NAV

Metenkefalin

Identification

Summary

Metenkefalin is an investigational endogenous opioid being studied for the treatment of COVID-19.

Generic Name
Metenkefalin
DrugBank Accession Number
DB12668
Background

Metenkefalin is an endogenous opioid and beta-endorphin.2 It has been shown to reduce chromosomal abberations in patients with multiple sclerosis.1 Metenkefalin, along with tridecactide, are under investigation as an immunomodulatory therapy for moderate to severe COVID-19.5,6

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 573.67
Monoisotopic: 573.225719661
Chemical Formula
C27H35N5O7S
Synonyms
  • [met5]-enkephalin
  • Metenkefalin
  • Methionine Enkephalin
External IDs
  • INNO-105
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Pharmacology

Indication

Metenkefalin is indicated in Bosnia for the treatment of relapsing-remitting multiple sclerosis.7

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Metenkefalin is an agonist of µ and δ opioid receptors.3 It also causes immunostimulation at low doses and immunosuppression at higher doses.3 Metenkefalin can also inhibit the production of aldosterone, deoxycorticosterone, and corticosterone.4 Unfortunately, the mechanisms by which these effects occur have not been well described in the literature.

TargetActionsOrganism
UDelta-type opioid receptor
agonist
Humans
UMu-type opioid receptor
agonist
Humans
Absorption

Metenkefalin reaches a Cmax of 1266.14pg/mL, with a Tmax of 0.16h, and an AUC of 360.64pg*h/mL.7

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The half life of metenkefalin is 4.2-39 minutes.7

Clearance

Not Available

Adverse Effects
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Toxicity

Data regarding overdoses of metenkefalin are not readily available.7 Animal overdose studies have not determined an LD50.7

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Metenkefalin acetateRBM01752JM82362-17-2Not applicable

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Tyrosine and derivatives / Phenylalanine and derivatives / Methionine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Amphetamines and derivatives / Thia fatty acids / Hydroxy fatty acids / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids
show 12 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound
show 32 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
peptide (CHEBI:6618)
Affected organisms
Not Available

Chemical Identifiers

UNII
9JEZ9OD3AS
CAS number
58569-55-4
InChI Key
YFGBQHOOROIVKG-FKBYEOEOSA-N
InChI
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
IUPAC Name
(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
SMILES
CSCC[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O

References

General References
  1. Rakanovic-Todic M, Ibrulj S, Brunazovic-Ristic L, Catovic A, Aganovic-Musinovic I, Kusturica J: Cytogenetic effects of combination of tridecactide and met-enkephalin on lymphocytes of patients with multiple sclerosis Journal of Health Sciences. 2014 Apr 6;5(1):5-10. [Article]
  2. Zoccali C: Elimination of plasma metenkephalin. Nephrol Dial Transplant. 1989;4(3):236. doi: 10.1093/oxfordjournals.ndt.a091862. [Article]
  3. Rakanovic-Todic M, Burnazovic-Ristic L, Ibrulj S, Mulbegovic N: Effect of met-enkephalin on chromosomal aberrations in the lymphocytes of the peripheral blood of patients with multiple sclerosis. Bosn J Basic Med Sci. 2014 May;14(2):75-80. doi: 10.17305/bjbms.2014.2267. [Article]
  4. Racz K, Varga I, Glaz E, Kiss R, Vida S, Lada G, di Gleria K, Medzihradszky K, Lichtwald K, Vecsei P: Met-enkephalin inhibits mineralocorticoid production in isolated human aldosteronoma cells. J Clin Endocrinol Metab. 1982 Mar;54(3):656-60. doi: 10.1210/jcem-54-3-656. [Article]
  5. NIH: Clinical Trial to Evaluate the Efficacy and Safety of an Immunomodulatory Therapy for the Treatment of Patients With Moderate to Severe COVID-19 Infection (NCT04374032) [Link]
  6. Bosna Lijek: Enkorten Metenkefalin and Tridecactide Injection [Link]
  7. Bosna Lijek: Enkorten Summary of Product Characteristics [Link]
KEGG Compound
C11684
PubChem Compound
443363
PubChem Substance
347828872
ChemSpider
391597
BindingDB
50019056
RxNav
1349278
ChEBI
189868
ChEMBL
CHEMBL13786
ZINC
ZINC000004102171
Wikipedia
Met-enkephalin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Covid 19 Infection1
1CompletedTreatmentLiver Cancer1
1TerminatedTreatmentTumor1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0196 mg/mLALOGPS
logP0.28ALOGPS
logP-2.5Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.61Chemaxon
pKa (Strongest Basic)7.73Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area199.95 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity149.01 m3·mol-1Chemaxon
Polarizability58.85 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0901150000-e75c22524ff0d6d461e7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0h90-0011490000-5df96bdae398f4a41fd6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-1579570000-db3bb035e45a5e578c50
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9334540000-06603f77aeee89d19ed9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-024i-8851900000-868672720464bd17a24a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9222100000-1eeb096a09779141e10c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-249.3977708
predicted
DarkChem Lite v0.1.0
[M-H]-220.88329
predicted
DeepCCS 1.0 (2019)
[M+H]+249.0619708
predicted
DarkChem Lite v0.1.0
[M+H]+222.73257
predicted
DeepCCS 1.0 (2019)
[M+Na]+250.6795708
predicted
DarkChem Lite v0.1.0
[M+Na]+228.5085
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Delta-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Rakanovic-Todic M, Burnazovic-Ristic L, Ibrulj S, Mulbegovic N: Effect of met-enkephalin on chromosomal aberrations in the lymphocytes of the peripheral blood of patients with multiple sclerosis. Bosn J Basic Med Sci. 2014 May;14(2):75-80. doi: 10.17305/bjbms.2014.2267. [Article]
Details2. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Rakanovic-Todic M, Burnazovic-Ristic L, Ibrulj S, Mulbegovic N: Effect of met-enkephalin on chromosomal aberrations in the lymphocytes of the peripheral blood of patients with multiple sclerosis. Bosn J Basic Med Sci. 2014 May;14(2):75-80. doi: 10.17305/bjbms.2014.2267. [Article]

Enzymes

Details1. Carboxypeptidase A6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
May be involved in the proteolytic inactivation of enkephalins and neurotensin in some brain areas. May convert inactive angiotensin I into the biologically active angiotensin II (PubMed:18178555). Releases a C-terminal amino acid, with preference for large hydrophobic C-terminal amino acids and shows only very weak activity toward small amino acids and histidine (PubMed:20855895).
Specific Function
Metallocarboxypeptidase activity
Gene Name
CPA6
Uniprot ID
Q8N4T0
Uniprot Name
Carboxypeptidase A6
Molecular Weight
51007.48 Da
References
  1. Lyons PJ, Callaway MB, Fricker LD: Characterization of carboxypeptidase A6, an extracellular matrix peptidase. J Biol Chem. 2008 Mar 14;283(11):7054-63. doi: 10.1074/jbc.M707680200. Epub 2008 Jan 4. [Article]

Drug created at October 20, 2016 23:33 / Updated at December 13, 2022 10:46