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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O.5H2O.H2O4S
Molecular Weight 482.546
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE SULFATE PENTAHYDRATE

SMILES

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

InChI

InChIKey=GJDGKSUZTWTYIX-RQGZUYDISA-N
InChI=1S/C19H22N2O.H2O4S.5H2O/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;1-5(2,3)4;;;;;/h2-7,9,13-14,18-19,22H,1,8,10-12H2;(H2,1,2,3,4);5*1H2/t13-,14-,18-,19+;;;;;;/m0....../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
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
Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts.
2001 Nov 7
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
2002 Aug 14
Adsorption mode of cinchonidine on Cu(111) surface.
2002 Dec 4
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
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
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
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.
2003 Jan
Determination of enantiomeric excess using the ultraviolet-circular dichroism and the high-performance liquid chromatography-circular dichroism methods.
2003 Jul
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
Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy.
2003 Nov 5
Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling.
2003 Oct 31
Direct STM investigation of cinchona alkaloid adsorption on Cu(III).
2004 Apr 13
Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine.
2004 Apr 16
Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique.
2004 May 5
Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion.
2004 Nov 26
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
Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers.
2005 Feb
Cobalt complexes with cinchonidine and quinidine: effect of C8/C9 stereochemistry and 6'-substitution on intermolecular interactions.
2005 Feb
Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.
2005 Feb 10
Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase.
2005 Jun
Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase.
2006 Apr
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
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
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
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.
2007 Dec 26
Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.
2007 Jul 17
Acceptability and efficacy of intra-rectal quinine alkaloids as a pre-transfer treatment of non-per os malaria in peripheral health care facilities in Mopti, Mali.
2007 May 22
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
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.
2007 Nov 8
Phthalocyanine-based molecularly imprinted polymers as nucleoside receptors.
2008
Highly enantioselective synthesis of isoxazoline N-oxides.
2008 Feb 14
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.
2008 Mar
An improved synthesis of 10,11-didehydro Cinchona alkaloids.
2008 Mar
A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers.
2008 Sep 5
Experimental and theoretical analysis of asymmetric induction in heterogeneous catalysis: diastereoselective hydrogenation of chiral alpha-hydroxyketones over Pt catalyst.
2009 Apr 1
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
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
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 Wed Jul 05 22:33:15 UTC 2023
Edited
by admin
on Wed Jul 05 22:33:15 UTC 2023
Record UNII
P424MD870D
Record Status Validated (UNII)
Record Version
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Name Type Language
CINCHONIDINE SULFATE PENTAHYDRATE
Common Name English
CINCHONIDINE, SULFATE (1:1), PENTAHYDRATE
Common Name English
CINCHONAN-9-OL, (8.ALPHA.,9R)-, SULFATE (1:1) (SALT), PENTAHYDRATE
Systematic Name English
Code System Code Type Description
SMS_ID
300000018271
Created by admin on Wed Jul 05 22:33:15 UTC 2023 , Edited by admin on Wed Jul 05 22:33:15 UTC 2023
PRIMARY
PUBCHEM
71586828
Created by admin on Wed Jul 05 22:33:15 UTC 2023 , Edited by admin on Wed Jul 05 22:33:15 UTC 2023
PRIMARY
FDA UNII
P424MD870D
Created by admin on Wed Jul 05 22:33:15 UTC 2023 , Edited by admin on Wed Jul 05 22:33:15 UTC 2023
PRIMARY
CAS
5907-43-7
Created by admin on Wed Jul 05 22:33:15 UTC 2023 , Edited by admin on Wed Jul 05 22:33:15 UTC 2023
PRIMARY
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ANHYDROUS->SOLVATE
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ACTIVE MOIETY