APOVINCAMINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O2
Molecular Weight	336.4275
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(=C2)C(=O)OC

InChI

InChIKey=OZDNDGXASTWERN-CTNGQTDRSA-N

InChI=1S/C21H24N2O2/c1-3-21-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(18(15)19(21)22)17(13-21)20(24)25-2/h4-5,7-8,13,19H,3,6,9-12H2,1-2H3/t19-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H24N2O2
Molecular Weight	336.4275
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20576577 | https://www.sciencedirect.com/science/article/pii/S0040403901916788

Apovincamine is a vinca alkaloid derivative, which is structurally related to vinpocetine. Apovincamine is produced when vincamine, an alkaloid constituent of Vinca species, is heated to 220°C. Apovincamine suppresses melanogenesis in B16 mouse melanoma cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacteria 7 Target ID: CHEMBL612490 Sources: http://kanaya.naist.jp/MetaboliteActivity/result.jsp?conditions=exact&sname0=cid&cid=C00001688	Inhibitor 8504
Melanogenesis 5 Target ID: map04916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20576577	Inhibitor 8504

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 06:51:55 GMT 2025` Edited by `admin` on `Wed Apr 02 06:51:55 GMT 2025`
Record UNII	504R182ZX7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APOVINCAMINE

Official Name

English

VINPOCETINE RELATED COMPOUND B

Preferred Name

English

VINPOCETINE IMPURITY B [EP IMPURITY]

Common Name

English

(+)-APOVINCAMINE

Common Name

English

CIS-APOVINCAMINE

Common Name

English

EBURNAMENINE-14-CARBOXYLIC ACID, METHYL ESTER, (3.ALPHA.,16.ALPHA.)-

Systematic Name

English

METHYL(3.ALPHA.,16.ALPHA.)-EBURNAMENINE-14-CARBOXYLATE

Common Name

English

VINPOCETINE RELATED COMPOUND B [USP IMPURITY]

Common Name

English

apovincamine [INN]

Common Name

English

VINPOCETINE RELATED COMPOUND B [USP-RS]

Common Name

English

(+)-CIS-APOVINCAMINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707