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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 of VINCAMINE

SMILES

[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N4C5=C(C=CC=C5)C(CC3)=C24)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

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

Schlittler, E.|Furlenmeier, A.
4
Sources: E. Schlittler, A. Furlenmeier Vincamine, ein alkaloid aus Vinca minor L. Apocynaceae Helv. Chim. Acta, 36 (1953), pp. 2017-2020
Curator's Comment: Vincamine was first isolated from Vinca minor. reference retrieved from https://www.sciencedirect.com/science/article/pii/S0040403900709774

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
 1.9 µM [IC50]
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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.
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
[Nimodipine, nifedipine and vincamine improve amnesia induced by anisodine and sodium nitrite in rats and mice].
1986 Oct
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
1997 Jul
Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compounds.
2001
[Investigation of vasoactive agents with indole skeletons at Richter Ltd].
2002
Vinpocetine is a potent blocker of rat NaV1.8 tetrodotoxin-resistant sodium channels.
2003 Aug
Enhanced tail pinch-induced activation of catecholamine metabolism in the pericerulean area of RU 24722-treated rats.
2004 Dec 24
Eburnamine derivatives and the brain.
2005 Nov
Development and application of an automated solution stability assay for drug discovery.
2006 Feb
Effect of vinpocetine on retrograde axoplasmic transport.
2007
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 Oct
Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport.
2008
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.
2008 Mar-Apr
Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model.
2009 Summer
Aggressive behavior during social interaction in mice is controlled by the modulation of tyrosine hydroxylase expression in the prefrontal cortex.
2010 Dec 15
WITHDRAWN: Interventions for normal tension glaucoma.
2010 Feb 17
Antinociceptive effect of vinpocetine--a comprehensive survey.
2010 May 30
Patents

Patents

JP2002511777A
414
JPH0892041A
6
JPS5762277A
4

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 Fri Dec 15 15:12:02 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:02 GMT 2023
Record UNII
996XVD0JHT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VINCAMINE
HSDB   INN   MART.   MI   WHO-DD  
INN  
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
CETAL RETARD
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
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DSLD 2937 (Number of products:1)
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WHO-ATC C04AX07
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WHO-VATC QC04AX07
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Code System Code Type Description
NSC
91998
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PRIMARY
WIKIPEDIA
VINCAMINE
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PRIMARY
DRUG BANK
DB13374
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PRIMARY
PUBCHEM
15376
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PRIMARY
EVMPD
SUB00054MIG
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PRIMARY
SMS_ID
100000091936
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PRIMARY
CHEBI
9985
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PRIMARY
FDA UNII
996XVD0JHT
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PRIMARY
MERCK INDEX
m11450
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PRIMARY Merck Index
DRUG CENTRAL
3643
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PRIMARY
INN
2714
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PRIMARY
NCI_THESAURUS
C87697
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PRIMARY
ChEMBL
CHEMBL1165342
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PRIMARY
CAS
1617-90-9
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PRIMARY
HSDB
7150
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PRIMARY
EPA CompTox
DTXSID9040134
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PRIMARY
ECHA (EC/EINECS)
216-576-3
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PRIMARY
RXCUI
11201
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PRIMARY RxNorm
MESH
D014749
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PRIMARY
Related Record Type Details
Structure of VINCAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of VINCAMINE TARTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of VINCAMINE
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