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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015667
Secondary Accession Numbers
  • HMDB15667
Metabolite Identification
Common NameSulfaphenazole
DescriptionSulfaphenazole, also known as sulfabid or sulphafenazol, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Sulfaphenazole is a drug which is used for the treatment bacterial infections. Based on a literature review a small amount of articles have been published on Sulfaphenazole.
Structure
Data?1582753321
Synonyms
ValueSource
1-Phenyl-5-sulfanilamidopyrazoleChEBI
3-(p-Aminobenzenesulfonamido)-2-phenylpyrazoleChEBI
5-Sulfanilamido-1-phenylpyrazoleChEBI
N'-(1-phenylpyrazol-5-yl)sulfanilamideChEBI
N(1)-(1-Phenylpyrazol-5-yl)sulfanilamideChEBI
SulfabidChEBI
SulfafenazolChEBI
SulfaphenazolChEBI
SulfaphenazolumChEBI
SulphaphenazoleChEBI
1-Phenyl-5-sulphanilamidopyrazoleGenerator
3-(p-Aminobenzenesulphonamido)-2-phenylpyrazoleGenerator
5-Sulphanilamido-1-phenylpyrazoleGenerator
N'-(1-phenylpyrazol-5-yl)sulphanilamideGenerator
N(1)-(1-Phenylpyrazol-5-yl)sulphanilamideGenerator
SulphabidGenerator
SulphafenazolGenerator
SulphaphenazolGenerator
SulphaphenazolumGenerator
PhenylsulfapyrazoleHMDB
SulfaphenazonHMDB
SulfaphenylpipazolHMDB
SulfaphenylpyrazolHMDB
SulfaphenylpyrazoleHMDB
SulfonylpyrazolHMDB
SulphenazoleHMDB
Chemical FormulaC15H14N4O2S
Average Molecular Weight314.362
Monoisotopic Molecular Weight314.083746402
IUPAC Name4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzene-1-sulfonamide
Traditional Namemerian
CAS Registry Number526-08-9
SMILES
NC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C1
InChI Identifier
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
InChI KeyQWCJHSGMANYXCW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Phenylpyrazole
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Monocyclic benzene moiety
  • Benzenoid
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.52HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available170.011http://allccs.zhulab.cn/database/detail?ID=AllCCS00001142
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.83931661259
DarkChem[M-H]-173.83131661259
DeepCCS[M+H]+170.41230932474
DeepCCS[M-H]-168.05430932474
DeepCCS[M-2H]-201.89730932474
DeepCCS[M+Na]+177.18630932474
AllCCS[M+H]+173.632859911
AllCCS[M+H-H2O]+170.332859911
AllCCS[M+NH4]+176.632859911
AllCCS[M+Na]+177.532859911
AllCCS[M-H]-169.832859911
AllCCS[M+Na-2H]-169.332859911
AllCCS[M+HCOO]-168.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfaphenazoleNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C14617.9Standard polar33892256
SulfaphenazoleNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C13122.3Standard non polar33892256
SulfaphenazoleNC1=CC=C(C=C1)S(=O)(=O)NC1=CC=NN1C1=CC=CC=C13095.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfaphenazole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C13122.2Semi standard non polar33892256
Sulfaphenazole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C13032.7Standard non polar33892256
Sulfaphenazole,1TMS,isomer #1C[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C14093.6Standard polar33892256
Sulfaphenazole,1TMS,isomer #2C[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C13010.2Semi standard non polar33892256
Sulfaphenazole,1TMS,isomer #2C[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C12956.6Standard non polar33892256
Sulfaphenazole,1TMS,isomer #2C[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C14311.6Standard polar33892256
Sulfaphenazole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C2997.8Semi standard non polar33892256
Sulfaphenazole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C3096.4Standard non polar33892256
Sulfaphenazole,2TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C3891.9Standard polar33892256
Sulfaphenazole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C13040.7Semi standard non polar33892256
Sulfaphenazole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C13062.1Standard non polar33892256
Sulfaphenazole,2TMS,isomer #2C[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C13800.4Standard polar33892256
Sulfaphenazole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C1)[Si](C)(C)C2999.6Semi standard non polar33892256
Sulfaphenazole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C1)[Si](C)(C)C3149.7Standard non polar33892256
Sulfaphenazole,3TMS,isomer #1C[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C)C=C1)[Si](C)(C)C3638.0Standard polar33892256
Sulfaphenazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C13321.7Semi standard non polar33892256
Sulfaphenazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C13253.9Standard non polar33892256
Sulfaphenazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C14136.5Standard polar33892256
Sulfaphenazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C13239.5Semi standard non polar33892256
Sulfaphenazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C13176.3Standard non polar33892256
Sulfaphenazole,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=NN1C1=CC=CC=C1)S(=O)(=O)C1=CC=C(N)C=C14261.2Standard polar33892256
Sulfaphenazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C3445.7Semi standard non polar33892256
Sulfaphenazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C3509.1Standard non polar33892256
Sulfaphenazole,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)NC2=CC=NN2C2=CC=CC=C2)C=C1)[Si](C)(C)C(C)(C)C3898.3Standard polar33892256
Sulfaphenazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C13451.6Semi standard non polar33892256
Sulfaphenazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C13502.5Standard non polar33892256
Sulfaphenazole,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C13867.1Standard polar33892256
Sulfaphenazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3610.0Semi standard non polar33892256
Sulfaphenazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3784.5Standard non polar33892256
Sulfaphenazole,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC=C(S(=O)(=O)N(C2=CC=NN2C2=CC=CC=C2)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3746.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfaphenazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bu0-5950000000-0cc1951df9ab2bdd46752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfaphenazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfaphenazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 10V, Positive-QTOFsplash10-014j-0369000000-abf75c05199abdf7dc002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 20V, Positive-QTOFsplash10-0a4i-1931000000-5ab680fc3ed5a09f23862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 40V, Positive-QTOFsplash10-0006-9100000000-f48bf2b095d990894ea02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 10V, Negative-QTOFsplash10-03di-0019000000-8f511cbfebf17d64870f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 20V, Negative-QTOFsplash10-0bt9-1957000000-f98142e1f3bb59e625612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 40V, Negative-QTOFsplash10-0a4i-3900000000-5a7bf1e5e310f28b21ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 10V, Positive-QTOFsplash10-014i-0009000000-8d0af0efab416cc5ca812021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 20V, Positive-QTOFsplash10-07vi-0906000000-b06561ce36f4b03191882021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 40V, Positive-QTOFsplash10-03dl-9820000000-bf5f1c3818380fd877d42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 10V, Negative-QTOFsplash10-03di-0009000000-2c8716213a23f0f4f8732021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 20V, Negative-QTOFsplash10-03di-0009000000-5421c12fd130b6aad3362021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfaphenazole 40V, Negative-QTOFsplash10-0a4l-8941000000-6ea16e7d043301a176c42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06729 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06729 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06729
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfaphenazole
METLIN IDNot Available
PubChem Compound5335
PDB IDNot Available
ChEBI ID77780
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot 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 ]