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130-95-0 molecular structure
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(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

ChemBase ID: 351
Molecular Formular: C20H24N2O2
Molecular Mass: 324.41676
Monoisotopic Mass: 324.18377802
SMILES and InChIs

SMILES:
O[C@@H]([C@H]1N2C[C@@H](C(C1)CC2)C=C)c1c2c(ncc1)ccc(OC)c2
Canonical SMILES:
C=C[C@H]1CN2CCC1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)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-VOMFEXJBSA-N

Cite this record

CBID:351 http://www.chembase.cn/molecule-351.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(R)-[(2S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
IUPAC Traditional name
quinine
Brand Name
Aflukin
Chinin
Chinine
Coco-Quinine
None
Quinine Dab
Synonyms
6'-Methoxycinchonidine
6'-Methoxycinchonine
Quinine, Anhydrous
Quinineanhydrous
Quinoline Alkaloid
Quinine sulfate
Quinine
(1R)-(6-methoxyquinolin-4-yl)((2S,5R)-5-vinylquinuclidin-2-yl)methanol
CAS Number
130-95-0
PubChem SID
160963814
PubChem CID
8549

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
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CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.892048  H Acceptors
H Donor LogD (pH = 5.5) -0.7213722 
LogD (pH = 7.4) 0.863951  Log P 2.513464 
Molar Refractivity 94.6936 cm3 Polarizability 38.350784 Å3
Polar Surface Area 45.59 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.82  LOG S -2.99 
Solubility (Water) 3.34e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
500 mg/L expand Show data source
Hydrophobicity(logP)
2.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00468 external link
Item Information
Drug 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. [PubChem]
Indication For the treatment of malaria and leg cramps
Pharmacology Quinine is used parenterally to treat life-threatening infections caused by chloroquine-resistant Plasmodium falciparum malaria. Quinine acts as a blood schizonticide although it also has gametocytocidal activity against P. vivax and P. malariae. Because it is a weak base, it is concentrated in the food vacuoles of P. falciparum. It is thought to act by inhibiting heme polymerase, thereby allowing accumulation of its cytotoxic substrate, heme. As a schizonticidal drug, it is less effective and more toxic than chloroquine. However, it has a special place in the management of severe falciparum malaria in areas with known resistance to chloroquine.
Toxicity Quinine is a documented causative agent of drug induced thrombocytopenia (DIT). Thrombocytopenia is a low amount of platelets in the blood. Quinine induces production of antibodies against glycoprotein (GP) Ib-IX complex in the majority of cases of DIT, or more rarely, the platelet-glycoprotein complex GPIIb-IIIa. Increased antibodies against these complexes increases platelet clearance, leading to the observed thrombocytopenia.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic, over 80% metabolized by the liver.
Absorption 76 - 88%
Half Life Approximately 18 hours
Protein Binding Approximately 70%
Elimination Quinine is eliminated primarily via hepatic biotransformation. Approximately 20% of quinine is excreted unchanged in urine.
Distribution * 1.43 ± 0.18 L/kg [Healthy Pediatric Controls]
* 0.87 ± 0.12 L/kg [P. falciparum Malaria Pediatric Patients]
* 2.5 to 7.1 L/kg [healthy subjects who received a single oral 600 mg dose]
Clearance * 0.17 L/h/kg [healthy]
* 0.09 L/h/kg [patients with uncomplicated malaria]
* 18.4 L/h [healthy adult subjects with administration of multiple-dose activated charcoal]
* 11.8 L/h [healthy adult subjects without administration of multiple-dose activated charcoal]
* Oral cl=0.06 L/h/kg [elderly subjects]
References
Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23. [Pubmed]
External Links
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REFERENCES

REFERENCES

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  • • Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23. Pubmed
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