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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

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

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
Cinchoninium L-tartrate tetrahydrate.
2001 Dec
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
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
Cobalt complex of cinchonine: intermolecular interactions in two crystalline modifications.
2002 Nov-Dec
[Preparation of molecularly imprinted chiral monolithic column and its applications for separation of diastereomers].
2002 Sep
Highly enantioselective reformatsky reaction of ketones: chelation-assisted enantioface discrimination.
2002 Sep 5
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
Conformational spaces of Cinchona alkaloids.
2003 Aug
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
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Evidence for the 2:1 molecular recognition and inclusion behaviour between beta- and gamma-cyclodextrins and cinchonine.
2004 Aug
Short columns with molecularly imprinted monolithic stationary phases for rapid separation of diastereomers and enantiomers.
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
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
Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives.
2005 Sep 21
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.
2006 Dec 27
Highly enantioselective cyanation of aldehydes catalyzed by a multicomponent titanium complex.
2006 Jul 21
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
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
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
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
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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 10:44:10 UTC 2023
Edited
by admin
on Thu Jul 06 10:44:10 UTC 2023
Record UNII
V43X79NZCD
Record Status Validated (UNII)
Record Version
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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 Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID6045082
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
CAS
118-10-5
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
MERCK INDEX
M3560
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY Merck Index
SMS_ID
100000080110
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
CHEBI
27509
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
PUBCHEM
90454
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
NSC
6176
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-234-6
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
MESH
C010086
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
NCI_THESAURUS
C75265
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
WIKIPEDIA
CINCHONINE
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
EVMPD
SUB13375MIG
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
FDA UNII
V43X79NZCD
Created by admin on Thu Jul 06 10:44:10 UTC 2023 , Edited by admin on Thu Jul 06 10:44:10 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY