Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H22N2O |
Molecular Weight | 294.3908 |
Optical Activity | ( - ) |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=C4C=CC=CC4=NC=C3
InChI
InChIKey=KMPWYEUPVWOPIM-KODHJQJWSA-N
InChI=1S/C19H22N2O/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/t13-,14-,18-,19+/m0/s1
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 |
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 |
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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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Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid. | 2001 Aug 15 |
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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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In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense. | 2001 Oct |
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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 |
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Hydrogenation of cinchona alkaloids over supported Pt catalyst. | 2003 |
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Conformational spaces of Cinchona alkaloids. | 2003 Aug |
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Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and molecular modeling. | 2003 Oct 31 |
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Enantioselective iodolactonization catalyzed by chiral quaternary ammonium salts derived from cinchonidine. | 2004 Apr 16 |
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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 |
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Polymer-supported Cinchona alkaloid-derived ammonium salts as recoverable phase-transfer catalysts for the asymmetric synthesis of alpha-amino acids. | 2004 Apr 30 |
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Large-scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] anion. | 2004 Nov 26 |
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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 |
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Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers. | 2005 Feb |
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Stereospecific oxidation of the (S)-enantiomer of RS-8359, a selective and reversible monoamine oxidase A (MAO-A) inhibitor, by aldehyde oxidase. | 2005 Jun |
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Competition at chiral metal surfaces: fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum. | 2005 Jun 15 |
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Cinchonidine adsorption on gold and gold-containing bimetallic platinum metal surfaces: an attenuated total reflection infrared and density functional theory study. | 2006 Aug 31 |
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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 |
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Effect of ultrasound in enantioselective hydrogenation of 1-phenyl-1,2-propanedione: comparison of catalyst activation, solvents and supports. | 2006 Jan |
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Solvent-induced conformational changes of O-phenyl-cinchonidine: a theoretical and VCD spectroscopy study. | 2006 Jan 26 |
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Improved asymmetric S(N)Ar reaction of beta-dicarbonyl compounds catalyzed by quaternary ammonium salts derived from cinchona alkaloids. | 2006 Jun 23 |
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Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS. | 2006 Mar 21 |
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The origin of chemo- and enantioselectivity in the hydrogenation of diketones on platinum. | 2006 Mar 29 |
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Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals. | 2006 Nov 2 |
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Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation. | 2006 Oct 27 |
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Cinchonidinium chloride monohydrate. | 2007 Dec 6 |
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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 |
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Phase-transfer-catalyzed asymmetric acylimidazole alkylation. | 2007 Nov 8 |
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Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. | 2008 Aug |
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Rational combination of two privileged chiral backbones: highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones. | 2008 Aug 1 |
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Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids. | 2008 Jan |
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Hydrogen-bonding interactions in cinchonidine-2-methyl-2-hexenoic acid complexes: a combined spectroscopic and theoretical study. | 2008 Jul 10 |
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Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis. | 2008 Oct 1 |
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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 |
|
Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. | 2010 Mar 21 |
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Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum. | 2012 May 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
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1U622LRA8Z
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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