NAV

Vincamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Vincamine
DrugBank Accession Number
DB13374
Background

Vincamine is a monoterpenoid indole alkaloid obtained from the leaves of Vinca minor with a vasodilatory property. Studies indicate that vincamine increases the regional cerebral blood flow.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 354.45
Monoisotopic: 354.194342705
Chemical Formula
C21H26N2O3
Synonyms
  • Vincamina
  • Vincamine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbaloparatideAbaloparatide may increase the hypotensive activities of Vincamine.
AcebutololAcebutolol may increase the hypotensive activities of Vincamine.
AceclofenacThe therapeutic efficacy of Vincamine can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Vincamine can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Vincamine.
Food Interactions
Not Available

Products

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Categories

ATC Codes
C04AX07 — Vincamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Eburnan-type alkaloids
Sub Class
Not Available
Direct Parent
Eburnan-type alkaloids
Alternative Parents
Indolonaphthyridine alkaloids / Beta carbolines / 3-alkylindoles / Alpha amino acids and derivatives / Naphthyridines / Aralkylamines / Piperidines / Benzenoids / Pyrroles / Methyl esters
show 9 more
Substituents
3-alkylindole / Alkanolamine / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, methyl ester, hemiaminal, alkaloid ester, vinca alkaloid (CHEBI:9985) / Indole alkaloids (C09251)
Affected organisms
Not Available

Chemical Identifiers

UNII
996XVD0JHT
CAS number
1617-90-9
InChI Key
RXPRRQLKFXBCSJ-GIVPXCGWSA-N
InChI
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
IUPAC Name
methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
SMILES
[H][C@]12N3CCC[C@@]1(CC)C[C@@](O)(N1C4=CC=CC=C4C(CC3)=C21)C(=O)OC

References

General References
  1. Hagstadius S, Gustafson L, Risberg J: The effects of bromvincamine and vincamine on regional cerebral blood flow and mental functions in patients with multi-infarct dementia. Psychopharmacology (Berl). 1984;83(4):321-6. [Article]
KEGG Compound
C09251
PubChem Compound
15376
PubChem Substance
347829295
ChemSpider
14635
RxNav
11201
ChEBI
9985
ChEMBL
CHEMBL1165342
ZINC
ZINC000001069082
Wikipedia
Vincamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Solution / drops
Tablet
Capsule
Tablet20 MG
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.216 mg/mLALOGPS
logP2.62ALOGPS
logP3.39Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.52Chemaxon
pKa (Strongest Basic)6.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.7 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity99.57 m3·mol-1Chemaxon
Polarizability39.39 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0092000000-7408330df526558920e8
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0009000000-8f742bc50bb6ffaadcf1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0009000000-e477ed23d437d91bcacc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4j-0019000000-856c214b29871969e3ec
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001c-0593000000-3e0598831094cc184110
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-40b09b0bad70d7dedfbf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-38790bcb9a5aab91b895
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0019000000-a4a9563945d69e5b1aeb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-0009000000-c98daa362817a0eb2f0f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0971000000-3917829e225ae665156d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f95-0090000000-fe3210eb7663bbd0004e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.1036023
predicted
DarkChem Lite v0.1.0
[M-H]-191.4597023
predicted
DarkChem Lite v0.1.0
[M-H]-192.9644
predicted
DeepCCS 1.0 (2019)
[M+H]+180.5192808
predicted
DarkChem Lite v0.1.0
[M+H]+192.5107023
predicted
DarkChem Lite v0.1.0
[M+H]+195.36018
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.0554709
predicted
DarkChem Lite v0.1.0
[M+Na]+191.6877023
predicted
DarkChem Lite v0.1.0
[M+Na]+201.27269
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:40 / Updated at February 21, 2021 18:54