Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H22N2O.2ClH |
| Molecular Weight | 367.313 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)C3=C4C=CC=CC4=NC=C3
InChI
InChIKey=ZDBQDNUZNQOCTH-OPMVAYRNSA-N
InChI=1S/C19H22N2O.2ClH/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;2*1H/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 |
| 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 |
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 |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|---|---|---|---|---|
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 |
|
1.41 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 |
|
2.19 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 |
|
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 |
|
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 |
|
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 |
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 |
|---|---|---|
| Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum. | 2012-05-15 |
|
| Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate. | 2010-06 |
|
| Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. | 2010-03-15 |
|
| Empire and alternatives: Swietenia febrifuga and the Cinchona substitutes. | 2010-01 |
|
| Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine. | 2010-01 |
|
| Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids. | 2009-08-27 |
|
| Metal complexes of cinchonine as chiral building blocks: a strategy for the construction of nanotubular architectures and helical coordination polymers. | 2009-04-22 |
|
| Resolution of (+)-cinchonine and (-)-cinchonidine by phase-modulation fluorescence spectroscopy. | 2009-04-20 |
|
| 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. | 2009-02 |
|
| Highly enantioselective radical addition to N-benzoyl hydrazones using chiral ammonium salts. | 2008-12-03 |
|
| Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. | 2008-11-05 |
|
| Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis. | 2008-10-01 |
|
| Performance of electrospun nanofibers for SPE of drugs from aqueous solutions. | 2008-10 |
|
| A combined NMR, DFT, and X-ray investigation of some cinchona alkaloid O-ethers. | 2008-09-05 |
|
| Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. | 2008-08 |
|
| An improved synthesis of 10,11-didehydro Cinchona alkaloids. | 2008-03 |
|
| 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. | 2008-01-25 |
|
| Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids. | 2008-01 |
|
| Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication. | 2008-01 |
|
| Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces. | 2007-12-26 |
|
| 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. | 2007-11-15 |
|
| Increased uptake of quinine into the brain by inhibition of P-glycoprotein. | 2007-10 |
|
| Highly enantioselective direct aldol reaction catalyzed by cinchona derived primary amines. | 2007-09-21 |
|
| 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. | 2007-05-22 |
|
| Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones. | 2007-03-07 |
|
| Resolution and stereochemistry of tert-butylphenylphosphinous acid-borane. | 2007-02-02 |
|
| Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. | 2007-02 |
|
| Asymmetric activation of tropos 2,2'-biphenol with cinchonine generates an effective catalyst for the asymmetric strecker reaction of N-tosyl-protected aldimines and ketoimines. | 2007 |
|
| Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces. | 2006-12-27 |
|
| Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals. | 2006-11-02 |
|
| Liquid chromatographic analysis of cinchona alkaloids in beverages. | 2006-08-19 |
|
| Highly enantioselective cyanation of aldehydes catalyzed by a multicomponent titanium complex. | 2006-07-21 |
|
| Pharmacological strategies for overcoming multidrug resistance. | 2006-07 |
|
| Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts. | 2006-04-07 |
|
| Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative. | 2006-03-21 |
|
| Stimulation of choline/Mg2+ antiport in rat erythrocytes by mefloquine. | 2006-03 |
|
| Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives. | 2005-09-21 |
|
| Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. | 2005-08-17 |
|
| Evaluation of magnesium fluxes in rat erythrocytes using a stable isotope of magnesium. | 2005-05-01 |
|
| Bioactive cinchona alkaloids from Remijia peruviana. | 2005-03-23 |
|
| Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry. | 2005-02 |
|
| 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. | 2005-01-13 |
|
| Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. | 2004-10-01 |
|
| Five new alkaloids from the leaves of Remijia peruviana. | 2004-10 |
|
| Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine. | 2004-08 |
|
| Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. | 2004-05-05 |
|
| Direct STM investigation of cinchona alkaloid adsorption on Cu(III). | 2004-04-13 |
|
| In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand. | 2003 |
|
| [Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers]. | 2002-09 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
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
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Edited
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| Record UNII |
J2H993JF5Q
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| Record Status |
Validated (UNII)
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| Record Version |
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m3560
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70004430
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J2H993JF5Q
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524-55-0
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ACTIVE MOIETY |