Acyline

Short description: Chemical compound

Acyline

Clinical data
Other names| MER-104
Routes of
administration| Subcutaneous injection[1][2]
Drug class| GnRH 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|

* 170157-13-8

PubChem CID|

* 16137348

DrugBank|

* DB11906

ChemSpider|

* 17293858

UNII|

* S3439D3B35

ChEMBL|

* ChEMBL262747

Chemical and physical data
Formula| C80H102ClN15O14
Molar mass| 1533.24 g·mol−1
3D model (JSmol)|

* Interactive image

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

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]

## See also

* Gonadotropin-releasing hormone receptor § Antagonists

## References

1. ↑ 1.0 1.1 1.2 1.3 "Acyline: the first study in humans of a potent, new gonadotropin-releasing hormone antagonist". J. Clin. Endocrinol. Metab. 87 (7): 3215–20. July 2002. doi:10.1210/jcem.87.7.8675. PMID 12107227.
2. ↑ 2.0 2.1 2.2 2.3 "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. December 2004. doi:10.1210/jc.2003-032123. PMID 15579744.
3. ↑ 3.0 3.1 3.2 "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. August 2009. doi:10.1007/s00280-009-1038-1. PMID 19479252.

* v
* t
* e

GnRH and gonadotropins

GnRH modulators
(incl. analogues)|

| Agonists|

* Peptide: Azagly-nafarelin
* Buserelin
* Deslorelin
* Fertirelin
* Gonadorelin
* Goserelin
* Histrelin
* Lecirelin
* Leuprorelin (leuprolide)
* Nafarelin
* Peforelin
* Triptorelin

|

Antagonists|

* Peptide: Abarelix
* Cetrorelix
* Degarelix
* Ganirelix

* Non-peptide: Elagolix
* Linzagolix†
* Relugolix†

Gonadotropins|

| Preparations|

* Follicle-stimulating hormone
* Human chorionic gonadotropin
* Luteinizing hormone
* Menotropin
* Urofollitropin

|

Others
(indirect)|

| Progonadotropins|

* Sex steroid antagonists (via disinhibition of the HPG axis): Antiandrogens (e.g., flutamide, bicalutamide, enzalutamide)
* Antiestrogens/SERMs (e.g., tamoxifen, Chemistry:Clomifene

|

Antigonadotropins|

* Sex steroid agonists (via negative feedback on the HPG axis): Androgens/anabolic steroids (e.g., testosterone, nandrolone esters, oxandrolone)
* D2 receptor antagonists (prolactin releasers) (incl., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
* Estrogens (incl., bifluranol, estradiol, estradiol esters, ethinylestradiol, diethylstilbestrol, paroxypropione)
* Progestogen|Progestogens (incl. progestins, e.g., Chemistry:Chlormadinone acetate

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

See also
GnRH and gonadotropin receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
Progestogens and antiprogestogens

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*[CID]: Compound ID
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*[t]: Discuss this template
*[e]: Edit this template
*[GnRH]: gonadotropin-releasing hormone
*[HPG]: hypothalamic–pituitary–gonadal
*[SERMs]: Selective estrogen receptor modulators