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Details

Stereochemistry ACHIRAL
Molecular Formula C15H14N4O2S
Molecular Weight 314.362
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAPHENAZOLE

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC2=CC=NN2C3=CC=CC=C3

InChI

InChIKey=QWCJHSGMANYXCW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Sulfaphenazole is an oral antibiotic, which was used for the treatment of bacterial infections under the name Sulfabid. The drug was found to block folate synthesis in bacterias by inhibiting the enzyme dihydropteroate synthase. Sulfaphenazole is also known to inhibit CYP2C9 with high potency and specificity. Sulfabid is no longer marketed in the USA.

Approval Year

1963
72
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.94 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
SULFABID

Approved Use

Unknown

Launch Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2091020/
439 mg single, oral
dose: 439 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAPHENAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
731 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2091020/
439 mg single, oral
dose: 439 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAPHENAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2091020/
439 mg single, oral
dose: 439 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAPHENAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/2091020/
439 mg single, oral
dose: 439 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAPHENAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

CYP2B6
926

CYP2C8
1057

CYP2C19
2057

CYP2E1
1060
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
911
 little or no effect
CYP2B6
1160
 little
CYP2E1
1146
 little
CYP3A4
2633
 little
CYP2C9
2497
 yes [IC50 0.5 uM]
CYP2C8
1117
 yes [IC50 172 uM]
CYP2C19
2141
 yes [IC50 379 uM]
CYP2D6
2546
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:77780
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:77780
ChemicalBook
CB4160540
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4160540
eMolecules
594162
https://www.emolecules.com/cgi-bin/more?vid=594162
MolPort
MolPort-002-070-488
https://www.molport.com/shop/molecule-link/MolPort-002-070-488
ZINC
ZINC000000057490
http://zinc15.docking.org/substances/ZINC000000057490
PubMed

PubMed

TitleDatePubMed
Territrems B and C metabolism in human liver microsomes: major role of CYP3A4 and CYP3A5.
2006-02-01
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2006-01-03
Human cytochrome p450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol.
2006-01
Cytochrome P450 epoxygenases 2C8 and 2C9 are implicated in hypoxia-induced endothelial cell migration and angiogenesis.
2005-12-01
Functional characterization and expression of endothelin receptors in rat carotid artery: involvement of nitric oxide, a vasodilator prostanoid and the opening of K+ channels in ETB-induced relaxation.
2005-11
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes.
2005-11
Modulation of the Ca2 permeable cation channel TRPV4 by cytochrome P450 epoxygenases in vascular endothelium.
2005-10-28
Cytochrome p450 2C inhibition reduces post-ischemic vascular dysfunction.
2005-10
Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein.
2005-08
Urotensin II-induced hypotensive responses in Wistar-Kyoto (Wky) and spontaneously hypertensive (Shr) rats.
2005-08
Metabolism of the alpha,beta-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites.
2005-08
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
2005-08
Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous torasemide in rats.
2005-07-14
Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism.
2005-07
Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors.
2005-06-02
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.
2005-06
The effect of ketoconazole on the pharmacokinetics of a selective alpha 1A-adrenoceptor antagonist.
2005-06
Detection of a novel reactive metabolite of diclofenac: evidence for CYP2C9-mediated bioactivation via arene oxides.
2005-06
SuperLigands - a database of ligand structures derived from the Protein Data Bank.
2005-05-19
Electrochemical characterisation of the human cytochrome P450 CYP2C9.
2005-05-15
Chlorpropamide 2-hydroxylation is catalysed by CYP2C9 and CYP2C19 in vitro: chlorpropamide disposition is influenced by CYP2C9, but not by CYP2C19 genetic polymorphism.
2005-05
Nitric oxide- and EDHF-mediated arteriolar tone in uremia is unaffected by selective inhibition of vascular cytochrome P450 2C9.
2005-05
Identification of the cytochrome P450 enzymes involved in the metabolism of domperidone.
2005-04-02
Role of human liver cytochrome P450 2C9 in the metabolism of a novel alpha4beta1/alpha4beta7 dual antagonist, TR-14035.
2005-04
Effect of enzyme inducers and inhibitors on the pharmacokinetics of oltipraz in rats.
2005-04
The synthesis of 20-HETE in small porcine coronary arteries antagonizes EDHF-mediated relaxation.
2005-02-01
Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells.
2005-02
Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants.
2004-12-14
Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo.
2004-12
The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol.
2004-11
Inhibition of cardiac cytochrome P450: a new approach to cardiac ischaemia and reperfusion damage.
2004-10
Biphasic effect of hydrogen peroxide on skeletal muscle arteriolar tone via activation of endothelial and smooth muscle signaling pathways.
2004-09
Drug-drug interactions of Z-338, a novel gastroprokinetic agent, with terfenadine, comparison with cisapride, and involvement of UGT1A9 and 1A8 in the human metabolism of Z-338.
2004-08-23
Tolbutamide uptake via pH- and membrane-potential-dependent transport mechanism in mouse brain capillary endothelial cell line.
2004-08
Identification of the main human cytochrome P450 enzymes involved in safrole 1'-hydroxylation.
2004-08
Validated assays for human cytochrome P450 activities.
2004-06
The mechanism of EDHF-mediated responses in subcutaneous small arteries from healthy pregnant women.
2004-06
Stereoselective glucuronidation and hydroxylation of etodolac by UGT1A9 and CYP2C9 in man.
2004-05
Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone.
2004-04
Effects of the dietary flavonoid chrysin in isolated rat mesenteric vascular bed.
2004-03-05
In vitro sulfoxidation of thioether compounds by human cytochrome P450 and flavin-containing monooxygenase isoforms with particular reference to the CYP2C subfamily.
2004-03
Utility of microtiter plate assays for human cytochrome P450 inhibition studies in drug discovery: application of simple method for detecting quasi-irreversible and irreversible inhibitors.
2004-02
Mediators of bradykinin-induced vasorelaxation in human coronary microarteries.
2004-02
Inhibition of cytochrome P450 2C9 improves endothelium-dependent, nitric oxide-mediated vasodilatation in patients with coronary artery disease.
2004-01-20
Identification of the human cytochrome P450s responsible for the in vitro metabolism of a leukotriene B4 receptor antagonist, CP-195,543.
2003-12
Involvement of CYP 2C9 in mediating the proinflammatory effects of linoleic acid in vascular endothelial cells.
2003-12
Aged spontaneously hypertensive rats exhibit a selective loss of EDHF-mediated relaxation in the renal artery.
2003-10
Demethylation of radiolabelled dextromethorphan in rat microsomes and intact hepatocytes.
2003-09
Role of human hepatic cytochrome P-450s in territrem A metabolism.
2003-07-11
Major cytochrome P450 enzymes responsible for microsomal aldehyde oxygenation of 11-oxo-Delta8-tetrahydrocannabinol and 9-anthraldehyde in human liver.
2002

Sample Use Guides

In Vivo Use Guide
1 g suspension given orally.
Route of Administration: Oral
In Vitro Use Guide
The minimal inhibitory concentrations of sulfaphenazole were 64 ug/ml for A. fumigatus and 4-8 ug/ml for C. neoformans var grubii.
Name Type Language
SULFAPHENAZOLE
INN   JAN   MART.   MI   ORANGE BOOK   WHO-DD  
INN  
Official Name English
SULFABID
Preferred Name English
SULFAFENAZOL
Common Name English
SULFAPHENAZOLE [JAN]
Common Name English
NSC-757859
Code English
Sulfaphenazole [WHO-DD]
Common Name English
SULFAPHENAZOLE [MI]
Common Name English
SULFAPHENAZOLE [MART.]
Common Name English
N(SUP 1)-(1-PHENYLPYRAZOL-5-YL)SULFANILAMIDE
Systematic Name English
SULFAPHENAZOLE [ORANGE BOOK]
Common Name English
SULPHAPHENAZOLE
Common Name English
sulfaphenazole [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01AB05
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
NCI_THESAURUS C29739
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
WHO-ATC S01AB05
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
WHO-VATC QJ01EQ08
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
WHO-ATC J01ED08
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C66569
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
CAS
526-08-9
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
EVMPD
SUB10721MIG
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-384-3
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
WIKIPEDIA
Sulfaphenazole
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
DRUG BANK
DB06729
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
ChEMBL
CHEMBL1109
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
PUBCHEM
5335
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
MERCK INDEX
m10336
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY Merck Index
CHEBI
77780
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
FDA UNII
0J8L4V3F81
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
DRUG CENTRAL
2523
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
SMS_ID
100000083295
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
NSC
757859
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
EPA CompTox
DTXSID2044131
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
INN
912
Created by admin on Mon Mar 31 18:16:16 GMT 2025 , Edited by admin on Mon Mar 31 18:16:16 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of SULFAPHENAZOLE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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