CATHARANTHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H24N2O2
Molecular Weight	336.4275
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C[C@@H]2C[N@]3CCC4=C(NC5=CC=CC=C45)[C@@](C2)([C@@H]13)C(=O)OC

InChI

InChIKey=CMKFQVZJOWHHDV-NQZBTDCJSA-N

InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13-,19+,21-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23532933
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/13641069 | https://www.ncbi.nlm.nih.gov/pubmed/23532933

Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Transient receptor potential cation channel subfamily M member 8 18 Target ID: CHEMBL3108632 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25052206	Antagonist 2849	0.9 µM [IC50]
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25052206	Partial Agonist 297	9000.0 nM [EC50]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25052206	Partial Agonist 297	20.0 µM [EC50]
Voltage-gated L-type calcium channel 95 Target ID: CHEMBL2095177 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23532933	Inhibitor 8504	220.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
A note on the alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.). II. Catharanthine, lochnericine, vindolinine, and vindoline.	1959-04	13641069

Patents

Sample Use Guides

In Vivo Use Guide

Intravenous administration of catharanthine (0.5–20 mg/kg) to anesthetized rats induced rapid, dose-dependent decreases in blood pressure, heart rate, left ventricular blood pressure, cardiac contractility, and the slope of the end-systolic pressure-volume relationship curve.

Route of Administration: Intravenous

In Vitro Use Guide

Catharanthine evoked concentrationdependent decreases in endothelium-independent tonic responses of aortic rings to phenylephrine (PE) and KCl (IC50 = 5 28 uM for PE and IC50 =5 34 mM for KCl) and of thirdorder branches of the small mesenteric artery (IC50 = 3 mM for PE and IC50 = 6 mM for KCl)

Name

Type

Language

CATHARANTHINE

Common Name

English

(+)-3,4-DIDEHYDROCORONARIDINE

Preferred Name

English

IBOGAMINE-18-CARBOXYLIC ACID, 3,4-DIDEHYDRO-, METHYL ESTER,(2.ALPHA.,5.BETA.,6.ALPHA.,18.BETA.)-

Common Name

English

(+)-CATHARANTHINE

Common Name

English

CATHARANTHINE [MI]

Common Name

English

CATHARANTHIN

Common Name

English

CATHARANTHINE, (+)-

Common Name

English

Code System Code Type Description

CAS

2468-21-5