N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide

ID: ALA596

Chembl Id: CHEMBL596

Cas Number: 437-38-7

PubChem CID: 3345

Max Phase: Approved

First Approval: 1968

Molecular Formula: C22H28N2O

Molecular Weight: 336.48

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Abstral- | Durogesic d-trans | En3267 | Fendrop | Fentanest | Fentanyl | Fentora | Innovar | Ionsys | Phentanyl | Recuvyra | Sublimase | AD 923 | AD-923 | EN-3267 | IDS-NF-001 | N02AB03 | R 4263 | fentanyl|Phentanyl|Fentanil|Fentanest|Fentora|437-38-7|Duragesic|Durogesic|Fentanila|Fentanylum|Sentonil|Sublimase|Sublimaze|Matrifen|Duragesic-100|Duragesic-12|Duragesic-25|Duragesic-50|Duragesic-75|Fentanyl-12|Fentanyl-25|Fentanyl-50|Fentanyl-75|Recuvyra|N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionaShow More

Synonyms from Alternative Forms(21): Fentanyl citrate | Fentanyl buccal | Instanyl | Kw-2246 | Leptanal | MCN-JR-4263-49 | R-4263 | Abstral | Actiq | Fentanyl | Fentanyl citrate preservative free | Fentora | Lazanda | Onsolis | Sublimaze | Sublimaze preservative free | Thalamonal | Fentanyl citrate cii | Fentanyl hydrochloride | Fentanyl hcl | Ionsys

Trade Names(39): Abstral | Actiq | Breakyl | Duragesic-100 | Duragesic-12 | Duragesic-25 | Duragesic-37 | Duragesic-50 | Duragesic-75 | Durogesic | Durogesic dtrans | Effentora | Fencino | Fentalis reservoir | Fentanyl-100 | Fentanyl-12 | Fentanyl-25 | Fentanyl-37 | Fentanyl-50 | Fentanyl-62 | Fentanyl-75 | Fentanyl-87 | Fentora | Ionsys | Leptanal | Matrifen | Mezolar matrix | Mylafent | Opiodur | Oralet | Osmach | Osmanil | Pecfent | Recivit | Sublimaze | Subsys | Tilofyl | Victanyl | Yemex

Canonical SMILES:  CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1

Standard 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

Standard InChI Key:  PJMPHNIQZUBGLI-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

    ALA596

    FENTANYL
  2. Alternative Forms:

Associated Targets(Human)

OPRM1 Tclin Mu opioid receptor (19785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Tclin Kappa opioid receptor (16155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRD1 Tclin Delta opioid receptor (15096 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase (395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Skin (286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC22A1 Tchem Solute carrier family 22 member 1 (646 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH1 Tclin Histamine H1 receptor (7573 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Whole blood (398 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR1I2 Tchem Pregnane X receptor (6667 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Tclin Sigma opioid receptor (6358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD4 Tchem Dopamine D4 receptor (7907 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NR3C1 Tclin Glucocorticoid receptor (14987 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA1 Tclin Adenosine A1 receptor (17603 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADORA2A Tclin Adenosine A2a receptor (16305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SCN5A Tclin Sodium channel protein type V alpha subunit (3462 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GHSR Tclin Ghrelin receptor (6229 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EDNRA Tclin Endothelin receptor ET-A (5008 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MC3R Tchem Melanocortin receptor 3 (5659 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MLNR Tchem Motilin receptor (1724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGR Tclin Progesterone receptor (8562 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (6060 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oryctolagus cuniculus (11301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Opioid receptor (994 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRM1 Mu opioid receptor (3620 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OPRK1 Kappa opioid receptor (4577 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cavia porcellus (23802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3911 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprd1 Delta opioid receptor (3127 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei (78846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichomonas vaginalis (2376 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Toxoplasma gondii (4585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pneumocystis carinii (749 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania mexicana (936 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania major (2877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania infantum (5912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania amazonensis (3813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Entamoeba histolytica (2676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptosporidium parvum (1150 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Luciferin 4-monooxygenase (66902 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hrh1 Histamine H1 receptor (251 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nr1i2 Nuclear receptor subfamily 1 group I member 2 (641 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Oprm1 Mu opioid receptor (1674 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIGMAR1 Sigma-1 receptor (3326 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sigmar1 Sigma opioid receptor (1607 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ptgs1 Cyclooxygenase-1 (1373 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ar Androgen Receptor (5522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: YesChemical Probe: NoParenteral: Yes
Molecule Type: Small moleculeTopical: YesFirst In Class: NoBlack Box: Yes
Chirality: YesAvailability: YesProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 336.48Molecular Weight (Monoisotopic): 336.2202AlogP: 4.14#Rotatable Bonds: 6
Polar Surface Area: 23.55Molecular Species: BASEHBA: 2HBD:
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.77CX LogP: 3.82CX LogD: 2.43
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.79Np Likeness Score: -1.26

References

1. Burke TR, Jacobson AE, Rice KC, Silverton JV, Simonds WF, Streaty RA, Klee WA..  (1986)  Probes for narcotic receptor mediated phenomena. 12. cis-(+)-3-Methylfentanyl isothiocyanate, a potent site-directed acylating agent for delta opioid receptors. Synthesis, absolute configuration, and receptor enantioselectivity.,  29  (6): [PMID:3012085] [10.1021/jm00156a030]
2. Kudzma LV, Evans SM, Turnbull SP, Severnak SA, Ezell EF.  (1995)  Octahydro-1,2,3,4,4a,5,11,11a-pyrido[3,4-c][1,5]benzoxazepines: conformationally restricted fentanyl analogs,  (11): [10.1016/0960-894X(95)00190-5]
3. Lombardo F, Obach RS, Shalaeva MY, Gao F..  (2004)  Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics.,  47  (5): [PMID:14971904] [10.1021/jm030408h]
4. Brine GA, Stark PA, Liu Y, Carroll FI, Singh P, Xu H, Rothman RB..  (1995)  Enantiomers of diastereomeric cis-N-[1-(2-hydroxy-2-phenylethyl)- 3-methyl-4-piperidyl]-N-phenylpropanamides: synthesis, X-ray analysis, and biological activities.,  38  (9): [PMID:7739013] [10.1021/jm00009a015]
5. Mićović IV, Ivanović MD, Vuckovic SM, Prostran MS, Dosen-Mićović L, Kiricojević VD..  (2000)  The synthesis and preliminary pharmacological evaluation of 4-methyl fentanyl.,  10  (17): [PMID:10987438] [10.1016/s0960-894x(00)00394-2]
6. Feldman PL, James MK, Brackeen MF, Bilotta JM, Schuster SV, Lahey AP, Lutz MW, Johnson MR, Leighton HJ..  (1991)  Design, synthesis, and pharmacological evaluation of ultrashort- to long-acting opioid analgetics.,  34  (7): [PMID:2066993] [10.1021/jm00111a041]
7. Janssens F, Torremans J, Janssen PA..  (1986)  Synthetic 1,4-disubstituted-1,4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: alfentanil (R 39209), a potent, extremely short-acting narcotic analgesic.,  29  (11): [PMID:2878076] [10.1021/jm00161a027]
8. Kudzma LV, Severnak SA, Benvenga MJ, Ezell EF, Ossipov MH, Knight VV, Rudo FG, Spencer HK, Spaulding TC..  (1989)  4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents.,  32  (12): [PMID:2585442] [10.1021/jm00132a007]
9. Wang C, McFadyen IJ, Traynor JR, Mosberg HI..  (1998)  Design of a high affinity peptidomimetic opioid agonist from peptide pharmacophore models.,  (19): [PMID:9873603] [10.1016/s0960-894x(98)00472-7]
10. Lombardo F, Obach RS, Shalaeva MY, Gao F..  (2002)  Prediction of volume of distribution values in humans for neutral and basic drugs using physicochemical measurements and plasma protein binding data.,  45  (13): [PMID:12061889] [10.1021/jm0200409]
11. Lalinde N, Moliterni J, Wright D, Spencer HK, Ossipov MH, Spaulding TC, Rudo FG..  (1990)  Synthesis and pharmacological evaluation of a series of new 3-methyl-1,4-disubstituted-piperidine analgesics.,  33  (10): [PMID:2170652] [10.1021/jm00172a032]
12. Poulain R, Horvath D, Bonnet B, Eckhoff C, Chapelain B, Bodinier MC, Déprez B..  (2001)  From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands.,  44  (21): [PMID:11585443] [10.1021/jm010877o]
13. Essawi MY, Portoghese PS..  (1983)  Synthesis and evaluation of 1- and 2-substituted fentanyl analogues for opioid activity.,  26  (3): [PMID:6827557] [10.1021/jm00357a007]
14. Subramanian G, Paterlini MG, Portoghese PS, Ferguson DM..  (2000)  Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor.,  43  (3): [PMID:10669565] [10.1021/jm9903702]
15. Dardonville C, Jagerovic N, Callado LF, Callado LF, Meana JJ..  (2004)  Fentanyl derivatives bearing aliphatic alkaneguanidinium moieties: a new series of hybrid molecules with significant binding affinity for mu-opioid receptors and I2-imidazoline binding sites.,  14  (2): [PMID:14698188] [10.1016/j.bmcl.2003.10.048]
16. Bishop MJ, Garrido DM, Boswell GE, Collins MA, Harris PA, McNutt RW, O'Neill SJ, Wei K, Chang KJ..  (2003)  3-(alphaR)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-alkyl-N-arylbenzamides: potent, non-peptidic agonists of both the micro and delta opioid receptors.,  46  (4): [PMID:12570383] [10.1021/jm020395s]
17. Bagley JR, Wynn RL, Rudo FG, Doorley BM, Spencer HK, Spaulding T..  (1989)  New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties.,  32  (3): [PMID:2563773] [10.1021/jm00123a028]
18. Lobbezoo MW, Soudijn W, van Wijngaarden I..  (1981)  Opiate receptor interaction of compounds derived from or structurally related to fentanyl.,  24  (7): [PMID:6268786] [10.1021/jm00139a003]
19. Bagley JR, Thomas SA, Rudo FG, Spencer HK, Doorley BM, Ossipov MH, Jerussi TP, Benvenga MJ, Spaulding T..  (1991)  New 1-(heterocyclylalkyl)-4-(propionanilido)-4-piperidinyl methyl ester and methylene methyl ether analgesics.,  34  (2): [PMID:1847432] [10.1021/jm00106a051]
20. Maryanoff BE, McComsey DF, Taylor RJ, Gardocki JF..  (1981)  Synthesis and stereochemistry of 7-phenyl-2-propionanilidobenzo[a]quinolizidine derivatives. Structural probes of fentanyl analgesics.,  24  (1): [PMID:6259354] [10.1021/jm00133a017]
21. Finney ZG, Riley TN..  (1980)  4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogues.,  23  (8): [PMID:7190616] [10.1021/jm00182a016]
22. Maryanoff BE, Simon EJ, Gioannini T, Gorissen H..  (1982)  Potential affinity labels for the opiate receptor based on fentanyl and related compounds.,  25  (8): [PMID:6288945] [10.1021/jm00350a006]
23. Colapret JA, Diamantidis G, Spencer HK, Spaulding TC, Rudo FG..  (1989)  Synthesis and pharmacological evaluation of 4,4-disubstituted piperidines.,  32  (5): [PMID:2709383] [10.1021/jm00125a008]
24. Wang YH, Li Y, Li YH, Yang SL, Yang L..  (2005)  Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.,  15  (18): [PMID:15990295] [10.1016/j.bmcl.2005.06.015]
25. Tobita M, Nishikawa T, Nagashima R..  (2005)  A discriminant model constructed by the support vector machine method for HERG potassium channel inhibitors.,  15  (11): [PMID:15911273] [10.1016/j.bmcl.2005.03.080]
26. Morphy R, Rankovic Z..  (2005)  Designed multiple ligands. An emerging drug discovery paradigm.,  48  (21): [PMID:16220969] [10.1021/jm058225d]
27. Baert B, Deconinck E, Van Gele M, Slodicka M, Stoppie P, Bodé S, Slegers G, Vander Heyden Y, Lambert J, Beetens J, De Spiegeleer B..  (2007)  Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.,  15  (22): [PMID:17827020] [10.1016/j.bmc.2007.07.050]
28. Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergström CA, Artursson P..  (2008)  Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.,  51  (19): [PMID:18788725] [10.1021/jm8003152]
29. Varma MV, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A..  (2009)  Physicochemical determinants of human renal clearance.,  52  (15): [PMID:19445515] [10.1021/jm900403j]
30. Weltrowska G, Chung NN, Lemieux C, Guo J, Lu Y, Wilkes BC, Schiller PW..  (2010)  "Carba"-analogues of fentanyl are opioid receptor agonists.,  53  (7): [PMID:20218625] [10.1021/jm9019068]
31. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]
32. Alelyunas YW, Empfield JR, McCarthy D, Spreen RC, Bui K, Pelosi-Kilby L, Shen C..  (2010)  Experimental solubility profiling of marketed CNS drugs, exploring solubility limit of CNS discovery candidate.,  20  (24): [PMID:21055935] [10.1016/j.bmcl.2010.10.068]
33. Obach RS, Lombardo F, Waters NJ..  (2008)  Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.,  36  (7): [PMID:18426954] [10.1124/dmd.108.020479]
34. Jolivette LJ, Ward KW..  (2005)  Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.,  94  (7): [PMID:15920768] [10.1002/jps.20373]
35. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]
36. Matthews EJ, Kruhlak NL, Weaver JL, Benz RD, Contrera JF..  (2004)  Assessment of the health effects of chemicals in humans: II. Construction of an adverse effects database for QSAR modeling.,  (4): [PMID:16472241] [10.2174/1570163043334794]
37. Unpublished dataset, 
38. PubChem BioAssay data set, 
39.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 
40. Abraham MH, Ibrahim A, Acree WE..  (2008)  Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs.,  43  (3): [PMID:17544548] [10.1016/j.ejmech.2007.04.002]
41. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]
42. Sun H, Scott DO..  (2011)  Metabolism of 4-Aminopiperidine Drugs by Cytochrome P450s: Molecular and Quantum Mechanical Insights into Drug Design.,  (8): [PMID:21841964] [10.1021/ml200117z]
43. Wandel C, Kim R, Wood M, Wood A..  (2002)  Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein.,  96  (1): [PMID:11964599] [10.1097/00000542-200204000-00019]
44. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 
45. Vasudevan SR, Moore JB, Schymura Y, Churchill GC..  (2012)  Shape-based reprofiling of FDA-approved drugs for the H₁ histamine receptor.,  55  (16): [PMID:22793499] [10.1021/jm300671m]
46. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P..  (2012)  Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.,  55  (10): [PMID:22541068] [10.1021/jm300212s]
47. Noorizadeh H, Noorizadeh M, Farmany A.  (2012)  Advanced QSRR models of toxicological screening of basic drugs in whole blood by UPLC-TOFMS,  21  (12): [10.1007/s00044-012-9977-1]
48. Gupta PK, Yadav SK, Bhutia YD, Singh P, Rao P, Gujar NL, Ganesan K, Bhattacharya R.  (2013)  Synthesis and comparative bioefficacy of N-(1-phenethyl-4-piperidinyl)propionanilide (fentanyl) and its 1-substituted analogs in Swiss albino mice,  22  (8): [10.1007/s00044-012-0390-6]
49. PubChem BioAssay data set, 
50. Petrov RR, Lee YS, Vardanyan RS, Liu L, Ma SW, Davis P, Lai J, Porreca F, Vanderah TW, Hruby VJ..  (2013)  Effect of anchoring 4-anilidopiperidines to opioid peptides.,  23  (11): [PMID:23623418] [10.1016/j.bmcl.2013.03.065]
51. Settimo L, Bellman K, Knegtel RM..  (2013)  Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.,  [PMID:24249037] [10.1007/s11095-013-1232-z]
52. Andurkar SV, Reniguntala MS, Gulati A, DeRuiter J..  (2014)  Synthesis and antinociceptive properties of N-phenyl-N-(1-(2-(thiophen-2-yl)ethyl)azepane-4-yl)propionamide in the mouse tail-flick and hot-plate tests.,  24  (2): [PMID:24360563] [10.1016/j.bmcl.2013.11.069]
53. Mosberg HI, Yeomans L, Anand JP, Porter V, Sobczyk-Kojiro K, Traynor JR, Jutkiewicz EM..  (2014)  Development of a bioavailable μ opioid receptor (MOPr) agonist, δ opioid receptor (DOPr) antagonist peptide that evokes antinociception without development of acute tolerance.,  57  (7): [PMID:24641190] [10.1021/jm5002088]
54. Berger JG, Davidson F, Langford GE..  (1977)  Synthesis of some conformationally restricted analogues of fentanyl.,  20  (4): [PMID:850249] [10.1021/jm00214a035]
55. Shukla SJ, Sakamuru S, Huang R, Moeller TA, Shinn P, Vanleer D, Auld DS, Austin CP, Xia M..  (2011)  Identification of clinically used drugs that activate pregnane X receptors.,  39  (1): [PMID:20966043] [10.1124/dmd.110.035105]
56. Deekonda S, Wugalter L, Kulkarni V, Rankin D, Largent-Milnes TM, Davis P, Bassirirad NM, Lai J, Vanderah TW, Porreca F, Hruby VJ..  (2015)  Discovery of 5-substituted tetrahydronaphthalen-2yl-methyl with N-phenyl-N-(piperidin-4-yl)propionamide derivatives as potent opioid receptor ligands.,  23  (18): [PMID:26299827] [10.1016/j.bmc.2015.07.071]
57. Deekonda S, Wugalter L, Rankin D, Largent-Milnes TM, Davis P, Wang Y, Bassirirad NM, Lai J, Kulkarni V, Vanderah TW, Porreca F, Hruby VJ..  (2015)  Design and synthesis of novel bivalent ligands (MOR and DOR) by conjugation of enkephalin analogues with 4-anilidopiperidine derivatives.,  25  (20): [PMID:26323872] [10.1016/j.bmcl.2015.07.064]
58. Canale V, Kurczab R, Partyka A, Satała G, Słoczyńska K, Kos T, Jastrzębska-Więsek M, Siwek A, Pękala E, Bojarski AJ, Wesołowska A, Popik P, Zajdel P..  (2016)  N-Alkylated arylsulfonamides of (aryloxy)ethyl piperidines: 5-HT(7) receptor selectivity versus multireceptor profile.,  24  (2): [PMID:26706111] [10.1016/j.bmc.2015.11.041]
59. Deekonda S, Rankin D, Davis P, Lai J, Vanderah TW, Porecca F, Hruby VJ..  (2016)  Design synthesis and structure-activity relationship of 5-substituted (tetrahydronaphthalen-2yl)methyl with N-phenyl-N-(piperidin-2-yl)propionamide derivatives as opioid ligands.,  24  (2): [PMID:26712115] [10.1016/j.bmc.2015.11.030]
60. Waszkielewicz AM, Gunia-Krzyżak A, Powroźnik B, Słoczyńska K, Pękala E, Walczak M, Bednarski M, Żesławska E, Nitek W, Marona H..  (2016)  Design, physico-chemical properties and biological evaluation of some new N-[(phenoxy)alkyl]- and N-{2-[2-(phenoxy)ethoxy]ethyl}aminoalkanols as anticonvulsant agents.,  24  (8): [PMID:26988801] [10.1016/j.bmc.2016.03.006]
61. WHO Anatomical Therapeutic Chemical Classification, 
62. British National Formulary (72nd edition), 
63. DailyMed|setid=578def77-4959-4392-83a8-0abfcbf1d023 | FENTANYL - fentanyl patch, extended release|Bryant Ranch Prepack, 
64. DailyMed|setid=491dd1b2-b91a-4bd9-b022-159b8717699e | FENTANYL - fentanyl patch, extended release|Lake Erie Medical DBA Quality Care Products LLC, 
65. Prezzavento O, Arena E, Sánchez-Fernández C, Turnaturi R, Parenti C, Marrazzo A, Catalano R, Amata E, Pasquinucci L, Cobos EJ..  (2017)  (+)-and (-)-Phenazocine enantiomers: Evaluation of their dual opioid agonist/σ1 antagonist properties and antinociceptive effects.,  125  [PMID:27721146] [10.1016/j.ejmech.2016.09.077]
66. Unpublished dataset, 
67. Rosas R, Huang XP, Roth BL, Dockendorff C..  (2019)  β-Fluorofentanyls Are pH-Sensitive Mu Opioid Receptor Agonists.,  10  (9): [PMID:31531209] [10.1021/acsmedchemlett.9b00335]
68. Meyer MJ, Neumann VE, Friesacher HR, Zdrazil B, Brockmöller J, Tzvetkov MV..  (2019)  Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.,  62  (21): [PMID:31597043] [10.1021/acs.jmedchem.9b01301]
69. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]
70. Tan L, Yan W, McCorvy JD, Cheng J..  (2018)  Biased Ligands of G Protein-Coupled Receptors (GPCRs): Structure-Functional Selectivity Relationships (SFSRs) and Therapeutic Potential.,  61  (22): [PMID:29939744] [10.1021/acs.jmedchem.8b00435]
71. Lipiński PFJ, Szűcs E, Jarończyk M, Kosson P, Benyhe S, Misicka A, Dobrowolski JC, Sadlej J..  (2019)  Affinity of fentanyl and its derivatives for the σ1-receptor.,  10  (7): [PMID:31391893] [10.1039/C9MD00222G]
72. Obeng S, Kamble SH, Reeves ME, Restrepo LF, Patel A, Behnke M, Chear NJ, Ramanathan S, Sharma A, León F, Hiranita T, Avery BA, McMahon LR, McCurdy CR..  (2020)  Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.,  63  (1): [PMID:31834797] [10.1021/acs.jmedchem.9b01465]
73. Hsu FL, Walz AJ, Myslinski JM, Kong L, Feasel MG, Goralski TDP, Rose T, Cooper NJ, Roughley N, Timperley CM..  (2019)  Synthesis and μ-Opioid Activity of the Primary Metabolites of Carfentanil.,  10  (11): [PMID:31749912] [10.1021/acsmedchemlett.9b00404]
74. Johnson BM, Shu YZ, Zhuo X, Meanwell NA..  (2020)  Metabolic and Pharmaceutical Aspects of Fluorinated Compounds.,  63  (12): [PMID:32182061] [10.1021/acs.jmedchem.9b01877]
75. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]
76. Faouzi A,Uprety R,Gomes I,Massaly N,Keresztes AI,Le Rouzic V,Gupta A,Zhang T,Yoon HJ,Ansonoff M,Allaoa A,Pan YX,Pintar J,Morón JA,Streicher JM,Devi LA,Majumdar S.  (2020)  Synthesis and Pharmacology of a Novel μ-δ Opioid Receptor Heteromer-Selective Agonist Based on the Carfentanyl Template.,  63  (22): [PMID:33170687] [10.1021/acs.jmedchem.0c00901]
77. Zhang M,Xu B,Li N,Liu H,Shi X,Zhang Q,Shi Y,Xu K,Xiao J,Chen D,Zhu H,Sun Y,Zhang T,Zhang R,Fang Q.  (2020)  Synthesis and Biological Characterization of Cyclic Disulfide-Containing Peptide Analogs of the Multifunctional Opioid/Neuropeptide FF Receptor Agonists That Produce Long-Lasting and Nontolerant Antinociception.,  63  (24): [PMID:33271020] [10.1021/acs.jmedchem.0c01367]
78. Xiong J,Jin J,Gao L,Hao C,Liu X,Liu BF,Chen Y,Zhang G.  (2020)  Piperidine propionamide as a scaffold for potent sigma-1 receptor antagonists and mu opioid receptor agonists for treating neuropathic pain.,  191  [PMID:32087465] [10.1016/j.ejmech.2020.112144]
79. Chakraborty S, DiBerto JF, Faouzi A, Bernhard SM, Gutridge AM, Ramsey S, Zhou Y, Provasi D, Nuthikattu N, Jilakara R, Nelson MNF, Asher WB, Eans SO, Wilson LL, Chintala SM, Filizola M, van Rijn RM, Margolis EB, Roth BL, McLaughlin JP, Che T, Sames D, Javitch JA, Majumdar S..  (2021)  A Novel Mitragynine Analog with Low-Efficacy Mu Opioid Receptor Agonism Displays Antinociception with Attenuated Adverse Effects.,  64  (18.0): [PMID:34505767] [10.1021/acs.jmedchem.1c01273]
80. Xiong J, Zhuang T, Ma Y, Xu J, Ye J, Ma R, Zhang S, Liu X, Liu BF, Hao C, Zhang G, Chen Y..  (2021)  Optimization of bifunctional piperidinamide derivatives as σ1R Antagonists/MOR agonists for treating neuropathic pain.,  226  [PMID:34628236] [10.1016/j.ejmech.2021.113879]
81. Bonifazi A, Battiti FO, Sanchez J, Zaidi SA, Bow E, Makarova M, Cao J, Shaik AB, Sulima A, Rice KC, Katritch V, Canals M, Lane JR, Newman AH..  (2021)  Novel Dual-Target μ-Opioid Receptor and Dopamine D3 Receptor Ligands as Potential Nonaddictive Pharmacotherapeutics for Pain Management.,  64  (11.0): [PMID:34011153] [10.1021/acs.jmedchem.1c00611]
82. Zhuang T, Xiong J, Ren X, Liang L, Qi Z, Zhang S, Du W, Chen Y, Liu X, Zhang G..  (2022)  Benzylaminofentanyl derivates: Discovery of bifunctional μ opioid and σ1 receptor ligands as novel analgesics with reduced adverse effects.,  241  [PMID:35961067] [10.1016/j.ejmech.2022.114649]
83. Callis TB, Garrett TR, Montgomery AP, Danon JJ, Kassiou M..  (2022)  Recent Scaffold Hopping Applications in Central Nervous System Drug Discovery.,  65  (20.0): [PMID:36206553] [10.1021/acs.jmedchem.2c00969]
84. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]