Macimorelin

DRACPC ID  DRACPC0079

Active Ingredients   Macimorelin

Description  An orally available synthetic mimetic of the growth hormone (GH) secretagogue ghrelin with potential anti-cachexia activity. Upon oral administration, macimorelin mimics endogenous ghrelin by stimulating appetite and binds to the growth hormone secretagogue receptor GHSR in the central nervous system, thereby mimicking the GH-releasing effects of ghrelin from the pituitary gland. Stimulation of GH secretion increases insulin-like growth factor-I (IGF-I) levels which may further stimulate protein synthesis. In addition, ghrelin reduces the production of pro-inflammatory cytokines, which may play a direct role in cancer-related loss of appetite.

Synonyms  AEZS-130; D-Tryptophanamide,2-methylalanyl-N-[(1R)-1-(formylamino)-2-(1H-indol-3-yl)ethyl]-; EP 1572; JMV 1843; Macimorelin; Solorel

Type  Small Molecule

Disease  AGHD, Cancer Cachexia

Classification

  

Peptide and derivative

Structure Information


Molecular Formula  C26H30N6O3

Molecular Weight  474.565

Active Sequence  Xw

Sequence Length  2

Modification  X=Aib

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2R)-2-(2-amino-2-methylpropanamido)-3-(1H-indol-3-yl)-N-[(1R)-2-(1H-indol-3-yl)-1-formamidoethyl]propanamide

InChI  InChI=1S/C26H30N6O3/c1-26(2,27)25(35)31-22(11-16-13-28-20-9-5-3-7-18(16)20)24(34)32-23(30-15-33)12-17-14-29-21-10-6-4-8-19(17)21/h3-10,13-15,22-23,28-29H,11-12,27H2,1-2H3,(H,30,33)(H,31,35)(H,32,34)/t22-,23-/m1/s1

InChI_Key UJVDJAPJQWZRFR-DHIUTWEWSA-N

SMILES  O=C(N[C@@H](NC=O)CC1=CNC2=C1C=CC=C2)[C@H](NC(C(C)(N)C)=O)CC3=CNC4=C3C=CC=C4

External Codes


PubChem CID  9804938

DrugBank Accession Number  DB13074

NCI Thesaurus Code  C95123  

UNII  8680B21W73   GSRS

CAS  381231-18-1



Drug approval


Drug indication
    Indicated for the diagnosis of adult growth hormone deficiency (AGHD). Macimorelin has investigated for use/treatment in Cancer Cachexia.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Macrilen eq 60mg base/pouch For Solution; Oral Novo Prescription NDA: 205598 2017
Ghryvelin (Previously Macimorelin Aeterna Zentaris) 0.5 mg per kg body weight Granules Dissolved; Oral Consilient Health Limited Prescription EMEA/H/C/004660 2019

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT01614990 Cancer Cachexia Cancer Cachexia Phase 2 Treatment
NCT03844217 Copeptin After an Oral Stimulation With Macimorelin in Healthy Volunteers - The Macicop-Study Polyuria-polydipsia Syndrome Not Applicable Diagnostic

    More clinical information is obtained from ClinicalTrials.gov.





DRACP is developed by Dr.Zheng's team.