Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H22N2O.ClH.2H2O |
| Molecular Weight | 366.882 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.Cl.[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)C3=C4C=CC=CC4=NC=C3
InChI
InChIKey=OLUIHQWPFXMZOA-MHVIFZQSSA-N
InChI=1S/C19H22N2O.ClH.2H2O/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;1H;2*1H2/t13-,14-,18+,19-;;;/m0.../s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| 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 | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22512909 |
https://www.ncbi.nlm.nih.gov/pubmed/20768740
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22512909 |
https://www.ncbi.nlm.nih.gov/pubmed/20768740
Cinchonine is cinchona bark alkaloid, which was used to treat malaria. Cinchonine is more efficient than quinine in increasing the intracellular accumulation and restoring the cytotoxicity of doxorubicin, mitoxantrone and vincristine on well-characterized multidrug resistance (MDR) cell lines. In the phase I of clinical trial was investigated the properties of cinchonine combined with the CHVP (cyclophosphamide, doxorubicin, vinblastine, methylprednisolone) regimen in relapsed and refractory lymphoproliferative syndromes.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4302 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2120 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1298088 |
200 mg 3 times / day multiple, intravenous dose: 200 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: QUININE |
CINCHONINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
420 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1298088 |
133 mg 3 times / day multiple, intravenous dose: 133 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: QUININE |
CINCHONINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
13.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
20 mg/kg 1 times / 4 weeks other, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
15 mg/kg 1 times / 4 weeks other, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
23.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
30 mg/kg 1 times / 4 weeks other, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
29.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
25 mg/kg 1 times / 4 weeks other, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
35.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
35 mg/kg 1 times / 4 weeks other, intravenous dose: 35 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1298088 |
133 mg 3 times / day multiple, intravenous dose: 133 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: QUININE |
CINCHONINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.41 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
20 mg/kg 1 times / 4 weeks other, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.98 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
15 mg/kg 1 times / 4 weeks other, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
30 mg/kg 1 times / 4 weeks other, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
25 mg/kg 1 times / 4 weeks other, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: DOXORUBICIN |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11187897 |
35 mg/kg 1 times / 4 weeks other, intravenous dose: 35 mg/kg route of administration: Intravenous experiment type: OTHER co-administered: |
CINCHONINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
40% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16695641 |
3 g 1 times / day multiple, oral dose: 3 g route of administration: Oral experiment type: MULTIPLE co-administered: |
CINCHONINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells. | 2001 Jul |
|
| New crystalline complex of quinine and quinidine. | 2002 Nov-Dec |
|
| Cobalt complex of cinchonine: intermolecular interactions in two crystalline modifications. | 2002 Nov-Dec |
|
| 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 |
|
| The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach. | 2003 Feb 17 |
|
| Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases. | 2003 Jan |
|
| Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin. | 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 |
|
| Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials. | 2003 Nov-Dec |
|
| Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. | 2004 May 5 |
|
| 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 |
|
| Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces. | 2006 Dec 27 |
|
| Pharmacological strategies for overcoming multidrug resistance. | 2006 Jul |
|
| Liquid chromatographic analysis of cinchona alkaloids in beverages. | 2006 Jul-Aug |
|
| Stimulation of choline/Mg2+ antiport in rat erythrocytes by mefloquine. | 2006 Mar |
|
| Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals. | 2006 Nov 2 |
|
| Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. | 2007 Feb |
|
| Resolution and stereochemistry of tert-butylphenylphosphinous acid-borane. | 2007 Feb 2 |
|
| Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones. | 2007 Mar 7 |
|
| 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 |
|
| Increased uptake of quinine into the brain by inhibition of P-glycoprotein. | 2007 Oct |
|
| 1-[(Diethyl-amino-carbon-yl)meth-yl]-2-[hydr-oxy(6-methoxy-quinolin-4-yl)meth-yl]-5-vinyl-1-azoniabicyclo-[2.2.2]octane chloride monohydrate. | 2008 Jan 25 |
|
| Resolution of (+)-cinchonine and (-)-cinchonidine by phase-modulation fluorescence spectroscopy. | 2009 Apr 20 |
|
| Metal complexes of cinchonine as chiral building blocks: a strategy for the construction of nanotubular architectures and helical coordination polymers. | 2009 Apr 22 |
|
| Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids. | 2009 Aug 27 |
|
| Separation of Cinchona alkaloids on a novel strong cation-exchange-type chiral stationary phase-comparison with commercially available strong cation exchanger and reversed-phase packing materials. | 2009 Feb |
|
| Empire and alternatives: Swietenia febrifuga and the Cinchona substitutes. | 2010 Jan |
|
| Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine. | 2010 Jan |
|
| Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate. | 2010 Jun |
|
| Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. | 2010 Mar 15 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/20769234 | https://www.ncbi.nlm.nih.gov/pubmed/3321829
relapsed and refractory lymphoproliferative syndromes: Cinchonine dihydrochloride was given as a continuous i.v. infusion from day 1 to day 3, over a 48-h period. The first dose level was 15 mg/kg/d. The following steps were defined by a 5 mg/kg/d increase of cinchonine dose over the previous step.
malaria: it was injected 7(1/2) grains of cinichonine bihydrochloride into the deltoid muscle on the day before an attack was due, and warned the patient that this could not be expected to stop completely the attack due the next day
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:40:52 GMT 2023
by
admin
on
Fri Dec 15 16:40:52 GMT 2023
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| Record UNII |
2NB0197ROW
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| Record Status |
Validated (UNII)
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| Record Version |
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2NB0197ROW
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m3560
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PRIMARY | Merck Index |
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |