Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H27FN2O2 |
Molecular Weight | 370.4604 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(F)C=CC=C3
InChI
InChIKey=NYISTOZKVCMVEL-UHFFFAOYSA-N
InChI=1S/C22H27FN2O2/c1-27-17-22(26)25(21-10-6-5-9-20(21)23)19-12-15-24(16-13-19)14-11-18-7-3-2-4-8-18/h2-10,19H,11-17H2,1H3
Ocfentanil, a compound structurally similar to the opioid analgesic fentanyl, was developed in the early 1990’s with the hope that it would provide a better clinical safety profile than fentanyl. The receptor pharmacology of ocfentanil appears to share pharmacodynamic effects with fentanyl and other μ opioid agonists, including analgesia, sedation, and respiratory depression. In rodents, ocfentanil was approximately 2.5 times more potent as an analgesic than fentanyl and had a shorter duration of action. Because the preclinical research suggested that ocfentanil had a better safety profile than fentanyl, it was selected for clinical evaluation. Like other μ opioid agonists, ocfentanil has been reported to produce itching, nausea, sedation, and severe respiratory depression. Chest pain, psychosis, and agitation have also been reported. In humans, however, ocfentanil had a similar potency (3 ug/kg ocfentanil produced effects that were comparable to 5 ug/kg fentanyl) and side-effects profile as fentanyl so further clinical development was discontinued. Ocfentanil is not approved in any country for medical useand is under national control in Canada, the United Kingdom, and China.
Approval Year
Sample Use Guides
Ocfentanil was evaluated as a supplement to anesthesia in a study involving 60 patients who were 18-65 years of age and undergoing elective surgery. Intravenous doses of 1, 3, and 5 ug/kg ocfentanil were compared to 5 ug/kg fentanyl. Under these conditions, the 3 ug/kg dose of ocfentanil produced effects (analgesia and sedation) that were comparable to 5 ug/kg fentanyl.
Route of Administration:
Intravenous
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DEA NO. |
9838
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WIKIPEDIA |
List_of_fentanyl_analogues
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NCI_THESAURUS |
C67413
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101343-69-5
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C84024
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60575
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100000083857
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OCFENTANIL
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PRIMARY | In human volunteers ocfentanil induces effective analgesia at 1 .MU.g/kg, while in doses up to 3 .MU.g/kg, analgesia and respiratory depression occurred in a dose-dependent manner. While a further study suggests that ocfentanil may be as effective as morphine in post-operative relief,(4) Ocfentanil was also studied as a supplement to general anaesthesia, in which the researchers concluded that it appears to be similar in action to fentanyl, with 3 .MU.g/kg of ocfentanil approximately equivalent to 5 .MU.g/kg of fentanyl. | ||
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DTXSID00869356
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MX52WBC8EV
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C071395
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SUB09396MIG
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CHEMBL2110917
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6448
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OCFENTANIL
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)