METENKEFALIN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19634861 | https://www.ncbi.nlm.nih.gov/pubmed/15806307

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 Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12437765 \| https://www.ncbi.nlm.nih.gov/pubmed/8393575	Agonist 2678	22.0 nM [IC50]
Mu opioid receptor 221 Target ID: CHEMBL270 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8114680	Agonist 2678	0.65 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL3614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8234341	Agonist 2678	1.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 97 Sources: https://clinicaltrials.gov/ct2/show/NCT00109941 http://adisinsight.springer.com/drugs/800004141	Primary	Phase II 1132	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: http://adisinsight.springer.com/drugs/800004141 https://clinicaltrials.gov/ct2/show/NCT00706576	Primary	Phase II 1132	Unknown Approved Use Unknown
Head and neck cancer 50 Sources: http://adisinsight.springer.com/drugs/800004141 https://clinicaltrials.gov/ct2/show/NCT00982696	Primary	Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

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
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

Title	Date	PubMed
Enhancement of the generation of cytotoxic T cells by endogenous opiates.	1986 Jul	2940263

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:15:44 UTC 2023` Edited by `admin` on `Fri Dec 15 17:15:44 UTC 2023`
Record UNII	9JEZ9OD3AS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METENKEFALIN

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

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