CINCHONIDINE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Optical Activity	( - )
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=C4C=CC=CC4=NC=C3

InChI

InChIKey=KMPWYEUPVWOPIM-KODHJQJWSA-N

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Cinchonidine is an alkaloid found in Cinchona officinalis and Gongronema latifolium. Cinchonidine is an antimalarial drug which has been used clinically in malaria caused by Plasmodium falciparum. Cinchonidine is reported as an ingredient of Quinimax in a number of countries. Quinimax is a combination of four alkaloids (quinine, quinidine, cinchoine and cinchonidine).

Approval Year

Targets

Primary Target	Pharmacology	Potency
Plasmodium falciparum 74	Inhibitor 8,297	225.0 nM [EC50]
Trypanosoma brucei brucei 12	Inhibitor 8,297
Leishmania mexicana mexicana 8	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95	Primary		Approved 8,429	Quinimax

PubMed

Show entries

Title	Date	PubMed
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.	2001 Nov 7	11686738
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].	2002 Sep	16358696
Conformational spaces of Cinchona alkaloids.	2003 Aug	12840830
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.	2003 Feb	12697166
Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone.	2003 Jun 13	12790606

Showing 1 to 5 of 30 entries

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Patents

Sample Use Guides

In Vivo Use Guide

Fifty-five children were given 20 mg/kg of the diluted injectable form of Quinimax (a quinine, quinidine, cinchonine, cinchonidine association) intrarectally. A further 11 children with malaria were treated with 12.5 mg/kg of the same Quinimax solution by the intramuscular route. All the children were treated twice a day for 3 d.

Route of Administration: Other

In Vitro Use Guide

Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml