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

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
Structure of OCFENTANIL

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

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

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
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 Thu Jul 06 00:08:54 UTC 2023
Edited
by admin
on Thu Jul 06 00:08:54 UTC 2023
Record UNII
MX52WBC8EV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OCFENTANIL
INN  
INN  
Official Name English
N-(2-FLUOROPHENYL)-2-METHOXY-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)ACETAMIDE
Systematic Name English
2'-FLUORO-2-METHOXY-N-(1-PHENETHYL)-4-PIPERIDYL)ACETANILIDE
Common Name English
ACETAMIDE, N-(2-FLUOROPHENYL)-2-METHOXY-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-
Systematic Name English
OCFENTANYL
Common Name English
ocfentanil [INN]
Common Name English
A 3217
Code English
Classification Tree Code System Code
DEA NO. 9838
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
NCI_THESAURUS C67413
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
Code System Code Type Description
CAS
101343-69-5
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
NCI_THESAURUS
C84024
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
PUBCHEM
60575
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
SMS_ID
100000083857
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
WIKIPEDIA
OCFENTANIL
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
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.
EPA CompTox
DTXSID00869356
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
FDA UNII
MX52WBC8EV
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
MESH
C071395
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
EVMPD
SUB09396MIG
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110917
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
INN
6448
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
WEB RESOURCE
OCFENTANIL
Created by admin on Thu Jul 06 00:08:54 UTC 2023 , Edited by admin on Thu Jul 06 00:08:54 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY