QI9

Quinine

Created:	2014-10-15
Last modified:	2020-06-05

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5 entries where QI9 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	48
Chiral Atom Count	5
Bond Count	51
Aromatic Bond Count	11

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Chemical Component Summary
Name	Quinine
Synonyms	(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol
Systematic Name (OpenEye OEToolkits)	(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Formula	C₂₀ H₂₄ N₂ O₂
Molecular Weight	324.417
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O(c4cc1c(nccc1C(O)C2N3CCC(C2)C(/C=C)C3)cc4)C
SMILES	CACTVS	3.385	COc1ccc2nccc([CH](O)[CH]3C[CH]4CC[N]3C[CH]4C=C)c2c1
SMILES	OpenEye OEToolkits	1.9.2	COc1ccc2c(c1)c(ccn2)C(C3CC4CCN3CC4C=C)O
Canonical SMILES	CACTVS	3.385	COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)c2c1
Canonical SMILES	OpenEye OEToolkits	1.9.2	COc1ccc2c(c1)c(ccn2)[C@H]([C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O
InChI	InChI	1.03	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	InChI	1.03	LOUPRKONTZGTKE-WZBLMQSHSA-N

Drug Info: DrugBank

DrugBank ID	DB00468
Name	Quinine
Groups	approved
Description	An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.
Synonyms	6'-Methoxycinchonidine Quinina Quinine hydrochloride (R)-(−)-quinine Chinin (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol Chininum Quinine (-)-Quinine (8S,9R)-quinine Quinine phosphate Quinine sulfate Chinine Quinine citrate (−)-quinine
Brand Names	Qualaquin Apo-quinine Quinine Sulfate Cap 300mg Quinine Sulfate Quinine Sulfate Capsules 300mg Jamp-quinine Pro-quinine - 200 Quinine - Odan Teva-quinine Quinine Sulfate Cap 200mg Pro-quinine - 300 Quinine Sulfate Capsules 200mg
Indication	For the treatment of malaria and leg cramps
Categories	Agents that produce neuromuscular block (indirect) Agents that reduce seizure threshold Alkaloids Analgesics Analgesics, Non-Narcotic Anti-Infective Agents Antimalarial methanolquinolines Antimalarials Antiparasitic Agents Antiparasitic Products, Insecticides and Repellents Antiprotozoals Blood Glucose Lowering Agents Central Nervous System Agents Central Nervous System Depressants Cinchona Alkaloids Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (strength unknown) Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Herbs (Hypotensive Properties) Heterocyclic Compounds, Fused-Ring Highest Risk QTc-Prolonging Agents Hypoglycemia-Associated Agents Methemoglobinemia Associated Agents Muscle Relaxants Muscle Relaxants, Centrally Acting Agents Musculo-Skeletal System Neuromuscular Agents OATP1B1/SLCO1B1 Inhibitors OCT1 inhibitors OCT1 substrates OCT2 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Peripheral Nervous System Agents QTc Prolonging Agents Quinolines Quinuclidines Sensory System Agents
ATC-Code	M09AA72 P01BC01
CAS number	130-95-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Fe(II)-protoporphyrin IX	-	unknown	antagonist
Platelet glycoprotein IX	MPAWGALFLLWATAEATKDCPSPCTCRALETMGLWVDCRGHGLTALPALP...	unknown	other
Intermediate conductance calcium-activated potassium channel protein 4	MGGDLVLGLGALRRRKRLLEQEKSLAGWALVLAGTGIGLMVLHAEMLWFG...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor,inducer
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	inhibitor,inducer
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate,inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate,inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	substrate,inhibitor
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
Solute carrier family 22 member 4	MRDYDEVIAFLGEWGPFQRLIFFLLSASIIPNGFNGMSVVFLAGTPEHRC...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682