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Details

Stereochemistry ACHIRAL
Molecular Formula C22H24N4O2
Molecular Weight 376.4516
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIRFENTANIL

SMILES

O=C(N(C1CCN(CCC2=CC=CC=C2)CC1)C3=NC=CN=C3)C4=CC=CO4

InChI

InChIKey=BJZZDOLVVLWFHN-UHFFFAOYSA-N
InChI=1S/C22H24N4O2/c27-22(20-7-4-16-28-20)26(21-17-23-11-12-24-21)19-9-14-25(15-10-19)13-8-18-5-2-1-3-6-18/h1-7,11-12,16-17,19H,8-10,13-15H2

HIDE SMILES / InChI

Molecular Formula C22H24N4O2
Molecular Weight 376.4516
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Mirfentanil was developed as CNS analgesic with a short duration of action. It induced antinociception predominately through mu opioid receptors. It was shown that at doses larger than those, which exert opioid effects, mirfentanil had nonopioid analgesic effects. The drug was successfully encapsulated in liposomes having a variety of compositions. The lipid composition of the formulation was varied to optimize the stabilization of liposomes and the encapsulation of solutes. Mirfentanil participated in phase II clinical trials for the treatment of pain. However, this study was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9MYW9
Gene ID: 574141.0
Gene Symbol: OPRM1
Target Organism: Macaca mulatta (Rhesus macaque)
PubMed

PubMed

TitleDatePubMed
Mirfentanil: pharmacological profile of a novel fentanyl derivative with opioid and nonopioid effects.
1991 Aug
Mirfentanil antagonizes morphine-induced suppression of splenic NK activity in mice.
1996 Aug
Mirfentanil and A-4334: Tritiation at high specific activity.
2010 Jan
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:15:42 UTC 2023
Edited
by admin
on Thu Jul 06 02:15:42 UTC 2023
Record UNII
Q2U943H24P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIRFENTANIL
INN  
INN  
Official Name English
N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-N-2-PYRAZINYL-2-FURANCARBOXAMIDE
Systematic Name English
OHM 10579
Code English
MIRFENTANYL
Common Name English
A 3508
Code English
mirfentanil [INN]
Common Name English
MS 32 (RECEPTOR BINDER)
Code English
2-FURANCARBOXAMIDE, N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-N-2-PYRAZINYL-
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
Code System Code Type Description
EVMPD
SUB08988MIG
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
CAS
117523-47-4
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
FDA UNII
Q2U943H24P
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL161084
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
SMS_ID
100000080644
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
NCI_THESAURUS
C174864
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID10151799
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
WEB RESOURCE
MIRFENTANIL
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
INN
6690
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
WIKIPEDIA
MIRFENTANIL
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY Mirfentanil, at high doses, exhibits analgesic activity which is not fully reversed by opioid antagonists, suggesting that the drug has both opioid and non-opioid mechanisms of action. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.
MESH
C069209
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
PUBCHEM
60698
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
DRUG BANK
DB09175
Created by admin on Thu Jul 06 02:15:42 UTC 2023 , Edited by admin on Thu Jul 06 02:15:42 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY