Sulfaphenazole

drug
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Also known as NSC-757859OrisulfSulfabidSulfafenazolSulfaphenazolSID11111774SID11111775SID26732624SID26747662SID50106998sulphenazoleSID50100344SID46500353SID85267855SulphaphenazoleSID174006203SID144203813SID170465185SID90340933

Summary

Sulfaphenazole (CHEMBL1109) is an approved small-molecule antibacterial drug (ATC J01ED08) targeting CYP2C9; indicated across 2 conditions including bacterial infectious disease and eye infectious disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: J01ED08 (+1 more)
  • Targets: 1 (CYP2C9)
  • Indications: 2 conditions
  • Chemistry: 314.4 Da · C15H14N4O2S

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1109
NameSulfaphenazole
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID5335
ChEBICHEBI:77780
ATCJ01ED08, S01AB05
Molecular formulaC15H14N4O2S
Molecular weight314.4
InChIKeyQWCJHSGMANYXCW-UHFFFAOYSA-N

SMILES: C1=CC=C(C=C1)N2C(=CC=N2)NS(=O)(=O)C3=CC=C(C=C3)N

IUPAC name: 4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide

ChEBI definition: 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.

Pharmacological roles (ChEBI): antibacterial drug, EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor, EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor, P450 inhibitor.

Also known as: NSC-757859, Orisulf, Sulfabid, Sulfafenazol, Sulfaphenazol, Sulfaphenazole, sulfaphenazole, SID11111774, SID11111775, SID26732624, SID26747662, SID50106998

Patent coverage: 1,186 distinct patent families (4,065 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CYP2C9CYP2C9Inhibition6.520%P11712

Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Prelamin-A/C, Ferritin light chain, Thrombopoietin, Thyrotropin receptor, DNA polymerase beta, Cytochrome P450 2C18, Muscarinic acetylcholine receptor M1, Nuclear factor NF-kappa-B p105 subunit, Cytochrome P450 2C9, Cytochrome P450 3A4, Cytochrome P450 2C19, 3-hydroxyacyl-CoA dehydrogenase type-2, Neuropeptide S receptor.

Bioactivity

ChEMBL activities: 84 potent at pChembl ≥ 5 of 90 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P084827.65Potency22.4nMCHEMBL_ACT_4807446
CYP2C97.3Potency50.1nMCHEMBL_ACT_5037596
CYP2C97.3AC5050.12nMCHEMBL_ACT_5993352
CYP2C97.1IC5080nMCHEMBL_ACT_15766269
CYP3A46.9Potency125.9nMCHEMBL_ACT_4977890
CYP3A46.9Potency125.9nMCHEMBL_ACT_5046918
CYP2C96.85IC50140nMCHEMBL_ACT_24925858
CYP2C96.75IC50180nMCHEMBL_ACT_14710053
CYP2C96.75IC50180nMCHEMBL_ACT_15026112
CYP2C96.75IC50180nMCHEMBL_ACT_16584257
CYP2C96.7Ki200nMCHEMBL_ACT_1107467
CYP2C96.7IC50200nMCHEMBL_ACT_7812141
CYP2C96.69IC50205nMCHEMBL_ACT_18015048
CYP2C96.68IC50210nMCHEMBL_ACT_26718731
CYP2C96.61IC50245nMCHEMBL_ACT_24742467
CYP2C96.61IC50245nMCHEMBL_ACT_25000957
CYP2C96.6IC50250nMCHEMBL_ACT_2154813
CYP2C96.6IC50250nMCHEMBL_ACT_5186918
CYP2C96.59IC50258nMCHEMBL_ACT_25672239
CYP2C96.57IC50270nMCHEMBL_ACT_17692366
CYP2C96.57IC50270nMCHEMBL_ACT_17718291
CYP2C96.57IC50270nMCHEMBL_ACT_26002620
CYP2C96.55IC50280nMCHEMBL_ACT_19315064
CYP2C96.5IC50318nMCHEMBL_ACT_2224894
CYP2C96.5IC50318nMCHEMBL_ACT_2361511
CYP2C96.5IC50318nMCHEMBL_ACT_6164119
CYP2C96.46IC50350nMCHEMBL_ACT_1814583
CYP2C96.43IC50367nMCHEMBL_ACT_23174367
CYP2C96.43IC50369.4nMCHEMBL_ACT_24807946
CYP2C96.4Potency398.1nMCHEMBL_ACT_5025372
CYP2C96.4AC50398.1nMCHEMBL_ACT_5990070
CYP2C96.33IC50462nMCHEMBL_ACT_18590814
CYP2C96.33IC50470nMCHEMBL_ACT_29116823
CYP2C96.31IC50487nMCHEMBL_ACT_25508207
CYP2C96.31IC50487nMCHEMBL_ACT_26142476
CYP2C96.31IC50487nMCHEMBL_ACT_29097765
CYP2C96.3Ki500nMCHEMBL_ACT_377367
CYP2C96.28IC50529nMCHEMBL_ACT_25698248
CYP2C96.28IC50527nMCHEMBL_ACT_29060059
CYP2C96.27IC50535nMCHEMBL_ACT_18278462
CYP2C96.25IC50567nMCHEMBL_ACT_24828452
CYP2C96.23IC50586nMCHEMBL_ACT_23259666
CYP2C96.23IC50585nMCHEMBL_ACT_24875742
CYP2C96.22IC50600nMCHEMBL_ACT_378600
CYP2C96.21IC50609nMCHEMBL_ACT_19156604
CYP2C96.21IC50609nMCHEMBL_ACT_22405888
CYP2C96.21IC50624nMCHEMBL_ACT_24868037
CYP2C96.2IC50630nMCHEMBL_ACT_22934680
CYP2C96.2IC50627nMCHEMBL_ACT_25453765
CYP2C96.19IC50641nMCHEMBL_ACT_24366297
CYP2C96.19IC50652nMCHEMBL_ACT_25935289
CYP2C96.18IC50660nMCHEMBL_ACT_19063367
CYP2C96.18IC50660nMCHEMBL_ACT_19109594
CYP2C96.18IC50656nMCHEMBL_ACT_24889668
CYP2C96.17IC50680nMCHEMBL_ACT_25968448
CYP2C96.17IC50681nMCHEMBL_ACT_26118142
CYP2C96.17IC50681nMCHEMBL_ACT_29186730
CYP2C96.17IC50676nMCHEMBL_ACT_29191725
CYP2C96.16IC50685nMCHEMBL_ACT_18924698
CYP2C96.15IC50704nMCHEMBL_ACT_16828579
CYP2C96.14IC50720nMCHEMBL_ACT_18295684
CYP2C96.13IC50740nMCHEMBL_ACT_16621040
CYP2C96.11IC50770nMCHEMBL_ACT_22879836
CYP2C96.07IC50847nMCHEMBL_ACT_19111622
CYP2C96.06IC50870nMCHEMBL_ACT_26153931
CYP2C96.05IC50893nMCHEMBL_ACT_22971657
POLB6.05Potency891.3nMCHEMBL_ACT_5047672
NPSR15.5Potency3162nMCHEMBL_ACT_4933065
CYP3A45.5Potency3162nMCHEMBL_ACT_4977684
CYP3A45.5Potency3162nMCHEMBL_ACT_5042917
CYP3A45.5AC503162nMCHEMBL_ACT_6049461
TSHR5.4Potency3981nMCHEMBL_ACT_3915150
TSHR5.4Potency3981nMCHEMBL_ACT_4699079
CYP2C95.38IC504200nMCHEMBL_ACT_15002185
CYP2C95.38IC504200nMCHEMBL_ACT_15105317
NFKB15.15Potency7080nMCHEMBL_ACT_3672612
NFKB15.15Potency7080nMCHEMBL_ACT_4585348
LMNA5.1Potency7943nMCHEMBL_ACT_3653893
CYP3A45.1Potency7943nMCHEMBL_ACT_5010217
CYP3A45.1Potency7943nMCHEMBL_ACT_5078631
CYP3A45.1AC507943nMCHEMBL_ACT_6049137
CYP2C95IC5010000nMCHEMBL_ACT_18125087
HSD17B105Potency10000nMCHEMBL_ACT_3709549
TDP15Potency10000nMCHEMBL_ACT_3932741

Target pathways

Aggregated over 1 target gene(s): CYP2C9.

Top Reactome pathways

6 total, by targets touching each:

PathwayTargetsGenes
Xenobiotics1CYP2C9
CYP2E1 reactions1CYP2C9
Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET)1CYP2C9
Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)1CYP2C9
Biosynthesis of maresin-like SPMs1CYP2C9
Aspirin ADME1CYP2C9

Dominant GO biological processes

GO termTargets
xenobiotic metabolic process1
steroid metabolic process1
cholesterol metabolic process1
estrogen metabolic process1
monoterpenoid metabolic process1
epoxygenase P450 pathway1
urea metabolic process1
monocarboxylic acid metabolic process1
xenobiotic catabolic process1
long-chain fatty acid biosynthetic process1
icosanoid biosynthetic process1
oxidative demethylation1
organofluorine metabolic process1
omega-hydroxylase P450 pathway1
lipid metabolic process1

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

IndicationPhaseMONDOEFO
bacterial infectious disease4MONDO:0005113EFO:0000771
eye infectious disorder4MONDO:0043885EFO:1001888

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

341 molecules share ≥1 primary target. Top 100 by shared-target count:

MoleculeSourceStatusShared targets
FEZOLINETANTChEMBL + PubChemPhase 4 (approved)CYP2C9
PAZOPANIBChEMBL + PubChemPhase 4 (approved)CYP2C9
AMIODARONEChEMBLPhase 4 (approved)CYP2C9
AMSACRINEChEMBLPhase 4 (approved)CYP2C9
APOMORPHINEChEMBLPhase 4 (approved)CYP2C9
BENZBROMARONEChEMBLPhase 4 (approved)CYP2C9
BENZTHIAZIDEChEMBLPhase 4 (approved)CYP2C9
BEPRIDILChEMBLPhase 4 (approved)CYP2C9
BISACODYLChEMBLPhase 4 (approved)CYP2C9
BUSPIRONEChEMBLPhase 4 (approved)CYP2C9
BUTAMBENChEMBLPhase 4 (approved)CYP2C9
CANNABIDIOLChEMBLPhase 4 (approved)CYP2C9
CELECOXIBChEMBLPhase 4 (approved)CYP2C9
CHLORHEXIDINEChEMBLPhase 4 (approved)CYP2C9
CILOSTAZOLChEMBLPhase 4 (approved)CYP2C9
CIPROFLOXACINChEMBLPhase 4 (approved)CYP2C9
CLEMASTINEChEMBLPhase 4 (approved)CYP2C9
CLOMETHIAZOLEChEMBLPhase 4 (approved)CYP2C9
CLOMIPHENEChEMBLPhase 4 (approved)CYP2C9
CLONIDINEChEMBLPhase 4 (approved)CYP2C9
CLOTRIMAZOLEChEMBLPhase 4 (approved)CYP2C9
CLOZAPINEChEMBLPhase 4 (approved)CYP2C9
COLCHICINEChEMBLPhase 4 (approved)CYP2C9
CYCLOSERINEChEMBLPhase 4 (approved)CYP2C9
CYCLOSPORINEChEMBLPhase 4 (approved)CYP2C9
DACLATASVIRChEMBLPhase 4 (approved)CYP2C9
DANAZOLChEMBLPhase 4 (approved)CYP2C9
DAPSONEChEMBLPhase 4 (approved)CYP2C9
DASATINIBChEMBLPhase 4 (approved)CYP2C9
DEFERIPRONEChEMBLPhase 4 (approved)CYP2C9
DEXIBUPROFENChEMBLPhase 4 (approved)CYP2C9
DEXMEDETOMIDINEChEMBLPhase 4 (approved)CYP2C9
DEXTROTHYROXINEChEMBLPhase 4 (approved)CYP2C9
DICHLORPHENAMIDEChEMBLPhase 4 (approved)CYP2C9
DICLOFENACChEMBLPhase 4 (approved)CYP2C9
DICUMAROLChEMBLPhase 4 (approved)CYP2C9
DICYCLOMINEChEMBLPhase 4 (approved)CYP2C9
DIENESTROLChEMBLPhase 4 (approved)CYP2C9
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)CYP2C9
DIPYRIDAMOLEChEMBLPhase 4 (approved)CYP2C9
DISULFIRAMChEMBLPhase 4 (approved)CYP2C9
DROPERIDOLChEMBLPhase 4 (approved)CYP2C9
DULOXETINEChEMBLPhase 4 (approved)CYP2C9
DYCLONINEChEMBLPhase 4 (approved)CYP2C9
ECONAZOLEChEMBLPhase 4 (approved)CYP2C9
ENOXACINChEMBLPhase 4 (approved)CYP2C9
ENOXIMONEChEMBLPhase 4 (approved)CYP2C9
ENTACAPONEChEMBLPhase 4 (approved)CYP2C9
ESCITALOPRAMChEMBLPhase 4 (approved)CYP2C9
ESTRONE SULFURIC ACIDChEMBLPhase 4 (approved)CYP2C9
ETHACRYNIC ACIDChEMBLPhase 4 (approved)CYP2C9
ETODOLACChEMBLPhase 4 (approved)CYP2C9
ETRAVIRINEChEMBLPhase 4 (approved)CYP2C9
FELODIPINEChEMBLPhase 4 (approved)CYP2C9
FENOFIBRATEChEMBLPhase 4 (approved)CYP2C9
FINASTERIDEChEMBLPhase 4 (approved)CYP2C9
FLUCONAZOLEChEMBLPhase 4 (approved)CYP2C9
FLUPIRTINEChEMBLPhase 4 (approved)CYP2C9
FLUSPIRILENEChEMBLPhase 4 (approved)CYP2C9
FLUTAMIDEChEMBLPhase 4 (approved)CYP2C9
FLUVASTATINChEMBLPhase 4 (approved)CYP2C9
FLUVOXAMINEChEMBLPhase 4 (approved)CYP2C9
GEMFIBROZILChEMBLPhase 4 (approved)CYP2C9
GLIPIZIDEChEMBLPhase 4 (approved)CYP2C9
GLYBURIDEChEMBLPhase 4 (approved)CYP2C9
GUANFACINEChEMBLPhase 4 (approved)CYP2C9
HALOPERIDOLChEMBLPhase 4 (approved)CYP2C9
HEXESTROLChEMBLPhase 4 (approved)CYP2C9
HYDROCHLOROTHIAZIDEChEMBLPhase 4 (approved)CYP2C9
HYDROFLUMETHIAZIDEChEMBLPhase 4 (approved)CYP2C9
IBRUTINIBChEMBLPhase 4 (approved)CYP2C9
IBUDILASTChEMBLPhase 4 (approved)CYP2C9
IBUPROFENChEMBLPhase 4 (approved)CYP2C9
IDEBENONEChEMBLPhase 4 (approved)CYP2C9
INAMRINONEChEMBLPhase 4 (approved)CYP2C9
INDOMETHACINChEMBLPhase 4 (approved)CYP2C9
ISRADIPINEChEMBLPhase 4 (approved)CYP2C9
ISTRADEFYLLINEChEMBLPhase 4 (approved)CYP2C9
KETANSERINChEMBLPhase 4 (approved)CYP2C9
KETOCONAZOLEChEMBLPhase 4 (approved)CYP2C9
LANSOPRAZOLEChEMBLPhase 4 (approved)CYP2C9
LEFLUNOMIDEChEMBLPhase 4 (approved)CYP2C9
LESINURADChEMBLPhase 4 (approved)CYP2C9
LIFITEGRASTChEMBLPhase 4 (approved)CYP2C9
LORATADINEChEMBLPhase 4 (approved)CYP2C9
LOSARTANChEMBLPhase 4 (approved)CYP2C9
LOXAPINEChEMBLPhase 4 (approved)CYP2C9
LUMACAFTORChEMBLPhase 4 (approved)CYP2C9
MARAVIROCChEMBLPhase 4 (approved)CYP2C9
MASOPROCOLChEMBLPhase 4 (approved)CYP2C9
MEBENDAZOLEChEMBLPhase 4 (approved)CYP2C9
MECLOFENAMATEChEMBLPhase 4 (approved)CYP2C9
MEFENAMIC ACIDChEMBLPhase 4 (approved)CYP2C9
MEGESTROLChEMBLPhase 4 (approved)CYP2C9
MENADIONEChEMBLPhase 4 (approved)CYP2C9
MESALAMINEChEMBLPhase 4 (approved)CYP2C9
METHAPYRILENEChEMBLPhase 4 (approved)CYP2C9
METHAZOLAMIDEChEMBLPhase 4 (approved)CYP2C9
METHSCOPOLAMINEChEMBLPhase 4 (approved)CYP2C9
MIBEFRADILChEMBLPhase 4 (approved)CYP2C9