Home > Compound List > Compound details
437-38-7 molecular structure
click picture or here to close

N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

ChemBase ID: 692
Molecular Formular: C22H28N2O
Molecular Mass: 336.47052
Monoisotopic Mass: 336.22016353
SMILES and InChIs

SMILES:
O=C(N(C1CCN(CC1)CCc1ccccc1)c1ccccc1)CC
Canonical SMILES:
CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1
InChI:
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
InChIKey:
PJMPHNIQZUBGLI-UHFFFAOYSA-N

Cite this record

CBID:692 http://www.chembase.cn/molecule-692.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
IUPAC Traditional name
fentanyl
Brand Name
Actiq
Duragesic
Duragesic-100
Durogesic
Fentanest
Fentanil
Pentanyl
Phentanyl
Sentonil
Sublimaze
Nasalfent
Rapinyl
Synonyms
N-(Phenyl)-N-(1-[2-phenylethyl]-4-piperidinyl)propanamide
1-Phenethyl-4-(N-phenylpropionamido)piperidine
Durogesic
Durogesic D-Trans
Durotep MT
Fentanest
Fentanil
Fentora
Matrifen
Phentanyl
R 4263
Sublimase
Fentanila [INN-Spanish]
Fentanyl citrate
Fentanylum [INN-Latin]
fentanyl
Fentanyl
CAS Number
437-38-7
PubChem SID
160964155
46506372
PubChem CID
3345
CHEBI ID
119915
ATC CODE
N01AH01
N02AB03
CHEMBL
596
Chemspider ID
3228
DrugBank ID
DB00813
IUPHAR ligand ID
1626
KEGG ID
D00320
Unique Ingredient Identifier
UF599785JZ
Wikipedia Title
Fentanyl

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
F274990 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.7473339  LogD (pH = 7.4) 2.432824 
Log P 3.8154986  Molar Refractivity 103.4825 cm3
Polarizability 40.300232 Å3 Polar Surface Area 23.55 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.12  LOG S -4.15 
Solubility (Water) 2.40e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
200 mg/L expand Show data source
Chloroform expand Show data source
Dichloromethane expand Show data source
DMSO,Hexane expand Show data source
MethanolDichloromethane expand Show data source
Apperance
Pale Brown Solid expand Show data source
Melting Point
83-84°C expand Show data source
87.5°C (189.5°F) expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
Storage Condition
Controlled Substance, -20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
TD, IM, IV, oral, sublingual, buccal expand Show data source
Bioavailability
92% (transdermal)
89% (intranasal)
50% (buccal)
33% (ingestion)
expand Show data source
Dependency Liability
Moderate - High expand Show data source
Excretion
60% Urinary (metabolites, <10% unchanged drug) expand Show data source
Half Life
(IV)= 2.5 minutes
Intranasal = 6.5 mins
Transdermal = 7 hours (range 3–12 h)
expand Show data source
Metabolism
hepatic, primarily by CYP3A4 expand Show data source
Protein Bound
80-85% expand Show data source
Legal Status
Class A (UK) expand Show data source
Schedule II (US) expand Show data source
Pregnancy Category
C (US) expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00813 external link
Item Information
Drug Groups illicit; approved; investigational
Description A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
Indication For the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy.
Pharmacology Fentanyl is an opioid analgesic. Fentanyl interacts predominately with the opioid mu-receptor but also binds to kappa and delta-type opioid receptors. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, Fentanyl exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Fentanyl may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Fentanyl depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
Toxicity Fentanyl has an LD50 of 3.1 milligrams per kilogram in rats, and, 0.03 milligrams per kilogram in monkeys. The LD50 in humans is not known.
Affected Organisms
Humans and other mammals
Biotransformation Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system.
Absorption Bioavailability is 92% following transdermal administration and 50% following buccal administration.
Half Life 7 (range 3-12) hours
Protein Binding 80-85%
Elimination Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system and mostly eliminated in urine. Within 72 hours of IV fentanyl administration, approximately 75% of the dose is excreted in urine, mostly as metabolites with less than 10% representing unchanged drug.
Distribution * 3 to 8 L/kg [Surgical Patients]
* 0.8 to 8 [Hepatically Impaired Patients]
Clearance * 27 – 75 L/h [Surgical Patients receving IV administration]
* 3 – 80 L/h [Hepatically Impaired Patients receving IV administration]
* 30 – 78 L/h [Renally Impaired Patients receving IV administration]
References
Van Bever WF, Niemegeers CJ, Janssen PA: Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J Med Chem. 1974 Oct;17(10):1047-51. [Pubmed]
Messina J, Darwish M, Fine PG: Fentanyl buccal tablet. Drugs Today (Barc). 2008 Jan;44(1):41-54. [Pubmed]
Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [Pubmed]
Simpson DM, Messina J, Xie F, Hale M: Fentanyl buccal tablet for the relief of breakthrough pain in opioid-tolerant adult patients with chronic neuropathic pain: a multicenter, randomized, double-blind, placebo-controlled study. Clin Ther. 2007 Apr;29(4):588-601. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - F274990 external link
Used as an analgesic. Controlled Substance.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Van Bever WF, Niemegeers CJ, Janssen PA: Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J Med Chem. 1974 Oct;17(10):1047-51. Pubmed
  • • Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. Pubmed
  • • Simpson DM, Messina J, Xie F, Hale M: Fentanyl buccal tablet for the relief of breakthrough pain in opioid-tolerant adult patients with chronic neuropathic pain: a multicenter, randomized, double-blind, placebo-controlled study. Clin Ther. 2007 Apr;29(4):588-601. Pubmed
  • • Messina J, Darwish M, Fine PG: Fentanyl buccal tablet. Drugs Today (Barc). 2008 Jan;44(1):41-54. Pubmed
  • • Zernig, G., et al.: Life Sci., 57, 2113 (1995)
  • • Bot, G., et al.: J. Pharmacol. Exper. Therap., 285, 1207 (1995)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle