Drug Information

General Information
Drug ID
DR00054
Drug Name
Quinine
Synonyms
(+)-Quinidine; (-)-Quinine; (1R)-(6-Methoxyquinolin-4-yl)((1S,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (3A,8A,9r)-6'-methoxycinchonan-9-ol; (5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol; (8-alpha,9R)-6'-Methoxycinchonan-9-ol; (8.alpha.,9R)-6'-Methoxycinchonan-9-ol; (8S,9R)-6'-Methoxycinchonan-9-ol; (8S,9R)-Quinine; (9R)-6'-methoxy-8alpha-cinchonan-9-ol; (R)-(-)-Quinine, 6-methoxycinchonidine; (R)-(-)-quinine; (R)-(6-Methoxy-quinolin-4-yl)-((2S,5S)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol; (R)-[(2S,4R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; (R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; (S)-(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methanol; (S)-[(2R,4R,5S)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; 6'-Methoxycinchonan-9-ol; 6'-Methoxycinchonidine; 6'-Methoxycinchonine; 6-Methoxycinchonine; Aflukin; Alpha-(6-Methoxy-4-quinoyl)-5-vinyl-2-quinclidinemethanol; Beta-Quinine; Biquinate (*Bisulfate heptathydrate*); Chinin; Chinin [German]; Chinine; Chininum; Cin-Quin; Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-, sulfate; Coco-Quinine; Conchinin; Conquinine; Dentojel (*Bisulfate heptathydrate*); IBS-L0034250; Kinder Quinina; Kinder Quinina (TN); LT00645788;Q0028; Legatrin (TN); QUININE MONO HCL; Quinamm (*2:1 Sulfate salt*), dihydrate; Quindan; Quine (*2:1 Sulfate salt*, dihydrate); Quinidex; Quinidine; Quinimax; Quinina; Quinine (BAN); Quinine Dab; Quinine [BAN]; Quinine anhydrous; Quinine bisulfate; Quinine sulfate; Quinine sulphate; Quinine, Anhydrous; Quinine, polymers; Quinine, tannate; Quinineanhydrous; Quinoline alkaloid; Quinora; Quinsan (*2:1 Sulfate salt*), dihydrate; Quniacridine; SB01652
Drug Type
Small molecular drug
Indication Malaria [ICD11:1F40] Approved [1]
Therapeutic Class
Antimalarials
Structure
3D MOL 2D MOL
Formula
C20H24N2O2
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
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
InChIKey
LOUPRKONTZGTKE-WZBLMQSHSA-N
CAS Number
CAS 130-95-0
Pharmaceutical Properties Molecular Weight 324.4 Topological Polar Surface Area 45.6
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
XLogP
2.9
PubChem CID
3034034
PubChem SID
10047893 ,103401549 ,104014717 ,104179003 ,111635622 ,117498515 ,126609105 ,127305362 ,127305363 ,127305364 ,127305365 ,127305366 ,127305367 ,127305368 ,127305369 ,127305370 ,128520104 ,128520105 ,134973208 ,135231014 ,135652709 ,136076620 ,136202233 ,136904085 ,137019039 ,137224223 ,139072192 ,142847474 ,14797229 ,152164544 ,152248148 ,160846349 ,162178599 ,162202314 ,162224671 ,29204524 ,44424807 ,46507493 ,49681219 ,50077764 ,56480783 ,57309160 ,598422 ,7980452 ,80217992 ,8145105 ,83100521 ,87623901 ,92308761 ,92310322
ChEBI ID
ChEBI:15854
TTD Drug ID
D03DDR
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
2-Oct Transporter Info Organic cation transporter 2 Substrate [3]
BGT1 Transporter Info Na(+)/Cl(-) betaine/GABA transporter Substrate [4]
OCTN1 Transporter Info Organic cation/carnitine transporter 1 Substrate [5]
OCTN2 Transporter Info Organic cation/carnitine transporter 2 Substrate [6]
P-GP Transporter Info P-glycoprotein 1 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 2-Oct Transporter Info Km =2.6 microM Oocytes-OCT2 [3]
P-GP Transporter Info Km =10 microM Chinese hamster ovary AA8 cells-MDR1 [8]
P-GP Transporter Info Km =5.42 microM High five cells-MDR1 [9]
References
1 Quinine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
3 Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81.
4 The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 2.A.22.3.1)
5 Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73.
6 Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84.
7 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
8 Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71.
9 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.

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