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
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
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 |
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.
Originator
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095171 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8957220 |
1.9 µM [IC50] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Oxybral Approved UseOxybral (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 |
|
[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 |
|
[Neuroprotection strategies: effect of vinpocetine in vitro oxidative stress models]. | 2003 Nov-Dec |
|
Enhanced tail pinch-induced activation of catecholamine metabolism in the pericerulean area of RU 24722-treated rats. | 2004 Dec 24 |
|
Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade. | 2007 Aug 16 |
|
Allosteric modulation of muscarinic acetylcholine receptors. | 2007 Sep |
|
Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport. | 2008 |
|
Effects of Vinpocetine on mitochondrial function and neuroprotection in primary cortical neurons. | 2008 Dec |
|
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 |
|
Simultaneous determination of piracetam and vincamine by spectrophotometric and high-performance liquid chromatographic methods. | 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 |
|
Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy. | 2010 Dec 15 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3386330
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
Edited
Fri Dec 15 15:12:02 UTC 2023
by
admin
on
Fri Dec 15 15:12:02 UTC 2023
|
Record UNII |
996XVD0JHT
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C47795
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
||
|
DSLD |
2937 (Number of products:1)
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
||
|
WHO-ATC |
C04AX07
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
||
|
WHO-VATC |
QC04AX07
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
91998
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
VINCAMINE
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
DB13374
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
15376
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
SUB00054MIG
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
100000091936
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
9985
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
996XVD0JHT
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
m11450
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | Merck Index | ||
|
3643
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
2714
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
C87697
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
CHEMBL1165342
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
1617-90-9
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
7150
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
DTXSID9040134
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
216-576-3
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | |||
|
11201
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY | RxNorm | ||
|
D014749
Created by
admin on Fri Dec 15 15:12:02 UTC 2023 , Edited by admin on Fri Dec 15 15:12:02 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |