ACYLINE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C80H102ClN15O14
Molecular Weight	1533.211
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

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

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

Name

Type

Language

ACYLINE

Common 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

MER-104

Code

English

Code System Code Type Description

EPA CompTox

DTXSID60168812