Vinpocetine

Summary

Vinpocetine (CHEMBL71752) is an approved small molecule (ATC N06BX18) targeting PDE1A and PDE1C; indicated across 3 conditions including attention deficit-hyperactivity disorder and diabetic kidney disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N06BX18
• Targets: 2 (PDE1A, PDE1C)
• Indications: 3 conditions
• Clinical trials: 5
• Chemistry: 350.5 Da · C22H26N2O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL71752
Name	Vinpocetine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	443955
ATC	N06BX18
Molecular formula	C22H26N2O2
Molecular weight	350.5
InChIKey	DDNCQMVWWZOMLN-IRLDBZIGSA-N

SMILES: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC

IUPAC name: ethyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate

Also known as: Apovincaminic acid ethyl ester, AY-27,255, AY-27255, Bravinton, Cavinton, Ceractin, NSC-760093, Rgh 4405, Tcv 3b, Ultra-vinca, Vinpocetina, Vinpocetine

Patent coverage: 2,969 distinct patent families (8,194 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 8,023 (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
PDE1A	phosphodiesterase 1A	Inhibition	5.1	0%	P54750
PDE1C	phosphodiesterase 1C	Inhibition	4.3	0.5%	Q14123

Broader ChEMBL bioactivity targets: 28 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, RecQ-like DNA helicase BLM, 4’-phosphopantetheinyl transferase ffp, Peripheral myelin protein 22, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Menin/Histone-lysine N-methyltransferase MLL, Phosphodiesterase 1, Phosphodiesterase 1, Muscarinic acetylcholine receptor M2, Adenosine receptor A1, Sodium-dependent serotonin transporter, D(3) dopamine receptor, Sodium-dependent dopamine transporter.

Bioactivity

ChEMBL activities: 14 potent at pChembl ≥ 5 of 37 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
KCNH2	7.41	IC50	39	nM	CHEMBL_ACT_18051517
KCNH2	7.26	AC50	54.8	nM	CHEMBL_ACT_25117426
BLM	6.1	Potency	794.3	nM	CHEMBL_ACT_4745895
BLM	6.1	Potency	794.3	nM	CHEMBL_ACT_4921837
ADRA2C	5.96	AC50	1100	nM	CHEMBL_ACT_25147578
ADRA2B	5.62	AC50	2400	nM	CHEMBL_ACT_25143411
SMN1	5.6	Potency	2512	nM	CHEMBL_ACT_3885090
HIF1A	5.2	Potency	6310	nM	CHEMBL_ACT_4127968
HIF1A	5.2	Potency	6310	nM	CHEMBL_ACT_4520577
PDE1B	5.1	IC50	7990	nM	CHEMBL_ACT_22905733
PDE4D	5.06	AC50	8800	nM	CHEMBL_ACT_25185026
SLC6A4	5.05	AC50	9000	nM	CHEMBL_ACT_25150048
MAPT	5.05	Potency	8912	nM	CHEMBL_ACT_4514788
PDE1A	5	IC50	10000	nM	CHEMBL_ACT_24982972

Target pathways

Aggregated over 2 target gene(s): PDE1A, PDE1C.

Top Reactome pathways

3 total, by targets touching each:

Pathway	Targets	Genes
Cam-PDE 1 activation	2	PDE1A, PDE1C
cGMP effects	1	PDE1A
G alpha (s) signalling events	1	PDE1A

Dominant GO biological processes

GO term	Targets
signal transduction	2
negative regulation of cAMP/PKA signal transduction	2
regulation of smooth muscle cell apoptotic process	1
cGMP catabolic process	1
regulation of smooth muscle cell proliferation	1

Indications & clinical

Indications

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

Indication	Phase	MONDO	EFO
attention deficit-hyperactivity disorder	4	MONDO:0007743	EFO:0003888

2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
diabetic kidney disease	2	MONDO:0005016	EFO:0000401
epilepsy	1	MONDO:0005027	EFO:0000474

Clinical trials

Total trials: 5.

Phase distribution

Phase	Trials
PHASE2/PHASE3	3
PHASE1/PHASE2	1
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06441591	PHASE2/PHASE3	RECRUITING	Clinical Outcome of Vinpocetine in Diabetic Nephropathy
NCT07229664	PHASE2/PHASE3	RECRUITING	Vinpocetine in Patients With Parkinsonian Disease
NCT02878772	PHASE2/PHASE3	COMPLETED	Vinpocetine Inhibits NF-κB-dependent Inflammation in Acute Ischemic Stroke Patients
NCT02011971	PHASE1/PHASE2	SUSPENDED	Cognitive Effects of Vinpocetine in Healthy Adults and Patients With Epilepsy
NCT06635746	PHASE1	NOT_YET_RECRUITING	Dose Escalation Study of Vinpocetine in Healthy Volunteers

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.

20 molecules share ≥1 primary target. Top 20 by shared-target count:

Molecule	Source	Status	Shared targets
DIPYRIDAMOLE	ChEMBL + PubChem	Phase 4 (approved)	PDE1A, PDE1C
NIMODIPINE	ChEMBL + PubChem	Phase 4 (approved)	PDE1A, PDE1C
SILDENAFIL	ChEMBL + PubChem	Phase 4 (approved)	PDE1A, PDE1C
VARDENAFIL	ChEMBL + PubChem	Phase 4 (approved)	PDE1A, PDE1C
PAPAVERINE	ChEMBL	Phase 3	PDE1A, PDE1C
BUFROLIN	ChEMBL	Phase 2	PDE1A, PDE1C
CILOSTAMIDE	ChEMBL	Phase 2	PDE1A, PDE1C
EDELINONTRINE	ChEMBL	Phase 2	PDE1A, PDE1C
ETAZOLATE	ChEMBL	Phase 2	PDE1A, PDE1C
IDOXIFENE	ChEMBL	Phase 2	PDE1A, PDE1C
OXAGRELATE	ChEMBL	Phase 2	PDE1A, PDE1C
ROLIPRAM	ChEMBL	Phase 2	PDE1A, PDE1C
ZAPRINAST	ChEMBL	Phase 2	PDE1A, PDE1C
Cilostazol	PubChem	Approved	PDE1A, PDE1C
Milrinone	PubChem	Approved	PDE1A, PDE1C
Tadalafil	PubChem	Approved	PDE1A, PDE1C
theophylline	PubChem	Approved	PDE1A, PDE1C
CRISABOROLE	ChEMBL + PubChem	Phase 4 (approved)	PDE1A
NITRENDIPINE	ChEMBL	Phase 3	PDE1C
TOVINONTRINE	ChEMBL	Phase 2	PDE1A