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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 of CINCHONIDINE

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

Description
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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Quinimax

Approved Use

Indications: malaria
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid.
2001 Aug 15
A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species.
2001 Dec
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.
2001 Nov 7
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
Adsorption mode of cinchonidine on Cu(111) surface.
2002 Dec 4
Highly selective hydroformylation of the cinchona alkaloids.
2002 Jul 12
Optical resolution by preferential crystallization of (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid and its use in synthesizing optically active 2-amino-2-methyl-3-phenylpropanoic acid.
2002 Oct
Observation of high enantioselectivity for the gas phase hydrogenation of methyl pyruvate using supported Pt catalysts pre-modified with cinchonidine.
2003 Aug 7
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.
2003 Jan
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.
2003 Jan
Determination of enantiomeric excess using the ultraviolet-circular dichroism and the high-performance liquid chromatography-circular dichroism methods.
2003 Jul
Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling.
2003 Oct 31
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Efficient synthesis of 4-(3'-furanyl)butenolide derivatives via PdII-catalyzed oxidative heterodimeric cyclization reaction of 2,3-allenoic acids and 1,2-allenyl ketones.
2004 Apr 19
Polymer-supported Cinchona alkaloid-derived ammonium salts as recoverable phase-transfer catalysts for the asymmetric synthesis of alpha-amino acids.
2004 Apr 30
On the existence of ordered organic adlayers at the Cu(111)/electrolyte interface.
2004 Mar 30
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.
2004 May 5
Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers.
2004 May 5
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
Signaling molecularly imprinted polymers: molecular recognition-based sensing materials.
2005
Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids.
2005 Aug 17
Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.
2005 Feb 10
Effect of protonation on the conformation of cinchonidine.
2006 Dec 13
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
2006 Feb
Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.
2006 Jan 26
Liquid chromatographic analysis of cinchona alkaloids in beverages.
2006 Jul-Aug
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.
2007 Aug 29
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.
2007 Dec 26
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
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.
2008
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
2008 Aug
Highly enantioselective synthesis of isoxazoline N-oxides.
2008 Feb 14
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.
2008 Sep 5
Resolution of (+)-cinchonine and (-)-cinchonidine by phase-modulation fluorescence spectroscopy.
2009 Apr 20
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.
2009 Aug 27
Construction of expression system of rabbit aldehyde oxidase cDNA for the clarification of species differences.
2009 Jul-Sep
Shape-selective enantioselective hydrogenation on Pt nanoparticles.
2009 Sep 2
Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine.
2010 Feb 15
Chiral recognition in cinchona alkaloid protonated dimers: mass spectrometry and UV photodissociation studies.
2010 Mar 11
Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization.
2010 Mar 15
Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum.
2012 May 15
Patents

Sample Use Guides

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
Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:14:42 UTC 2023
Edited
by admin
on Fri Dec 15 16:14:42 UTC 2023
Record UNII
1U622LRA8Z
Record Status Validated (UNII)
Record Version
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Name Type Language
CINCHONIDINE
MI   WHO-DD   WHO-IP  
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
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID60883396
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
WIKIPEDIA
CINCHONIDINE
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
CAS
485-71-2
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
SMS_ID
100000080090
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
MERCK INDEX
m3559
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-622-3
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
MESH
C041622
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
FDA UNII
1U622LRA8Z
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
PUBCHEM
101744
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
CHEBI
3703
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
NCI_THESAURUS
C75264
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
EVMPD
SUB13374MIG
Created by admin on Fri Dec 15 16:14:42 UTC 2023 , Edited by admin on Fri Dec 15 16:14:42 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> IMPURITY
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
Not Specified
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
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ACTIVE MOIETY