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Details

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

SHOW SMILES / InChI
Structure of CINCHONIDINE

SMILES

O[C@@H]([C@@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Quinimax
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].
2002 Sep
Conformational spaces of Cinchona alkaloids.
2003 Aug
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.
2003 Feb
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion.
2004 Nov 26
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
Effect of protonation on the conformation of cinchonidine.
2006 Dec 13
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.
2006 Dec 27
Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids.
2006 Jun 23
The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.
2006 Mar 29
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.
2007
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
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.
2008
Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.
2008 Aug 1
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.
2008 Sep 5
Preparative resolution of etodolac enantiomers by preferential crystallization method.
2009 Oct
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
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
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: intrarectally, IM
In Vitro Use Guide
Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml
Name Type Language
CINCHONIDINE
MI   WHO-DD   WHO-IP  
Common Name English
CINCHONIDINE [MI]
Common Name English
CINCHONIDINE [WHO-DD]
Common Name English
QUININE BISULFATE IMPURITY B [WHO-IP]
Common Name English
QUININE BISULFATE HEPTAHYDRATE IMPURITY B [WHO-IP]
Common Name English
.ALPHA.-QUINIDINE
Common Name English
QUININE SULFATE IMPURITY B [EP]
Common Name English
QUININE HYDROCHLORIDE IMPURITY B [EP]
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
WIKIPEDIA
CINCHONIDINE
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
CAS
485-71-2
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
MERCK INDEX
M3559
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
207-622-3
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
MESH
C041622
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
PUBCHEM
101744
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
NCI_THESAURUS
C75264
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY
EVMPD
SUB13374MIG
Created by admin on Mon Oct 21 22:34:54 UTC 2019 , Edited by admin on Mon Oct 21 22:34:54 UTC 2019
PRIMARY