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Chemistry

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Also known as: Ncgc00166281-01, Dsstox_cid_24280, Dsstox_rid_80140, Dsstox_gsid_44280, 130-95-0, Cas-130-95-0

Molecular Formula

C₂₀H₂₄N₂O₂

Molecular Weight

324.4 g/mol

InChI Key

LOUPRKONTZGTKE-VOMFEXJBSA-N

1 2D Structure

Quinine Sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

2.1.2 InChI

InChI=1S/C20H24N2O2/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/t13-,14?,19-,20+/m0/s1

2.1.3 InChI Key

LOUPRKONTZGTKE-VOMFEXJBSA-N

2.1.4 Canonical SMILES

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

2.1.5 Isomeric SMILES

COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3CC4CCN3C[C@@H]4C=C)O

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Ncgc00166281-01

2. Dsstox_cid_24280

3. Dsstox_rid_80140

4. Dsstox_gsid_44280

5. 130-95-0

6. Cas-130-95-0

7. Sr-01000075160

8. Quinine (ban)

9. Kinder Quinina (tn)

10. Lopac0_001029

11. Mls001304041

12. Chembl387326

13. Schembl12310700

14. Hms2233l08

15. Tox21_112389

16. Bdbm50411276

17. Akos015955637

18. Tox21_112389_1

19. Ncgc00274071-01

20. Smr000718748

21. C06526

22. D08460

23. Sr-01000075160-1

24. Sr-01000075160-12

25. (alphar,2s)-alpha-(6-methoxy-4-quinolyl)-5beta-vinyl-2alpha-quinuclidinemethanol

2.3 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄N₂O₂
Molecular Weight	324.4 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	324.183778013 g/mol
Monoisotopic Mass	324.183778013 g/mol
Topological Polar Surface Area	45.6 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	457
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Quinine sulfate
Drug Label	Quinine sulfate is a cinchona alkaloid chemically described as cinchonan-9-ol, 6'-methoxy-, (8, 9R)-, sulfate (2:1) (salt), dihydrate with a molecular formula of (C20H24N2O2)2H2SO42H2O and a molecular weight of 782.96.The structural formula o...
Active Ingredient	Quinine sulfate
Dosage Form	Capsule
Route	Oral
Strength	324mg
Market Status	Prescription
Company	Mylan Pharms; Teva Pharms

2 of 2
Drug Name	Quinine sulfate
Drug Label	Quinine sulfate is a cinchona alkaloid chemically described as cinchonan-9-ol, 6'-methoxy-, (8, 9R)-, sulfate (2:1) (salt), dihydrate with a molecular formula of (C20H24N2O2)2H2SO42H2O and a molecular weight of 782.96.The structural formula o...
Active Ingredient	Quinine sulfate
Dosage Form	Capsule
Route	Oral
Strength	324mg
Market Status	Prescription
Company	Mylan Pharms; Teva Pharms

4.2 Therapeutic Uses

Analgesics, Non-Narcotic; Antimalarials; Muscle Relaxants, Central

National Library of Medicine's Medical Subject Headings. Quinine. Online file (MeSH, 2014). Available from, as of August 28, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html

Qualaquin (quinine sulfate) is an antimalarial drug indicated only for treatment of uncomplicated Plasmodium falciparum malaria. Quinine sulfate has been shown to be effective in geographical regions where resistance to chloroquine has been documented. /Included in US product label/

NIH; DailyMed. Current Medication Information for Qualaquin (Quinine Sulfate) Capsule (Revised: April 2013). Available from, as of November 20, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=1f66fba7-4026-4504-918d-4c88f2835cc0

Oral quinine sulfate is used in conjunction with IV or oral clindamycin for the treatment of babesiosis caused by Babesia microti. /NOT included in US product label/

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

Although quinine sulfate is not approved by the FDA for the treatment of severe or complicated malaria, the CDC states that oral quinine sulfate can be used in conjunction with doxycycline, tetracycline, or clindamycin for follow-up treatment after an appropriate initial parenteral regimen.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

For more Therapeutic Uses (Complete) data for QUININE (8 total), please visit the HSDB record page.

4.3 Drug Warning

/BOXED WARNING/ WARNING: Qualaquin use for the treatment or prevention of nocturnal leg cramps may result in serious and life-threatening hematologic reactions, including thrombocytopenia and hemolytic uremic syndrome/thrombotic thrombocytopenic purpura (HUS/TTP). Chronic renal impairment associated with the development of TTP has been reported. The risk associated with Qualaquin use in the absence of evidence of its effectiveness in the treatment or prevention of nocturnal leg cramps outweighs any potential benefit.

Serious hypersensitivity reactions, including anaphylactic shock, anaphylactoid reactions, urticaria, serious skin rashes (e.g., Stevens-Johnson syndrome, toxic epidermal necrolysis), angioedema, facial edema, bronchospasm, and pruritus, have been reported with quinine. In addition, thrombocytopenia, hemolytic uremic syndrome/thrombotic thrombocytopenic purpura (HUS/TTP), immune thrombocytopenic purpura, blackwater fever, disseminated intravascular coagulation, leukopenia, neutropenia, granulomatous hepatitis, and acute interstitial nephritis have been reported and may also be due to hypersensitivity reactions to the drug.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

Potentially fatal cardiac arrhythmias, including torsades de pointes and ventricular fibrillation, have been reported rarely during quinine therapy. At least 1 case of fatal ventricular arrhythmia has been reported in a geriatric patient with preexisting prolonged QT interval treated with IV quinine sulfate for Plasmodium falciparum malaria.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

Serious, life-threatening, and sometimes fatal hematologic reactions, including thrombocytopenia and thrombocytopenia, hemolytic uremic syndrome/thrombotic thrombocytopenic purpura (HUS/TTP), have been reported in patients receiving quinine, especially patients using the drug for unlabeled indications (prevention or treatment of leg cramps or restless leg syndrome). Subsequent development of chronic renal impairment has occurred in patients with quinine-associated TTP.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

For more Drug Warnings (Complete) data for QUININE (37 total), please visit the HSDB record page.

4.4 Minimum/Potential Fatal Human Dose

The average fatal dose for an adult is about 8 g although deaths have been reported from as little as 1.5 g in an adult and 900 mg in a child.

IPCS; UK Poison Information Documents (UKPID) for Quinine (Last updated March 1996). Available from, as of November 20, 2014: https://www.inchem.org/pages/ukpids.html

A lethal dose of quinine has not been clearly defined, but fatalities have been reported after the ingestion of 2 to 8 grams in adults.

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Following oral administration of a single 600-mg dose of quinine sulfate in healthy adults, the mean plasma clearance was 0.08-0.47 L/hour per kg (median: 0.17 L/hour per kg) and the mean plasma elimination half-life was 9.7-12.5 hours. Following oral administration of 10 mg/kg of quinine sulfate in patients with uncomplicated malaria, mean total clearance of quinine was decreased (approximately 0.09 L/hour per kg) during the acute phase of the infection and increased (approximately 0.16 L/hour per kg) during the recovery or convalescent phase.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

Following oral administration of a single 600-mg dose of quinine sulfate in geriatric and younger adults, the mean clearance of the drug was decreased (0.06 versus 0.08 L/hour per kg) and the mean elimination half-life was significantly increased (18.4 versus 10.5 hours) in geriatric adults compared with younger adults. Although renal clearance of quinine was similar in geriatric and younger adults, geriatric adults excreted a larger proportion of the dose in urine as unchanged drug compared with younger adults (16.6 versus 11.2%). The steady-state pharmacokinetics after a quinine sulfate dosage of 648 mg 3 times daily for 7 days were similar in healthy geriatric adults 65-78 years of age and healthy younger adults 20-39 years of age; however, the mean elimination half-life was 24 hours in the geriatric individuals compared with 20 hours in the younger adults.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

Following oral administration of a single dose of 10 mg/kg of quinine sulfate in healthy children or pediatric patients 1.5-12 years of age with uncomplicated Plasmodium falciparum malaria, the mean total clearance (0.06 versus 0.3 L/hour per kg) is reduced and the plasma elimination half-life increased (12.1 versus 3.21 hours) in pediatric patients with malaria as compared to that observed in healthy children.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

In 15 patients with uncomplicated malaria who received a 10 mg/kg oral dose of quinine sulfate, the mean total clearance of quinine was slower (approximately 0.09 L/hr/kg) during the acute phase of the infection, and faster (approximately 0.16 L/hr/kg) during the recovery or convalescent phase.

For more Absorption, Distribution and Excretion (Complete) data for QUININE (19 total), please visit the HSDB record page.

5.2 Metabolism/Metabolites

In vitro studies using human liver microsomes and recombinant P450 enzymes have shown that quinine is metabolized mainly by CYP3A4. Depending on the in vitro experimental conditions, other enzymes, including CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP2E1 were shown to have some role in the metabolism of quinine.

Quinine is metabolized almost exclusively via hepatic oxidative cytochrome P450 (CYP) pathways, resulting in four primary metabolites, 3-hydroxyquinine, 2'-quinone, O-desmethylquinine, and 10,11-dihydroxydihydroquinine. Six secondary metabolites result from further biotransformation of the primary metabolites. The major metabolite, 3-hydroxyquinine, is less active than the parent drug.

5.3 Biological Half-Life

Compared with administration of quinine alone, administration of a single 600-mg dose of quinine sulfate in healthy individuals who were receiving ritonavir (200 mg every 12 hours) resulted in an increased quinine mean elimination half-life (11.2 hours versus 13.4 hours).

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

The plasma elimination half-life of quinine reportedly averages 8-21 hours in adults with malaria and 7-12 hours in healthy or convalescing adults.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

The steady-state pharmacokinetics after a quinine sulfate dosage of 648 mg 3 times daily for 7 days were similar in healthy geriatric adults 65-78 years of age and healthy younger adults 20-39 years of age; however, the mean elimination half-life was 24 hours in the geriatric individuals compared with 20 hours in the younger adults.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

In children 1-12 years of age, the plasma elimination half-life of quinine reportedly averages 11-12 hours in those with malaria and 6 hours in those convalescing from the disease.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

At toxic levels elimination half life is reported to be 26.5 + or - 5.8 hrs.

IPCS; UK Poison Information Documents (UKPID) for Quinine (Last updated March 1996). Available from, as of November 20, 2014: https://www.inchem.org/pages/ukpids.html

5.4 Mechanism of Action

Quinine has a local anesthetic action and analgesic, antipyretic, and oxytocic effects. Quinine also has cardiovascular effects similar to those of quinidine.

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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ACTIVE PHARMA INGREDIENTS

17 API Suppliers

7 USDMF

4 CEP/COS

4 EU WC

6 NDC API

7 Listed Suppliers

$ API Reference Price

FINISHED DOSAGE FORMULATIONS

32 FDF Dossiers

6 FDA Orange Book

3 Europe

5 Canada

1 Australia

3 South Africa

14 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc

4 SPI Pharma

8 DKSH

1 Pharm-RX Chemical

7 Faran Shimi Pharmaceutical

1 Boai NKY Pharmaceuticals Ltd

12 Gangwal Healthcare

1 Nanjing Well Pharmaceutical

1 Pfanstiehl

4 ACG Worldwide

3 Actylis

1 Aeon Procare

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

17 BASF

1 Bioplus Life Sciences

3 DFE Pharma

1 Finar

7 Gangwal Chemicals

1 Ideal Cures Pvt Ltd

3 Ingredion Pharma Solutions

7 Kerry

3 Lonza Capsugel

11 Microlex e.U

1 Novo Excipients

2 Pharmatrans-Sanaq

9 Pluviaendo

3 Prachin Chemical

1 Qualicaps

19 Roquette

2 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

10 Sigachi Industries

1 Valens Pharmachem

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

49 Fillers, Diluents & Binders

26 Direct Compression

21 Thickeners and Stabilizers

19 Disintegrants & Superdisintegrants

18 Lubricants & Glidants

18 Coating Systems & Additives

17 Granulation

13 Co-Processed Excipients

12 Taste Masking

12 Controlled & Modified Release

10 Film Formers & Plasticizers

8 Solubilizers

8 Parenteral

8 Empty Capsules

6 Topical

5 Chewable & Orodispersible Aids

4 Emulsifying Agents

3 Coloring Agents

2 Rheology Modifiers

2 API Stability Enhancers

1 Surfactant & Foaming Agents

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