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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.74 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
80.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26640742/
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:
https://pubmed.ncbi.nlm.nih.gov/28472437
unhealthy
n = 343
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 343
Sources:
https://pubmed.ncbi.nlm.nih.gov/28472437
Other AEs: Hyperglycemia...
Other AEs:
Hyperglycemia (1.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28472437
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:
https://pubmed.ncbi.nlm.nih.gov/28472437
unhealthy
n = 343
Health Status: unhealthy
Condition: NSCLC
Sex: M+F
Food Status: UNKNOWN
Population Size: 343
Sources:
https://pubmed.ncbi.nlm.nih.gov/28472437
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P002QL2
https://www.1pchem.com/search?query=1P002QL2
1PlusChem LLC
1P00GUHJ
https://www.1pchem.com/search?query=1P00GUHJ
AChemBlock
10265
http://www.achemblock.com/catalogsearch/result/?q=10265
AK Scientific
3157AH
https://aksci.com/item_detail.php?cat=3157AH
AK Scientific
3444AH
https://aksci.com/item_detail.php?cat=3444AH
AK Scientific
3445AH
https://aksci.com/item_detail.php?cat=3445AH
AbovChem LLC
HY-14734B
http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-14734B
Alfa Chemistry
ACM249921195
http://www.alfa-chemistry.com/search.aspx?q=ACM249921195
AstaTech
40205
http://astatechinc.com/CPSResult.php?CRNO=40205
BLD Pharm
BD630587
http://www.bldpharm.com/search/Search.html?keyword=BD630587
BLD Pharm
BD630658
http://www.bldpharm.com/search/Search.html?keyword=BD630658
BLD Pharm
BD630916
http://www.bldpharm.com/search/Search.html?keyword=BD630916
BOC Sciences
249921-19-5
http://www.bocsci.com/description.asp?cas=249921-19-5
Chem Scene
CS-1037
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1037
ChemShuttle
169531
https://www.chemshuttle.com/catalogsearch/result/?q=169531
Debye Scientific
DA-35327
https://www.debyesci.com/index.php?id=product&ext[cno]=DA-35327
Excenen
EX-A154
http://www.excenen.com/searchresultlist.php?id=EX-A154
KeyOrganics
AS-75284
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75284
MedChem Express
HY-14734
https://www.medchemexpress.com/search.html?q=HY-14734A&ft=&fa=&fp=
MedChem Express
HY-14734A
https://www.medchemexpress.com/search.html?q=HY-14734A&ft=&fa=&fp=
MolPort
MolPort-039-139-550
https://www.molport.com/shop/molecule-link/MolPort-039-139-550
MolPort
MolPort-039-139-551
https://www.molport.com/shop/molecule-link/MolPort-039-139-551
Molnova
M13734
https://www.molnova.com/en/serch-list.html?keywords=M13734
Molnova
M14150
https://www.molnova.com/en/serch-list.html?keywords=M14150
Molnova
M16239
https://www.molnova.com/en/serch-list.html?keywords=M16239
MuseChem
I002848
https://www.musechem.com/product/I002848.html
MuseChem
I003228
https://www.musechem.com/product/I003228.html
PI Chemicals
PI-39497
http://www.pipharm.com/catalog_products/PI-39497.html
Selleck Chemicals
S4980
http://www.selleckchem.com/search.html?searchDTO.searchParam=S4980
ShangHai Biochempartner
BCP000666
http://www.biochempartner.com/search_BCP000666
ShangHai Biochempartner
BCP06108
http://www.biochempartner.com/search_BCP06108
ShangHai Biochempartner
BCP15207
http://www.biochempartner.com/search_BCP15207
ShangHai Biochempartner
BCP23985
http://www.biochempartner.com/search_BCP23985
Toronto Research Chemicals
A637225
https://www.trc-canada.com/product-detail/?CatNum=A637225
Toronto Research Chemicals
A656510
https://www.trc-canada.com/product-detail/?CatNum=A656510
Toronto Research Chemicals
E922033
https://www.trc-canada.com/product-detail/?CatNum=E922033
Toronto Research Chemicals
P139920
https://www.trc-canada.com/product-detail/?CatNum=P139920
eMolecules
266610513
https://orderbb.emolecules.com/search/#?query=266610513
eMolecules
300754452
https://orderbb.emolecules.com/search/#?query=300754452
eMolecules
44811280
https://orderbb.emolecules.com/search/#?query=44811280
eMolecules
44811298
https://orderbb.emolecules.com/search/#?query=44811298
eMolecules
44811505
https://orderbb.emolecules.com/search/#?query=44811505
mcule
MCULE-1447077543
https://mcule.com/MCULE-1447077543/
mcule
MCULE-5103186823
https://mcule.com/MCULE-5103186823/
mcule
MCULE-7006267405
https://mcule.com/MCULE-7006267405/
PubMed

PubMed

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

Patents

US20150072934
2
WO2013158874A1
2

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
Created
by admin
on Fri Dec 15 15:28:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:28:41 UTC 2023
Record UNII
DD5RBA1NKF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANAMORELIN
INN   WHO-DD  
INN  
Official Name English
3-PIPERIDINECARBOXYLIC ACID, 1-(2-METHYLALANYL-D-TRYPTOPHYL)-3-(PHENYLMETHYL)-, TRIMETHYLHYDRAZIDE, (3R)-
Common Name English
ANAMORELIN [MI]
Common Name English
ST-1291
Code English
Anamorelin [WHO-DD]
Common Name English
ONO-7643
Code English
RC-1291
Code English
(3R)-1-((2R)-2-((2-AMINO-2-METHYLPROPANOYL)AMINO)-3-(INDOL-3-YL)PROPANOYL)-3-BENZYL-N,N',N'-TRIMETHYLPIPERIDINE-3-CARBOHYDRAZIDE
Systematic Name English
anamorelin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1935
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
Code System Code Type Description
PUBCHEM
9828911
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
WIKIPEDIA
Anamorelin
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
EVMPD
SUB178986
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110579
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
DRUG BANK
DB06645
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
FDA UNII
DD5RBA1NKF
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID20179702
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
CAS
249921-19-5
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
INN
8846
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
MERCK INDEX
m12067
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
NCI_THESAURUS
C52197
Created by admin on Fri Dec 15 15:28:41 UTC 2023 , Edited by admin on Fri Dec 15 15:28:41 UTC 2023
PRIMARY
Related Record Type Details
Structure of ANAMORELIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
GROWTH HORMONE SECRETAGOGUE RECEPTOR TYPE 1A
TARGET -> AGONIST
Related Record Type Details
Structure of ANAMORELIN
ACTIVE MOIETY
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