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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H42N6O3
Molecular Weight 546.7036
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANAMORELIN

SMILES

CN(C)N(C)C(=O)[C@@]2(CC1=CC=CC=C1)CCCN(C2)C(=O)[C@@H](CC3=CNC4=CC=CC=C34)NC(=O)C(C)(C)N

InChI

InChIKey=VQPFSIRUEPQQPP-MXBOTTGLSA-N
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

HIDE SMILES / InChI

Molecular Formula C31H42N6O3
Molecular Weight 546.7036
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Anamorelin is a first-in-class, orally active ghrelin receptor agonist that binds and stimulates the growth hormone secretagogue receptor centrally, thereby mimicking the appetite-enhancing and anabolic effects of ghrelin. Anamorelin is under development by Helsinn Therapeutics for the treatment of cancer cachexia and anorexia. Anamorelin has completed phase III clinical trials for the treatment of cancer cachexia and anorexia associated with non-small-cell lung carcinoma. Results of the studies were positive, and the drug is now in preregistration with the European Medicines Agency.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.74 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
80.6 ng/mL
25 mg single, oral
ANAMORELIN plasma
Homo sapiens
184 ng/mL
25 mg single, oral
ANAMORELIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
197 ng × h/mL
25 mg single, oral
ANAMORELIN plasma
Homo sapiens
366 ng × h/mL
25 mg single, oral
ANAMORELIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.03 h
25 mg single, oral
ANAMORELIN plasma
Homo sapiens
6.08 h
25 mg single, oral
ANAMORELIN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
100 mg orally administered daily at least one hour before meal
Route of Administration: Oral
In Vitro Use Guide
Anamorelin showed significant agonist activity on the ghrelin receptor with EC50 value of 0.74 nM
Substance Class Chemical
Record UNII
DD5RBA1NKF
Record Status Validated (UNII)
Record Version