ACYLINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C80H102ClN15O14
Molecular Weight	1533.214
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@H](NC(=O)[C@@H](CC1=CC=C(NC(C)=O)C=C1)NC(=O)[C@H](CC2=CC=C(NC(C)=O)C=C2)NC(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(Cl)C=C4)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N7CCC[C@H]7C(=O)N[C@H](C)C(N)=O

InChI

InChIKey=ZWNUQDJANZGVFO-YHSALVGYSA-N

InChI=1S/C80H102ClN15O14/c1-46(2)37-63(72(102)89-62(18-11-12-35-84-47(3)4)80(110)96-36-14-19-70(96)79(109)85-48(5)71(82)101)90-74(104)66(40-53-23-30-60(31-24-53)86-49(6)98)92-76(106)67(41-54-25-32-61(33-26-54)87-50(7)99)94-78(108)69(45-97)95-77(107)68(43-56-15-13-34-83-44-56)93-75(105)65(39-52-21-28-59(81)29-22-52)91-73(103)64(88-51(8)100)42-55-20-27-57-16-9-10-17-58(57)38-55/h9-10,13,15-17,20-34,38,44,46-48,62-70,84,97H,11-12,14,18-19,35-37,39-43,45H2,1-8H3,(H2,82,101)(H,85,109)(H,86,98)(H,87,99)(H,88,100)(H,89,102)(H,90,104)(H,91,103)(H,92,106)(H,93,105)(H,94,108)(H,95,107)/t48-,62+,63+,64-,65-,66-,67+,68-,69+,70+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C80H102ClN15O14
Molecular Weight	1533.214
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://mct.aacrjournals.org/content/6/11_Supplement/B83 | https://www.ncbi.nlm.nih.gov/pubmed/15579744 | https://adisinsight.springer.com/drugs/800025851

Merrion Pharmaceuticals was developing an oral tablet formulation of acyline, a gonadotropin-releasing hormone (GnRH) antagonist, referred to as MER 104. MER-104 effectively suppresses luteinizing hormone (LH) and follicle-stimulating hormone (FSH) secretion in man. Acyline has been investigated for the prevention and treatment of hypogonadism and contraception. Injectable forms have been administered successfully in man in Phase II studies as part of a potential contraceptive regimen. MER-104 is an enteric coated acyline tablet developed by Merrion Pharmaceuticals using GIPET™ I technology to enable the oral administration of this decapeptide. The development of acyline appears to have been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Hormonal suppression restores fertility in irradiated mice from both endogenous and donor-derived stem spermatogonia.	2010-09	20584762
Insights into male germ cell apoptosis due to depletion of gonadotropins caused by GnRH antagonists.	2007-06	17268770
Intraprostatic androgens and androgen-regulated gene expression persist after testosterone suppression: therapeutic implications for castration-resistant prostate cancer.	2007-05-15	17510436
Effect of medical castration on CD4+ CD25+ T cells, CD8+ T cell IFN-gamma expression, and NK cells: a physiological role for testosterone and/or its metabolites.	2006-05	16352669
A single dose of the potent gonadotropin-releasing hormone antagonist acyline suppresses gonadotropins and testosterone for 2 weeks in healthy young men.	2004-12	15579744

Sample Use Guides

In Vivo Use Guide

Prostate cancer :10, 20 and 40 mg doses of GIPET-enhanced oral acyline

Route of Administration: Oral

In Vitro Use Guide

Acyline had antagonistic potency IC50 = 0.52 nM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:54 GMT 2025`
Record UNII	S3439D3B35
Record Status	`FAILED`
Record Version

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Name

Type

Language

ACYLINE

Common Name

English

MER-104

Preferred Name

English

D-ALANINAMIDE, N-ACETYL-3-(2-NAPHTHALENYL)-D-ALANYL-4-CHLORO-D-PHENYLALANYL-3-(3-PYRIDINYL)-D-ALANYL-L-SERYL-4-(ACETYLAMINO)-L-PHENYLALANYL-4-(ACETYLAMINO)-D-PHENYLALANYL-L-LEUCYL-N6-(1-METHYLETHYL)-L-LYSYL-L-PROLYL-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID60168812