MACIMORELIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H30N6O3
Molecular Weight	474.5548
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=UJVDJAPJQWZRFR-DHIUTWEWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C26H30N6O3
Molecular Weight	474.5548
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

Macimorelin (AEZS 130) is an orally active, small-molecule, peptidomimetic growth hormone secretagogue receptor (GHSR1A) agonist (ghrelin analogue), being developed by AEterna Zentaris for the diagnosis of adult growth hormone deficiency (AGHD; somatotropin deficiency), and for the treatment of cachexia associated with chronic disease such as AIDS and cancer. Macimorelin was approved by the FDA in December 2017 under the market name Macrilen for oral solution. Macimorelin stimulates GH release by activating growth hormone secretagogue receptors present in the pituitary and hypothalamus. Macimorelin has been granted orphan drug designation by the FDA for diagnosis of AGHD.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ghrelin receptor 15	Agonist 2,678		123.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Growth hormone deficiency 5	Diagnostic		Approved 8,429	MACRILEN

C_max

Value	Dose	Analyte	Population
9.24 ng/mL	0.5 mg single, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
10.6 μg/L	0.5 mg/kg 1 times / day multiple, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
9.17 ng/mL	0.5 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens
21.9 ng/mL	2 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
38 ng × h/mL	0.5 mg single, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
32 μg × h/L	0.5 mg/kg 1 times / day multiple, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
59.45 ng × h/mL	0.5 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens
75.7 ng × h/mL	2 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.51 h	0.5 mg single, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
3.9 h	0.5 mg/kg 1 times / day multiple, oral	[NO STEREO] MACIMORELIN plasma	Homo sapiens
3.76 h	0.5 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens
7.23 h	2 mg/kg single, oral	MACIMORELIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
22%	0.5 mg/kg 1 times / day multiple, oral		[NO STEREO] MACIMORELIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
2 mg/kg 1 times / day single, oral Highest studied dose	healthy, adult n = 9	Other AEs: Diarrhoea, Pain...
0.5 mg/kg 1 times / day single, oral Recommended	unhealthy, adult n = 52	Disc. AE: Vein collapse...

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AEs

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AE	Significance	Dose	Population
Diarrhoea	11.1%	2 mg/kg 1 times / day single, oral Highest studied dose	healthy, adult n = 9
Pain	11.1%	2 mg/kg 1 times / day single, oral Highest studied dose	healthy, adult n = 9
Headache	44.4%	2 mg/kg 1 times / day single, oral Highest studied dose	healthy, adult n = 9
Vein collapse	1.9% Disc. AE	0.5 mg/kg 1 times / day single, oral Recommended	unhealthy, adult n = 52

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	inhibitor 1,767 substrate 1,037	inhibitor 1,852 substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C8 911 CYP2C19 1,478 P-gp 1,461	CYP1A1 349 CYP1A2 1,054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity
CYP2C19 1,553	inhibitor 3,277	no [IC50 25 uM]
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no
CYP2A6 739	inhibitor 3,277	no
CYP2C8 965	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
CYP3A4 1,737	substrate 3,367	major
CYP1A1 349	substrate 3,367	no
CYP1A2 1,054	substrate 3,367	no
CYP2A6 543	substrate 3,367	no
CYP2B6 664	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Chemieliva Pharmaceutical Co., Ltd	PBCM1293258
Compound Cloud	71526737
Compound Cloud	9804938
Hairui	HR139802	http://www.hairuichem.com/en/product/381231-18-1.html
Lan Pharmatech	LAN-B38700

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PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

Recommended dose is 0.5 mg/kg as a single oral dose, after fasting for at least 8 hours

Route of Administration: Oral

In Vitro Use Guide

Macimorelin exhibited a high binding affinity to the cloned hGHS-R 1a receptor (IC50 value of 123 nM).

Substance Class	Chemical
Record UNII	8680B21W73
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

MACIMORELIN

Official Name

English

EP-1572

Code

English

MACIMORELIN [MI]

Common Name

English

D-87575

Code

English

JMV-1843

Code

English

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Classification Tree

Code System

Code

Tests for pituitary function

WHO-ATC

V04CD06

Therapeutic Hormone

NCI_THESAURUS

C76358

Established Pharmacologic Class

NDF-RT

N0000193785

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Code System

Code

Type

Description

PUBCHEM

9804938

PRIMARY

SMS_ID

100000175809

PRIMARY

DAILYMED

8680B21W73

PRIMARY

NCI_THESAURUS

C95123

PRIMARY

RXCUI

1999420

PRIMARY

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Related Record

Type

Details


					AQZ1003RMG

MACIMORELIN ACETATE

SALT/SOLVATE -> PARENT

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Amount:


					NUJ1I0OY8D

GROWTH HORMONE SECRETAGOGUE RECEPTOR TYPE 1A

TARGET -> AGONIST

Comments:

test for adult GH deficiency:

Amount:

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Related Record

Type

Details


					8680B21W73

MACIMORELIN

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Biological Half-life	PHARMACOKINETIC	4.1 hours (average)	ORAL ADMINISTRATION

Tmax	PHARMACOKINETIC	[0.5 to 1.5] hours (average)	ORAL ADMINISTRATION

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator