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Abarelix

Names

[ CAS No. ]:
183552-38-7

[ Name ]:
Abarelix

[Synonym ]:
Carbamic acid,acetyldithio-,methyl ester
Abarelix
Carbamodithioic acid,acetyl-,methyl ester
Ac-D-Nal-[D-(pCl)Phe]-D-Pal-Ser-[Nα-Me-Tyr]-D-Asn-Leu-ILys-Pro-DAla-NH2
acetyl-dithiocarbamic acid methyl ester
Abarelix Acetate
N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-N-methyl-L-tyrosyl-D-asparaginyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide
(2R)-N-[(2S)-1-{[(2S)-1-[(2S)-2-{[(2R)-1-Amino-1-oxopropan-2-yl]carbamoyl}pyrrolidin-1-yl]-6-(isopropylamino)-1-oxohexan-2-yl]amino}-4-methyl-1-oxopentan-2-yl]-2-{[(2S,5S,8R,11R,14R)-11-(4-chlorobenzyl)-2-(4-hydroxybenzyl)-5-(hydroxymethyl)-3-methyl-14-(2-naphthylmethyl)-4,7,10,13,16-pentaoxo-8-(pyridin-3-ylmethyl)-3,6,9,12,15-pentaazaheptadecan-1-oyl]amino}succinamide (non-preferred name)
Acetyl-dithiocarbamidsaeure-methylester
(2R)-N-[(2S)-1-{[(2S)-1-[(2S)-2-{[(2R)-1-Amino-1-oxo-2-propanyl]carbamoyl}-1-pyrrolidinyl]-6-(isopropylamino)-1-oxo-2-hexanyl]amino}-4-methyl-1-oxo-2-pentanyl]-2-{[(2S,5S,8R,11R,14R)-11-(4-chlorobe nzyl)-2-(4-hydroxybenzyl)-5-(hydroxymethyl)-3-methyl-14-(2-naphthylmethyl)-4,7,10,13,16-pentaoxo-8-(3-pyridinylmethyl)-3,6,9,12,15-pentaazaheptadecan-1-oyl]amino}succinamide

Biological Activity

[Description]:

Abarelix is a potent gonadotrophin-releasing hormone (GnRH) antagonist, used for prostate cancer treatment.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> GNRH Receptor
Peptides
Research Areas >> Cancer

[In Vitro]

Abarelix (30 and 300 µg/mL) and cetrorelix cause significantly increased histamine release[1]. Abarelix is the firstGnRH antagonist to be developed, and can produce rapid and sustained decreases in testosterone to castrate levels without the need for co-administration of an antiandrogen, and with a very low complication rate in the short term[2]. Abarelix demonstrates to promptly and substantially reduce follicle-stimulating hormone levels to lower than LHRH agonist. Abarelix does not cause a surge in serum testosterone that can precipitate a flare phenomenon or worsening of disease, particularly dangerous for patients with metastatic, symptomatic disease, and produces medical castration more quickly[3].

[References]

[1]. Koechling W, et al. Degarelix, a novel GnRH antagonist, causes minimal histamine release compared with cetrorelix, abarelix and ganirelix in an ex vivo model of human skin samples. Br J Clin Pharmacol. 2010 Oct;70(4):580-7.

[2]. Kirby RS, et al. Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4.

[3]. Debruyne F, et al. Abarelix for injectable suspension: first-in-class gonadotropin-releasing hormone antagonist for prostate cancer. Future Oncol. 2006 Dec;2(6):677-96.


[Related Small Molecules]

(Des-Gly10,D-Leu6,Pro-NHEt9)-LHRH acetate salt | Alarelin | Cetrorelix Acetate | [D-Trp6]-LH-RH | (D-Ser(tBu)6,AzaGly10)-LHRH acetate salt | Deslorelin | Buserelin (Acetate) | elagolix | Relugolix | (D-2-Nal6)-LHRH acetate salt | Gonadorelin Acetate | (Des-Gly10,tBu-D-Gly6,Pro-NHEt9)-LHRH trifluoroacetate salt | opigolix

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
1688.4±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C72H95ClN14O14

[ Molecular Weight ]:
1416.063

[ Flash Point ]:
974.9±34.3 °C

[ Exact Mass ]:
1414.684082

[ PSA ]:
424.98000

[ LogP ]:
5.18

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.601

[ Storage condition ]:
-20°C


Related Compounds