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    Chemistry

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    Also known as: 249921-19-5, Anamorelin [inn], Rc 1291, Rc-1291, Dd5rba1nkf, Ono-7643
    Molecular Formula
    C31H42N6O3
    Molecular Weight
    546.7  g/mol
    InChI Key
    VQPFSIRUEPQQPP-MXBOTTGLSA-N
    FDA UNII
    DD5RBA1NKF
    Anamorelin
    Anamorelin is a synthetic, orally bioavailable, small-molecule ghrelin mimetic with appetite-stimulating and anabolic activities. Anamorelin binds to and stimulates the growth hormone secretagogue receptor (GHSR) centrally, thereby mimicking the appetite-stimulating and growth hormone-releasing effects of ghrelin. Stimulation of GHSR may also reduce the production of the pro-inflammatory cytokines TNF-alpha and interleukin-6, which may play a direct role in cancer-related loss of appetite.
    1 2D Structure

    Anamorelin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-amino-N-[(2R)-1-[(3R)-3-benzyl-3-[dimethylamino(methyl)carbamoyl]piperidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide
    2.1.2 InChI
    InChI=1S/C31H42N6O3/c1-30(2,32)28(39)34-26(18-23-20-33-25-15-10-9-14-24(23)25)27(38)37-17-11-16-31(21-37,29(40)36(5)35(3)4)19-22-12-7-6-8-13-22/h6-10,12-15,20,26,33H,11,16-19,21,32H2,1-5H3,(H,34,39)/t26-,31-/m1/s1
    2.1.3 InChI Key
    VQPFSIRUEPQQPP-MXBOTTGLSA-N
    2.1.4 Canonical SMILES
    CC(C)(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)N3CCCC(C3)(CC4=CC=CC=C4)C(=O)N(C)N(C)C)N
    2.1.5 Isomeric SMILES
    CC(C)(C(=O)N[C@H](CC1=CNC2=CC=CC=C21)C(=O)N3CCC[C@](C3)(CC4=CC=CC=C4)C(=O)N(C)N(C)C)N
    2.2 Other Identifiers
    2.2.1 UNII
    DD5RBA1NKF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Anamorelin Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 249921-19-5

    2. Anamorelin [inn]

    3. Rc 1291

    4. Rc-1291

    5. Dd5rba1nkf

    6. Ono-7643

    7. St-1291

    8. 3-piperidinecarboxylic Acid, 1-[(2r)-2-[(2-amino-2-methyl-1-oxopropyl)amino]-3-(1h-indol-3-yl)-1-oxopropyl]-3-(phenylmethyl)-, 1,2,2-trimethylhydrazide, (3r)-

    9. 2-amino-n-[(2r)-1-[(3r)-3-benzyl-3-[dimethylamino(methyl)carbamoyl]piperidin-1-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide

    10. 3-piperidinecarboxylic Acid, 1-(2-methylalanyl-d-tryptophyl)-3-(phenylmethyl)-, Trimethylhydrazide, (3r)-

    11. Unii-dd5rba1nkf

    12. Anamorelin [mi]

    13. Ono-7643;anamorelin

    14. Anamorelin [who-dd]

    15. Schembl935751

    16. Chembl2110579

    17. Dtxsid20179702

    18. Ex-a154

    19. Bcp06108

    20. Mfcd11973671

    21. Ono-7643rc-1291

    22. S4980

    23. Zinc43130908

    24. Akos030526752

    25. Ccg-269985

    26. Db06645

    27. Ncgc00378854-01

    28. Ac-33703

    29. As-75284

    30. Hy-14734

    31. 921a195

    32. Q20707542

    33. (3r)-1-((2r)-2-((2-amino-2-methylpropanoyl)amino)-3-(indol-3-yl)propanoyl)-3-benzyl-n,n',n'-trimethylpiperidine-3-carbohydrazide

    34. 2-amino-n-[(2r)-1-[(3r)-3-benzyl-3-(n,n',n'-trimethylhydrazinecarbonyl)piperidin-1-yl]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]-2-methylpropanamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 546.7 g/mol
    Molecular Formula C31H42N6O3
    XLogP32.8
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count9
    Exact Mass546.33183922 g/mol
    Monoisotopic Mass546.33183922 g/mol
    Topological Polar Surface Area115 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity904
    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

    Investigated for use/treatment in cachexia and anorexia.

    Treatment of anorexia, cachexia or unintended weight loss in adult patients with non-small cell lung cancer (NSCLC)

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    V03

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