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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22N2O.ClH
Molecular Weight 330.852
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONINE HYDROCHLORIDE

SMILES

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=IMUHWLVEEVGMBC-BKUXTCEESA-N
InChI=1S/C19H22N2O.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Flexibility of CuCl4-tetrahedra in bis[cinchoninium tetrachlorocuprate(II)]trihydrate single crystals. X-ray diffraction and EPR studies.
2001 Aug 27
Cinchoninium L-tartrate tetrahydrate.
2001 Dec
Apoptosis induced by doxorubicin and cinchonine in P388 multidrug-resistant cells.
2001 Jul
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
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
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
Conformational spaces of Cinchona alkaloids.
2003 Aug
Highly stereoselective, uniformly sized molecularly imprinted polymers for cinchona alkaloids in hydro-organic mobile phases.
2003 Jan
Transformation of Cinchona alkaloids into 1-N-oxide derivatives by endophytic Xylaria sp isolated from Cinchona pubescens.
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
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
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
Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts.
2006 Apr 7
Pharmacological strategies for overcoming multidrug resistance.
2006 Jul
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
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
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
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
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
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
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 Fri Dec 15 17:20:26 GMT 2023
Edited
by admin
on Fri Dec 15 17:20:26 GMT 2023
Record UNII
4PSQ7YHS4T
Record Status Validated (UNII)
Record Version
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Name Type Language
CINCHONINE HYDROCHLORIDE
Common Name English
(+)-CINCHONINE HYDROCHLORIDE
Common Name English
CINCHONINE, MONOHYDROCHLORIDE
Common Name English
CINCHONAN-9-OL, MONOHYDROCHLORIDE, (9S)-
Common Name English
CINCHONINE HCL
Common Name English
NSC-215195
Code English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C95051
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
FDA UNII
4PSQ7YHS4T
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
NSC
215195
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
SMS_ID
100000091316
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
EVMPD
SUB26925
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
CAS
5949-11-1
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID801339696
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
PUBCHEM
90453
Created by admin on Fri Dec 15 17:20:26 GMT 2023 , Edited by admin on Fri Dec 15 17:20:26 GMT 2023
PRIMARY
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ACTIVE MOIETY