VINCAMINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26N2O3
Molecular Weight	354.4427
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]12CCCN3CCC4=C([C@H]13)N(C5=C4C=CC=C5)[C@](O)(C2)C(=O)OC

InChI

InChIKey=RXPRRQLKFXBCSJ-GIVPXCGWSA-N

InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H26N2O3
Molecular Weight	354.4427
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.biofarm.ro/Vincamine-SR-s29-p178-en.htm | https://nootopics.com/vincamine-dosage/ | http://www.hnkeyuan.com/anti_cancer/Vincamine.html

Vincamine is the major alkaloid of Vinca minor. Although vincamine has been used therapeutically for almost three decades, the exact mechanisms of action and its effects are still unknown. Vincamine is a peripheral vasodilator that increases blood flow to the brain. Vincamine is beneficial to the nervous system's cells feeding and protecting processes and is utilized as an adjuvant in case of cerebrovascular insufficiency, age-related psycho-behavioral disorders, post concussion syndrome in head trauma, in case of post-stroke sequels. Vincamine may be used as a dietary nootropic supplement.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunits; brain (Types I, II, III) 28 Target ID: CHEMBL2095171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8957220	Blocker 555		1.9 µM [IC50]
vasodilation 8 Target ID: GO:0042311 Sources: https://elitenootropics.com/vincamine-natural-brain-nootropic/ \| https://www.covex.com/products/api/vincamine/ \| https://nootriment.com/vincamine/	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cerebrovascular insufficiency 15 Sources: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0004-282X1975000100003 https://www.ncbi.nlm.nih.gov/pubmed/351463 https://www.ncbi.nlm.nih.gov/pubmed/6500776 https://www.ncbi.nlm.nih.gov/pubmed/6389380 https://www.ncbi.nlm.nih.gov/pubmed/3949275	Primary		Approved 8583	Oxybral Approved Use Oxybral (Vincamine) is indicated to normalize and adapt the cerebral blood flow according to the metabolic needs and in turn improves, regulates and maintains all the brain functions, reflecting better performance physically and intellectually. Vincamine is beneficial to the nervous system's cells feeding and protecting processes and is utilized as an adjuvant in case of cerebrovascular insufficiency, age related psycho-behavioral disorders, post concussion syndrome in head trauma, in case of post-stroke sequels.

C_max

Value	Dose	Co-administered	Analyte	Population
155 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6654533/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
91.67 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10738641/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
443 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6654533/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
514.65 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10738641/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6654533/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
4.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10738641/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		VINCAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
36% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4010386/			VINCAMINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 4 times / day steady, oral Studied dose Dose: 20 mg, 4 times / day Route: oral Route: steady Dose: 20 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6436861/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6436861/	Sources: https://pubmed.ncbi.nlm.nih.gov/6436861/
30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	Other AEs: Gastrointestinal disorders, Hypotension... Other AEs: Gastrointestinal disorders (not severe, 12 patients) Hypotension (not severe, 12 patients) Nervousness (not severe, 12 patients) Insomnia (not severe, 12 patients) Vertigo (not severe, 12 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/

AEs

AE	Significance	Dose	Population
Gastrointestinal disorders	not severe, 12 patients	30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/
Hypotension	not severe, 12 patients	30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/
Insomnia	not severe, 12 patients	30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/
Nervousness	not severe, 12 patients	30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/
Vertigo	not severe, 12 patients	30 mg 2 times / day steady, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8884757/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OATP1B1 1079 CYP2C19 2057 P-gp 1741 CYP19A1 429 CYP1A2 2153	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 13.0	no [EC50 43.6486 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 146.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 223.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 225.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 15.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 8.0	yes [EC50 12.5893 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 4.0	yes [IC50 7.7619 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 5.0	yes [IC50 8.709 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUzNDIifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUzNDIifX0=	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 9 \| 195	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/15376#section=Biological-Test-Results Page: 1.0

PubMed

Title	Date	PubMed
Aggressive behavior during social interaction in mice is controlled by the modulation of tyrosine hydroxylase expression in the prefrontal cortex.	2010-12-15	20923695
Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy.	2010-12-15	20724093
Brain trace element concentration of rats treated with the plant alkaloid, vincamine.	2010-09	19902161
Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora.	2010-06-15	20576577
Antinociceptive effect of vinpocetine--a comprehensive survey.	2010-05-30	20648783
WITHDRAWN: Interventions for normal tension glaucoma.	2010-02-17	20166063
Exercise as an intervention for the age-related decline in neural metabolic support.	2010	20802804
Adenylate kinase and AMP signaling networks: metabolic monitoring, signal communication and body energy sensing.	2009-04-17	19468337
Seco-tabersonine alkaloids from Tabernaemontana corymbosa.	2009-02	19217125
Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model.	2009	19492990
Development and validation of an adsorptive stripping voltammetric method for the quantification of vincamine in its formulations and human serum using a Nujol-based carbon paste electrode.	2008-12	19043234
Effects of Vinpocetine on mitochondrial function and neuroprotection in primary cortical neurons.	2008-12	18793690
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.	2008-06	18830442
Simultaneous determination of piracetam and vincamine by spectrophotometric and high-performance liquid chromatographic methods.	2008-05-15	18476342
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.	2008-05-15	18476341
Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport.	2008	18413267
In vitro anticholinesterase activity of various alkaloids.	2007-12-12	18069241
Application of unsymmetrical indirect covariance NMR methods to the computation of the (13)C <--> (15)N HSQC-IMPEACH and (13)C <--> (15)N HMBC-IMPEACH correlation spectra.	2007-10	17729230
Allosteric modulation of muscarinic acetylcholine receptors.	2007-09	19305798
Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.	2007-08-16	17658832
Impaired cognition and attention in adults: pharmacological management strategies.	2007-02	19300541
Effect of vinpocetine on retrograde axoplasmic transport.	2007	17319607
Catharanthus roseus flower extract has wound-healing activity in Sprague Dawley rats.	2006-12-21	17184528
Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine.	2006-05-12	16674048
Development and application of an automated solution stability assay for drug discovery.	2006-02	16234336
Eburnamine derivatives and the brain.	2005-11	16158388
Measurement and pharmacokinetics of vincamine in rat blood and brain using microdialysis.	2005-09-23	16130744
Processing methods for differential analysis of LC/MS profile data.	2005-07-18	16026613
Catalytic N-sulfonyliminium ion-mediated cyclizations to alpha-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis.	2005-07-08	15989333
Stability-indicating methods for determination of vincamine in presence of its degradation product.	2005-06-01	15907622
[Neuroprotection strategies: effect of vinpocetine in vitro oxidative stress models].	2005-01-06	15631851
Enhanced tail pinch-induced activation of catecholamine metabolism in the pericerulean area of RU 24722-treated rats.	2004-12-24	15567332
Vinpocetine is a potent blocker of rat NaV1.8 tetrodotoxin-resistant sodium channels.	2003-08	12730276
Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography.	2003-05-09	12830921
Interventions for normal tension glaucoma.	2003	14583947
[Investigation of vasoactive agents with indole skeletons at Richter Ltd].	2002	12426785
[Open-angle glaucoma clinical presentation and management].	2001-12	11802456
Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compounds.	2001	11746802
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997-07	9224827
[Nimodipine, nifedipine and vincamine improve amnesia induced by anisodine and sodium nitrite in rats and mice].	1986-10	2952309
Screening for new compounds with antiherpes activity.	1984-10	6517562

Patents

Sample Use Guides

In Vivo Use Guide

Oxybral (Vincamine) Capsule contains 30 mg of vincamine in a sustained release pellet form. Oxybral (Vincamine) Ampoule for parenteral administration contains 15 mg of vincamine. Dosage in Adult: 1 capsule twice daily, 1 ampoule once or twice daily by IM or slow IV infusion

Route of Administration: Other

In Vitro Use Guide

Metabolic changes in alveolar macrophages and cell injury were evaluated in three studies carried out after 24 hr of gaseous phase culture in normoxia and in anaerobiosis with a possible treatment with 0.01 ug/ml vincamine: 1) ATP content assay by bioluminescence, the witness of cell vitality which decreases significantly in anaerobiosis; 2) Lactate assay which shows the metabolism derivation towards the anaerobic pathways; and 3) Tritiated deoxyglucose (DOG) incorporation, which shows glucose requirements after hypoxic incubation, maintaining or recovering a certain level of energetic activity.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:56 GMT 2025`
Record UNII	996XVD0JHT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CETAL RETARD

Preferred Name

English

VINCAMINE

Official Name

English

ANGIOPAC

Brand Name

English

VINCIMAX

Brand Name

English

vincamine [INN]

Common Name

English

(3.ALPHA.,14.BETA.,16.ALPHA.)-14,15-DIHYDRO-14-HYDROXYEBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER

Common Name

English

VINCAMINE [HSDB]

Common Name

English

Vincamine [WHO-DD]

Common Name

English

VINCAMINE [MART.]

Common Name

English

PERVINCAMINE

Brand Name

English

CETAL

Brand Name

English

VRAAP

Brand Name

English

ARTERIOVINCA

Brand Name

English

VINCAFOR

Brand Name

English

VINCAMINE [EP MONOGRAPH]

Common Name

English

VINCAGIL

Brand Name

English

VINCAMINE [MI]

Common Name

English

OXYGERON

Brand Name

English

NSC-91998

Code

English

ALKALOID OBTAINED FROM VINCA MINOR

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47795