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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

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 225.0 nM [EC50]
Inhibitor
8228
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
Quinimax

Approved Use

Indications: malaria
PubMed

PubMed

TitleDatePubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
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
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
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
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
Conformational spaces of Cinchona alkaloids.
2003 Aug
Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling.
2003 Oct 31
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
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
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
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.
2005 Feb
Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.
2005 Jun
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.
2005 Jun 15
Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study.
2006 Aug 31
Effect of protonation on the conformation of cinchonidine.
2006 Dec 13
Enantioseparation of secondary alcohols by diastereoisomeric salt formation.
2006 Feb
Effect of ultrasound in enantioselective hydrogenation of 1-phenyl-1,2-propanedione: comparison of catalyst activation, solvents and supports.
2006 Jan
Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.
2006 Jan 26
Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids.
2006 Jun 23
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.
2006 Mar 21
The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum.
2006 Mar 29
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation.
2006 Oct 27
Cinchonidinium chloride monohydrate.
2007 Dec 6
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
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.
2007 Nov 8
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
2008 Aug
Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones.
2008 Aug 1
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.
2008 Jan
Hydrogen-bonding interactions in cinchonidine-2-methyl-2-hexenoic acid complexes: a combined spectroscopic and theoretical study.
2008 Jul 10
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
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
Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency.
2010 Mar 21
Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum.
2012 May 15
Patents

Patents

04001301
10
JPH01254661A
8
JPS62158268A
8
WO1993014426A1
8

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 Wed Jul 05 23:41:59 UTC 2023
Edited
by admin
on Wed Jul 05 23:41:59 UTC 2023
Record UNII
1U622LRA8Z
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID60883396
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
WIKIPEDIA
CINCHONIDINE
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
CAS
485-71-2
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
SMS_ID
100000080090
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
MERCK INDEX
M3559
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-622-3
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
MESH
C041622
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
FDA UNII
1U622LRA8Z
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
PUBCHEM
101744
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
CHEBI
3703
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
NCI_THESAURUS
C75264
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
EVMPD
SUB13374MIG
Created by admin on Wed Jul 05 23:42:00 UTC 2023 , Edited by admin on Wed Jul 05 23:42:00 UTC 2023
PRIMARY
Related Record Type Details
Structure of CINCHONIDINE SULFATE PENTAHYDRATE
SALT/SOLVATE -> PARENT
Structure of CINCHONIDINE SALICYLATE
SALT/SOLVATE -> PARENT
Structure of CINCHONIDINE SULFATE TRIHYDRATE
SALT/SOLVATE -> PARENT
Structure of CINCHONIDINE DIHYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of CINCHONIDINE SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of QUININE BISULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of QUININE SULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of QUININE BISULFATE HEPTAHYDRATE
PARENT -> IMPURITY
Not Specified
Structure of QUININE SULFATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of QUININE HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of QUINIDINE SULFATE
PARENT -> IMPURITY
Not Specified
Related Record Type Details
Structure of CINCHONIDINE
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