Acyline

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201823

CAS#: 170157-13-8

Description: Acyline is a novel GnRH antagonist found in animal studies to be a potent suppressor of circulating gonadotropin and testosterone (T) levels. Acyline inhibits basal and GnRH-stimulated serum testosterone concentrations in male dogs. Acyline prevented ovulation, but did not affect ovarian follicular development or gestational corpora lutea in the domestic cat. A single dose of the potent gonadotropin-releasing hormone antagonist acyline suppresses gonadotropins and testosterone for 2 weeks in healthy young men.


Chemical Structure

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Acyline
CAS# 170157-13-8

Theoretical Analysis

MedKoo Cat#: 201823
Name: Acyline
CAS#: 170157-13-8
Chemical Formula: C80H102ClN15O14
Exact Mass: 1531.74192
Molecular Weight: 1533.21
Elemental Analysis: C, 62.67; H, 6.71; Cl, 2.31; N, 13.70; O, 14.61

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Synonym: Acyline; MER104; MER-104; MER 104.

IUPAC/Chemical Name: (S)-N-((R)-1-amino-1-oxopropan-2-yl)-1-((2S,5S,8R,11S,14S,17R,20R,23R)-8,11-bis(4-acetamidobenzyl)-20-(4-chlorobenzyl)-14-(hydroxymethyl)-5-isobutyl-2-(4-(isopropylamino)butyl)-23-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22,25-octaoxo-17-(pyridin-3-ylmethyl)-3,6,9,12,15,18,21,24-octaazahexacosan-1-oyl)pyrrolidine-2-carboxamide

InChi Key: ZWNUQDJANZGVFO-YHSALVGYSA-N

InChi Code: 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

SMILES Code: O=C([C@H]1N(C([C@H](CCCCNC(C)C)NC([C@H](CC(C)C)NC([C@@H](CC2=CC=C(NC(C)=O)C=C2)NC([C@H](CC3=CC=C(NC(C)=O)C=C3)NC([C@H](CO)NC([C@@H](CC4=CC=CN=C4)NC([C@@H](CC5=CC=C(Cl)C=C5)NC([C@@H](CC6=CC=C7C=CC=CC7=C6)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC1)N[C@H](C)C(N)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1533.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Zysling DA, Park SU, McMillan EL, Place NJ. Photoperiod-gonadotropin mismatches induced by treatment with acyline or FSH in Siberian hamsters: impacts on ovarian structure and function. Reproduction. 2012 Nov;144(5):603-16. doi: 10.1530/REP-12-0155. Epub 2012 Aug 30. PubMed PMID: 22936286.

2: Garcia Romero G, Fernández PE, Gimeno E, Barbeito C, Gobello C. Effects of the GnRH antagonist acyline on the testis of the domestic cat (Felis catus). Vet J. 2012 Jul;193(1):279-82. doi: 10.1016/j.tvjl.2011.09.028. Epub 2011 Nov 8. PubMed PMID: 22070915.

3: García Romero G, Mattioli G, Rosa D, Diaz JD, Abeyá M, Gobello C. A single administration of the GnRH antagonist acyline inhibits basal and GnRH-stimulated serum testosterone concentrations in male dogs. Reprod Domest Anim. 2012 Jun;47(3):e32-5. doi: 10.1111/j.1439-0531.2011.01898.x. Epub 2011 Nov 1. PubMed PMID: 22044671.

4: Risso A, Valiente C, Corrada Y, Romero GG, Blanco PG, de la Sota PE, Diaz JD, Gobello C. The GnRH antagonist acyline prevented ovulation, but did not affect ovarian follicular development or gestational corpora lutea in the domestic cat. Theriogenology. 2010 Apr 15;73(7):984-7. doi: 10.1016/j.theriogenology.2010.01.010. Epub 2010 Feb 19. PubMed PMID: 20171723.

5: Valiente C, Corrada Y, de la Sota PE, Blanco PG, Arias D, Gobello C. Comparison of two doses of the GnRH antagonist, acyline, for pregnancy termination in bitches. Reprod Domest Anim. 2009 Jul;44 Suppl 2:156-9. doi: 10.1111/j.1439-0531.2009.01397.x. PubMed PMID: 19754557.

6: Amory JK, Leonard TW, Page ST, O'Toole E, McKenna MJ, Bremner WJ. 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. 2009 Aug;64(3):641-5. doi: 10.1007/s00280-009-1038-1. Epub 2009 May 29. PubMed PMID: 19479252; PubMed Central PMCID: PMC2721900.

7: García Romero G, Valiente C, Aquilano D, Corrada Y, Gobello C. Endocrine effects of the GnRH antagonist, acyline, in domestic dogs. Theriogenology. 2009 May;71(8):1234-7. doi: 10.1016/j.theriogenology.2008.12.017. Epub 2009 Feb 3. PubMed PMID: 19193431.

8: Checura CM, Beg MA, Gastal EL, Gastal MO, Wiltbank MC, Parrish JJ, Ginther OJ. Effect of suppression of FSH with a GnRH antagonist (acyline) before and during follicle deviation in the mare. Reprod Domest Anim. 2009 Jun;44(3):504-11. doi: 10.1111/j.1439-0531.2008.01222.x. Epub 2008 Oct 10. PubMed PMID: 18954386.

9: Valiente C, Romero GG, Corrada Y, de la Sota PE, Hermo G, Gobello C. Interruption of the canine estrous cycle with a low and a high dose of the GnRH antagonist, acyline. Theriogenology. 2009 Feb;71(3):408-11. doi: 10.1016/j.theriogenology.2008.08.007. Epub 2008 Sep 11. PubMed PMID: 18789519.

10: Valiente C, Corrada Y, de la Sota PE, Gerez PG, Gobello C. Effect of the GnRH antagonist, acyline, on canine testicular characteristics. Theriogenology. 2007 Sep 15;68(5):687-92. Epub 2007 Jun 21. PubMed PMID: 17586037.



Additional Information

Acyline is currently being developed by Merrion Pharmaceuticals. Acyline is a GnRH antagonist that takes advantage of GIPET® technology and provides an oral dosage form alternative to current therapies, all of which are injectable. There are several GnRH antagonists either marketed or in development for the treatment of prostate cancer, endometriosis and benign prostatic hypertrophy (BPH). In general, these new compounds are less potent than the first generation agonists, and cause greater local tissue irritation when used in a long acting injection or subcutaneous implant delivery systems. The market adoption of the currently approved products has been low due to the fact that a small percentage of patients develop a severe allergic response to the large doses given by injection of subcutaneous depot. An oral product would eliminate the inconvenience of injection therapy, avoid the severe reactions, and allow tailored dosing regimens. Merrion has identified a potent GnRH antagonist with an attractive product profile for development as an oral dosage form for the treatment of prostate cancer as an initial indication. This compound is a novel chemical entity and has already been evaluated in Phase II clinical trials. s ee : http://www.merrionpharma.com/content/portfolio/mer104.asp