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Details

Stereochemistry ACHIRAL
Molecular Formula C22H27FN2O2.ClH
Molecular Weight 406.921
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OCFENTANIL HYDROCHLORIDE

SMILES

Cl.COCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=C(F)C=CC=C3

InChI

InChIKey=IUZMSSDQGOBJTG-UHFFFAOYSA-N
InChI=1S/C22H27FN2O2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C22H27FN2O2
Molecular Weight 370.4604
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil.
2018
Fatality involving ocfentanil documented by identification of metabolites.
2018 Jun
Patents

Patents

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:31:14 UTC 2023
Edited
by admin
on Fri Dec 15 15:31:14 UTC 2023
Record UNII
Z8T88FVW9V
Record Status Validated (UNII)
Record Version
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Name Type Language
OCFENTANIL HYDROCHLORIDE
USAN  
USAN  
Official Name English
OCFENTANIL HCL
Common Name English
A-3217
Code English
2'-FLUORO-2-METHOXY-N-(1-PHENETHYL)-4-PIPERIDYL)ACETANILIDE MONOHYDROCHLORIDE
Common Name English
OCFENTANIL HYDROCHLORIDE [USAN]
Common Name English
ACETAMIDE, N-(2-FLUOROPHENYL)-2-METHOXY-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-, MONOHYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID201037476
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
PUBCHEM
9931207
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
SMS_ID
300000047462
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110917
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
FDA UNII
Z8T88FVW9V
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
CAS
112964-97-3
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
MESH
C071395
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
NCI_THESAURUS
C76850
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
USAN
AA-61
Created by admin on Fri Dec 15 15:31:14 UTC 2023 , Edited by admin on Fri Dec 15 15:31:14 UTC 2023
PRIMARY
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