Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H26N2O3.C5H6O5 |
| Molecular Weight | 500.5409 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(=O)C(O)=O.[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N4C5=CC=CC=C5C(CC3)=C24)C(=O)OC
InChI
InChIKey=ZZIDXUJHLCRNJB-YAFGAGFVSA-N
InChI=1S/C21H26N2O3.C5H6O5/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;6-3(5(9)10)1-2-4(7)8/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3;1-2H2,(H,7,8)(H,9,10)/t18-,20+,21+;/m1./s1
| Molecular Formula | C5H6O5 |
| Molecular Weight | 146.0981 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095171 |
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 |
|
| Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compounds. | 2001 |
|
| [Open-angle glaucoma clinical presentation and management]. | 2001 Dec |
|
| Interventions for normal tension glaucoma. | 2003 |
|
| [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 |
|
| Catalytic N-sulfonyliminium ion-mediated cyclizations to alpha-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis. | 2005 Jul 8 |
|
| Stability-indicating methods for determination of vincamine in presence of its degradation product. | 2005 Jun 1 |
|
| Eburnamine derivatives and the brain. | 2005 Nov |
|
| Measurement and pharmacokinetics of vincamine in rat blood and brain using microdialysis. | 2005 Sep 23 |
|
| Development and application of an automated solution stability assay for drug discovery. | 2006 Feb |
|
| Syntheses of vinca alkaloids and related compounds. 104. A concise synthesis of (-)-vincapusine. | 2006 May 12 |
|
| Effect of vinpocetine on retrograde axoplasmic transport. | 2007 |
|
| Synthesis of (+/-)-3H-epivincamine via a Rh(II)-triggered cyclization/cycloaddition cascade. | 2007 Aug 16 |
|
| Impaired cognition and attention in adults: pharmacological management strategies. | 2007 Feb |
|
| 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 |
|
| Allosteric modulation of muscarinic acetylcholine receptors. | 2007 Sep |
|
| In vitro anticholinesterase activity of various alkaloids. | 2007 Sep-Oct |
|
| Mitigation of nociception via transganglionic degenerative atrophy: possible mechanism of vinpocetine-induced blockade of retrograde axoplasmic transport. | 2008 |
|
| 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 |
|
| 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 |
|
| Smart stability-indicating spectrophotometric methods for determination of binary mixtures without prior separation. | 2008 Mar-Apr |
|
| Adenylate kinase and AMP signaling networks: metabolic monitoring, signal communication and body energy sensing. | 2009 Apr 17 |
|
| Seco-tabersonine alkaloids from Tabernaemontana corymbosa. | 2009 Feb |
|
| Neuroprotective effects of vinpocetine and its major metabolite cis-apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesion model. | 2009 Summer |
|
| Exercise as an intervention for the age-related decline in neural metabolic support. | 2010 |
|
| Aggressive behavior during social interaction in mice is controlled by the modulation of tyrosine hydroxylase expression in the prefrontal cortex. | 2010 Dec 15 |
|
| Separation of vinca alkaloid enantiomers by capillary electrophoresis applying cyclodextrin derivatives and characterization of cyclodextrin complexes by nuclear magnetic resonance spectroscopy. | 2010 Dec 15 |
|
| WITHDRAWN: Interventions for normal tension glaucoma. | 2010 Feb 17 |
|
| Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora. | 2010 Jun 15 |
|
| Antinociceptive effect of vinpocetine--a comprehensive survey. | 2010 May 30 |
|
| Brain trace element concentration of rats treated with the plant alkaloid, vincamine. | 2010 Sep |
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
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
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| Record UNII |
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