U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O.2ClH
Molecular Weight 367.313
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE DIHYDROCHLORIDE

SMILES

Cl.Cl.[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=C4C=CC=CC4=NC=C3

InChI

InChIKey=ZDBQDNUZNQOCTH-WESSAKMQSA-N
InChI=1S/C19H22N2O.2ClH/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;2*1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
Highly selective hydroformylation of the cinchona alkaloids.
2002 Jul 12
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.
2003 Jan
Direct STM investigation of cinchona alkaloid adsorption on Cu(III).
2004 Apr 13
Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers.
2004 May 5
Signaling molecularly imprinted polymers: molecular recognition-based sensing materials.
2005
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.
2005 Feb
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
Michael reactions carried out using a bench-top flow system.
2006 Feb 7
Effect of ultrasound in enantioselective hydrogenation of 1-phenyl-1,2-propanedione: comparison of catalyst activation, solvents and supports.
2006 Jan
Liquid chromatographic analysis of cinchona alkaloids in beverages.
2006 Jul-Aug
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
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.
2007 Feb 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
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.
2009 Aug 27
Preparative resolution of etodolac enantiomers by preferential crystallization method.
2009 Oct
Shape-selective enantioselective hydrogenation on Pt nanoparticles.
2009 Sep 2
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
Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.
2010 Jan 20
Chiral recognition in cinchona alkaloid protonated dimers: mass spectrometry and UV photodissociation studies.
2010 Mar 11
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 Sat Dec 16 06:43:31 GMT 2023
Edited
by admin
on Sat Dec 16 06:43:31 GMT 2023
Record UNII
QNY56C6XYZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHONIDINE DIHYDROCHLORIDE
MI   WHO-DD  
Common Name English
CINCHONIDINE DIHYDROCHLORIDE [MI]
Common Name English
Cinchonidine dihydrochloride [WHO-DD]
Common Name English
CINCHONAN-9-OL, DIHYDROCHLORIDE, (8.ALPHA.,9R)-
Common Name English
Code System Code Type Description
CAS
524-54-9
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
EVMPD
SUB125748
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID70200414
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
PUBCHEM
45073521
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
SMS_ID
100000146237
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
FDA UNII
QNY56C6XYZ
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY
MERCK INDEX
m3559
Created by admin on Sat Dec 16 06:43:31 GMT 2023 , Edited by admin on Sat Dec 16 06:43:31 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY