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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O
Molecular Weight 294.3908
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINBURNINE

SMILES

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

InChI

InChIKey=WYJAPUKIYAZSEM-MOPGFXCFSA-N
InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1

HIDE SMILES / InChI
Molecular Formula C19H22N2O
Molecular Weight 294.3908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2287808

Vinburnine is a nutritional product, which is semi-synthesized from vincamine. It is a peripheral vasodilator with cerebral activities that also act as a cerebral metabolic stimulant and appears to be able to relax the smooth muscle cells within the walls of blood vessels. Some evidence also suggests that vinburnine stimulates acetylcholine neurotransmission. Acetylcholine is a very important neurotransmitter responsible for a number of cognitive functions, such as memory and learning.

CNS Activity

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Muscarinic acetylcholine receptor M2
121
Target ID: P08172
Gene ID: 1129.0
Gene Symbol: CHRM2
Target Organism: Homo sapiens (Human)
Modulator
828
 68.9 µM [Kd]
Muscarinic acetylcholine receptor M1
169
Target ID: P11229
Gene ID: 1128.0
Gene Symbol: CHRM1
Target Organism: Homo sapiens (Human)
Modulator
828
 7.54 µM [Kd]
Muscarinic acetylcholine receptor M3
159
Target ID: P20309
Gene ID: 1131.0
Gene Symbol: CHRM3
Target Organism: Homo sapiens (Human)
Modulator
828
 6.67 µM [Kd]
Muscarinic acetylcholine receptor M4
86
Target ID: P08173
Gene ID: 1132.0
Gene Symbol: CHRM4
Target Organism: Homo sapiens (Human)
Positive Allosteric Modulator
179
 23.7 µM [Kd]
acetylcholine neurotransmission
2
Target ID: acetylcholine neurotransmission
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CERVOXAN

Approved Use

Cerebrovascular diseases
PubMed

PubMed

TitleDatePubMed
GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.
1965 Apr 5
Metabolism of vincamine in the rat in vivo and in vitro.
1980
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
1997 Jul
Patents

Patents

CA1252467A
2
JP2008017734A
4
US3888865
2

Sample Use Guides

In Vivo Use Guide
The recommended dosage is 60 mg taken twice a day.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Different concentrations of the drugs: vincamine, vinpocetine and eburnamonine (VINBURNINE) (4, 20 and 100 µM) induced minimal stimulation of the ATPase activity of the Bcrp and Pgp membrane transporters. The relative metabolic stability of eburnamonine compared to the other alkaloids suggests the use of eburnamonine or its derivatives as lead compounds for the development of antitumor and nootropic agents that need to cross the BBB and produce their pharmacological effects in the CNS.
Different concentrations of the three drugs, vincamine, vinpocetine, and eburnamonine, (4, 20 and 100 uM) induced minimal stimulation of the ATPase activity of the Bcrp and Pgp membrane transporters.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:43:03 GMT 2023
Edited
by admin
on Sat Dec 16 17:43:03 GMT 2023
Record UNII
G54D0HMY25
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VINBURNINE
INN   MART.   WHO-DD  
INN  
Official Name English
3.ALPHA.,16.ALPHA.-EBURNAMONINE
Common Name English
EBURNAMONINE (-)-FORM
MI  
Common Name English
EBURNAMONINE (-)-FORM [MI]
Common Name English
Vinburnine [WHO-DD]
Common Name English
VINBURNINE [MART.]
Common Name English
NSC-322920
Code English
vinburnine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C932
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
WHO-VATC QC04AX17
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
NCI_THESAURUS C29707
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
WHO-ATC C04AX17
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152880
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
NSC
322920
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
FDA UNII
G54D0HMY25
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
DRUG BANK
DB13793
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL1892145
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
RXCUI
57954
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY RxNorm
CAS
4880-88-0
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
MESH
C016422
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
INN
4976
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
EVMPD
SUB00053MIG
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
DRUG CENTRAL
2824
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
225-490-5
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
PUBCHEM
71203
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
MERCK INDEX
m4804
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY Merck Index
SMS_ID
100000079106
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID6045119
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
WIKIPEDIA
VINBURNINE
Created by admin on Sat Dec 16 17:43:03 GMT 2023 , Edited by admin on Sat Dec 16 17:43:03 GMT 2023
PRIMARY
Related Record Type Details
Structure of VINBURNINE
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