QUININE HYDROBROMIDE ANHYDROUS

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2.BrH
Molecular Weight	405.329
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of QUININE HYDROBROMIDE ANHYDROUS

Structure Search

SMILES

Br.[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3

InChI

InChIKey=HDZGBIRSORQVNB-DSXUQNDKSA-N

InChI=1S/C20H24N2O2.BrH/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/t13-,14-,19-,20+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Charge	0
Count

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

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdfhttps://onlinelibrary.wiley.com/doi/abs/10.1002/jps.3080010617
Curator's Comment: description was created based on several sources, including http://www.fda.gov/downloads/ForHealthProfessionals/LearningActivities/UCM317816.pdf

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 43 Target ID: CHEMBL613897 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14967191	Antagonist 2760

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021799s024lbl.pdf	Curative		Approved 8360	QUALAQUIN Approved Use is a cinchona alkaloid indicated for treatment of uncomplicated Plasmodium falciparum malaria Launch Date 1.12380477E12

C_max

Value	Dose	Co-administered	Analyte	Population
3.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
28 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
8% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021799s029lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		QUININE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 g single, oral Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2566088	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2566088	Other AEs: Respiratory distress... Other AEs: Respiratory distress (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2566088
1.8 g single, oral Overdose Dose: 1.8 g Route: oral Route: single Dose: 1.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/28778932	unhealthy, 46 years n = 1 Health Status: unhealthy Age Group: 46 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/28778932	Other AEs: Hearing loss... Other AEs: Hearing loss (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/28778932
16250 mg single, oral Overdose Dose: 16250 mg Route: oral Route: single Dose: 16250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8340583	unhealthy, 49 years n = 1 Health Status: unhealthy Age Group: 49 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8340583	Other AEs: Cardiotoxicity... Other AEs: Cardiotoxicity (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8340583
9.75 g single, oral Dose: 9.75 g Route: oral Route: single Dose: 9.75 g Sources: https://pubmed.ncbi.nlm.nih.gov/14640479	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14640479	Other AEs: Tachycardia... Other AEs: Tachycardia (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/14640479

AEs

AE	Significance	Dose	Population
Respiratory distress	grade 5, 1 patient	5 g single, oral Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/2566088	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2566088
Hearing loss	1 patient	1.8 g single, oral Overdose Dose: 1.8 g Route: oral Route: single Dose: 1.8 g Sources: https://pubmed.ncbi.nlm.nih.gov/28778932	unhealthy, 46 years n = 1 Health Status: unhealthy Age Group: 46 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/28778932
Cardiotoxicity	1 patient	16250 mg single, oral Overdose Dose: 16250 mg Route: oral Route: single Dose: 16250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8340583	unhealthy, 49 years n = 1 Health Status: unhealthy Age Group: 49 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8340583
Tachycardia	grade 5	9.75 g single, oral Dose: 9.75 g Route: oral Route: single Dose: 9.75 g Sources: https://pubmed.ncbi.nlm.nih.gov/14640479	unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14640479

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15854	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15854
MolPort	MolPort-000-146-082	https://www.molport.com/shop/molecule-link/MolPort-000-146-082
ZINC	ZINC000003831404	http://zinc15.docking.org/substances/ZINC000003831404
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

PubMed

Title	Date	PubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.	2001	11444722
Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography.	2001 Apr 15	11318427
[Plasmodium vivax: therapy update].	2001 Apr 21	11360746
Soa genotype selectively affects mouse gustatory neural responses to sucrose octaacetate.	2001 Apr 27	11328963
BK channels in human glioma cells.	2001 Feb	11160513
Taste receptor cells that discriminate between bitter stimuli.	2001 Feb 23	11222863
Comparative expression of hedonic impact: affective reactions to taste by human infants and other primates.	2001 Jan	11166078
Babesiosis.	2001 Jan	11165832
Redox systems as conduits for antimalarial compounds.	2001 Jan	11152448
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.	2001 Jan 1	11169615
Effect of extracellular Ca2+ on the quinine-activated current of bullfrog taste receptor cells.	2001 Jan 15	11208971
[Fulminant course of falciparum malaria].	2001 Jan 26	11218564
The applicability of rat and human liver slices to the study of mechanisms of hepatic drug uptake.	2001 Jan-Feb	11489665
Taste responses in sons of male alcoholics.	2001 Jan-Feb	11139421
Covariation in individuals' sensitivities to bitter compounds: evidence supporting multiple receptor/transduction mechanisms.	2001 Jul	11521845
Sapid solutions and food intake in repeated dehydration and rehydration periods in rats.	2001 Jul	11445828
A comparison of the in vivo kinetics of Plasmodium falciparum ring-infected erythrocyte surface antigen-positive and -negative erythrocytes.	2001 Jul 15	11435316
Myosin II-dependent cylindrical protrusions induced by quinine in Dictyostelium: antagonizing effects of actin polymerization at the leading edge.	2001 Jun	11493651
Influence of quinine on catecholamine release evoked by cholinergic stimulation and membrane depolarization from the rat adrenal gland.	2001 Jun	11440085
Transfusion-transmitted babesiosis in Ontario: first reported case in Canada.	2001 Jun 12	11450217
Dynamic and multimodal responses of gustatory cortical neurons in awake rats.	2001 Jun 15	11404435
Effects of hydroxypyridinone iron chelators in combination with antimalarial drugs on the in vitro growth of Plasmodium falciparum.	2001 Mar	11485097
Persistence of Plasmodium falciparum in the placenta after apparently effective quinidine/clindamycin therapy.	2001 Mar	11324359
Effect of compound sequence on bitterness enhancement.	2001 May	11369676
Chemistry. Synthetic lessons from quinine.	2001 May 24	11373659
Clinical trial of beta-arteether versus quinine for the treatment of cerebral malaria in children in Yaounde, Cameroon.	2001 May-Jun	11463108
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand.	2001 Sep 1	11495642
HPLC of basic drugs on microparticulate strong cation-exchange materials - a review.	2001 Sep 15	11516893
Properties and regulation of organic cation transport in freshly isolated human proximal tubules.	2001 Sep 7	11447227

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 Created by `admin` on `Wed Jul 05 23:01:51 UTC 2023` Edited by `admin` on `Wed Jul 05 23:01:51 UTC 2023`
Record UNII	VWF36Q4G6V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUININE HYDROBROMIDE ANHYDROUS

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, HYDROBROMIDE (1:1), (8.ALPHA.,9R)-

Common Name

English

Quinine hydrobromide [WHO-DD]

Common Name

English

QUININE HBR

Common Name

English

QUININE HYDROBROMIDE

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, HBR (1:1), (8.ALPHA.,9R)-

Common Name

English

QUININE, MONOHYDROBROMIDE

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, MONOHYDROBROMIDE, (8.ALPHA.,9R)-

Common Name

English

QUININE, MONOHBR

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, MONOHBR, (8.ALPHA.,9R)-

Common Name

English

ANHYDROUS QUININE HYDROBROMIDE

Common Name

English

ANHYDROUS QUININE HYDROBROMIDE [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547