METENKEFALIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H35N5O7S
Molecular Weight	573.661
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC2=CC=C(O)C=C2)C(O)=O

InChI

InChIKey=YFGBQHOOROIVKG-FKBYEOEOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H35N5O7S
Molecular Weight	573.661
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Metenkephalin (Met-enkephalin) is an endogenous opioid peptide that acts as an agonist at μ-opioid receptors (μORs) and δ-opioid receptors (δORs). Met-enkephalin exhibits neuromodulatory, antinociceptive/analgesic, antidepressant, and gastrointestinal motility modulating activities. Like other endogenous opioids, met-enkephalin modulates expression of opioid receptors and plays a role in reward/reinforcement signaling. Met-enkephalin is also involved in exercise-induced reversal of neuropathic pain and in animals undergoing the forced swim test, decreases immobility time. Met-enkephalin inhibits gastrointestinal muscle contractility, inhibiting motility and gastric emptying. Additionally, analogs of this peptide display anticancer and antiepileptic/anticonvulsant activities.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Delta opioid receptor 77	Agonist 2,678	22.0 nM [IC50]
Mu opioid receptor 221	Agonist 2,678	0.65 nM [Ki]
Kappa opioid receptor 108	Agonist 2,678	1.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 97	Primary	Phase II 1,132	Unknown
Hepatocellular carcinoma 83	Primary	Phase II 1,132	Unknown
Head and neck cancer 50	Primary	Phase II 1,132	Unknown

Doses

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Dose	Population	Adverse events
250 ug/kg single, intravenous MTD	unhealthy, ADULT n = 3	DLT: Hypotension...
50 ug/kg 2 times / day multiple, subcutaneous Studied dose	unhealthy, ADULT n = 6

Showing 1 to 2 of 2 entries

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AEs

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AE	Significance	Dose	Population
Hypotension	grade 3, 66.7% DLT	250 ug/kg single, intravenous MTD	unhealthy, ADULT n = 3

Showing 1 to 1 of 1 entries

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Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
001 Chemical	DY435264	https://www.001chemical.com/chem/search?q=DY435264
1PlusChem LLC	1P00E96O	https://www.1pchem.com/search?query=1P00E96O
A2B Chem	AG64288	http://a2bchem.com/prod/AG64288
Ambeed	A313396	http://www.ambeed.com/search/Search.html?keyword=A313396
AstaTech	C75740	http://astatechinc.com/CPSResult.php?CRNO=C75740

Showing 1 to 5 of 29 entries

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PubMed

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Title	Date	PubMed
Enhancement of the generation of cytotoxic T cells by endogenous opiates.	1986 Jul	2940263
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.	1993 Jul 15	8393575

Showing 1 to 2 of 2 entries

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Patents

Sample Use Guides

In Vivo Use Guide

All subjects treated with met-enkephalin 250 ug/kg iv weekly over 45 minutes

Route of Administration: Intravenous

In Vitro Use Guide

Treatment with Metenkephalin (M-ENK) caused a significant increase in apoptotic cells after 18 h of culture: *0 M (control) versus 10(-10) M, p < or = 0.02; **10(-10) M versus 10(-10) M, p < or = 0.02.