Noscapine
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Also known as (-)-.alpha.-narcotine(-)-narcotineMethoxyhydrastineNarcotinumNoscapinaNoscapinumNSC-5366SID11113349SID50104123SID855860SID90341457SID49645498SID71491SID144203964SID170465539Alpha-noscapineCO-ADD:0137169NarcosineNarcotine
Summary
Noscapine (CHEMBL364713) is an approved small-molecule antineoplastic agent (ATC R05DA07) targeting CYP2C9 and CYP3A4; indicated across 3 conditions including plasma cell myeloma and b-cell chronic lymphocytic leukemia.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: R05DA07
- Targets: 2 (CYP2C9, CYP3A4)
- Indications: 3 conditions
- Clinical trials: 1
- Chemistry: 413.4 Da · C22H23NO7
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL364713 |
| Name | Noscapine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 275196 |
| ChEBI | CHEBI:73237 |
| ATC | R05DA07 |
| Molecular formula | C22H23NO7 |
| Molecular weight | 413.4 |
| InChIKey | AKNNEGZIBPJZJG-MSOLQXFVSA-N |
SMILES: CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
IUPAC name: (3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
ChEBI definition: A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.
Pharmacological roles (ChEBI): antitussive, antineoplastic agent, apoptosis inducer.
Other ChEBI roles (chemical / environmental): plant metabolite.
Also known as: (-)-.alpha.-narcotine, (-)-narcotine, Methoxyhydrastine, Narcotinum, Noscapina, Noscapine, Noscapinum, NSC-5366, noscapine, SID11113349, SID50104123, SID855860
Parent form; salt/anhydrous children: CHEMBL2106732
Patent coverage: 4,032 distinct patent families (14,987 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 14,756 (98%) of the total. 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 | 0% | P11712 | |
| CYP3A4 | CYP3A4 | Inhibition | 0% | P08684 |
Broader ChEMBL bioactivity targets: 21 (assay-derived). Sample: Ras-related protein Rab-9A, Solute carrier family 22 member 2, Multidrug and toxin extrusion protein 1, Beta-lactamase, Menin/Histone-lysine N-methyltransferase MLL, Tubulin, Beta-1 adrenergic receptor, Motilin receptor, 5-hydroxytryptamine receptor 2A, Type-1 angiotensin II receptor.
Bioactivity
ChEMBL activities: 16 potent at pChembl ≥ 5 of 27 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| CYP2C9 | 6.9 | Potency | 125.9 | nM | CHEMBL_ACT_5017136 |
| CYP2C9 | 6.9 | AC50 | 125.9 | nM | CHEMBL_ACT_5989915 |
| CYP2C19 | 6.8 | Potency | 158.5 | nM | CHEMBL_ACT_4019441 |
| CYP2C19 | 6.8 | AC50 | 158.5 | nM | CHEMBL_ACT_6039577 |
| GHSR | 6.49 | AC50 | 326 | nM | CHEMBL_ACT_25172794 |
| CYP2C19 | 6.4 | IC50 | 400.3 | nM | CHEMBL_ACT_7744376 |
| TUBB8B | 6.24 | Kd | 579 | nM | CHEMBL_ACT_22400876 |
| AGTR1 | 6.2 | AC50 | 627 | nM | CHEMBL_ACT_25177030 |
| TUBB4A | 5.73 | Kd | 1860 | nM | CHEMBL_ACT_15658190 |
| CYP3A4 | 5.7 | Potency | 1995 | nM | CHEMBL_ACT_4973788 |
| CYP3A4 | 5.7 | Potency | 1995 | nM | CHEMBL_ACT_5042814 |
| CYP3A4 | 5.6 | AC50 | 2512 | nM | CHEMBL_ACT_6036261 |
| SLC22A2 | 5.58 | IC50 | 2600 | nM | CHEMBL_ACT_12636187 |
| CYP2C9 | 5.09 | IC50 | 8177 | nM | CHEMBL_ACT_7744378 |
| PTGS2 | 5.08 | AC50 | 8400 | nM | CHEMBL_ACT_25166234 |
| ADRB1 | 5.06 | AC50 | 8699 | nM | CHEMBL_ACT_25121817 |
Target pathways
Aggregated over 2 target gene(s): CYP2C9, CYP3A4.
Top Reactome pathways
10 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Xenobiotics | 2 | CYP2C9, CYP3A4 |
| Biosynthesis of maresin-like SPMs | 2 | CYP2C9, CYP3A4 |
| Aspirin ADME | 2 | CYP2C9, CYP3A4 |
| Phase I - Functionalization of compounds | 1 | CYP3A4 |
| CYP2E1 reactions | 1 | CYP2C9 |
| Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET) | 1 | CYP2C9 |
| Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) | 1 | CYP2C9 |
| Aflatoxin activation and detoxification | 1 | CYP3A4 |
| Atorvastatin ADME | 1 | CYP3A4 |
| Prednisone ADME | 1 | CYP3A4 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| xenobiotic metabolic process | 2 |
| steroid metabolic process | 2 |
| cholesterol metabolic process | 2 |
| estrogen metabolic process | 2 |
| monoterpenoid metabolic process | 2 |
| xenobiotic catabolic process | 2 |
| long-chain fatty acid biosynthetic process | 2 |
| oxidative demethylation | 2 |
| lipid metabolic process | 2 |
| epoxygenase P450 pathway | 1 |
| urea metabolic process | 1 |
| monocarboxylic acid metabolic process | 1 |
| icosanoid biosynthetic process | 1 |
| organofluorine metabolic process | 1 |
| omega-hydroxylase P450 pathway | 1 |
Indications & clinical
Indications
3 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| plasma cell myeloma | 1 | MONDO:0009693 | EFO:0001378 |
| B-cell chronic lymphocytic leukemia | 1 | MONDO:0004948 | EFO:0000095 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 1.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00183950 | PHASE1/PHASE2 | TERMINATED | Study of Noscapine for Patients With Low Grade Non Hodgkin’s Lymphoma or Chronic Lymphocytic Leukemia Refractory to Chemotherapy |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
725 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Carfilzomib | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FEZOLINETANT | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9, CYP3A4 |
| PAZOPANIB | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9, CYP3A4 |
| saxagliptin | ChEMBL + PubChem | Phase 4 (approved) | CYP2C9, CYP3A4 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| BENZTHIAZIDE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| BUTAMBEN | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| COLCHICINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| CYCLOSPORINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DACLATASVIR | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DAPSONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DASATINIB | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DICLOFENAC | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DICUMAROL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DICYCLOMINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DIENESTROL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DROPERIDOL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DULOXETINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| DYCLONINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| ENOXIMONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| ESCITALOPRAM | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| ETODOLAC | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| ETRAVIRINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FENOFIBRATE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FINASTERIDE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FLUCONAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FLUPIRTINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| FLUSPIRILENE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| GLIPIZIDE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| GLYBURIDE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| IBRUTINIB | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| IBUDILAST | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| IDEBENONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| INAMRINONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| ISRADIPINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| KETANSERIN | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| KETOCONAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| LANSOPRAZOLE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| LESINURAD | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| LOSARTAN | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| LOXAPINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MARAVIROC | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MASOPROCOL | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MECLOFENAMATE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MEFENAMIC ACID | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MENADIONE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| MESALAMINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
| METHSCOPOLAMINE | ChEMBL | Phase 4 (approved) | CYP2C9, CYP3A4 |
Related Atlas pages
- Genes: CYP2C9, CYP3A4
- Drugs: Carfilzomib, Fezolinetant, Pazopanib, saxagliptin, Amiodarone, Amsacrine, Apomorphine, Benzbromarone, Benzthiazide, Bepridil, Buspirone, Butamben, Cannabidiol, Celecoxib, Clemastine, Clotrimazole, Clozapine, Colchicine, Cyclosporine, Daclatasvir, Dapsone, Dasatinib, Diclofenac, Dicumarol, Dicyclomine, Dienestrol, Diethylstilbestrol, Droperidol, Duloxetine, Dyclonine, Enoximone, Escitalopram, Etodolac, Etravirine, Fenofibrate, Finasteride, Fluconazole, Flupirtine, Fluspirilene, Glipizide, Glyburide, Haloperidol, Ibrutinib, Ibudilast, Idebenone, Inamrinone, Isradipine, Ketanserin, Ketoconazole, Lansoprazole, Lesinurad, Losartan, Loxapine, Maraviroc, Masoprocol, Meclofenamate, Mefenamic Acid, Menadione, Mesalamine, Methscopolamine