Acyline

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.[1][2][3] It has been shown to suppress gonadotropin and testosterone levels in men.[1][2][3] Acyline is a peptide and under normal circumstances is not orally active.[3] For this reason, it has instead been administered by subcutaneous injection.[1][2]

Acyline
Clinical data
Other namesMER-104
Routes of
administration		Subcutaneous injection[1][2]
Drug classGnRH antagonist
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC80H102ClN15O14
Molar mass1533.24 g·mol−1
3D model (JSmol)
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
InChI
  • 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
  • Key:ZWNUQDJANZGVFO-YHSALVGYSA-N

See also
  • Gonadotropin-releasing hormone receptor § Antagonists

References
  1. Herbst KL, Anawalt BD, Amory JK, Bremner WJ (July 2002). "Acyline: the first study in humans of a potent, new gonadotropin-releasing hormone antagonist". J. Clin. Endocrinol. Metab. 87 (7): 3215–20. doi:10.1210/jcem.87.7.8675. PMID 12107227.
  2. Herbst KL, Coviello AD, Page S, Amory JK, Anawalt BD, Bremner WJ (December 2004). "A single dose of the potent gonadotropin-releasing hormone antagonist acyline suppresses gonadotropins and testosterone for 2 weeks in healthy young men". J. Clin. Endocrinol. Metab. 89 (12): 5959–65. doi:10.1210/jc.2003-032123. PMID 15579744.
  3. Amory JK, Leonard TW, Page ST, O'Toole E, McKenna MJ, Bremner WJ (August 2009). "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". Cancer Chemother. Pharmacol. 64 (3): 641–5. doi:10.1007/s00280-009-1038-1. PMC 2721900. PMID 19479252.



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