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Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N2O
Molecular Weight 336.4705
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENTANYL

SMILES

CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3

InChI

InChIKey=PJMPHNIQZUBGLI-UHFFFAOYSA-N
InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3

HIDE SMILES / InChI

Molecular Formula C22H28N2O
Molecular Weight 336.4705
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fentanyl is a potent agonist of mu opioid receptor. It is used to relieve severe pain, such as after surgery or during cancer treatment, and breakthrough pain (flare-ups of intense pain despite round-the-clock narcotic treatment). Fentanyl is an extremely powerful analgesic, 50–100-times more potent than morphine. Fentanyl harbors massive risk for addiction and abuse regardless of its prescription form. Fentanyl abuse is especially dangerous to those without a tolerance to opioids. The substance’s already elevated risk of overdose is multiplied when someone without a tolerance abuses it.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.15 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DURAGESIC-100

Cmax

ValueDoseCo-administeredAnalytePopulation
0.91 ng/mL
100 μg single, intravenous
FENTANYL plasma
Homo sapiens
0.61 ng/mL
400 μg single, oral transmucosal
FENTANYL plasma
Homo sapiens
0.81 ng/mL
400 μg single, sublingual
FENTANYL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.76 ng × h/mL
100 μg single, intravenous
FENTANYL plasma
Homo sapiens
4.18 ng × h/mL
400 μg single, oral transmucosal
FENTANYL plasma
Homo sapiens
5.76 ng × h/mL
400 μg single, sublingual
FENTANYL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.5 h
100 μg single, intravenous
FENTANYL plasma
Homo sapiens
7.9 h
400 μg single, oral transmucosal
FENTANYL plasma
Homo sapiens
10 h
400 μg single, sublingual
FENTANYL plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Dosage should be individualized. Some of the factors to be considered in determining the dose are age, body weight, physical status, underlying pathological condition, use of other drugs, type of anesthesia to be used and the surgical procedure involved. Dosage should be reduced in elderly or debilitated patients (see PRECAUTIONS). Vital signs should be monitored routinely. I. Premedication — Premedication (to be appropriately modified in the elderly, debilitated and those who have received other depressant drugs) — 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly 30 to 60 minutes prior to surgery. II. Adjunct to General Anesthesia — See Dosage Range Chart III. Adjunct to Regional Anesthesia - 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly or slowly intravenously, over one to two minutes, when additional analgesia is required. IV. Postoperatively (recovery room) - 50 to 100 mcg (0.05 to 0.1 mg) (1 to 2 mL) may be administered intramuscularly for the control of pain, tachypnea and emergence delirium. The dose may be repeated in one to two hours as needed
Route of Administration: Other
In Vitro Use Guide
0.5 - 5 ng/ml fentanyl inhibited viability of SW1990 cells in vitro.
Substance Class Chemical
Record UNII
UF599785JZ
Record Status Validated (UNII)
Record Version