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AM001746

AM001746

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

1 NDC API

1 NDC API

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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

AM001746

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 Formula	C₂₇H₃₅N₅O₇S
Molecular Weight	573.7 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	16
Exact Mass	573.22571965 g/mol
Monoisotopic Mass	573.22571965 g/mol
Topological Polar Surface Area	225 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	847
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 C_max of 1266.14pg/mL, with a T_max 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.