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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
Structure of METENKEFALIN

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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 22.0 nM [IC50]
Agonist
2678
 0.65 nM [Ki]
Agonist
2678
 1.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
250 ug/kg single, intravenous
MTD
Dose: 250 ug/kg
Route: intravenous
Route: single
Dose: 250 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15014352
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:
https://pubmed.ncbi.nlm.nih.gov/15014352
Page: p.206
DLT: Hypotension...
Dose limiting toxicities:
Hypotension (grade 3, 66.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15014352
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:
https://pubmed.ncbi.nlm.nih.gov/15014352
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:
https://pubmed.ncbi.nlm.nih.gov/15014352
Page: p.206
Sources:
https://pubmed.ncbi.nlm.nih.gov/15014352
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:
https://pubmed.ncbi.nlm.nih.gov/15014352
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:
https://pubmed.ncbi.nlm.nih.gov/15014352
Page: p.206
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
BLD Pharm
BD133990
http://www.bldpharm.com/search/Search.html?keyword=BD133990
BOC Sciences
58569-55-4
http://www.bocsci.com/description.asp?cas=58569-55-4
BOC Sciences
82362-17-2
http://www.bocsci.com/description.asp?cas=82362-17-2
Bachem
H-2785
https://shop.bachem.com/catalogsearch/result/?q=H-2785
Chem Scene
CS-5426
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5426
Chem-Impex International
32953
http://www.chemimpex.com/category/search/32953/2?filter=&search=32953&type=q&keywordoption=ANY&cid=2&fltrdesc=
Combi-Blocks
QV-2574
http://www.combi-blocks.com/cgi-bin/find.cgi?QV-2574
Hairui
HR145106
http://www.hairuichem.com/en/product/search.do?q=HR145106
Indofine
04-1131
https://indofinechemical.com/details.aspx?Sku=04-1131
KeyOrganics
AS-58159
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-58159
MedChem Express
HY-P0073
https://www.medchemexpress.com/search.html?q=HY-P0073&ft=&fa=&fp=
MolPort
MolPort-003-938-143
https://www.molport.com/shop/molecule-link/MolPort-003-938-143
Molcore
MC435264
http://www.molcore.com/CatMC435264.html
TargetMol
T7211
https://www.targetmol.com/search?keyword=T7211
Tetrahedron
TS73338
http://www.thsci.com/search.do?q=TS73338
TimTec
ST45400121
http://www.echemstore.com/catalogsearch/result/?q=ST45400121
Toronto Research Chemicals
H245648
https://www.trc-canada.com/product-detail/?CatNum=H245648
Toronto Research Chemicals
M225485
https://www.trc-canada.com/product-detail/?CatNum=M225485
eMolecules
29549689
https://orderbb.emolecules.com/search/#?query=29549689
eMolecules
299995770
https://orderbb.emolecules.com/search/#?query=299995770
eMolecules
50418795
https://orderbb.emolecules.com/search/#?query=50418795
eMolecules
526422
https://orderbb.emolecules.com/search/#?query=526422
eNovation Chemicals
D766196
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D766196&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-7306161950
https://mcule.com/MCULE-7306161950/
PubMed

PubMed

TitleDatePubMed
Enhancement of the generation of cytotoxic T cells by endogenous opiates.
1986 Jul
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.
1993 Jul 15
Cloning and pharmacological characterization of a rat kappa opioid receptor.
1993 Nov 1
Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors.
1994 Feb
Patents

Patents

04374928
2

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
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 Fri Dec 15 17:15:44 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:44 GMT 2023
Record UNII
9JEZ9OD3AS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METENKEFALIN
INN  
INN  
Official Name English
TYR-GLY-GLY-PHE-MET
Common Name English
OPIOID GROWTH FACTOR
Common Name English
MET-ENKEPHALIN
Common Name English
(MET5)-ENKEPHALIN
Common Name English
METHIONINE ENKEPHALIN
Common Name English
ENKEPHALIN-(5-L-METHIONINE)
Common Name English
NSC-374896
Code English
SH-PENTAPEPTIDE-19
INCI  
INCI  
Official Name English
Metenkefalin [WHO-DD]
Common Name English
INNO-105
Code English
L-TYROSYLGLYCYLGLYCYL-L-PHENYLALANYL-L-METHIONINE .BETA.-ENDORPHIN HUMAN-(1-5)-PEPTIDE
Common Name English
SH-PENTAPEPTIDE-19 [INCI]
Common Name English
metenkefalin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C308
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
FDA ORPHAN DRUG 388312
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
FDA ORPHAN DRUG 333011
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
NCI_THESAURUS C274
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
FDA ORPHAN DRUG 392213
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
Code System Code Type Description
WIKIPEDIA
Met-enkephalin
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
FDA UNII
9JEZ9OD3AS
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
RXCUI
1349278
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2108291
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
DAILYMED
9JEZ9OD3AS
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
DRUG BANK
DB12668
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-335-8
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
PUBCHEM
443363
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
CAS
58569-55-4
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
NCI_THESAURUS
C91011
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
NSC
374896
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
INN
8875
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
SMS_ID
300000034342
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID90974125
Created by admin on Fri Dec 15 17:15:44 GMT 2023 , Edited by admin on Fri Dec 15 17:15:44 GMT 2023
PRIMARY
Related Record Type Details
DELTA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Opioid growth factor receptor
TARGET -> AGONIST
Structure of METENKEFALIN ACETATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of METENKEFALIN
ACTIVE MOIETY
NIH
NCATS
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