U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H35N5O7S.C2H4O2
Molecular Weight 633.713
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METENKEFALIN ACETATE

SMILES

CC(O)=O.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=YWBMODPHGARALU-SGIIKHNDSA-N
InChI=1S/C27H35N5O7S.C2H4O2/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;1-2(3)4/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39);1H3,(H,3,4)/t20-,21-,22-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C27H35N5O7S
Molecular Weight 573.661
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Doses

Doses

DosePopulationAdverse events​
250 ug/kg single, intravenous
MTD
Dose: 250 ug/kg
Route: intravenous
Route: single
Dose: 250 ug/kg
Sources: Page: p.206
unhealthy, ADULT
n = 3
Health Status: unhealthy
Condition: pancreatic cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 3
Sources: Page: p.206
DLT: Hypotension...
Dose limiting toxicities:
Hypotension (grade 3, 66.7%)
Sources: Page: p.206
50 ug/kg 2 times / day multiple, subcutaneous
Studied dose
Dose: 50 ug/kg, 2 times / day
Route: subcutaneous
Route: multiple
Dose: 50 ug/kg, 2 times / day
Sources: Page: p.206
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: pancreatic cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.206
AEs

AEs

AESignificanceDosePopulation
Hypotension grade 3, 66.7%
DLT
250 ug/kg single, intravenous
MTD
Dose: 250 ug/kg
Route: intravenous
Route: single
Dose: 250 ug/kg
Sources: Page: p.206
unhealthy, ADULT
n = 3
Health Status: unhealthy
Condition: pancreatic cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 3
Sources: Page: p.206
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cloning and pharmacological characterization of a rat kappa opioid receptor.
1993 Nov 1
Patents

Patents

Sample Use Guides

All subjects treated with met-enkephalin 250 ug/kg iv weekly over 45 minutes
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: Isolated from human peripheral blood, neutrophils were incubated in the presence or absence of 10(-6) to 10(-10) M of Metenkephalin (M-ENK) and beta-END for 12 and 18 h. Apoptosis of neutrophils was determined in vitro by flow cytometric analysis of cellular DNA content and Annexin V-FITC protein binding to the cell surface.
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:04:04 UTC 2023
Edited
by admin
on Sat Dec 16 15:04:04 UTC 2023
Record UNII
RBM01752JM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METENKEFALIN ACETATE
Common Name English
(MET5)ENKEPHALIN ACETATE SALT
Common Name English
L-METHIONINE, L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-, ACETATE (1:1)
Common Name English
Code System Code Type Description
FDA UNII
RBM01752JM
Created by admin on Sat Dec 16 15:04:04 UTC 2023 , Edited by admin on Sat Dec 16 15:04:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID80332078
Created by admin on Sat Dec 16 15:04:04 UTC 2023 , Edited by admin on Sat Dec 16 15:04:04 UTC 2023
PRIMARY
CAS
82362-17-2
Created by admin on Sat Dec 16 15:04:04 UTC 2023 , Edited by admin on Sat Dec 16 15:04:04 UTC 2023
PRIMARY
PUBCHEM
51355594
Created by admin on Sat Dec 16 15:04:04 UTC 2023 , Edited by admin on Sat Dec 16 15:04:04 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY