U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CINCHONINE

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-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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2120 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
13.4 μg × h/mL
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.8 h
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
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
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Cinchoninium L-tartrate tetrahydrate.
2001 Dec
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane.
2001 Mar
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
2002 Aug 14
Catalytic enantioselective fluorination of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.
2002 Feb 21
A selective PVC membrane for di- or trinitrophenol based on N,N-dibenzyl-3,3',5,5'-tetramethylbenzidine.
2002 Jan
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
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
In-vitro response of Plasmodium falciparum to the main alkaloids of Cinchona in northwestern Thailand.
2003
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach.
2003 Feb 17
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.
2003 Jan
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.
2003 Mar 5
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
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
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
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
Increased uptake of quinine into the brain by inhibition of P-glycoprotein.
2007 Oct
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
2008 Aug
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
Performance of electrospun nanofibers for SPE of drugs from aqueous solutions.
2008 Oct
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
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
Patents

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
In Vitro Use Guide
Cinchonine at 5-10 uM induced a rapid and significant increase in the accumulation of doxorubicin, mitoxantrone, and vincristine in MDR-expressing human leukemic cell line K562/ADM.
Name Type Language
CINCHONINE
MI   WHO-DD  
Common Name English
NSC-6176
Code English
(8R,9S)-CINCHONINE
Common Name English
Cinchonine [WHO-DD]
Common Name English
CINCHONINE [MI]
Common Name English
(9S)-CINCHONAN-9-OL
Common Name English
CINCHONAN-9-OL, (9S)-
Common Name English
2-QUINUCLIDINEMETHANOL, .ALPHA.-(5-VINYL-2-QUINOLYL)-
Systematic Name English
D-CINCHONINE
Common Name English
(+)-CINCONINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID6045082
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
CAS
118-10-5
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
MERCK INDEX
m3560
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY Merck Index
SMS_ID
100000080110
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
CHEBI
27509
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
PUBCHEM
90454
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
NSC
6176
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-234-6
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
MESH
C010086
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
NCI_THESAURUS
C75265
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
WIKIPEDIA
CINCHONINE
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
EVMPD
SUB13375MIG
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY
FDA UNII
V43X79NZCD
Created by admin on Sat Dec 16 04:54:42 GMT 2023 , Edited by admin on Sat Dec 16 04:54:42 GMT 2023
PRIMARY