QUININE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2.ClH.2H2O
Molecular Weight	396.908
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.O.Cl.COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1

InChI

InChIKey=MPQKYZPYCSTMEI-FLZPLBAKSA-N

InChI=1S/C20H24N2O2.ClH.2H2O/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;1H;2*1H2/t13-,14-,19-,20+;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Quinine soluble salts possess the extremely bitter taste, that may have a perplexing problem especially to children. That is why the most common combinations which are administered in this way are the sulphate, salicylate, tannate and certain esters. Quinine tannate, an insoluble quinine salt has been known in medicine for a very long time. However, many experiments have revealed that quinine tannate was practically inert as a medicinal substance.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ferriprotoporphyrin IX 44	Antagonist 2,849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63	Curative		Approved 8,583	QUALAQUIN

C_max

Value	Dose	Co-administered	Analyte	Population
3.2 μg/mL	8.7 mg/kg single, oral		QUININE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
28 μg × h/mL	8.7 mg/kg single, oral		QUININE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.5 h	8.7 mg/kg single, oral		QUININE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
8%	8.7 mg/kg single, oral		QUININE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
5 g single, oral	unhealthy, 17 years	Other AEs: Respiratory distress...
1.8 g single, oral Overdose	unhealthy, 46 years	Other AEs: Hearing loss...
16250 mg single, oral Overdose	unhealthy, 49 years	Other AEs: Cardiotoxicity...
9.75 g single, oral	unhealthy, adult	Other AEs: Tachycardia...

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AEs

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AE	Significance	Dose	Population
Respiratory distress	grade 5, 1 patient	5 g single, oral	unhealthy, 17 years
Hearing loss	1 patient	1.8 g single, oral Overdose	unhealthy, 46 years
Cardiotoxicity	1 patient	16250 mg single, oral Overdose	unhealthy, 49 years
Tachycardia	grade 5	9.75 g single, oral	unhealthy, adult

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15854	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15854
eMolecules	29549573	https://www.emolecules.com/cgi-bin/more?vid=29549573
eMolecules	30151887	https://www.emolecules.com/cgi-bin/more?vid=30151887
eMolecules	6843708	https://www.emolecules.com/cgi-bin/more?vid=6843708
MolPort	MolPort-000-146-082	https://www.molport.com/shop/molecule-link/MolPort-000-146-082

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PubMed

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Title	Date	PubMed
Olfactory learning induces differential long-lasting changes in rat central olfactory pathways.	2001	11226666
Quinine-induced alterations of electrically evoked otoacoustic emissions and cochlear potentials in guinea pigs.	2001 Apr	11423223
Cell volume-induced changes in K+ transport across the rat colon.	2001 Apr	11421860
Patterns of Plasmodium falciparum drug resistance in nonimmune travellers to Africa.	2001 Apr	11399022
HPTLC method for the estimation of alkaloids of Cinchona officinalis stem bark and its marketed formulations.	2001 Apr	11345710

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Patents

Sample Use Guides

In Vivo Use Guide

in adults: 648 mg (two capsules) every 8 hours for 7 days

Route of Administration: Oral

In Vitro Use Guide

Quinine (0-100 uM) stimulates adipogenesis through ERK/S6 (extracellular-signal-regulated kinase/Ribosomal protein S6) signaling, which at least partly functions via taste receptor, type 2, member 106 (T2R106)

Substance Class	Chemical
Record UNII	711S8Y0T33
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUININE HYDROCHLORIDE DIHYDRATE

Preferred Name

English

QUININE HYDROCHLORIDE

Common Name

English

QUININE HYDROCHLORIDE [FCC]

Common Name

English

QUININI HYDROCHLORIDUM [WHO-IP LATIN]

Common Name

English

(8.ALPHA.,9R)-6'-METHOXYCINCHONAN-9-OL HYDROCHLORIDE DIHYDRATE

Common Name

English

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Classification Tree

Code System

Code

FUNCTIONAL CLASSIFICATION

JECFA EVALUATION

QUININE HYDROCHLORIDE

Subpart E--Requirements for Specific New Drugs or Devices

CFR

21 CFR 310.547

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Code System

Code

Type

Description

RXCUI

9074

PRIMARY

RxNorm

EVMPD

SUB15093MIG

PRIMARY

EPA CompTox

DTXSID2047694

PRIMARY

MERCK INDEX

m9447

PRIMARY

Merck Index

DRUG BANK

DBSALT001044

PRIMARY

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PARENT -> SALT/SOLVATE


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ANHYDROUS->SOLVATE

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IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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Amount:

[<5] PERCENT PEAK AREA (limits)

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QUININE

ACTIVE MOIETY

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SMILES

InChI

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound