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Macimorelin

Synopsis, Chemistry

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Also known as: Ard-07, Aezs-130, 381231-18-1, Ep-1572, Jmv-1843, Ard 07

Molecular Formula

C₂₆H₃₀N₆O₃

Molecular Weight

474.6 g/mol

InChI Key

UJVDJAPJQWZRFR-DHIUTWEWSA-N

FDA UNII

8680B21W73

Macimorelin is an orally available synthetic mimetic of the growth hormone (GH) secretagogue ghrelin with potential anti-cachexia activity. Upon oral administration, macimorelin mimics endogenous ghrelin by stimulating appetite and binds to the growth hormone secretagogue receptor GHSR in the central nervous system, thereby mimicking the GH-releasing effects of ghrelin from the pituitary gland. Stimulation of GH secretion increases insulin-like growth factor-I (IGF-I) levels which may further stimulate protein synthesis. In addition, ghrelin reduces the production of pro-inflammatory cytokines, which may play a direct role in cancer-related loss of appetite.

Macimorelin is a Growth Hormone Secretagogue Receptor Agonist. The mechanism of action of macimorelin is as a Growth Hormone Secretagogue Receptor Agonist.

1 2D Structure

Macimorelin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-N-[(2R)-1-[[(1R)-1-formamido-2-(1H-indol-3-yl)ethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide

2.1.2 InChI

InChI=1S/C26H30N6O3/c1-26(2,27)25(35)31-22(11-16-13-28-20-9-5-3-7-18(16)20)24(34)32-23(30-15-33)12-17-14-29-21-10-6-4-8-19(17)21/h3-10,13-15,22-23,28-29H,11-12,27H2,1-2H3,(H,30,33)(H,31,35)(H,32,34)/t22-,23-/m1/s1

2.1.3 InChI Key

UJVDJAPJQWZRFR-DHIUTWEWSA-N

2.1.4 Canonical SMILES

CC(C)(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC3=CNC4=CC=CC=C43)NC=O)N

2.1.5 Isomeric SMILES

CC(C)(C(=O)N[C@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC3=CNC4=CC=CC=C43)NC=O)N

2.2 Other Identifiers

2.2.1 UNII

8680B21W73

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aezs-130

2. Aib-dtrp-dgtrp-cho

3. Aib-trp-gtrp-cho

4. Aminoisobutyryl-tryptophyl-tryptophanamine-formyl

5. Ard-07

6. Ep 1572

7. Ep-1572

8. Ep1572

9. Jmv 1843

10. Jmv-1843

11. Jmv1843

12. Macimorelin Acetate

13. Macrilen

2.3.2 Depositor-Supplied Synonyms

1. Ard-07

2. Aezs-130

3. 381231-18-1

4. Ep-1572

5. Jmv-1843

6. Ard 07

7. Jmv 1843

8. Ep 1572

9. Ep-01572

10. Chembl278623

11. 381231-18-1 (free Base)

12. Ep1572

13. Macimorelin (usan)

14. 8680b21w73

15. Macimorelin [usan]

16. D-87575

17. 2-amino-n-((r)-1-(((r)-1-formamido-2-(1h-indol-3-yl)ethyl)amino)-3-(1h-indol-3-yl)-1-oxopropan-2-yl)-2-methylpropanamide

18. 2-amino-n-[(2r)-1-[[(1r)-1-formamido-2-(1h-indol-3-yl)ethyl]amino]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide

19. Macimorelin [inn]

20. Macimorelin [usan:inn]

21. Unii-8680b21w73

22. Aib-dtrp-dgtrp-cho

23. Macimorelin [mi]

24. Aezs130

25. Macimorelin [who-dd]

26. Gtpl9745

27. Schembl1984708

28. Jmv1843

29. Umv1843

30. Dtxsid601045766

31. Glxc-25240

32. Bdbm50125886

33. Db13074

34. Ep01572

35. Hy-14820

36. Cs-0003577

37. D10563

38. Aminoisobutyryl-tryptophyl-tryptophanamine-formyl

39. Q15624037

40. 2-amino-n-{(r)-1-[(r)-1-formylamino-2-(1h-indol-3-yl)-ethylcarbamoyl]-2-1h-indol-3-yl-ethyl}-2-methyl-propionamide

41. N(sup 2)-(2-amino-2-methylpropanoyl-n1-((1r)-1-formamido-2-(1h-indol-3-yl)ethyl)-d-tryptophanamide

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₀N₆O₃
Molecular Weight	474.6 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	9
Exact Mass	474.23793884 g/mol
Monoisotopic Mass	474.23793884 g/mol
Topological Polar Surface Area	145 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	761
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Indicated for the diagnosis of adult growth hormone deficiency (AGHD).

FDA Label

This medicinal product is for diagnostic use only. GHRYVELIN is indicated for the diagnosis of growth hormone deficiency (GHD) in adults.

Diagnosis of growth hormone deficiency

5 Pharmacology and Biochemistry

5.1 Pharmacology

Maximum GH levels from stimulation are observed between 30 to 90 minutes after administration of macimorelin. Increase in the QTcF interval may be observed from macimorelin administration.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

MACIMORELIN

5.2.2 FDA UNII

8680B21W73

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Growth Hormone Secretagogue Receptor Agonists

5.3 ATC Code

V04CD06

V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CD - Tests for pituitary function

V04CD06 - Macimorelin

5.4 Absorption, Distribution and Excretion

Absorption

Macimorelin is a novel, synthetic ghrelin agonist, which is readily absorbed from the gastrointestinal tract. The maximum plasma concentration (Cmax) was observed between 0.5 and 1.5 hours following oral administration of 0.5mg/kg macimorelin to patients with AGHD under fasting for at least 8 hours. Higher doses of drug demonstrate a dose-proportional increase in plasma concentrations. A liquid meal decreased the macimorelin Cmax and AUC by 55% and 49%, respectively.

Volume of Distribution

Following a single oral dose of 0.5 mg/kg macimorelin, the mean volume of distribution of the central compartment is 5,733.4 565.7L.

Clearance

Following a single oral dose of 0.5 mg/kg macimorelin, the mean clearance over the fraction absorbed (Cl/F) was 37,411.0 4,554.6 mL/min.

5.5 Metabolism/Metabolites

Macimorelin predominantly undergoes CYP3A4-mediated metabolism according to an *in vitro* human liver microsomes study.

5.6 Biological Half-Life

The mean terminal half-life (T1/2) is 4.1 hours following administration of a single oral dose of 0.5 mg macimorelin/kg body weight in healthy subjects.

5.7 Mechanism of Action

Ghrelin is an endogenous ligand for the GH secretagogue receptor that is also called the ghrelin receptor (GHS-R1a). Upon activation of the receptor, ghrelin serves to increase growth hormone (GH) secretion. Macimorelin mimics the actions of ghrelin by stimulating GH release. As a synthetic agonist, it activates growth hormone secretagogue receptors present in the pituitary and hypothalamus.