VINCAMINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26N2O3.ClH
Molecular Weight	390.904
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N4C5=CC=CC=C5C(CC3)=C24)C(=O)OC

InChI

InChIKey=YGKAKNJJNTVSKB-YAFGAGFVSA-N

InChI=1S/C21H26N2O3.ClH/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;1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 537		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 1430

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 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

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
[Nimodipine, nifedipine and vincamine improve amnesia induced by anisodine and sodium nitrite in rats and mice].	1986 Oct	2952309
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997 Jul	9224827
Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compounds.	2001	11746802
[Open-angle glaucoma clinical presentation and management].	2001 Dec	11802456
[Investigation of vasoactive agents with indole skeletons at Richter Ltd].	2002	12426785
Interventions for normal tension glaucoma.	2003	14583947
Vinpocetine is a potent blocker of rat NaV1.8 tetrodotoxin-resistant sodium channels.	2003 Aug	12730276
Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography.	2003 May 9	12830921
[Neuroprotection strategies: effect of vinpocetine in vitro oxidative stress models].	2003 Nov-Dec	15631851
Enhanced tail pinch-induced activation of catecholamine metabolism in the pericerulean area of RU 24722-treated rats.	2004 Dec 24	15567332
Processing methods for differential analysis of LC/MS profile data.	2005 Jul 18	16026613
Catalytic N-sulfonyliminium ion-mediated cyclizations to alpha-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis.	2005 Jul 8	15989333
Stability-indicating methods for determination of vincamine in presence of its degradation product.	2005 Jun 1	15907622
Eburnamine derivatives and the brain.	2005 Nov	16158388
Measurement and pharmacokinetics of vincamine in rat blood and brain using microdialysis.	2005 Sep 23	16130744
Catharanthus roseus flower extract has wound-healing activity in Sprague Dawley rats.	2006 Dec 21	17184528
Development and application of an automated solution stability assay for drug discovery.	2006 Feb	16234336
Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine.	2006 May 12	16674048
Effect of vinpocetine on retrograde axoplasmic transport.	2007	17319607
Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade.	2007 Aug 16	17658832
Impaired cognition and attention in adults: pharmacological management strategies.	2007 Feb	19300541
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	17729230
Allosteric modulation of muscarinic acetylcholine receptors.	2007 Sep	19305798
In vitro anticholinesterase activity of various alkaloids.	2007 Sep-Oct	18069241
Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport.	2008	18413267
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 Dec	19043234
Effects of Vinpocetine on mitochondrial function and neuroprotection in primary cortical neurons.	2008 Dec	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 Jun	18830442
Simultaneous determination of piracetam and vincamine by spectrophotometric and high-performance liquid chromatographic methods.	2008 Mar-Apr	18476342
Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation.	2008 Mar-Apr	18476341
Adenylate kinase and AMP signaling networks: metabolic monitoring, signal communication and body energy sensing.	2009 Apr 17	19468337
Seco-tabersonine alkaloids from Tabernaemontana corymbosa.	2009 Feb	19217125
Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model.	2009 Summer	19492990
Exercise as an intervention for the age-related decline in neural metabolic support.	2010	20802804
Aggressive behavior during social interaction in mice is controlled by the modulation of tyrosine hydroxylase expression in the prefrontal cortex.	2010 Dec 15	20923695
Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy.	2010 Dec 15	20724093
WITHDRAWN: Interventions for normal tension glaucoma.	2010 Feb 17	20166063
Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora.	2010 Jun 15	20576577
Antinociceptive effect of vinpocetine--a comprehensive survey.	2010 May 30	20648783
Brain trace element concentration of rats treated with the plant alkaloid, vincamine.	2010 Sep	19902161

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 `Fri Dec 15 18:47:57 GMT 2023` Edited by `admin` on `Fri Dec 15 18:47:57 GMT 2023`
Record UNII	X9XM85R7QQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VINCAMINE HYDROCHLORIDE

Common Name

English

Vincamine hydrochloride [WHO-DD]

Common Name

English

ESBERIDIN

Brand Name

English

VINCAMINE HYDROCHLORIDE [MI]

Common Name

English

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

Common Name

English

Code System Code Type Description

SMS_ID

100000087882