Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H22N2O |
| Molecular Weight | 294.3908 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)C3=C4C=CC=CC4=NC=C3
InChI
InChIKey=KMPWYEUPVWOPIM-QAMTZSDWSA-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 |
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 |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| [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 |
|
| Direct STM investigation of cinchona alkaloid adsorption on Cu(III). | 2004 Apr 13 |
|
| Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine. | 2004 Aug |
|
| Synthetic cinchonidine receptors obtained by cross-linking linear poly(methacrylic acid) derivatives as an alternative molecular imprinting technique. | 2004 May 5 |
|
| Five new alkaloids from the leaves of Remijia peruviana. | 2004 Oct |
|
| Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. | 2004 Oct 1 |
|
| Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. | 2005 Aug 17 |
|
| Carbon nanotubes as adsorbent of solid-phase extraction and matrix for laser desorption/ionization mass spectrometry. | 2005 Feb |
|
| 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 |
|
| Bioactive cinchona alkaloids from Remijia peruviana. | 2005 Mar 23 |
|
| Evaluation of magnesium fluxes in rat erythrocytes using a stable isotope of magnesium. | 2005 May 1 |
|
| Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives. | 2005 Sep 21 |
|
| Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts. | 2006 Apr 7 |
|
| 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 |
|
| Highly enantioselective cyanation of aldehydes catalyzed by a multicomponent titanium complex. | 2006 Jul 21 |
|
| Liquid chromatographic analysis of cinchona alkaloids in beverages. | 2006 Jul-Aug |
|
| Stimulation of choline/Mg2+ antiport in rat erythrocytes by mefloquine. | 2006 Mar |
|
| 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 Mar 21 |
|
| Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals. | 2006 Nov 2 |
|
| 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 |
|
| Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces. | 2007 Dec 26 |
|
| 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 |
|
| 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 |
|
| Increased uptake of quinine into the brain by inhibition of P-glycoprotein. | 2007 Oct |
|
| Highly enantioselective direct aldol reaction catalyzed by cinchona derived primary amines. | 2007 Sep 21 |
|
| Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. | 2008 Aug |
|
| Highly enantioselective radical addition to N-benzoyl hydrazones using chiral ammonium salts. | 2008 Dec 3 |
|
| Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids. | 2008 Jan |
|
| Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication. | 2008 Jan |
|
| 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 |
|
| An improved synthesis of 10,11-didehydro Cinchona alkaloids. | 2008 Mar |
|
| Chiral squaramide derivatives are excellent hydrogen bond donor catalysts. | 2008 Nov 5 |
|
| Performance of electrospun nanofibers for SPE of drugs from aqueous solutions. | 2008 Oct |
|
| 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 |
|
| 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 |
|
| Investigating the activity of quinine analogues versus chloroquine resistant Plasmodium falciparum. | 2012 May 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
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Edited
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| Record UNII |
V43X79NZCD
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C271
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118-10-5
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m3560
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100000080110
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27509
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C010086
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C75265
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CINCHONINE
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SUB13375MIG
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ACTIVE MOIETY |
