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.COC1=CC2=C(C=CN=C2C=C1)[C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C

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 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A8 37 UGT1A9 148 UGT1A10 37 P-gp 1741 CYP1A2 2153 BCRP 910 BSEP 550 MRP1 116 MRP2 499 MRP3 246 MRP4 290 UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A7 23 UGT2B7 197 UGT2B15 84 OCT1 620 OCT2 779 OCT3 159	P-gp 2052 CYP1A2 1197 CYP2C8 810 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 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 554	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-360	not significant
MRP1 232	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-361	not significant
MRP2 625	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-362	not significant
MRP3 326	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-363	not significant
MRP4 345	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-364	not significant
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 13 uM]
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 1355 uM]
UGT2B15 84	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 212 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 23 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 322 uM]
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 3290 uM]
OCT3 161	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16263091/	yes [IC50 37 uM]
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 388 uM]
P-gp 1932	inhibitor 4027 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 46	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 717 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 861 uM]
UGT1A7 25	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 970 uM]
UGT1A8 49	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 977 uM]
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0	yes [IC50 >5000 uM]
BCRP 985	inhibitor 4027 Sources: https://malariajournal.biomedcentral.com/articles/10.1186/1475-2875-13-359	yes [Inhibition 100 uM]
CYP2D6 2546	inhibitor 4027 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 2633	inhibitor 4027 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 1946	substrate 4014 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 810	substrate 4014 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2C9 1193	substrate 4014 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2D6 1388	substrate 4014 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP2E1 729	substrate 4014 Sources: https://www.sdrugs.com/?c=ing&s=quinine%20hypophosphite	minor
CYP1A2 1197	substrate 4014 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 2052	substrate 4014 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 `Mon Mar 31 18:08:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:35 GMT 2025`
Record UNII	9GXO2WE49Z
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

QUININE PHOSPHINATE

Preferred Name

English

QUININE HYPOPHOSPHITE

Common Name

English

QUININE PHOSPHINATE (1:1) (SALT)

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547