Compound monograph
Macimorelin
Macimorelin is an orally active gem-diamino peptidomimetic agonist at the ghrelin receptor.
01
Identity & nomenclature
Macimorelin is an orally active gem-diamino peptidomimetic agonist at the ghrelin receptor.
Macimorelin is neither a ghrelin fragment nor an ordinary unmodified tripeptide; the peptidomimetic connectivity is what defines it. Acetate in a salt preparation must not become a covalent N-acetyl modification in the structural record.
Declared aliases and development codes: AEZS-130, JMV 1843, EP-1572.
02
Molecular properties
| Molecular formula | C26H30N6O3 |
|---|---|
| Molecular mass | 474.56 Da |
| CAS Registry Number | 381231-18-1 |
| PubChem CID | 9804938 |
| UNII | 8680B21W73 |
No conventional amino-acid sequence string exists for this molecule and none is published here. It is a gem-diamino peptidomimetic: an Aib-derived unit and a D-Trp-derived unit connected to an R-configured, indole-containing gem-diamino terminus bearing an N-formyl group. A terminal 'CHO' abbreviation is a formamide arrangement, not a free peptide aldehyde.
03
Structural characteristics
A cryo-EM structure of the ghrelin receptor bound to macimorelin, determined alongside an anamorelin-bound structure, shows both occupying a bifurcated pocket divided by a conserved salt bridge, with mutagenesis identifying the residues behind their differing affinities. That permits a direct structural comparison rather than an assumption that all ghrelin mimetics bind alike. An assay-independent signalling-bias designation is not established.
- gem-diamino linkage
- D-tryptophan-derived unit
Terminal features: N-formyl gem-diamino terminus.
04
Molecular targets & mechanisms
05
Analytical considerations
An amino-acid composition result or a peptide search-engine match is insufficient for this terminus. NMR is needed to establish gem-diamino connectivity and N-formyl placement, with a chiral method for the defined stereocentres. Counterion content for acetate material is a separate measurement; the parent ion establishes neither acetate stoichiometry nor peptide-equivalent content.
06
Verified bibliography
- New active series of growth hormone secretagogues.current
Guerlavais V, Boeglin D, Mousseaux D, Oiry C, Heitz A, Deghenghi R, Locatelli V, Torsello A, Ghé C, Catapano F, Muccioli G, Galleyrand JC, Fehrentz JA, Martinez J
Journal of medicinal chemistry · 2003-03-27 · Journal Article
- Molecular recognition of two approved drugs Macimorelin and Anamorelin by the growth hormone secretagogue receptor.current
Wang RL, Sun J, Liu H, Guo SM, Zhang Y, Hu W, Wang J, Liu H, Zhuang YW, Jiang Y, Xie X, Xu HE, Wang Y
Acta pharmacologica Sinica · 2025-06-20 · Journal Article
- Molecular recognition of an acyl-peptide hormone and activation of ghrelin receptor.current
Wang Y, Guo S, Zhuang Y, Yun Y, Xu P, He X, Guo J, Yin W, Xu HE, Xie X, Jiang Y
Nature communications · 2021-08-20 · Journal Article
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Methodology & citation verification
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