VINBURNINE

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 Search

SMILES

CC[C@@]12CCCN3CCC4=C([C@H]13)N(C5=C4C=CC=C5)C(=O)C2

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2263666https://www.ncbi.nlm.nih.gov/pubmed/2263666 | https://www.exercise.com/supplements/vinburnine | http://www.drugfuture.com/chemdata/eburnamonine.html | https://www.ncbi.nlm.nih.gov/pubmed/14306194 | https://ir.nctu.edu.tw/bitstream/11536/25464/1/000233154200020.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2287808

Vinburnine is a nutritional product, 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. (+/-)-Eburnamonine is the racemate of the alkaloid Vinburnine. Dextrorotatory, levorotatory, and racemic forms of eburnamonine exist in nature. The (-)-form, also known as vincamone (isolated from Vinca minor), is a drug that possesses a stimulating activity for muscle and is used as cerebrotonic, whereas both enantiomers have hypotensive effects.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M2 121 Target ID: P08172 Gene ID: 1129.0 Gene Symbol: CHRM2 Target Organism: Homo sapiens (Human) Sources: http://drugcentral.org/drugcard/2824	Modulator 846	68.9 µM [Kd]
Muscarinic acetylcholine receptor M1 168 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Modulator 846	7.54 µM [Kd]
Muscarinic acetylcholine receptor M3 160 Target ID: P20309 Gene ID: 1131.0 Gene Symbol: CHRM3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Modulator 846	6.67 µM [Kd]
Muscarinic acetylcholine receptor M4 87 Target ID: P08173 Gene ID: 1132.0 Gene Symbol: CHRM4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Positive Allosteric Modulator 186	23.7 µM [Kd]
acetylcholine neurotransmission 2 Target ID: acetylcholine neurotransmission Sources: https://www.ncbi.nlm.nih.gov/pubmed/2263666	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cerebrovascular diseases 9 Sources: http://en.pharmacodia.com/web/drug/1_11912.html http://www.mims.com/india/drug/info/vinburnine?mtype=generic	Primary		Approved 8583	CERVOXAN Approved Use Cerebrovascular diseases
Unknown 2596

PubMed

Title	Date	PubMed
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997-07	9224827
Metabolism of vincamine in the rat in vivo and in vitro.	1980	7192994
GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.	1965-04-05	14306194

Patents

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

Unknown

Name

Type

Language

VINBURNINE

Official Name

English

EBURNAMONINE (-)-FORM

Preferred Name

English

3.ALPHA.,16.ALPHA.-EBURNAMONINE

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