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.[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)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
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 |
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| 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 |
|
| HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations. | 2001 Apr |
|
| In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense. | 2001 Oct |
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| Catalytic enantioselective fluorination of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts. | 2002 Feb 21 |
|
| Asymmetric Weitz-Scheffer epoxidation of isoflavones with hydroperoxides mediated by optically active phase-transfer catalysts. | 2002 Jan 11 |
|
| Unexpected change of the sense of the enantioselective hydrogenation of ethyl pyruvate catalyzed by a Pt-alumina-cinchona alkaloid system. | 2002 May 21 |
|
| [Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers]. | 2002 Sep |
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| Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens. | 2003 Jan |
|
| 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 |
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| Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives. | 2003 Mar 5 |
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| Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids. | 2005 Aug 17 |
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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 |
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| Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts. | 2006 Apr 7 |
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| 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 |
|
| 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 |
|
| Crystal and molecular structures of trichloro-cobalt(II) complexes of epiquinine, epiquinidine, and epidihydrocinchonine. | 2007 Feb |
|
| 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 |
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| Increased uptake of quinine into the brain by inhibition of P-glycoprotein. | 2007 Oct |
|
| Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes. | 2008 Aug |
|
| Temperature-dependent time-resolved fluorescence study of cinchonine alkaloid dication. | 2008 Jan |
|
| Performance of electrospun nanofibers for SPE of drugs from aqueous solutions. | 2008 Oct |
|
| 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 |
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
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m3560
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admin on Fri Dec 15 16:44:53 GMT 2023 , Edited by admin on Fri Dec 15 16:44:53 GMT 2023
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70004430
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J2H993JF5Q
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524-55-0
Created by
admin on Fri Dec 15 16:44:53 GMT 2023 , Edited by admin on Fri Dec 15 16:44:53 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
