U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H27NO
Molecular Weight 285.4238
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPREFADOL

SMILES

[H][C@@]12CCCC[C@]1(CCN(CC3CC3)C2)C4=CC(O)=CC=C4

InChI

InChIKey=KFIQKMINEHFZSM-HKUYNNGSSA-N
InChI=1S/C19H27NO/c21-18-6-3-5-16(12-18)19-9-2-1-4-17(19)14-20(11-10-19)13-15-7-8-15/h3,5-6,12,15,17,21H,1-2,4,7-11,13-14H2/t17-,19-/m0/s1

HIDE SMILES / InChI
Ciprefadol is an opioid analgesic drug. It binds with a high affinity to mu (Ki 4.2 nM) and kappa (Ki 2.5 nM) opioid receptors. In vivo, ciprefadol displays mixed antagonist/agonist activity in the mouse writhing and the rat tail heat tests: in low doses, the compound inhibits the analgesic effect of morphine, while at higher doses it displays analgesic effect. Chronic administration of ciprefadol to rhesus monkeys produced a marked physical dependence more severe than that of morphine, and its effect was consistent with what would be expected of a potent, long-lasting morphine-like agonist.

Approval Year

Name Type Language
CIPREFADOL
INN  
INN  
Official Name English
PHENOL, 3-((4AR,8AR)-2-(CYCLOPROPYLMETHYL)OCTAHYDRO-4A(2H)-ISOQUINOLINYL)-
Common Name English
(-)-M-(2-(CYCLOPROPYLMETHYL)-1,3,4,5,6,7,8,8A.ALPHA.-OCTAHYDRO-4A.BETA.(2H)-ISOQUINOLYL)PHENOL
Common Name English
ciprefadol [INN]
Common Name English
PHENOL, 3-(2-(CYCLOPROPYLMETHYL)OCTAHYDRO-4A(2H)-ISOQUINOLINYL-, TRANS, (-)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
Code System Code Type Description
EVMPD
SUB07467MIG
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
PRIMARY
INN
4454
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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ChEMBL
CHEMBL2111073
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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SMS_ID
100000081539
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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WIKIPEDIA
Ciprefadol
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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CAS
59889-36-0
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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NCI_THESAURUS
C79933
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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EPA CompTox
DTXSID00208605
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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FDA UNII
L6RFK0CJ8K
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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PUBCHEM
333483
Created by admin on Fri Dec 15 16:09:16 GMT 2023 , Edited by admin on Fri Dec 15 16:09:16 GMT 2023
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