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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O.C7H6O3
Molecular Weight 432.5115
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE SALICYLATE

SMILES

OC(=O)C1=C(O)C=CC=C1.[H][C@]2(C[C@@H]3CC[N@]2C[C@@H]3C=C)[C@H](O)C4=C5C=CC=CC5=NC=C4

InChI

InChIKey=LGWVGYMSUILBFM-YYXOUSRLSA-N
InChI=1S/C19H22N2O.C7H6O3/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;8-6-4-2-1-3-5(6)7(9)10/h2-7,9,13-14,18-19,22H,1,8,10-12H2;1-4,8H,(H,9,10)/t13-,14-,18-,19+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C7H6O3
Molecular Weight 138.1207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
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
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.
2003
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.
2003 Feb
The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach.
2003 Feb 17
Preparation of enantiopure 1-azabicyclo[3.2.2]nonanes functionalized at carbon C3, from cinchonine and cinchonidine. stereoselective solvolysis and an easily enolizable ketone.
2003 Jun 13
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.
2003 Mar 5
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.
2003 Nov 5
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
Phase-transfer-catalyzed asymmetric glycolate alkylation.
2004 Jun 24
On the existence of ordered organic adlayers at the Cu(111)/electrolyte interface.
2004 Mar 30
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
Cobalt complexes with cinchonidine and quinidine: effect of C8/C9 stereochemistry and 6'-substitution on intermolecular interactions.
2005 Feb
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
Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum.
2005 Jun 15
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
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.
2006 Mar 21
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
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
Conformational behavior of cinchonidine revisited: a combined theoretical and experimental study.
2008 Aug 7
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.
2009 Aug 27
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
Construction of expression system of rabbit aldehyde oxidase cDNA for the clarification of species differences.
2009 Jul-Sep
Platinum nanoparticles: the crucial role of crystal face and colloid stabilizer in the diastereoselective hydrogenation of cinchonidine.
2010 Feb 15
Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization.
2010 Mar 15
Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency.
2010 Mar 21
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 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 15:01:19 UTC 2023
Edited
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on Fri Dec 15 15:01:19 UTC 2023
Record UNII
Q1Y52JQ86J
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Record Version
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Name Type Language
CINCHONIDINE SALICYLATE
Common Name English
CINCHONIDINE, MONOSALICYLATE (SALT)
Common Name English
CINCHONAN-9-OL, (8.ALPHA.,9R)-, MONO(2-HYDROXYBENZOATE) (SALT)
Common Name English
BENZOIC ACID, 2-HYDROXY-, COMPD. WITH (8.ALPHA.,9R)-CINCHONAN-9-OL (1:1)
Common Name English
Code System Code Type Description
PUBCHEM
23617083
Created by admin on Fri Dec 15 15:01:19 UTC 2023 , Edited by admin on Fri Dec 15 15:01:19 UTC 2023
PRIMARY
FDA UNII
Q1Y52JQ86J
Created by admin on Fri Dec 15 15:01:19 UTC 2023 , Edited by admin on Fri Dec 15 15:01:19 UTC 2023
PRIMARY
CAS
574-11-8
Created by admin on Fri Dec 15 15:01:19 UTC 2023 , Edited by admin on Fri Dec 15 15:01:19 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY
ACTIVE MOIETY