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

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H22N2O.H2O4S
Molecular Weight 686.86
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONIDINE SULFATE

SMILES

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=WBBHOISPYYYBTC-IDJJGHEZSA-N
InChI=1S/2C19H22N2O.H2O4S/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)/t2*13-,14-,18-,19+;/m00./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 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
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.
2001 Apr
Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid.
2001 Aug 15
An in situ attenuated total reflection infrared study of a chiral catalytic solid-liquid interface: cinchonidine adsorption on pt.
2001 Dec 5
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
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
Observation of high enantioselectivity for the gas phase hydrogenation of methyl pyruvate using supported Pt catalysts pre-modified with cinchonidine.
2003 Aug 7
Selective binding of chiral molecules of cinchona alkaloid by beta- and gamma-cyclodextrins and organoselenium-bridged bis(beta-cyclodextrin)s.
2003 Feb
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
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
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
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
Species differences in enantioselective 2-oxidations of RS-8359, a selective and reversible MAO-A inhibitor, and cinchona alkaloids by aldehyde oxidase.
2006 Apr
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
Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study.
2006 Jan 26
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
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites.
2007
Cinchonidinium chloride monohydrate.
2007 Dec 6
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
Experimental and theoretical analysis of asymmetric induction in heterogeneous catalysis: diastereoselective hydrogenation of chiral alpha-hydroxyketones over Pt catalyst.
2009 Apr 1
A single amino acid substitution confers high cinchonidine oxidation activity comparable with that of rabbit to monkey aldehyde oxidase 1.
2010 Feb
Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.
2010 Jan 20
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 Wed Jul 05 22:32:33 UTC 2023
Edited
by admin
on Wed Jul 05 22:32:33 UTC 2023
Record UNII
5JT77A1M4W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHONIDINE SULFATE
WHO-DD  
Common Name English
Cinchonidine sulfate [WHO-DD]
Common Name English
CINCHONIDINE, SULFATE (2:1) (SALT)
Common Name English
TCMDC-123934
Code English
CINCHONIDINE SULPHATE ANHYDROUS
Common Name English
CINCHONAN-9-OL, (8.ALPHA.,9R), SULFATE (2:1) (SALT)
Common Name English
CINCHONIDINE SULFATE ANHYDROUS
Common Name English
CINCHONIDINE SULFATE, ANHYDROUS
Common Name English
Code System Code Type Description
CAS
524-61-8
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
SMS_ID
100000183627
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL533841
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
PUBCHEM
57383488
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
FDA UNII
5JT77A1M4W
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-362-3
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID20966811
Created by admin on Wed Jul 05 22:32:33 UTC 2023 , Edited by admin on Wed Jul 05 22:32:33 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE