CINCHONIDINE DIHYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22N2O.2ClH
Molecular Weight	367.313
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CINCHONIDINE DIHYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=ZDBQDNUZNQOCTH-WESSAKMQSA-N

InChI=1S/C19H22N2O.2ClH/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;2*1H/t13-,14-,18-,19+;;/m0../s1

HIDE SMILES / InChI

Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Charge	0
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.medicatione.com/?c=drug&s=quinimax
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500012185.pdf https://www.ncbi.nlm.nih.gov/pubmed/9776305

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 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15508779	Inhibitor 8297	225.0 nM [EC50]
Trypanosoma brucei brucei 12 Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880	Inhibitor 8297
Leishmania mexicana mexicana 8 Target ID: CHEMBL613214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95 Sources: http://www.ndrugs.com/?s=quinimax	Primary		Approved 8429	Quinimax Approved Use Indications: malaria

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.	2001 Apr	11345710
Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid.	2001 Aug 15	11534709
A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species.	2001 Dec	11745025
An in situ attenuated total reflection infrared study of a chiral catalytic solid-liquid interface: cinchonidine adsorption on pt.	2001 Dec 5	11724616
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.	2001 Nov 7	11686738
Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids.	2002 Mar 15	11921227
New crystalline complex of quinine and quinidine.	2002 Nov-Dec	12643316
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].	2002 Sep	16358696
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.	2003 Feb	12697166
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.	2003 Jan	12520132
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.	2003 Nov 5	14583014
Polymer-supported Cinchona alkaloid-derived ammonium salts as recoverable phase-transfer catalysts for the asymmetric synthesis of alpha-amino acids.	2004 Apr 30	18007436
On the existence of ordered organic adlayers at the Cu(111)/electrolyte interface.	2004 Mar 30	15835156
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.	2004 May 5	15093176
Study of fragmentation pattern and adsorption of 9-O-(triphenylsilyl)-10,11-dihydrocinchonidine on platinum by hydrogen/deuterium exchange using electrospray ionization ion-trap tandem mass spectrometry.	2005	16308850
Signaling molecularly imprinted polymers: molecular recognition-based sensing materials.	2005	16211586
Role of the solvent in the adsorption-desorption equilibrium of cinchona alkaloids between solution and a platinum surface: correlations among solvent polarity, cinchona solubility, and catalytic performance.	2005 Jan 13	16851030
Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase.	2006 Apr	16400710
Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study.	2006 Aug 31	16928003
Effect of protonation on the conformation of cinchonidine.	2006 Dec 13	17147361
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.	2006 Feb	16385616
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.	2006 Mar 21	16633613
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.	2007	17763490
Cinchonidinium chloride monohydrate.	2007 Dec 6	21200758
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.	2007 Feb 21	17287883
Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.	2007 Jul 17	17583922
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.	2007 Nov 8	17944480
Hydrogen-bonding interactions in cinchonidine-2-methyl-2-hexenoic acid complexes: a combined spectroscopic and theoretical study.	2008 Jul 10	18557603
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.	2008 Mar	19325758
An improved synthesis of 10,11-didehydro Cinchona alkaloids.	2008 Mar	17853397
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.	2008 Oct 1	18774816
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.	2009 Aug 27	19845397
Preparative resolution of etodolac enantiomers by preferential crystallization method.	2009 Oct	19898806

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:43:31 GMT 2023` Edited by `admin` on `Sat Dec 16 06:43:31 GMT 2023`
Record UNII	QNY56C6XYZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CINCHONIDINE DIHYDROCHLORIDE

Common Name

English

CINCHONIDINE DIHYDROCHLORIDE [MI]

Common Name

English

Cinchonidine dihydrochloride [WHO-DD]

Common Name

English

CINCHONAN-9-OL, DIHYDROCHLORIDE, (8.ALPHA.,9R)-

Common Name

English

Code System Code Type Description

CAS

524-54-9