Details of the Drug

General Information of Drug (ID: DMC153X)

Drug Name
3-Methylthiofentanyl
Synonyms
3-Methylthiofentanyl; 3-Methyl-thiofentanyl; UNII-C9C204973M; 86052-04-2; CHEBI:53763; N-(3-Methyl-1-(2-thienyl)ethyl-4-piperidinyl)-N-phenylpropanamide; C9C204973M; Propanamide, N-(3-methyl-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenyl-; N-{3-methyl-1-[2-(2-thienyl)ethyl]piperidin-4-yl}-N-phenylpropanamide; DEA No. 9833; 3-Methylthiofentanil; Epitope ID:153515; AC1Q5I8I; AC1L1WU2; SCHEMBL1742151; CHEMBL2365680; DB01439; FT-0672232
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 356.5
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C21H28N2OS
IUPAC Name
N-[3-methyl-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-N-phenylpropanamide
Canonical SMILES
CCC(=O)N(C1CCN(CC1C)CCC2=CC=CS2)C3=CC=CC=C3
InChI
InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3
InChIKey
SRARDYUHGVMEQI-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
62296
ChEBI ID
CHEBI:53763
CAS Number
86052-04-2
DrugBank ID
DB01439
TTD ID
D00HIG

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Opioid receptor delta (OPRD1) TT27RFC OPRD_HUMAN Agonist [1]
Opioid receptor kappa (OPRK1) TTQW87Y OPRK_HUMAN Agonist [1]
Opioid receptor mu (MOP) TTKWM86 OPRM_HUMAN Agonist [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Opioid receptor mu (MOP) DTT OPRM1 5.94E-01 -0.02 -0.17
Opioid receptor delta (OPRD1) DTT OPRD1 5.52E-01 0.03 0.23
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 You HJ, Colpaert FC, Arendt-Nielsen L: The novel analgesic and high-efficacy 5-HT1A receptor agonist F 13640 inhibits nociceptive responses, wind-up, and after-discharges in spinal neurons and withdrawal reflexes. Exp Neurol. 2005 Jan;191(1):174-83.
2 Buprenorphine is a weak partial agonist that inhibits opioid receptor desensitization. J Neurosci. 2009 Jun 3;29(22):7341-8.
3 Antianalgesia: stereoselective action of dextro-morphine over levo-morphine on glia in the mouse spinal cord.J Pharmacol Exp Ther.2005 Sep;314(3):1101-8.
4 Clinical pipeline report, company report or official report of signaturerx.
5 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
6 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
7 Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. Pain. 2001 Mar;91(1-2):177-87.
8 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
9 Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.Biochem Pharmacol.2014 Dec 1;92(3):448-56.
10 Drug design and synthesis of a novel kappa opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology. Bioorg Med Chem Lett. 2010 Jan 1;20(1):121-4.
11 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 319).
12 Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16.
13 Identification of opioid ligands possessing mixed micro agonist/delta antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone [correction of hydropmorphone]. J Med Chem. 2004 Mar 11;47(6):1400-12.
14 Loperamide: evidence of interaction with mu and delta opioid receptors. Life Sci. 1983;33 Suppl 1:315-8.
15 Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307.
16 Wax PM, Becker CE, Curry SC: Unexpected gas casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5.
17 Molecular Mechanisms of Opioid Receptor-Dependent Signaling and Behavior. Anesthesiology. 2011 December; 115(6): 1363-1381.
18 Delta-opioid receptor agonists inhibit neuromuscular transmission in human colon. Eur J Pharmacol. 1994 Sep 1;262(1-2):33-9.
19 Preclinical pharmacology of AZD2327: a highly selective agonist of the delta-opioid receptor. J Pharmacol Exp Ther. 2011 Jul;338(1):195-204.
20 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
21 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
22 Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3.
23 Emerging drugs for irritable bowel syndrome. Expert Opin Emerg Drugs. 2006 May;11(2):293-313.
24 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
25 Nalbuphine: an autoradiographic opioid receptor binding profile in the central nervous system of an agonist/antagonist analgesic. J Pharmacol Exp Ther. 1988 Jan;244(1):391-402.
26 Peptide Kappa Opioid Receptor Ligands: Potential for Drug Development. AAPS J. 2009 June; 11(2): 312-322.