Anamorelin HCl

Synopsis, Chemistry

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Also known as: 861998-00-7, Anamorelin hcl, Anamorelin (hydrochloride), Anamorelin hydrochloride [usan], Rc-1291 hcl, Rc-1291 hydrochloride

Molecular Formula

C₃₁H₄₃ClN₆O₃

Molecular Weight

583.2 g/mol

InChI Key

VFYAEUWJFGTGGO-GHTUPXNNSA-N

FDA UNII

55F75LJQ0V

Anamorelin Hydrochloride is the orally bioavailable hydrochloride salt of a synthetic, 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 grhelin. 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 HCl

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;hydrochloride

2.1.2 InChI

InChI=1S/C31H42N6O3.ClH/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);1H/t26-,31-;/m1./s1

2.1.3 InChI Key

VFYAEUWJFGTGGO-GHTUPXNNSA-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.Cl

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.Cl

2.2 Other Identifiers

2.2.1 UNII

55F75LJQ0V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anamorelin

2.3.2 Depositor-Supplied Synonyms

1. 861998-00-7

2. Anamorelin Hcl

3. Anamorelin (hydrochloride)

4. Anamorelin Hydrochloride [usan]

5. Rc-1291 Hcl

6. Rc-1291 Hydrochloride

7. 55f75ljq0v

8. (3r)-1-((2r)-2-((2-amino-2-methylpropanoyl)amino)-3-(indol-3-yl)propanoyl)-3-benzyl-n,n',n'-trimethylpiperidine-3-carbohydrazide Hydrochloride

9. 3-piperidinecarboxylic Acid, 1-(2-methylalanyl-d-tryptophyl)-3-(phenylmethyl)-, Trimethylhydrazide, Monohydrochloride, (3r)-

10. Unii-55f75ljq0v

11. Ono-7643 Hydrochloride

12. Schembl4535148

13. Chembl2103794

14. Dtxsid70235443

15. Bcp15207

16. Anamorelin Hydrochloride (jan/usan)

17. Anamorelin Hydrochloride [mi]

18. Hy-14734a

19. Mfcd23098788

20. Anamorelin Hydrochloride [jan]

21. Akos030526940

22. Cs-1037

23. Anamorelin Hydrochloride [who-dd]

24. Ac-29222

25. D08856

26. Q27261306

27. 2-amino-n-((r)-1-((r)-3-benzyl-3-(1,2,2-trimethylhydrazine-1-carbonyl)piperidin-1-yl)-3-(1h-indol-3-yl)-1-oxopropan-2-yl)-2-methylpropanamide Hydrochloride

28. 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;hydrochloride

2.4 Create Date

2007-06-04

3 Chemical and Physical Properties

Molecular Formula	C₃₁H₄₃ClN₆O₃
Molecular Weight	583.2 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	9
Exact Mass	582.3085169 g/mol
Monoisotopic Mass	582.3085169 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	904
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	2