CINCHONIDINE

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

Structure Search

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

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
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.	2001 Nov 7	11686738
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.	2002 Aug 14	12167010
Highly selective hydroformylation of the cinchona alkaloids.	2002 Jul 12	12098330
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
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.	2003	15508779
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
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.	2003 Nov 5	14583014
Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling.	2003 Oct 31	14575453
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.	2004 Apr 16	15074944
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.	2004 May 5	15093176
Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion.	2004 Nov 26	15549835
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
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.	2005 Feb	15614815
Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.	2005 Jun	16192108
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.	2005 Jun 15	15941281
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
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.	2006 Dec 27	17177346
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.	2006 Feb	16385616
Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids.	2006 Jun 23	16776530
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.	2006 Mar 21	16633613
The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.	2006 Mar 29	16551114
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.	2006 Nov 2	17064139
Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation.	2006 Oct 27	17064051
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.	2007	17763490
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.	2007 Aug 29	17676845
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.	2007 Dec 26	18044897
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.	2007 Feb 21	17287883
Diastereo- and enantioselective synthesis of alpha,beta-epoxyketones using aqueous NaOCl in conjunction with dihydrocinchonidine derived phase-transfer catalysis at room temperature. Scope and limitations.	2007 Jul 21	17609760
Acceptability and efficacy of intra-rectal quinine alkaloids as a pre-transfer treatment of non-per os malaria in peripheral health care facilities in Mopti, Mali.	2007 May 22	17519031
Pilot feasibility study of an emergency paediatric kit for intra-rectal quinine administration used by the personnel of community-based health care units in Senegal.	2007 Nov 15	18005442
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.	2007 Nov 8	17944480
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.	2008	18288245
Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.	2008 Aug 1	18572922
Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.	2008 Aug 7	18636698
Highly enantioselective synthesis of isoxazoline N-oxides.	2008 Feb 14	18478708
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.	2008 Jan	17966123
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.	2008 Mar	19325758
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.	2008 Oct 1	18774816
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.	2008 Sep 5	18683975
Experimental and theoretical analysis of asymmetric induction in heterogeneous catalysis: diastereoselective hydrogenation of chiral alpha-hydroxyketones over Pt catalyst.	2009 Apr 1	19260682
Separation of Cinchona alkaloids on a novel strong cation-exchange-type chiral stationary phase-comparison with commercially available strong cation exchanger and reversed-phase packing materials.	2009 Feb	19107468
Preparative resolution of etodolac enantiomers by preferential crystallization method.	2009 Oct	19898806
Synthesis and biological activity of the calcium modulator (R) and (S)-3-methyl 5-pentyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.	2010 Feb 1	20064722
Chiral recognition in cinchona alkaloid protonated dimers: mass spectrometry and UV photodissociation studies.	2010 Mar 11	20058939

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

Name

Type

Language

CINCHONIDINE

Common Name

English

CINCHONIDINE [MI]

Common Name

English

QUININE BISULFATE IMPURITY B [WHO-IP]

Common Name

English

Cinchonidine [WHO-DD]

Common Name

English

QUININE SULFATE IMPURITY B [EP IMPURITY]

Common Name

English

QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]

Common Name

English

.ALPHA.-QUINIDINE

Common Name

English

QUININE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

CINCHOVATINE-

Common Name

English

CINCHONIDINE [WHO-IP]

Common Name

English

NSC-5364

Code

English

QUININE SULFATE IMPURITY B [WHO-IP]

Common Name

English

(R)-((2S,4S,5R)-5-ETHENYL-1-AZABICYCLO(2.2.2)OCT-2-YL)(QUINOLIN-4-YL)METHANOL [WHO-IP]

Systematic Name

English

Code System Code Type Description

NSC

5364