^-1ChemAxon Polarizability31.82 ųChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06729

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06729

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB06729 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

5144 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Slifaphenazole NuGOwiki Link

HMDB15667 Metagene Link

HMDB15667 METLIN ID

Not Available PubChem Compound

5335 PDB ID

Not Available ChEBI ID

253330

Product: Vanoxerine (dihydrochloride)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References Not Available

Enzymes

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.

Gene Name:

CYP2C9

Uniprot ID:

P11712

Molecular weight:

55627.365

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

General function:

Involved in monooxygenase activity

Specific function:

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.

Gene Name:

CYP2D6

Uniprot ID:

P10635

Molecular weight:

55768.94

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.

Gene Name:

CYP2B6

Uniprot ID:

P20813

Molecular weight:

56277.81

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).

Gene Name:

CYP2C8

Uniprot ID:

P10632

Molecular weight:

55824.275

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

General function:

Involved in monooxygenase activity

Specific function:

Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.

Gene Name:

CYP2A6

Uniprot ID:

P11509

Molecular weight:

56517.005

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

PMID: 24292392

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