Details of the Drug

General Information of Drug (ID: DMSZFTP)

Drug Name
Met-enkephalin
Synonyms
MET-enkephalin; H-Tyr-Gly-Gly-Phe-Met-OH; 58569-55-4; Tyr-Gly-Gly-Phe-Met-OH; METENKEFALIN; [Met]enkephalin; [5-Methionine]Enkephalin; TYR-GLY-GLY-PHE-MET; Enkephalin M; UNII-9JEZ9OD3AS; (Met5)-enkephalin; Lupex; 9JEZ9OD3AS; CHEMBL13786; CHEBI:6618; ENKEPHALIN, METHIONINE; Opioid growth factor; [Met5]-ENKEPHALIN; [Met5]Enkephalin acetate salt hydrate; Porcine beta-endorphin 1-5; (2S,5S,14S)-14-Amino-5-benzyl-15-(4-hydroxyphenyl)-2-(2-(methylthio)ethyl)-4,7,10,13-tetraoxo-3,6,9,12-tetraazapentadecan-1-oic
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Phase 2 [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 573.7
Topological Polar Surface Area (xlogp) -2.1
Rotatable Bond Count (rotbonds) 16
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 0.361 mcgh/L [3]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1266.14 ng/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.16 h [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.2 - 39 minutes [3]
Chemical Identifiers
Formula
C27H35N5O7S
IUPAC Name
(2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
Canonical SMILES
CSCC[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
InChI
InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
InChIKey
YFGBQHOOROIVKG-FKBYEOEOSA-N
Cross-matching ID
PubChem CID
443363
ChEBI ID
CHEBI:6618
CAS Number
58569-55-4
DrugBank ID
DB12668
TTD ID
D0V5WL

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 [4], [5]
Opioid receptor mu (MOP) TTKWM86 OPRM_HUMAN Inhibitor [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pain
ICD Disease Classification MG30-MG3Z
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 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. (Ligand id: 1614).
2 ClinicalTrials.gov (NCT00109941) Opioid Growth Factor in Treating Patients With Advanced Pancreatic Cancer That Cannot Be Removed By Surgery. U.S. National Institutes of Health.
3 Bosna Lijek: Enkorten Summary of Product Characteristics
4 Delta-opioid receptor agonists inhibit neuromuscular transmission in human colon. Eur J Pharmacol. 1994 Sep 1;262(1-2):33-9.
5 Further studies of tyrosine surrogates in opioid receptor peptide ligands. Bioorg Med Chem Lett. 2007 May 1;17(9):2656-60.
6 Buprenorphine is a weak partial agonist that inhibits opioid receptor desensitization. J Neurosci. 2009 Jun 3;29(22):7341-8.
7 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.
8 Clinical pipeline report, company report or official report of signaturerx.
9 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
10 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
11 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.
12 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
13 Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.Biochem Pharmacol.2014 Dec 1;92(3):448-56.
14 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.
15 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).
16 Butorphanol: effects of a prototypical agonist-antagonist analgesic on kappa-opioid receptors. J Pharmacol Sci. 2005 Jun;98(2):109-16.
17 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.
18 Loperamide: evidence of interaction with mu and delta opioid receptors. Life Sci. 1983;33 Suppl 1:315-8.
19 Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307.
20 Wax PM, Becker CE, Curry SC: Unexpected gas casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5.
21 Molecular Mechanisms of Opioid Receptor-Dependent Signaling and Behavior. Anesthesiology. 2011 December; 115(6): 1363-1381.
22 Preclinical pharmacology of AZD2327: a highly selective agonist of the delta-opioid receptor. J Pharmacol Exp Ther. 2011 Jul;338(1):195-204.
23 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: 317).