SULFAPHENAZOLE

US Previously Marketed

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17287722 | https://www.ncbi.nlm.nih.gov/pubmed/8973193

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

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 44 Target ID: CHEMBL2364668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23567760	Inhibitor 8297		0.94 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5241097	Curative		Approved 8429	SULFABID Approved Use Unknown Launch Date 1974

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882

Drug as perpetrator

Target	Modality	Activity
CYP2A6 739	inhibitor 3277 Sources: http://www.chinaphar.com/article/view/7596/8093#page=3 Page: 3.0	little or no effect
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	little
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	little
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	little
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	yes [IC50 0.5 uM]
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	yes [IC50 172 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10821163/ Page: 8.0	yes [IC50 379 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/8886607/ Page: 8.0	yes

Sourcing

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

PubMed

Title	Date	PubMed
Inhibition of phenytoin hydroxylation in human liver microsomes by several selective serotonin re-uptake inhibitors.	2001 Apr	11255075
Inhibition of cytochrome P450 2C9 activity in vitro by 5-hydroxytryptamine and adrenaline.	2001 Feb	11207028
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.	2001 Feb	11159802
Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries.	2001 Jan 19	11139472
Role of CYP2C9 polymorphism in losartan oxidation.	2001 Jul	11408373
Establishment of the transformants expressing human cytochrome P450 subtypes in HepG2, and their applications on drug metabolism and toxicology.	2001 Jun	11377097
Metabolic characterization of the major human small intestinal cytochrome p450s.	2001 Mar	11181505
Metabolism of vanoxerine, 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine, by human cytochrome P450 enzymes.	2001 Sep	11502731
Design and application of fluorometric assays for human cytochrome P450 inhibition.	2002	12424917
Dynamic modulation of interendothelial gap junctional communication by 11,12-epoxyeicosatrienoic acid.	2002 Apr 19	11964373
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.	2002 Feb	11834610
Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes.	2002 May	11950794
Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR).	2003 Apr	12586744
Substrate selectivity of human cytochrome P450 2C9: importance of residues 476, 365, and 114 in recognition of diclofenac and sulfaphenazole and in mechanism-based inactivation by tienilic acid.	2003 Jan 1	12464247
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Cytochrome p-450 epoxygenase products contribute to attenuated vasoconstriction after chronic hypoxia.	2003 Jul	12623785
Metabolism and metabolic inhibition of cilnidipine in human liver microsomes.	2003 Mar	12617777
Identification of the cytochrome P450 enzymes involved in the N-oxidation of voriconazole.	2003 May	12695341
Characterization of the endothelium-derived hyperpolarizing factor (EDHF) response in the human interlobar artery.	2003 May	12675850
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 Aug 23	15306208
Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo.	2004 Dec	15333513
Validated assays for human cytochrome P450 activities.	2004 Jun	15155557
In vitro sulfoxidation of thioether compounds by human cytochrome P450 and flavin-containing monooxygenase isoforms with particular reference to the CYP2C subfamily.	2004 Mar	14977868
Alteration in endothelial function and modulation by treatment with pioglitazone in rabbit renal artery from short-term hypercholesterolemia.	2005 Jun	15953770
The effect of ketoconazole on the pharmacokinetics of a selective alpha 1A-adrenoceptor antagonist.	2005 Jun	15901753
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 Nov	16151434
Human cytochrome p450 enzymes of importance for the bioactivation of methyleugenol to the proximate carcinogen 1'-hydroxymethyleugenol.	2006 Jan	16411663

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

Official 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

SULFABID

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QS01AB05