QUININE ASCORBATE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2.2C6H8O6
Molecular Weight	676.665
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO.[H][C@@]2(OC(=O)C(O)=C2O)[C@@H](O)CO.[H][C@]3(C[C@@H]4CCN3C[C@@H]4C=C)[C@H](O)C5=C6C=C(OC)C=CC6=NC=C5

InChI

InChIKey=CJHQUYQRCLIWSW-JPGAVJPLSA-N

InChI=1S/C20H24N2O2.2C6H8O6/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;2*7-1-2(8)5-3(9)4(10)6(11)12-5/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*2,5,7-10H,1H2/t13-,14-,19-,20+;2*2-,5+/m000/s1

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?CFRPart=310&showFR=1 | https://www.ncbi.nlm.nih.gov/pubmed/8008450 | https://www.drugs.com/ppa/quinine.html

Quinine ascorbate is a salt of antimalarial drug quinine and ascorbic acid (vitamin C). Ascorbate reduces the potency of quinolone-containing anti-malarial drugs. Quinine ascorbate was marketed as a component of over-the-counter smoking deterrent products but was not recognized as safe by the FDA regulation in 1993.

Approval Year

C_max

Value	Dose	Analyte	Population
10.6 μg/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intramuscular dose: 300 mg/m² route of administration: Intramuscular experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
9.7 μg/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
10.3 μg/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intragastric dose: 300 mg/m² route of administration: Intragastric experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
11.3 μg/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² 2 times / day multiple, intramuscular dose: 300 mg/m² route of administration: Intramuscular experiment type: MULTIPLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
3.2 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021799lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	QUININE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
8.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021799lbl.pdf	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	QUININE unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
87.2 μg × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intramuscular dose: 300 mg/m² route of administration: Intramuscular experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
90.5 μg × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
95.4 μg × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intragastric dose: 300 mg/m² route of administration: Intragastric experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
28 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021799lbl.pdf	8.7 mg/kg single, oral dose: 8.7 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	QUININE unknown	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
73 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021799lbl.pdf	10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	QUININE unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
8.4 h EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intramuscular dose: 300 mg/m² route of administration: Intramuscular experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
12.5 h EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
13.1 h EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² single, intragastric dose: 300 mg/m² route of administration: Intragastric experiment type: SINGLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN
9.8 h EXPERIMENT https://www.sciencedirect.com/science/article/abs/pii/S0022347685806922	300 mg/m² 2 times / day multiple, intramuscular dose: 300 mg/m² route of administration: Intramuscular experiment type: MULTIPLE co-administered:	QUININE serum	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	substrate 1037	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCTN1 29 OCT3 150 OCTN2 66 OCT2 647 OATP1B1 788 OATP1B3 706 OATP2B1 123 OCT1 512 BSEP 402 MRP2 383 MRP3 157 MRP4 204 P-gp 1461 OATP1A2 35 CYP2C8 911 CYP2C19 1478 CYP1A1 110	CYP2C19 991 CYP2E1 667 CYP3A7 110 P-gp 1537 CYP3A5 395 CYP1A2 1054 CYP2C8 693 OCT2 355 OCT1 327	CYP1A2 701

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [IC50 >133 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [IC50 >133 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [IC50 >133 uM]
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [Inhibition 20 uM]
OATP2B1 126	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI0IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	no [Inhibition 20 uM]
OCTN1 29	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	weak
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16610785/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTcwIn19	yes [IC50 1.8 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11716514/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes [IC50 22.6 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/,https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Njg1IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes [IC50 51.6 uM]
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes [Inhibition 20 uM]
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11136296/, https://go.drugbank.com/drugs/DB00468	yes [Inhibition 80 uM]
OCT2 648	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes [Ki 3.4 uM]
CYP1A1 218	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP1A2 1692	inducer 1573 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP2C19 1553	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP3A4 1925	inducer 1573 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP3A4 1925	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00468	yes
OATP1A2 35	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00468	yes
OCT3 150	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28811134/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjczIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes
OCTN2 71	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10525100/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMDczNjkzIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/001/632/original/FDA_label_Quinine.pdf?1537805198	likely
CYP2C19 991	substrate 3367 Sources: https://s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/001/632/original/FDA_label_Quinine.pdf?1537805198	likely
CYP2C8 693	substrate 3367 Sources: https://s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/001/632/original/FDA_label_Quinine.pdf?1537805198	likely
CYP2C9 1037	substrate 3367 Sources: https://s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/001/632/original/FDA_label_Quinine.pdf?1537805198	likely
CYP2E1 667	substrate 3367 Sources: https://s3-us-west-2.amazonaws.com/drugbank/cite_this/attachments/files/000/001/632/original/FDA_label_Quinine.pdf?1537805198	likely
P-gp 1537	substrate 3367 Sources: https://www.genome.jp/kegg/drug/br08309.html	yes [Km 10 uM]
OCT2 355	substrate 3367 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE3MCJ9fQ%3D%3D	yes [Km 2.6 uM]
CYP2D6 1217	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP3A5 395	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP3A7 110	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00468	yes
OCT1 327	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00468	yes
CYP3A4 1737	substrate 3367 Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021799s008lbl.pdf	yes	yes (co-administration study) Comment: Coadministration of Ketoconazole increased Quinine AUC by 45% and decreased a mean oral clearance of Quinine by 31%. Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021799s008lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEMBL	CHEMBL3707332
ChemIDplus	146407	https://chem.nlm.nih.gov/chemidplus/id/0000146407
PubChem	56840788	https://pubchem.ncbi.nlm.nih.gov/compound/56840788
Wikidata	Q27282158

Name

Type

Language

QUININE ASCORBATE

Official Name

English

QUININE ASCORBATE [MART.]

Common Name

English

L-ASCORBIC ACID, COMPOUND WITH QUININE (2:1)

Common Name

English

QUININE ASCORBATE [USAN]

Common Name

English

L-ASCORBIC ACID, COMPOUND WITH (8.ALPHA.,9R)-6'-METHOXYCINCHONAN-9-OL (2:1)

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547