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    Enkephalin M

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 58569-55-4, Methionine enkephalin, H-tyr-gly-gly-phe-met-oh, Tyr-gly-gly-phe-met-oh, Tyr-gly-gly-phe-met, [met]enkephalin
    Molecular Formula
    C27H35N5O7S
    Molecular Weight
    573.7  g/mol
    InChI Key
    YFGBQHOOROIVKG-FKBYEOEOSA-N
    FDA UNII
    9JEZ9OD3AS
    One of the endogenous pentapeptides with morphine-like activity. It differs from LEU-ENKEPHALIN by the amino acid METHIONINE in position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
    2.1.2 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
    2.1.3 InChI Key
    YFGBQHOOROIVKG-FKBYEOEOSA-N
    2.1.4 Canonical SMILES
    CSCCC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)N
    2.1.5 Isomeric SMILES
    CSCC[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=C(C=C2)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    9JEZ9OD3AS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5 Methionine Enkephalin

    2. 5-methionine Enkephalin

    3. Enkephalin, 5-methionine

    4. Enkephalin, Methionine

    5. Met Enkephalin

    6. Met(5)-enkephalin

    7. Methionine Enkephalin

    2.3.2 Depositor-Supplied Synonyms

    1. 58569-55-4

    2. Methionine Enkephalin

    3. H-tyr-gly-gly-phe-met-oh

    4. Tyr-gly-gly-phe-met-oh

    5. Tyr-gly-gly-phe-met

    6. [met]enkephalin

    7. [5-methionine]enkephalin

    8. (met5)-enkephalin

    9. Opioid Growth Factor

    10. Metenkefalin [inn]

    11. Metenkefalin

    12. 9jez9od3as

    13. Chembl13786

    14. Enkephalin, Methionine

    15. (2s)-2-[[(2s)-2-[[2-[[2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic Acid

    16. [met5]-enkephalin

    17. [met5]enkephalin Acetate Salt Hydrate

    18. (2s)-2-[[(2s)-2-[[2-[[2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenyl-propanoyl]amino]-4-methylsulfanyl-butanoic Acid

    19. Opioid Growth Factor (ogf)

    20. 82362-17-2

    21. Unii-9jez9od3as

    22. Chebi:6618

    23. Porcine Beta-endorphin 1-5

    24. Met-enkefalin

    25. Ccris 4225

    26. Met5-enkephalin

    27. Np2 Enkephalin

    28. Nsc-374896

    29. [met]-enkephalin

    30. Met-enk

    31. 1-5 Adrenorphin

    32. 2-[[2-[[2-[[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic Acid

    33. Einecs 261-335-8

    34. Sh-pentapeptide-19

    35. Nsc 374896

    36. Inno-105

    37. L-methionine, L-tyrosylglycylglycyl-l-phenylalanyl-

    38. 1-5-adrenorphin (human)

    39. Enkephalin-(5-l-methionine)

    40. Metenkefalin [who-dd]

    41. Schembl632433

    42. Gtpl1614

    43. Dtxsid80332078

    44. Irt-101

    45. Hy-p0073

    46. Sh-pentapeptide-19 [inci]

    47. Zinc4102171

    48. Bdbm50019056

    49. Mfcd00076415

    50. Cs-5426

    51. Db12668

    52. Ncgc00163683-01

    53. As-58159

    54. C75740

    55. 569t554

    56. A915141

    57. Met-enkephalin (h-l-tyr-gly-gly-l-phe-l-met-oh)

    58. N-(n-(n-(n-l-tyrosylglycyl)glycyl)-l-phenylalanyl)-l-methionine

    59. Adrenorphin (human), 6-de-l-arginine-7-de-l-arginine-8-de-l-valinamide-

    60. ([met]-enkephalin)2-[2-(2-{2-[2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric Acid([met]-enkephalin

    61. (s)-2-[(s)-2-(2-{2-[(s)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric Acid

    62. 2-[(s)-2-(2-{2-[(s)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-1-oxo-3-phenyl-propylamino]-4-methylsulfanyl-butyric Acid

    63. 2-[1-[1-amino-2-(4-hydroxyphenyl)-(1s)-ethylcarboxamidomethylcarboxamidomethylcarboxamido]-2-phenyl-(1s)-ethylcarboxamido]-4-methylsulfanyl-(2s)-butanoic Acid

    64. 2-[2-(2-{2-[2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyric Acid

    65. L-tyrosylglycylglycyl-l-phenylalanyl-l-methionine .beta.-endorphin Human-(1-5)-peptide

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 573.7 g/mol
    Molecular Formula C27H35N5O7S
    XLogP3-2.1
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count16
    Exact Mass573.22571965 g/mol
    Monoisotopic Mass573.22571965 g/mol
    Topological Polar Surface Area225 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity847
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Neurotransmitter Agents

    Substances used for their pharmacological actions on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function. (See all compounds classified as Neurotransmitter Agents.)

    5.2 Absorption, Distribution and Excretion

    Absorption

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

    5.3 Biological Half-Life

    The half life of metenkefalin is 4.2-39 minutes.

    5.4 Mechanism of Action

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