QUININE HYPOPHOSPHITE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2.HO2P
Molecular Weight	388.3973
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP=O.[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=JWAMXEJYDDQVAR-DSXUQNDKSA-N

InChI=1S/C20H24N2O2.HO2P/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;1-3-2/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H,1,2)/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	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	HO2P
Molecular Weight	63.9805
Charge	0
Count

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

Description
Sources: https://www.henriettes-herb.com/eclectic/bpc1911/cinchona_quin16.html

QUININE HYPOPHOSPHITE, a salt of quinine, was formerly used, along with the hypophosphites of sodium, potassium, calcium, and iron, in the treatment of phthisis and neurasthenic conditions.

Approval Year

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 36 UGT1A9 116 UGT1A10 32 P-gp 1461 CYP1A2 1524 BCRP 699 BSEP 402 MRP1 106 MRP2 383 MRP3 157 MRP4 204 UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A7 21 UGT2B7 146 UGT2B15 64 OCT1 512 OCT2 647 OCT3 150	P-gp 1537 CYP1A2 1054 CYP2C8 693 CYP2E1 667

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1692	inhibitor 3277 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	likely	weak (co-administration study) Comment: the mean theophylline AUC was 10% lower than when theophylline was given alone. More: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite
BSEP 403	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-360	not significant
MRP1 172	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-361	not significant
MRP2 475	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-362	not significant
MRP3 207	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-363	not significant
MRP4 238	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-364	not significant
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 13 uM]
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 1355 uM]
UGT2B15 64	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 212 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 23 uM]
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 322 uM]
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 3290 uM]
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 37 uM]
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 388 uM]
P-gp 1650	inhibitor 3277 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite; https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-359	yes [IC50 6.8 uM]	weak (co-administration study) Comment: a 33% increase in mean steady state AUC of digoxin and a 35% reduction in the steady state biliary clearance of digoxin were observed compared to digoxin alone More: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite; https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-359
UGT1A10 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 717 uM]
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 861 uM]
UGT1A7 23	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 970 uM]
UGT1A8 48	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 977 uM]
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 >5000 uM]
BCRP 773	inhibitor 3277 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-359	yes [Inhibition 100 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	yes	likely (co-administration study) Comment: Quinine Hypophosphite (750 mg/day for 2 days) decreased the metabolism of desipramine in patients who were extensive CYP2D6 metabolizers, but had no effect in patients who were poor CYP2D6 metabolizers. Lower doses (80 mg to 400 mg) of Quinine Hypophosphite did not significantly affect the pharmacokinetics of other CYP2D6 substrates, namely, debrisoquine, dextromethorphan, and methoxyphenamine More: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite
CYP3A4 1925	inhibitor 3277 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	yes	no (co-administration study) Comment: mean AUC and Cmax of midazolam and 1-hydroxymidazolam were not significantly affected More: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	major	yes (co-administration study) Comment: after 2 weeks of pretreatment with rifampin, the mean Quinine Hypophosphite AUC and Cmax decreased by 85% and 55%, respectively; a mean Quinine Hypophosphite AUC that was higher by 45% and a mean oral clearance of Quinine Hypophosphite that was 31% lower than after receiving Quinine Hypophosphite alone after administration with ketoconazole Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite
CYP2C8 693	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2C9 1037	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2D6 1217	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2E1 667	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP1A2 1054	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor	yes (co-administration study) Comment: In healthy male heavy smokers/cigarette smoking (CYP1A2 inducer), the mean Quinine Hypophosphite AUC following a single 600 mg dose was 44% lower, the mean Cmax was 18% lower. Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite
P-gp 1537	substrate 3367 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	yes

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	6119535	https://chem.nlm.nih.gov/chemidplus/id/0006119535
PubChem	76971661	https://pubchem.ncbi.nlm.nih.gov/compound/76971661
Wikidata	Q27272534

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:47:15 UTC 2023` Edited by `admin` on `Fri Dec 15 15:47:15 UTC 2023`
Record UNII	9GXO2WE49Z
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

QUININE HYPOPHOSPHITE

Common Name

English

QUININE PHOSPHINATE

Common Name

English

QUININE PHOSPHINATE (1:1) (SALT)

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547