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    Macimorelin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    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

    2D Structure

    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 Weight 474.6 g/mol
    Molecular Formula C26H30N6O3
    XLogP31.8
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count9
    Exact Mass474.23793884 g/mol
    Monoisotopic Mass474.23793884 g/mol
    Topological Polar Surface Area145 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity761
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    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.