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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H22N2O.3H2O.H2O4S
Molecular Weight 740.906
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE SULFATE TRIHYDRATE

SMILES

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.[H][C@]5(C[C@@H]6CC[N@]5C[C@@H]6C=C)[C@H](O)C7=C8C=CC=CC8=NC=C7

InChI

InChIKey=OURNGHKIKULCHM-DMMCLRCZSA-N
InChI=1S/2C19H22N2O.H2O4S.3H2O/c2*1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17;1-5(2,3)4;;;/h2*2-7,9,13-14,18-19,22H,1,8,10-12H2;(H2,1,2,3,4);3*1H2/t2*13-,14-,18-,19+;;;;/m00..../s1

HIDE SMILES / InChI

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

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

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
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
Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids.
2002 Mar 15
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].
2002 Sep
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.
2003
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
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
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
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
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
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
Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.
2005 Feb 10
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
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
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
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.
2007
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.
2007 Aug 29
Cinchonidinium chloride monohydrate.
2007 Dec 6
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.
2007 Feb 21
Surface processes occurring on Rh/alumina during chiral modification by cinchonidine: an ATR-IR spectroscopy study.
2007 Jul 17
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
Phase-transfer-catalyzed asymmetric acylimidazole alkylation.
2007 Nov 8
Hydrogen-bonding interactions in cinchonidine-2-methyl-2-hexenoic acid complexes: a combined spectroscopic and theoretical study.
2008 Jul 10
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
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
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
Preparative resolution of etodolac enantiomers by preferential crystallization method.
2009 Oct
Shape-selective enantioselective hydrogenation on Pt nanoparticles.
2009 Sep 2
Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization.
2010 Mar 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 15:01:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:15 GMT 2023
Record UNII
31029T62CS
Record Status Validated (UNII)
Record Version
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Name Type Language
CINCHONIDINE SULFATE TRIHYDRATE
MI  
Common Name English
CINCHONAN-9-OL, (8.ALPHA.,9R)-, SULFATE (2:1) (SALT), TRIHYDRATE
Common Name English
CINCHONIDINE SULFATE TRIHYDRATE [MI]
Common Name English
CINCHONIDINE SULPHATE TRIHYDRATE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10974884
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
FDA UNII
31029T62CS
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
CAS
5948-98-1
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
PUBCHEM
76965645
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY
MERCK INDEX
m3559
Created by admin on Fri Dec 15 15:01:15 GMT 2023 , Edited by admin on Fri Dec 15 15:01:15 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE