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

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
Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane.
2001 Mar
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.
2001 Oct
The enantioselective synthesis of alpha-amino acid derivatives via organoboranes.
2002 Aug 14
New crystalline complex of quinine and quinidine.
2002 Nov-Dec
Cobalt complex of cinchonine: intermolecular interactions in two crystalline modifications.
2002 Nov-Dec
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
Conformational spaces of Cinchona alkaloids.
2003 Aug
The characterisation of supported platinum nanoparticles on carbon used for enantioselective hydrogenation: a combined electrochemical-STM approach.
2003 Feb 17
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.
2003 Jan
Pharmacokinetics of idarubicin in the isolated perfused rat lung: effect of cinchonine and rutin.
2003 Jul
Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of beta-substituted alpha-amino acid derivatives.
2003 Mar 5
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
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
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
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
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
Organocatalytic enantioselective indole alkylations of alpha,beta-unsaturated ketones.
2007 Mar 7
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
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
Homochiral crystallization of microporous framework materials from achiral precursors by chiral catalysis.
2008 Oct 1
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:54:41 GMT 2023
Edited
by admin
on Sat Dec 16 04:54:41 GMT 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 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
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY