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
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
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 |
DescriptionSources: http://www.medicatione.com/?c=drug&s=quinimaxCurator'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
Sources: http://www.medicatione.com/?c=drug&s=quinimax
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15508779 |
225.0 nM [EC50] | ||
Target ID: CHEMBL612851 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880 |
|||
Target ID: CHEMBL613214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.ndrugs.com/?s=quinimax |
Primary | Quinimax Approved UseIndications: malaria |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations. | 2001 Apr |
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A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species. | 2001 Dec |
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Adsorption geometry of modifiers as key in imparting chirality to platinum catalysts. | 2001 Nov 7 |
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Enantioselective hydrogenation over cinchona-modified Pt: the special role of carboxylic acids. | 2002 Mar 15 |
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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 |
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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 |
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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 |
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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 |
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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 |
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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 |
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Chirally modified platinum generated by adsorption of cinchonidine ether derivatives: towards uncovering the chiral sites. | 2007 |
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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 |
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Phase-transfer-catalyzed asymmetric acylimidazole alkylation. | 2007 Nov 8 |
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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 |
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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 |
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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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7570885
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23816880
Cinchonidine inhibited P. falcifarum with IC₅₀=0.28 ug/ml
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
31029T62CS
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Record Status |
Validated (UNII)
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Record Version |
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |