Vincamine
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Also known as AngiopacArteriovincaCetalCetal retardNSC-91998OxygeronPervincamineVincaforVincagilVincaminaVincimaxVraapSID56463058SID56463369SID144204895SID144212285SID170466430(+)-Vincamine
Summary
Vincamine (CHEMBL1165342) is an approved small-molecule antihypertensive agent (ATC C04AX07) targeting CHRM1, CHRM2, and CHRM3; indicated across 1 condition including cardiovascular disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C04AX07
- Targets: 4 (CHRM1, CHRM2, CHRM3…)
- Indications: 1 condition
- Chemistry: 354.4 Da · C21H26N2O3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1165342 |
| Name | Vincamine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 15376 |
| ChEBI | CHEBI:9985 |
| ATC | C04AX07 |
| Molecular formula | C21H26N2O3 |
| Molecular weight | 354.4 |
| InChIKey | RXPRRQLKFXBCSJ-GIVPXCGWSA-N |
SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@](C2)(C(=O)OC)O
IUPAC name: methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
Pharmacological roles (ChEBI): antihypertensive agent, vasodilator agent.
Also known as: Angiopac, Arteriovinca, Cetal, Cetal retard, NSC-91998, Oxygeron, Pervincamine, Vincafor, Vincagil, Vincamina, Vincamine, Vincimax
Patent coverage: 2,518 distinct patent families (5,764 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 5,750 (100%) 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 |
|---|---|---|---|---|---|
| CHRM1 | M1 receptor | Neutral | 4.8 | 0.2% | P11229 |
| CHRM2 | M2 receptor | Neutral | 5.1 | 0% | P08172 |
| CHRM3 | M3 receptor | Neutral | 5.7 | 0% | P20309 |
| CHRM4 | M4 receptor | Positive | 4.2 | 1.6% | P08173 |
Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Voltage-gated inwardly rectifying potassium channel KCNH2.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 1 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| KCNH2 | 6.34 | AC50 | 460 | nM | CHEMBL_ACT_25117764 |
Target pathways
Aggregated over 4 target gene(s): CHRM1, CHRM2, CHRM3, CHRM4.
Top Reactome pathways
17 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| Signaling by GPCR | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| Class A/1 (Rhodopsin-like receptors) | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| Amine ligand-binding receptors | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| GPCR downstream signalling | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| Muscarinic acetylcholine receptors | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| GPCR ligand binding | 4 | CHRM1, CHRM2, CHRM3, CHRM4 |
| G alpha (q) signalling events | 2 | CHRM1, CHRM3 |
| G alpha (i) signalling events | 2 | CHRM2, CHRM4 |
| Metabolism | 1 | CHRM3 |
| Integration of energy metabolism | 1 | CHRM3 |
| Membrane Trafficking | 1 | CHRM2 |
| Acetylcholine regulates insulin secretion | 1 | CHRM3 |
| Regulation of insulin secretion | 1 | CHRM3 |
| Vesicle-mediated transport | 1 | CHRM2 |
| Cargo recognition for clathrin-mediated endocytosis | 1 | CHRM2 |
| Clathrin-mediated endocytosis | 1 | CHRM2 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| signal transduction | 4 |
| G protein-coupled receptor signaling pathway | 4 |
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 4 |
| adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway | 4 |
| G protein-coupled acetylcholine receptor signaling pathway | 4 |
| chemical synaptic transmission | 4 |
| phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathway | 3 |
| nervous system development | 3 |
| regulation of locomotion | 2 |
| saliva secretion | 2 |
| acetylcholine receptor signaling pathway | 2 |
| regulation of smooth muscle contraction | 2 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| neuromuscular synaptic transmission | 1 |
| positive regulation of monoatomic ion transport | 1 |
Indications & clinical
Indications
1 indication (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 |
|---|---|---|---|
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
Clinical trials
Total trials: 0.
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
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.
567 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| ACLIDINIUM BROMIDE | ChEMBL + PubChem | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| Mavorixafor | ChEMBL + PubChem | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| ACETYLCHOLINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| ATROPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| BETHANECHOL | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| BIPERIDEN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CARBACHOL | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CARBAMOYLCHOLINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CEVIMELINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CHLOROQUINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CLIDINIUM | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CYCLIZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DARIFENACIN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DESLORATADINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DEXCHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DICYCLOMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DIMENHYDRINATE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DIPHENHYDRAMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DIPHENIDOL | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| DOXEPIN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| EBASTINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| GLYCOPYRRONIUM BROMIDE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| HOMATROPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| HYDROXYCHLOROQUINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| IMIPRAMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| IPRATROPIUM | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| KETOTIFEN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| LOXAPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| MAPROTILINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| MEPAZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| METHSCOPOLAMINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| METHSCOPOLAMINE BROMIDE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| MIANSERIN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| MICONAZOLE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| NORTRIPTYLINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| OLANZAPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| ORPHENADRINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| OXYBUTYNIN | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PAROXETINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PERHEXILINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PILOCARPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PIRENZEPINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PROCHLORPERAZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
| PROMAZINE | ChEMBL | Phase 4 (approved) | CHRM1, CHRM2, CHRM3, CHRM4 |
Related Atlas pages
- Genes: CHRM1, CHRM2, CHRM3, CHRM4
- Diseases: cardiovascular disorder
- Drugs: Aclidinium Bromide, Mavorixafor, Acetylcholine, Amiodarone, Amitriptyline, Amoxapine, Astemizole, Atropine, Benztropine, Bethanechol, Biperiden, Carbachol, Cevimeline, Chloroquine, Chlorpromazine, Cinnarizine, Clemastine, Clidinium, Clomipramine, Clotrimazole, Clozapine, Cyclizine, Cyproheptadine, Darifenacin, Desloratadine, Dexchlorpheniramine, Dicyclomine, Dimenhydrinate, Diphenhydramine, Diphenidol, Doxepin, Ebastine, Econazole, Fluphenazine, Glycopyrronium Bromide, Haloperidol, Homatropine, Hydroxychloroquine, Imipramine, Ipratropium, Ketotifen, Loxapine, Maprotiline, Mepazine, Methscopolamine, Mianserin, Miconazole, Nortriptyline, Olanzapine, Orphenadrine, Oxybutynin, Paroxetine, Perhexiline, Pilocarpine, Pirenzepine, Prochlorperazine, Promazine