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

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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.addictioncenter.com/painkillers/fentanyl/ | https://www.ncbi.nlm.nih.gov/pubmed/24635521

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.15 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DURAGESIC-100

Approved Use

Fentanyl transdermal system is a transdermal formulation of fentanyl indicated for the management of persistent, moderate to severe chronic pain in opioid-tolerant patients 2 years of age and older when a continuous, around-the-clock opioid analgesic is required for an extended period of time, and the patient cannot be managed by other means such as non-steroidal analgesics, opioid combination products, or immediate-release opioids. Patients considered opioid-tolerant are those who are taking at least 60 mg of morphine daily, or at least 30 mg of oral oxycodone daily, or at least 8 mg of oral hydromorphone daily, or an equianalgesic dose of another opioid for a week or longer. Fentanyl transdermal system contains fentanyl, a full opioid agonist. Fentanyl transdermal system is indicated for the management of persistent, moderate to severe chronic pain in opioid‑tolerant patients 2 years of age and older when a continuous, around-the-clock opioid analgesic is needed for an extended period of time. (1) Fentanyl transdermal system is NOT intended for use as an as-needed analgesic. (1)

Launch Date

6.4998723E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.91 ng/mL
100 μg single, intravenous
dose: 100 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.61 ng/mL
400 μg single, oral transmucosal
dose: 400 μg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.81 ng/mL
400 μg single, sublingual
dose: 400 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.76 ng × h/mL
100 μg single, intravenous
dose: 100 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.18 ng × h/mL
400 μg single, oral transmucosal
dose: 400 μg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.76 ng × h/mL
400 μg single, sublingual
dose: 400 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.5 h
100 μg single, intravenous
dose: 100 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.9 h
400 μg single, oral transmucosal
dose: 400 μg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
10 h
400 μg single, sublingual
dose: 400 μg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
FENTANYL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Disc. AE: Apnea, Respiratory depression...
AEs leading to
discontinuation/dose reduction:
Apnea
Respiratory depression
Bradypnea
Tachycardia
Diaphoresis
Sources: Page: p.463
150 ug 1 times / hour multiple, transdermal
Overdose
Dose: 150 ug, 1 times / hour
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / hour
Sources:
unknown, 31
n = 1
Health Status: unknown
Age Group: 31
Sex: M
Population Size: 1
Sources:
Disc. AE: Respiratory arrest...
AEs leading to
discontinuation/dose reduction:
Respiratory arrest (grade 5)
Sources:
225 ug 1 times / hour multiple, transdermal
Overdose
Dose: 225 ug, 1 times / hour
Route: transdermal
Route: multiple
Dose: 225 ug, 1 times / hour
Sources: Page: p.51
unhealthy, 32
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 32
Sex: F
Population Size: 1
Sources: Page: p.51
Disc. AE: Syncope, Acute coronary syndrome...
AEs leading to
discontinuation/dose reduction:
Syncope
Acute coronary syndrome
Sources: Page: p.51
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 14
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 14
Other AEs: Hypoxia, Nausea...
Other AEs:
Hypoxia (50%)
Nausea (75%)
Sources: Page: p.13, 14
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 15
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 15
Other AEs: Somnolence...
Other AEs:
Somnolence (87.5%)
Sources: Page: p.13, 15
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 16
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 16
Other AEs: Vomiting...
Other AEs:
Vomiting (50%)
Sources: Page: p.13, 16
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Disc. AE: Somnolence, Dizziness...
AEs leading to
discontinuation/dose reduction:
Somnolence (3%)
Dizziness (3%)
Hallucinations (1.5%)
Dry mouth (1.5%)
Headache (1.5%)
Nausea (1.5%)
Vomiting (1.5%)
Sources: Page: p.309
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Disc. AE: Confusion, Restlessness...
AEs leading to
discontinuation/dose reduction:
Confusion (acute)
Restlessness (mild)
Visual hallucinations
Sweating
Miosis
Sources: Page: p.199
200 ug 6 times / day multiple, sublingual
Recommended
Dose: 200 ug, 6 times / day
Route: sublingual
Route: multiple
Dose: 200 ug, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain
Sources: Page: p.1
Disc. AE: Respiratory depression, Opioid abuse...
AEs leading to
discontinuation/dose reduction:
Respiratory depression (grade 4)
Opioid abuse
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Apnea Disc. AE
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Bradypnea Disc. AE
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Diaphoresis Disc. AE
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Respiratory depression Disc. AE
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Tachycardia Disc. AE
6 mg single, transdermal (total)
Overdose
Dose: 6 mg
Route: transdermal
Route: single
Dose: 6 mg
Sources: Page: p.463
healthy, 15
n = 1
Health Status: healthy
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.463
Respiratory arrest grade 5
Disc. AE
150 ug 1 times / hour multiple, transdermal
Overdose
Dose: 150 ug, 1 times / hour
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / hour
Sources:
unknown, 31
n = 1
Health Status: unknown
Age Group: 31
Sex: M
Population Size: 1
Sources:
Acute coronary syndrome Disc. AE
225 ug 1 times / hour multiple, transdermal
Overdose
Dose: 225 ug, 1 times / hour
Route: transdermal
Route: multiple
Dose: 225 ug, 1 times / hour
Sources: Page: p.51
unhealthy, 32
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 32
Sex: F
Population Size: 1
Sources: Page: p.51
Syncope Disc. AE
225 ug 1 times / hour multiple, transdermal
Overdose
Dose: 225 ug, 1 times / hour
Route: transdermal
Route: multiple
Dose: 225 ug, 1 times / hour
Sources: Page: p.51
unhealthy, 32
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 32
Sex: F
Population Size: 1
Sources: Page: p.51
Hypoxia 50%
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 14
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 14
Nausea 75%
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 14
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 14
Somnolence 87.5%
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 15
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 15
Vomiting 50%
800 ug single, sublingual
Higher than recommended
Dose: 800 ug
Route: sublingual
Route: single
Dose: 800 ug
Sources: Page: p.13, 16
healthy, 33.4
n = 8
Health Status: healthy
Age Group: 33.4
Sex: M+F
Population Size: 8
Sources: Page: p.13, 16
Dry mouth 1.5%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Hallucinations 1.5%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Headache 1.5%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Nausea 1.5%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Vomiting 1.5%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Dizziness 3%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Somnolence 3%
Disc. AE
1600 ug 1 times / 15 min multiple, sublingual (max)
Highest studied dose
Dose: 1600 ug, 1 times / 15 min
Route: sublingual
Route: multiple
Dose: 1600 ug, 1 times / 15 min
Sources: Page: p.309
unhealthy, 53±12
n = 65
Health Status: unhealthy
Condition: Pain
Age Group: 53±12
Sex: M+F
Population Size: 65
Sources: Page: p.309
Miosis Disc. AE
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Sweating Disc. AE
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Visual hallucinations Disc. AE
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Confusion acute
Disc. AE
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Restlessness mild
Disc. AE
5 mg single, intravenous
Accidental dose
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources: Page: p.199
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Pain
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.199
Opioid abuse Disc. AE
200 ug 6 times / day multiple, sublingual
Recommended
Dose: 200 ug, 6 times / day
Route: sublingual
Route: multiple
Dose: 200 ug, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain
Sources: Page: p.1
Respiratory depression grade 4
Disc. AE
200 ug 6 times / day multiple, sublingual
Recommended
Dose: 200 ug, 6 times / day
Route: sublingual
Route: multiple
Dose: 200 ug, 6 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pain
Sources: Page: p.1
OverviewDrug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
major
yes (co-administration study)
Comment: Rate: 61 pmol/min/mg protein; Activity (Fentanyl): 1.03 nmol/min/nmol CYP (Biochem Pharmacol, 53, 1613 (1997)); Coadministartion of Ritonavir (strong CYP3A inhibitor, PO) increased Fentanyl (IV) AUCinf by 2.74-fold.
Page: (Pharm) 17, 28, (PMDA) 17
minor
minor
minor
minor
no
no
no
yes
yes
yes
yes
yes
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Epidural analgesia in children with cerebral palsy.
1998 Dec
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine.
1999 Oct
Long-lasting hyperalgesia induced by fentanyl in rats: preventive effect of ketamine.
2000 Feb
Inhibition by neuropeptide Y of fentanyl-induced muscular rigidity at the locus coeruleus in rats.
2000 Feb 25
An assessment of the safety, efficacy, and acceptability of intranasal fentanyl citrate in the management of cancer-related breakthrough pain: a pilot study.
2000 Oct
Computerised advice on drug dosage to improve prescribing practice.
2001
Thoracic epidural anesthesia combined with general anesthesia: the preferred anesthetic technique for thoracic surgery.
2001 Apr
[Epileptogenic drugs in anesthesia].
2001 Feb
Comparison of the effects of clonidine and hydroxyzine on haemodynamic and catecholamine reactions to microlaryngoscopy.
2001 Feb
When should diclofenac be given in ambulatory surgery: preoperatively or postoperatively?
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
2001 Feb
[Anesthetic management of two patients with insulinoma using propofol--in association with rapid radioimmunoassay for insulin].
2001 Feb
A randomized prospective comparative study of general versus epidural anesthesia for transcervical hysteroscopic endometrial resection.
2001 Feb
Nociceptin/orphanin FQ exacerbates excitotoxic white-matter lesions in the murine neonatal brain.
2001 Feb
Effect of midazolam pretreatment on induction dose requirements of propofol in combination with fentanyl in younger and older adults.
2001 Feb
Postoperative sleep disturbance: influences of opioids and pain in humans.
2001 Feb 1
Spinal and supraspinal components of opioid antinociception in streptozotocin induced diabetic neuropathy in rats.
2001 Feb 1
The influence of halothane, isoflurane and sevoflurane on rocuronium infusion in children.
2001 Jan
The Combitube in elective surgery: a report of 200 cases.
2001 Jan
Buprenorphine substitution ameliorates spontaneous withdrawal in fentanyl-dependent rat pups.
2001 Jan
Distressing upper extremity phantom limb sensation during intravenous regional anesthesia.
2001 Jan-Feb
Comparison of midazolam with or without fentanyl for conscious sedation and hemodynamics in coronary angiography.
2001 Mar
The effect of the preemptive use of the NMDA receptor antagonist dextromethorphan on postoperative analgesic requirements.
2001 Mar
The addition of morphine prolongs fentanyl-bupivacaine spinal analgesia for the relief of labor pain.
2001 Mar
Patents

Sample Use Guides

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
0.5 - 5 ng/ml fentanyl inhibited viability of SW1990 cells in vitro.
Substance Class Chemical
Created
by admin
on Thu Jul 06 23:06:18 UTC 2023
Edited
by admin
on Thu Jul 06 23:06:18 UTC 2023
Record UNII
UF599785JZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENTANYL
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
DURAGESIC
Brand Name English
N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide
Systematic Name English
FENTANYL [HSDB]
Common Name English
N02AB03
Code English
FENTANYL CII
USP-RS  
Common Name English
FENTANYL [JAN]
Common Name English
MATRIFEN
Common Name English
FENTANYL [MI]
Common Name English
PHENTANYL
Common Name English
FENTANYL [EMA EPAR]
Common Name English
FENTANYL [MART.]
Common Name English
RECUVYRA
Brand Name English
FENTANYL [EP IMPURITY]
Common Name English
FENTANYL [USAN]
Common Name English
FENTANYL [GREEN BOOK]
Common Name English
AD 923
Code English
FENTANYL [ORANGE BOOK]
Common Name English
FENTANYL [VANDF]
Common Name English
PECFENT
Brand Name English
ABSTRAL-
Common Name English
EN3267
Common Name English
FENTANYL [EP MONOGRAPH]
Common Name English
AD-923
Code English
IDS-NF-001
Code English
Tranq component fentanyl
Common Name English
FENDROP
Common Name English
R 4263
Code English
EN-3267
Code English
FENTANYL [USP MONOGRAPH]
Common Name English
DUROGESIC D-TRANS
Common Name English
fentanyl [INN]
Common Name English
Fentanyl [WHO-DD]
Common Name English
FENTANYL CII [USP-RS]
Common Name English
SUBLIMASE
Common Name English
FENTANYL [EMA EPAR VETERINARY]
Common Name English
FENTANEST
Common Name English
PROPANAMIDE, N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)
Common Name English
Classification Tree Code System Code
WHO-VATC QN01AH51
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
NCI_THESAURUS C67413
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
NDF-RT N0000175684
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
LIVERTOX NBK548026
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
CFR 21 CFR 524.916
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-VATC QN02AB03
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-ATC N01AH01
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-VATC QN02AB53
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
NDF-RT N0000175690
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-ATC N01AH51
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-ATC N02AB03
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-VATC QN02AB73
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
WHO-VATC QN01AH01
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
EMA ASSESSMENT REPORTS EFFENTORA (AUTHORIZED: PAIN)
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
DEA NO. 9801
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
EMA ASSESSMENT REPORTS PECFENT (AUTHORIZED: PAIN)
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
NCI_THESAURUS C1506
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
Code System Code Type Description
PUBCHEM
3345
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
CHEBI
119915
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL596
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID9023049
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
RXCUI
4337
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY RxNorm
DAILYMED
UF599785JZ
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
MESH
D005283
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
HSDB
3329
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
FDA UNII
UF599785JZ
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
EVMPD
SUB07597MIG
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
SMS_ID
100000090377
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
LACTMED
Fentanyl
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
USAN
SS-102
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
IUPHAR
1626
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-113-6
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
DRUG BANK
DB00813
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
INN
1608
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
CAS
437-38-7
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
EMA VETERINARY ASSESSMENT REPORTS
RECUVYRA [AUTHORIZED]
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY DOGS
MERCK INDEX
M5298
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
1164
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
RS_ITEM_NUM
1269902
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
NCI_THESAURUS
C494
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
WIKIPEDIA
FENTANYL
Created by admin on Thu Jul 06 23:06:22 UTC 2023 , Edited by admin on Thu Jul 06 23:06:22 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
DERIVATIVE -> PARENT
CUMULATIVE EXCRETION
URINE
PRECURSOR->PARENT
TARGET -> AGONIST
HUMAN RECEPTOR
AGONIST
Ki
PRECURSOR->PARENT
PRECURSOR->PARENT
DERIVATIVE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Possible deadly drug interaction with CYP3A4 inhibitors
MAJOR
SALT/SOLVATE -> PARENT
OFF TARGET->NON-INHIBITOR
TARGET -> AGONIST
AGONIST
EC50
OFF TARGET->NON-INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BINDER->LIGAND
BINDING
PARENT -> DERIVATIVE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
CUMULATIVE EXCRETION
FECAL
EXCRETED UNCHANGED
FECAL; URINE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
URINE
METABOLITE INACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
PLASMA
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Relative Response Factor - 1.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
ED50(mg/kg) = 0.0061, LD50(mg/kg) = 62, Potency ratio to morphine = 54.1, Potency ratio to fentanyl = 1
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC