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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.O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
1.41 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
2.19 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
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
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
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
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
Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane.
2001 Mar
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
Conformational spaces of Cinchona alkaloids.
2003 Aug
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
Spectrophotometric method for estimation of alkaloids precipitable with Dragendorff's reagent in plant materials.
2003 Nov-Dec
Asymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloids.
2005 Aug 17
Evaluation of magnesium fluxes in rat erythrocytes using a stable isotope of magnesium.
2005 May 1
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.
2007 Dec 26
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
Ylide-initiated michael addition-cyclization reactions beyond cyclopropanes.
2008 Aug
Synthesis and optical resolution of an allenoic acid by diastereomeric salt formation induced by chiral alkaloids.
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
Influence of peripheral groups on the physical and chemical behavior of cinchona alkaloids.
2009 Aug 27
Self-association promoted conformational transition of (3R,4S,8R,9R)-9-[(3,5-bis(trifluoromethyl)phenyl))-thiourea](9-deoxy)-epi-cinchonine.
2010 Jan
Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.
2010 Jun
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 Mon Mar 31 18:45:00 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:00 GMT 2025
Record UNII
4PSQ7YHS4T
Record Status Validated (UNII)
Record Version
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Name Type Language
(+)-CINCHONINE HYDROCHLORIDE
Preferred 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 Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C95051
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
FDA UNII
4PSQ7YHS4T
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
NSC
215195
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
SMS_ID
100000091316
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
EVMPD
SUB26925
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
CAS
5949-11-1
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
EPA CompTox
DTXSID801339696
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
PUBCHEM
90453
Created by admin on Mon Mar 31 18:45:00 GMT 2025 , Edited by admin on Mon Mar 31 18:45:00 GMT 2025
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY