Vincamine

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

Identification

Name
Vincamine
Accession Number
DB13374
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
996XVD0JHT
CAS number
1617-90-9
Weight
Average: 354.45
Monoisotopic: 354.194342705
Chemical Formula
C21H26N2O3
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Vincamine.
AcebutololAcebutolol may increase the hypotensive activities of Vincamine.
AcemetacinThe therapeutic efficacy of Vincamine can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Vincamine can be decreased when used in combination with Acetylsalicylic acid.
AlfuzosinAlfuzosin may increase the hypotensive activities of Vincamine.
AliskirenAliskiren may increase the hypotensive activities of Vincamine.
AlprenololAlprenolol may increase the hypotensive activities of Vincamine.
AmbrisentanVincamine may increase the hypotensive activities of Ambrisentan.
AmifostineVincamine may increase the hypotensive activities of Amifostine.
AmlodipineAmlodipine may increase the hypotensive activities of Vincamine.
Food Interactions
Not Available

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. [PubMed:6436861]
External Links
KEGG Compound
C09251
PubChem Compound
15376
PubChem Substance
347829295
ChemSpider
14635
ChEBI
9985
ChEMBL
CHEMBL1165342
Wikipedia
Vincamine
ATC Codes
C04AX07 — Vincamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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
Eburna alkaloid / Indolo[3,2-1de][1,5]naphthyridine / Beta-carboline / Pyridoindole / Diazanaphthalene / Alpha-amino acid or derivatives / Naphthyridine / 3-alkylindole / Indole / Indole or derivatives
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)

Drug created on June 23, 2017 14:40 / Updated on October 01, 2018 15:30