Acyline

{{Short description|Chemical compound}}

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| IUPAC_name = (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-acetamidophenyl)propanoyl]amino]-3-(4-acetamidophenyl)propanoyl]amino]-4-methylpentanoyl]amino]-6-(propan-2-ylamino)hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

| image = Acyline.svg

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| routes_of_administration = Subcutaneous injection

| class = GnRH antagonist

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| CAS_number_Ref =

| CAS_number = 170157-13-8

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| PubChem = 16137348

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| DrugBank_Ref =

| DrugBank = DB11906

| UNII = S3439D3B35

| ChemSpiderID = 17293858

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| ChEMBL = 262747

| synonyms = MER-104

| C=80 | H=102 | Cl=1 | N=15 | O=14

| SMILES = C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCNC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC2=CC=C(C=C2)NC(=O)C)NC(=O)[C@H](CC3=CC=C(C=C3)NC(=O)C)NC(=O)[C@H](CO)NC(=O)[C@@H](CC4=CN=CC=C4)NC(=O)[C@@H](CC5=CC=C(C=C5)Cl)NC(=O)[C@@H](CC6=CC7=CC=CC=C7C=C6)NC(=O)C

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = ZWNUQDJANZGVFO-YHSALVGYSA-N

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Acyline (developmental code name MER-104) is a gonadotropin-releasing hormone analogue (GnRH analogue) and gonadotropin-releasing hormone antagonist (GnRH antagonist) which was never marketed.{{Cite journal |vauthors=Herbst KL, Anawalt BD, Amory JK, Bremner WJ |date=July 2002 |title=Acyline: the first study in humans of a potent, new gonadotropin-releasing hormone antagonist |journal=J. Clin. Endocrinol. Metab. |volume=87 |issue=7 |pages=3215–20 |doi=10.1210/jcem.87.7.8675 |pmid=12107227 |doi-access=free |hdl-access=free |hdl=1773/4394}}{{Cite journal |vauthors=Herbst KL, Coviello AD, Page S, Amory JK, Anawalt BD, Bremner WJ |date=December 2004 |title=A single dose of the potent gonadotropin-releasing hormone antagonist acyline suppresses gonadotropins and testosterone for 2 weeks in healthy young men |journal=J. Clin. Endocrinol. Metab. |volume=89 |issue=12 |pages=5959–65 |doi=10.1210/jc.2003-032123 |pmid=15579744 |doi-access=free |hdl-access=free |hdl=1773/4325}}{{Cite journal |vauthors=Amory JK, Leonard TW, Page ST, O'Toole E, McKenna MJ, Bremner WJ |date=August 2009 |title=Oral administration of the GnRH antagonist acyline, in a GIPET-enhanced tablet form, acutely suppresses serum testosterone in normal men: single-dose pharmacokinetics and pharmacodynamics |journal=Cancer Chemother. Pharmacol. |volume=64 |issue=3 |pages=641–5 |doi=10.1007/s00280-009-1038-1 |pmc=2721900 |pmid=19479252}} It has been shown to suppress gonadotropin and testosterone levels in men. Acyline is a peptide and under normal circumstances is not orally active. For this reason, it has instead been administered by subcutaneous injection.