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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H22N2O.2H2O.H2O4S
Molecular Weight 722.891
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHONINE SULFATE DIHYDRATE

SMILES

O.O.OS(O)(=O)=O.[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)C3=C4C=CC=CC4=NC=C3.[H][C@@]5(C[C@@H]6CC[N@]5C[C@@H]6C=C)[C@@H](O)C7=C8C=CC=CC8=NC=C7

InChI

InChIKey=LPXYGFYEGUEAQG-KKDFKURBSA-N
InChI=1S/2C19H22N2O.H2O4S.2H2O/c2*1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17;1-5(2,3)4;;/h2*2-7,9,13-14,18-19,22H,1,8,10-12H2;(H2,1,2,3,4);2*1H2/t2*13-,14-,18+,19-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Picric acid sensitive optode based on a fluorescence carrier covalently bound to membrane.
2001 Mar
Unexpected change of the sense of the enantioselective hydrogenation of ethyl pyruvate catalyzed by a Pt-alumina-cinchona alkaloid system.
2002 May 21
Hydrogenation of cinchona alkaloids over supported Pt catalyst.
2003
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
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
Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.
2004 Oct 1
Time-lapse STM studies of diastereomeric cinchona alkaloids on platinum metals.
2006 Nov 2
Resolution and stereochemistry of tert-butylphenylphosphinous acid-borane.
2007 Feb 2
Increased uptake of quinine into the brain by inhibition of P-glycoprotein.
2007 Oct
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
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 16:42:14 GMT 2023
Edited
by admin
on Fri Dec 15 16:42:14 GMT 2023
Record UNII
8V7A43GW58
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHONINE SULFATE DIHYDRATE
MI  
Common Name English
CINCHONAN-9-OL, (9S)-, SULFATE (2:1) (SALT), DIHYDRATE
Common Name English
CINCHONAN-9-OL, (9S)-, SULPHATE (2:1) (SALT), DIHYDRATE
Common Name English
CINCHONINE SULPHATE DIHYDRATE
Common Name English
CINCHONINE SULFATE DIHYDRATE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
76968827
Created by admin on Fri Dec 15 16:42:14 GMT 2023 , Edited by admin on Fri Dec 15 16:42:14 GMT 2023
PRIMARY
FDA UNII
8V7A43GW58
Created by admin on Fri Dec 15 16:42:14 GMT 2023 , Edited by admin on Fri Dec 15 16:42:14 GMT 2023
PRIMARY
MERCK INDEX
m3560
Created by admin on Fri Dec 15 16:42:14 GMT 2023 , Edited by admin on Fri Dec 15 16:42:14 GMT 2023
PRIMARY Merck Index
CAS
5949-17-7
Created by admin on Fri Dec 15 16:42:14 GMT 2023 , Edited by admin on Fri Dec 15 16:42:14 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY