METENKEFALIN ACETATE

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 Search

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

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
Cloning and functional comparison of kappa and delta opioid receptors from mouse brain.	1993 Jul 15	8393575

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 `Sat Dec 16 15:04:04 GMT 2023` Edited by `admin` on `Sat Dec 16 15:04:04 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 15:04:04 GMT 2023

PRIMARY

EPA CompTox

DTXSID80332078

Created by admin on Sat Dec 16 15:04:04 GMT 2023 , Edited by admin on Sat Dec 16 15:04:04 GMT 2023

PRIMARY

CAS

82362-17-2

Created by admin on Sat Dec 16 15:04:04 GMT 2023 , Edited by admin on Sat Dec 16 15:04:04 GMT 2023

PRIMARY

PUBCHEM

51355594

Created by admin on Sat Dec 16 15:04:04 GMT 2023 , Edited by admin on Sat Dec 16 15:04:04 GMT 2023

PRIMARY

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METENKEFALIN

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Amount:

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					9JEZ9OD3AS

METENKEFALIN

ACTIVE MOIETY

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

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