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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H42N6O3.ClH
Molecular Weight 583.165
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANAMORELIN HYDROCHLORIDE

SMILES

Cl.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=VFYAEUWJFGTGGO-GHTUPXNNSA-N
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

HIDE SMILES / InChI

Molecular Formula C31H42N6O3
Molecular Weight 546.7036
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/26386985 https://www.ncbi.nlm.nih.gov/pubmed/24472001 https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=460131

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.74 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
80.6 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
184 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
197 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
366 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.03 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.08 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANAMORELIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 343
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 343
Sources:
Other AEs: Hyperglycemia...
Other AEs:
Hyperglycemia (1.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hyperglycemia 1.2%
100 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy
n = 343
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 343
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Anamorelin hydrochloride in the treatment of cancer anorexia-cachexia syndrome.
2014 Apr
Patents

Sample Use Guides

100 mg orally administered daily at least one hour before meal
Route of Administration: Oral
Anamorelin showed significant agonist activity on the ghrelin receptor with EC50 value of 0.74 nM
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:19 GMT 2023
Record UNII
55F75LJQ0V
Record Status Validated (UNII)
Record Version
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Name Type Language
ANAMORELIN HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
ANAMORELIN HYDROCHLORIDE [JAN]
Common Name English
Anamorelin hydrochloride [WHO-DD]
Common Name English
3-PIPERIDINECARBOXYLIC ACID, 1-(2-METHYLALANYL-D-TRYPTOPHYL)-3-(PHENYLMETHYL)-, TRIMETHYLHYDRAZIDE, MONOHYDROCHLORIDE, (3R)-
Common Name English
(3R)-1-((2R)-2-((2-AMINO-2-METHYLPROPANOYL)AMINO)-3-(INDOL-3-YL)PROPANOYL)-3-BENZYL-N,N',N'-TRIMETHYLPIPERIDINE-3-CARBOHYDRAZIDE HYDROCHLORIDE
Systematic Name English
ANAMORELIN HYDROCHLORIDE [MI]
Common Name English
RC-1291 HCL
Code English
ANAMORELIN HCL
Common Name English
ANAMORELIN HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1935
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
Code System Code Type Description
MERCK INDEX
m12067
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
FDA UNII
55F75LJQ0V
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110579
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
NCI_THESAURUS
C72701
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
USAN
SS-21
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
PUBCHEM
16072155
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID70235443
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
CAS
861998-00-7
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
DRUG BANK
DBSALT002031
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
EVMPD
SUB179972
Created by admin on Fri Dec 15 15:56:19 GMT 2023 , Edited by admin on Fri Dec 15 15:56:19 GMT 2023
PRIMARY
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