7V7

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

Created: 2016-12-06
Last modified:  2017-10-04

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Chemical Details

Formal Charge0
Atom Count53
Chiral Atom Count0
Bond Count55
Aromatic Bond Count12
2D diagram of 7V7

Chemical Component Summary

NameN-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
Systematic Name (OpenEye OEToolkits)~{N}-phenyl-~{N}-[1-(2-phenylethyl)piperidin-4-yl]propanamide
FormulaC22 H28 N2 O
Molecular Weight336.471
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01C2CC(N(c1ccccc1)C(CC)=O)CCN2CCc3ccccc3
SMILESCACTVS3.385CCC(=O)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3
SMILESOpenEye OEToolkits2.0.6CCC(=O)N(c1ccccc1)C2CCN(CC2)CCc3ccccc3
Canonical SMILESCACTVS3.385 CCC(=O)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3
Canonical SMILESOpenEye OEToolkits2.0.6 CCC(=O)N(c1ccccc1)C2CCN(CC2)CCc3ccccc3
InChIInChI1.03 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
InChIKeyInChI1.03 PJMPHNIQZUBGLI-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00813 
NameFentanyl
Groups
  • investigational
  • approved
  • illicit
  • vet_approved
DescriptionFentanyl, a potent opioid agonist, was developed in the 1950s to fill a need for strong and rapid analgesia.[A179542] Because of these characteristics, fentanyl is commonly used to treat chronic cancer pain or in anesthesia.[Label,L6598,L6601,L6604,L6607,L922,L6610,L6613] Fentanyl is related to other opioids like [morphine] and [oxycodone]. Fentanyl's high potency has also made it a common adulterant in illicit drugs, especially heroin.[A179542] In 2017, 47600 overdose deaths in the United States involved some opioid (over 2/3 of all overdose deaths).[L6748] Opioid overdoses kill an average of 11 Canadians daily.[L6751] Fentanyl was FDA approved in 1968.[Label,L6598,L6601,L6604,L6607,L922,L6610,L6613]
Synonyms
  • Fentanyl hydrochloride
  • N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide
  • 1-phenethyl-4-N-propionylanilinopiperidine
  • N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide
  • N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide
Brand Names
  • Fentanyl Citrate Injection USP 50mcg/ml
  • Sublimaze Inj 50mcg/ml
  • Ran-fentanyl Matrix Patch
  • Pat-fentanyl Mat
  • Duragesic 12
IndicationFentanyl intravenous or intramuscular injections are indicated for short term analgesia during induction, maintenance, and recovery from general or regional anesthesia.[Label] These injections are also used with a neuroleptic for premedication, induction, and as an adjunct to maintenance of anesthesia.[Label] Finally, fentanyl intravenous or intramuscular injections are used with oxygen for anesthesia in high risk patients.[Label] Fentanyl sublingual tablets, transmucosal lozenges, buccal tablets, sublingual sprays, transdermal systems, and nasal sprays are indicated for the management of breakthrough pain in opioid tolerant cancer patients who require around the clock pain management.[L6598,L6601,L6604,L6607,L922,L6610]
Categories
  • Adjuvants
  • Adjuvants, Anesthesia
  • Agents that produce hypertension
  • Agents that reduce seizure threshold
  • Analgesics
ATC-Code
  • N01AH01
  • N02AB03
  • N01AH51
CAS number437-38-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Mu-type opioid receptorMDSSAAPTNASNCTDALAYSSCSPAPSPGSWVNLSHLDGNLSDPCGPNRT...unknownagonist
Delta-type opioid receptorMEPAPSAGAELQPPLFANASDAYPSACPSAGANASGPPGARSASSLALAI...unknownagonist
Kappa-type opioid receptorMDSPIQIFRGEPGPTCAPSACLPPNSSAWFPGWAEPDSNGSAGSEDAQLE...unknownagonist
ATP-dependent translocase ABCB1MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...unknown
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL596
PubChem 3345
ChEMBL CHEMBL596
ChEBI CHEBI:119915
CCDC/CSD UGIYEP
COD 1551786