Sulfaphenazole
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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
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1109 |
| Name | Sulfaphenazole |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 5335 |
| ChEBI | CHEBI:77780 |
| ATC | J01ED08, S01AB05 |
| Molecular formula | C15H14N4O2S |
| Molecular weight | 314.4 |
| InChIKey | QWCJHSGMANYXCW-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).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| CYP2C9 | CYP2C9 | Inhibition | 6.52 | 0% | 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):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P08482 | 7.65 | Potency | 22.4 | nM | CHEMBL_ACT_4807446 |
| CYP2C9 | 7.3 | Potency | 50.1 | nM | CHEMBL_ACT_5037596 |
| CYP2C9 | 7.3 | AC50 | 50.12 | nM | CHEMBL_ACT_5993352 |
| CYP2C9 | 7.1 | IC50 | 80 | nM | CHEMBL_ACT_15766269 |
| CYP3A4 | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_4977890 |
| CYP3A4 | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_5046918 |
| CYP2C9 | 6.85 | IC50 | 140 | nM | CHEMBL_ACT_24925858 |
| CYP2C9 | 6.75 | IC50 | 180 | nM | CHEMBL_ACT_14710053 |
| CYP2C9 | 6.75 | IC50 | 180 | nM | CHEMBL_ACT_15026112 |
| CYP2C9 | 6.75 | IC50 | 180 | nM | CHEMBL_ACT_16584257 |
| CYP2C9 | 6.7 | Ki | 200 | nM | CHEMBL_ACT_1107467 |
| CYP2C9 | 6.7 | IC50 | 200 | nM | CHEMBL_ACT_7812141 |
| CYP2C9 | 6.69 | IC50 | 205 | nM | CHEMBL_ACT_18015048 |
| CYP2C9 | 6.68 | IC50 | 210 | nM | CHEMBL_ACT_26718731 |
| CYP2C9 | 6.61 | IC50 | 245 | nM | CHEMBL_ACT_24742467 |
| CYP2C9 | 6.61 | IC50 | 245 | nM | CHEMBL_ACT_25000957 |
| CYP2C9 | 6.6 | IC50 | 250 | nM | CHEMBL_ACT_2154813 |
| CYP2C9 | 6.6 | IC50 | 250 | nM | CHEMBL_ACT_5186918 |
| CYP2C9 | 6.59 | IC50 | 258 | nM | CHEMBL_ACT_25672239 |
| CYP2C9 | 6.57 | IC50 | 270 | nM | CHEMBL_ACT_17692366 |
| CYP2C9 | 6.57 | IC50 | 270 | nM | CHEMBL_ACT_17718291 |
| CYP2C9 | 6.57 | IC50 | 270 | nM | CHEMBL_ACT_26002620 |
| CYP2C9 | 6.55 | IC50 | 280 | nM | CHEMBL_ACT_19315064 |
| CYP2C9 | 6.5 | IC50 | 318 | nM | CHEMBL_ACT_2224894 |
| CYP2C9 | 6.5 | IC50 | 318 | nM | CHEMBL_ACT_2361511 |
| CYP2C9 | 6.5 | IC50 | 318 | nM | CHEMBL_ACT_6164119 |
| CYP2C9 | 6.46 | IC50 | 350 | nM | CHEMBL_ACT_1814583 |
| CYP2C9 | 6.43 | IC50 | 367 | nM | CHEMBL_ACT_23174367 |
| CYP2C9 | 6.43 | IC50 | 369.4 | nM | CHEMBL_ACT_24807946 |
| CYP2C9 | 6.4 | Potency | 398.1 | nM | CHEMBL_ACT_5025372 |
| CYP2C9 | 6.4 | AC50 | 398.1 | nM | CHEMBL_ACT_5990070 |
| CYP2C9 | 6.33 | IC50 | 462 | nM | CHEMBL_ACT_18590814 |
| CYP2C9 | 6.33 | IC50 | 470 | nM | CHEMBL_ACT_29116823 |
| CYP2C9 | 6.31 | IC50 | 487 | nM | CHEMBL_ACT_25508207 |
| CYP2C9 | 6.31 | IC50 | 487 | nM | CHEMBL_ACT_26142476 |
| CYP2C9 | 6.31 | IC50 | 487 | nM | CHEMBL_ACT_29097765 |
| CYP2C9 | 6.3 | Ki | 500 | nM | CHEMBL_ACT_377367 |
| CYP2C9 | 6.28 | IC50 | 529 | nM | CHEMBL_ACT_25698248 |
| CYP2C9 | 6.28 | IC50 | 527 | nM | CHEMBL_ACT_29060059 |
| CYP2C9 | 6.27 | IC50 | 535 | nM | CHEMBL_ACT_18278462 |
| CYP2C9 | 6.25 | IC50 | 567 | nM | CHEMBL_ACT_24828452 |
| CYP2C9 | 6.23 | IC50 | 586 | nM | CHEMBL_ACT_23259666 |
| CYP2C9 | 6.23 | IC50 | 585 | nM | CHEMBL_ACT_24875742 |
| CYP2C9 | 6.22 | IC50 | 600 | nM | CHEMBL_ACT_378600 |
| CYP2C9 | 6.21 | IC50 | 609 | nM | CHEMBL_ACT_19156604 |
| CYP2C9 | 6.21 | IC50 | 609 | nM | CHEMBL_ACT_22405888 |
| CYP2C9 | 6.21 | IC50 | 624 | nM | CHEMBL_ACT_24868037 |
| CYP2C9 | 6.2 | IC50 | 630 | nM | CHEMBL_ACT_22934680 |
| CYP2C9 | 6.2 | IC50 | 627 | nM | CHEMBL_ACT_25453765 |
| CYP2C9 | 6.19 | IC50 | 641 | nM | CHEMBL_ACT_24366297 |
| CYP2C9 | 6.19 | IC50 | 652 | nM | CHEMBL_ACT_25935289 |
| CYP2C9 | 6.18 | IC50 | 660 | nM | CHEMBL_ACT_19063367 |
| CYP2C9 | 6.18 | IC50 | 660 | nM | CHEMBL_ACT_19109594 |
| CYP2C9 | 6.18 | IC50 | 656 | nM | CHEMBL_ACT_24889668 |
| CYP2C9 | 6.17 | IC50 | 680 | nM | CHEMBL_ACT_25968448 |
| CYP2C9 | 6.17 | IC50 | 681 | nM | CHEMBL_ACT_26118142 |
| CYP2C9 | 6.17 | IC50 | 681 | nM | CHEMBL_ACT_29186730 |
| CYP2C9 | 6.17 | IC50 | 676 | nM | CHEMBL_ACT_29191725 |
| CYP2C9 | 6.16 | IC50 | 685 | nM | CHEMBL_ACT_18924698 |
| CYP2C9 | 6.15 | IC50 | 704 | nM | CHEMBL_ACT_16828579 |
| CYP2C9 | 6.14 | IC50 | 720 | nM | CHEMBL_ACT_18295684 |
| CYP2C9 | 6.13 | IC50 | 740 | nM | CHEMBL_ACT_16621040 |
| CYP2C9 | 6.11 | IC50 | 770 | nM | CHEMBL_ACT_22879836 |
| CYP2C9 | 6.07 | IC50 | 847 | nM | CHEMBL_ACT_19111622 |
| CYP2C9 | 6.06 | IC50 | 870 | nM | CHEMBL_ACT_26153931 |
| CYP2C9 | 6.05 | IC50 | 893 | nM | CHEMBL_ACT_22971657 |
| POLB | 6.05 | Potency | 891.3 | nM | CHEMBL_ACT_5047672 |
| NPSR1 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4933065 |
| CYP3A4 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4977684 |
| CYP3A4 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_5042917 |
| CYP3A4 | 5.5 | AC50 | 3162 | nM | CHEMBL_ACT_6049461 |
| TSHR | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_3915150 |
| TSHR | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_4699079 |
| CYP2C9 | 5.38 | IC50 | 4200 | nM | CHEMBL_ACT_15002185 |
| CYP2C9 | 5.38 | IC50 | 4200 | nM | CHEMBL_ACT_15105317 |
| NFKB1 | 5.15 | Potency | 7080 | nM | CHEMBL_ACT_3672612 |
| NFKB1 | 5.15 | Potency | 7080 | nM | CHEMBL_ACT_4585348 |
| LMNA | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_3653893 |
| CYP3A4 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_5010217 |
| CYP3A4 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_5078631 |
| CYP3A4 | 5.1 | AC50 | 7943 | nM | CHEMBL_ACT_6049137 |
| CYP2C9 | 5 | IC50 | 10000 | nM | CHEMBL_ACT_18125087 |
| HSD17B10 | 5 | Potency | 10000 | nM | CHEMBL_ACT_3709549 |
| TDP1 | 5 | Potency | 10000 | nM | CHEMBL_ACT_3932741 |
Target pathways
Aggregated over 1 target gene(s): CYP2C9.
Top Reactome pathways
6 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Xenobiotics | 1 | CYP2C9 |
| CYP2E1 reactions | 1 | CYP2C9 |
| Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET) | 1 | CYP2C9 |
| Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) | 1 | CYP2C9 |
| Biosynthesis of maresin-like SPMs | 1 | CYP2C9 |
| Aspirin ADME | 1 | CYP2C9 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| xenobiotic metabolic process | 1 |
| steroid metabolic process | 1 |
| cholesterol metabolic process | 1 |
| estrogen metabolic process | 1 |
| monoterpenoid metabolic process | 1 |
| epoxygenase P450 pathway | 1 |
| urea metabolic process | 1 |
| monocarboxylic acid metabolic process | 1 |
| xenobiotic catabolic process | 1 |
| long-chain fatty acid biosynthetic process | 1 |
| icosanoid biosynthetic process | 1 |
| oxidative demethylation | 1 |
| organofluorine metabolic process | 1 |
| omega-hydroxylase P450 pathway | 1 |
| lipid metabolic process | 1 |
Indications & clinical
Indications
2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).
| Indication | Phase | MONDO | EFO |
|---|---|---|---|
| bacterial infectious disease | 4 | MONDO:0005113 | EFO:0000771 |
| eye infectious disorder | 4 | MONDO:0043885 | EFO: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.
Related molecules
Related molecules
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:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| FEZOLINETANT | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9 |
| PAZOPANIB | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BENZTHIAZIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BISACODYL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| BUTAMBEN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CILOSTAZOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CIPROFLOXACIN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLOMETHIAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLOMIPHENE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLONIDINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| COLCHICINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CYCLOSERINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| CYCLOSPORINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DACLATASVIR | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DANAZOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DAPSONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DASATINIB | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DEFERIPRONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DEXIBUPROFEN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DEXMEDETOMIDINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DEXTROTHYROXINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DICHLORPHENAMIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DICLOFENAC | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DICUMAROL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DICYCLOMINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DIENESTROL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DIPYRIDAMOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DISULFIRAM | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DROPERIDOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DULOXETINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| DYCLONINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ENOXACIN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ENOXIMONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ENTACAPONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ESCITALOPRAM | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ESTRONE SULFURIC ACID | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ETHACRYNIC ACID | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ETODOLAC | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ETRAVIRINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FELODIPINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FENOFIBRATE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FINASTERIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUCONAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUPIRTINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUSPIRILENE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUTAMIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUVASTATIN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| FLUVOXAMINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| GEMFIBROZIL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| GLIPIZIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| GLYBURIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| GUANFACINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| HEXESTROL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| HYDROCHLOROTHIAZIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| HYDROFLUMETHIAZIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| IBRUTINIB | ChEMBL | Phase 4 (approved) | CYP2C9 |
| IBUDILAST | ChEMBL | Phase 4 (approved) | CYP2C9 |
| IBUPROFEN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| IDEBENONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| INAMRINONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| INDOMETHACIN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ISRADIPINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| ISTRADEFYLLINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| KETANSERIN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| KETOCONAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LANSOPRAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LEFLUNOMIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LESINURAD | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LIFITEGRAST | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LORATADINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LOSARTAN | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LOXAPINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| LUMACAFTOR | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MARAVIROC | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MASOPROCOL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MEBENDAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MECLOFENAMATE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MEFENAMIC ACID | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MEGESTROL | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MENADIONE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MESALAMINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| METHAPYRILENE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| METHAZOLAMIDE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| METHSCOPOLAMINE | ChEMBL | Phase 4 (approved) | CYP2C9 |
| MIBEFRADIL | ChEMBL | Phase 4 (approved) | CYP2C9 |
Related Atlas pages
- Genes: CYP2C9
- Indicated for: bacterial infectious disease, eye infectious disorder
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