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MedKoo Cat#: 100255 | Name: Degarelix acetate
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Description:

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

Degarelix, also known as FE-200486 and ASP-3550, is a long-acting, synthetic peptide with gonadotrophin-releasing hormone (GnRH) antagonistic properties. Degarelix targets and blocks GnRH receptors located on the surfaces of gonadotroph cells in the anterior pituitary, thereby reducing secretion of luteinizing hormone (LH) by pituitary gonadotroph cells and so decreasing testosterone production by interstitial (Leydig) cells in the testes. Degarelix acetate was approved in 2008.

Chemical Structure

Degarelix acetate
Degarelix acetate
CAS#934246-14-7 (acetate)

Theoretical Analysis

MedKoo Cat#: 100255

Name: Degarelix acetate

CAS#: 934246-14-7 (acetate)

Chemical Formula: C84H107ClN18O18

Exact Mass: 0.0000

Molecular Weight: 1692.31

Elemental Analysis: C, 60.34; H, 6.36; Cl, 2.17; N, 15.45; O, 15.68

Price and Availability

Size Price Availability Quantity
5mg USD 120.00 Ready to ship
10mg USD 190.00 Ready to ship
25mg USD 350.00 Ready to ship
50mg USD 550.00 Ready to ship
100mg USD 950.00 Ready to ship
200mg USD 1,650.00 Ready to ship
500mg USD 3,650.00 Ready to ship
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Related CAS #
214766-78-6 (free base) 934246-14-7 (acetate)
Synonym
FE200486; FE-200486; FE 200486; ASP3550; ASP-3550; ASP 3550. Degarelix acetate; tradename Firmagon.
IUPAC/Chemical Name
(S)-N-(4-((2S,5S,8R,11R,14R)-2-(((R)-1-(((S)-1-(((S)-1-((S)-2-(((R)-1-amino-1-oxopropan-2-yl)carbamoyl)pyrrolidin-1-yl)-6-(isopropylamino)-1-oxohexan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-(4-ureidophenyl)propan-2-yl)carbamoyl)-11-(4-chlorobenzyl)-5-(hydroxymethyl)-14-(naphthalen-2-ylmethyl)-4,7,10,13,16-pentaoxo-8-(pyridin-3-ylmethyl)-3,6,9,12,15-pentaazaheptadecyl)phenyl)-2,6-dioxohexahydropyrimidine-4-carboxamide.
InChi Key
AUTFSFUMNFDPLH-KYMMNHPFSA-N
InChi Code
(S)-N-(4-((2S,5S,8R,11R,14R)-2-(((R)-1-(((S)-1-(((S)-1-((S)-2-(((R)-1-amino-1-oxopropan-2-yl)carbamoyl)pyrrolidin-1-yl)-6-(isopropylamino)-1-oxohexan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-1-oxo-3-(4-ureidophenyl)propan-2-yl)carbamoyl)-11-(4-chlorobenzyl)-5-(hydroxymethyl)-14-(naphthalen-2-ylmethyl)-4,7,10,13,16-pentaoxo-8-(pyridin-3-ylmethyl)-3,6,9,12,15-pentaazaheptadecyl)phenyl)-2,6-dioxohexahydropyrimidine-4-carboxamide acetate
SMILES Code
O=C([C@H](CC(N1)=O)NC1=O)NC2=CC=C(C[C@@H](C(N[C@H](CC3=CC=C(NC(N)=O)C=C3)C(N[C@@H](CC(C)C)C(N[C@@H](CCCCNC(C)C)C(N4[C@H](C(N[C@H](C)C(N)=O)=O)CCC4)=O)=O)=O)=O)NC([C@H](CO)NC([C@@H](CC5=CC=CN=C5)NC([C@@H](CC6=CC=C(Cl)C=C6)NC([C@@H](CC7=CC=C8C=CC=CC8=C7)NC(C)=O)=O)=O)=O)=O)C=C2.CC(O)=O
Appearance
White to off-white 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
>2 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
More Info
Related CAS# 214766-78-6 (Degarelix ); 934246-14-7 (Degarelix acetate)
Biological target:
Degarelix is a competitive and reversible gonadotropin-releasing hormone receptor (GnRHR) antagonist.
In vitro activity:
The direct effect of degarelix on human prostate cell growth was evaluated. Normal prostate myofibroblast WPMY-1 and epithelial WPE1-NA22 cells, benign prostatic hyperplasia (BPH)-1 cells, androgen-independent PC-3 and androgen-dependent LNCaP prostate cancer cells, as well as VCaP cells derived from a patient with castration-resistant prostate cancer were used. Discriminatory protein and lipid fingerprints of normal, hyperplastic, and cancer cells were generated by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS). The investigated cell lines express GNRHR1 and GNRHR2 and their endogenous ligands. Degarelix treatment reduced cell viability in all prostate cell lines tested, with the exception of the PC-3 cells; this can be attributed to increased apoptosis, as indicated by increased caspase 3/7, 8 and 9 levels. WPE1-NA22, BPH-1, LNCaP, and VCaP cell viability was not affected by treatment with the GnRH agonists leuprolide and goserelin. Using MALDI MS, changes were detected in m/z signals that were robust enough to create a complete discriminatory profile induced by degarelix. Transcriptomic analysis of BPH-1 cells provided a global map of genes affected by degarelix and indicated that the biological processes affected were related to cell growth, G-coupled receptors, the mitogen-activated protein kinase (MAPK) pathway, angiogenesis and cell adhesion. Taken together, these data demonstrate that (i) the GnRH antagonist degarelix exerts a direct effect on prostate cell growth through apoptosis; (ii) MALDI MS analysis provided a basis to fingerprint degarelix-treated prostate cells; and (iii) the clusters of genes affected by degarelix suggest that this compound, in addition to its known use in the treatment of prostate cancer, may be efficacious in BPH. Reference: PLoS One. 2015 Mar 26;10(3):e0120670. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/25811175/
In vivo activity:
The pharmacological profile in rats and monkeys of degarelix (FE200486), a member of a new class of long-acting gonadotropin-releasing hormone (GnRH) antagonists, was examined. At single subcutaneous injections of 0.3 to 10 microg/kg in rats, degarelix produced a dose-dependent suppression of the pituitary-gonadal axis as revealed by the decrease in plasma luteinizing hormone (LH) and testosterone levels. Duration of LH suppression increased with the dose: in the rat, significant suppression of LH lasted 1, 2, and 7 days after a single subcutaneous injection of degarelix at 12.5, 50, or 200 microg/kg, respectively. Degarelix fully suppressed plasma LH and testosterone levels in the castrated and intact rats as well as in the ovariectomized rhesus monkey for more than 40 days after a single 2-mg/kg subcutaneous injection. Reference: J Pharmacol Exp Ther. 2002 Apr;301(1):95-102. https://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11907162
Solvent mg/mL mM
Solubility
DMSO 10.0 6.13
Water 25.0 15.32
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,692.31 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
Formulation protocol:
In vitro protocol:
1. Sakai M, Martinez-Arguelles DB, Patterson NH, Chaurand P, Papadopoulos V. In search of the molecular mechanisms mediating the inhibitory effect of the GnRH antagonist degarelix on human prostate cell growth. PLoS One. 2015 Mar 26;10(3):e0120670. doi: 10.1371/journal.pone.0120670. PMID: 25811175; PMCID: PMC4374753.
In vivo protocol:
1. Broqua P, Riviere PJ, Conn PM, Rivier JE, Aubert ML, Junien JL. Pharmacological profile of a new, potent, and long-acting gonadotropin-releasing hormone antagonist: degarelix. J Pharmacol Exp Ther. 2002 Apr;301(1):95-102. doi: 10.1124/jpet.301.1.95. PMID: 11907162.
1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Degarelix. 2023 May 28. PMID: 31643893. 2: Zengerling F, Jakob JJ, Schmidt S, Meerpohl JJ, Blümle A, Schmucker C, Mayer B, Kunath F. Degarelix for treating advanced hormone-sensitive prostate cancer. Cochrane Database Syst Rev. 2021 Aug 5;8(8):CD012548. doi: 10.1002/14651858.CD012548.pub2. PMID: 34350976; PMCID: PMC8407409. 3: Devos G, Tosco L, Baldewijns M, Gevaert T, Goffin K, Petit V, Mai C, Laenen A, Raskin Y, Van Haute C, Goeman L, De Meerleer G, Berghen C, Devlies W, Claessens F, Van Poppel H, Everaerts W, Joniau S. ARNEO: A Randomized Phase II Trial of Neoadjuvant Degarelix with or Without Apalutamide Prior to Radical Prostatectomy for High-risk Prostate Cancer. Eur Urol. 2023 Jun;83(6):508-518. doi: 10.1016/j.eururo.2022.09.009. Epub 2022 Sep 24. PMID: 36167599. 4: Lopes RD, Higano CS, Slovin SF, Nelson AJ, Bigelow R, Sørensen PS, Melloni C, Goodman SG, Evans CP, Nilsson J, Bhatt DL, Clarke NW, Olesen TK, Doyle-Olsen BT, Kristensen H, Arney L, Roe MT, Alexander JH; PRONOUNCE Study Investigators. Cardiovascular Safety of Degarelix Versus Leuprolide in Patients With Prostate Cancer: The Primary Results of the PRONOUNCE Randomized Trial. Circulation. 2021 Oct 19;144(16):1295-1307. doi: 10.1161/CIRCULATIONAHA.121.056810. Epub 2021 Aug 30. Erratum in: Circulation. 2021 Oct 19;144(16):e273. PMID: 34459214; PMCID: PMC9004319. 5: Sari Motlagh R, Abufaraj M, Mori K, Aydh A, Rajwa P, Katayama S, Grossmann NC, Laukhtina E, Mostafai H, Pradere B, Quhal F, Karakiewicz PI, Enikeev DV, Shariat SF. The Efficacy and Safety of Relugolix Compared with Degarelix in Advanced Prostate Cancer Patients: A Network Meta-analysis of Randomized Trials. Eur Urol Oncol. 2022 Apr;5(2):138-145. doi: 10.1016/j.euo.2021.07.002. Epub 2021 Jul 21. PMID: 34301529. 6: Secin FP. Questionable oncologic benefits of degarelix. Urol Oncol. 2016 Oct;34(10):423-6. doi: 10.1016/j.urolonc.2016.05.029. Epub 2016 Jun 28. PMID: 27364704. 7: Doehn C, Sommerauer M, Jocham D. Degarelix for prostate cancer. Expert Opin Investig Drugs. 2009 Jun;18(6):851-60. doi: 10.1517/13543780902954713. PMID: 19453267. 8: Carter NJ, Keam SJ. Degarelix: a review of its use in patients with prostate cancer. Drugs. 2014 Apr;74(6):699-712. doi: 10.1007/s40265-014-0211-y. PMID: 24756432. 9: Steinberg M. Degarelix: a gonadotropin-releasing hormone antagonist for the management of prostate cancer. Clin Ther. 2009;31 Pt 2:2312-31. doi: 10.1016/j.clinthera.2009.11.009. PMID: 20110043. 10: Frampton JE, Lyseng-Williamson KA. Degarelix. Drugs. 2009 Oct 1;69(14):1967-76. doi: 10.2165/10484080-000000000-00000. PMID: 19747011. 11: Doehn C, Sommerauer M, Jocham D. Degarelix and its therapeutic potential in the treatment of prostate cancer. Clin Interv Aging. 2009;4():215-23. doi: 10.2147/cia.s3503. Epub 2009 May 14. PMID: 19503784; PMCID: PMC2685243. 12: Uttley L, Whyte S, Gomersall T, Ren S, Wong R, Chambers D, Tappenden P. Degarelix for Treating Advanced Hormone-Dependent Prostate Cancer: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoeconomics. 2017 Jul;35(7):717-726. doi: 10.1007/s40273-016-0481-1. PMID: 27943135. 13: Degarelix. More rapid medical castration, nothing more. Prescrire Int. 2010 Jun;19(107):106-8. PMID: 20738032. 14: Wallach JD, Deng Y, McCoy RG, Dhruva SS, Herrin J, Berkowitz A, Polley EC, Quinto K, Gandotra C, Crown W, Noseworthy P, Yao X, Shah ND, Ross JS, Lyon TD. Real-world Cardiovascular Outcomes Associated With Degarelix vs Leuprolide for Prostate Cancer Treatment. JAMA Netw Open. 2021 Oct 1;4(10):e2130587. doi: 10.1001/jamanetworkopen.2021.30587. PMID: 34677594; PMCID: PMC8536955. 15: Klotz L, Boccon-Gibod L, Shore ND, Andreou C, Persson BE, Cantor P, Jensen JK, Olesen TK, Schröder FH. The efficacy and safety of degarelix: a 12-month, comparative, randomized, open-label, parallel-group phase III study in patients with prostate cancer. BJU Int. 2008 Dec;102(11):1531-8. doi: 10.1111/j.1464-410X.2008.08183.x. PMID: 19035858. 16: Pyrgidis N, Hatzichristodoulou G, Sokolakis I. Behandlung des fortgeschrittenen hormonsensitiven Prostatakarzinoms mittels Degarelix [Treatment of advanced hormone-sensitive prostate cancer using degarelix]. Urologe A. 2022 Jan;61(1):63-67. German. doi: 10.1007/s00120-021-01735-x. Epub 2021 Dec 14. PMID: 34907463. 17: Degarelix (firmagon) for prostate cancer. Med Lett Drugs Ther. 2009 Oct 19;51(1323):82-3. PMID: 19838145. 18: Clinton TN, Woldu SL, Raj GV. Degarelix versus luteinizing hormone-releasing hormone agonists for the treatment of prostate cancer. Expert Opin Pharmacother. 2017 Jun;18(8):825-832. doi: 10.1080/14656566.2017.1328056. Epub 2017 May 19. PMID: 28480768; PMCID: PMC7171911. 19: Anderson J. Degarelix: a novel gonadotropin-releasing hormone blocker for the treatment of prostate cancer. Future Oncol. 2009 May;5(4):433-43. doi: 10.2217/fon.09.24. PMID: 19450172. 20: Cui Y, Zong H, Yan H, Li N, Zhang Y. Degarelix versus goserelin plus bicalutamide therapy for lower urinary tract symptom relief, prostate volume reduction and quality of life improvement in men with prostate cancer: a systematic review and meta-analysis. Urol Int. 2014;93(2):152-9. doi: 10.1159/000356272. Epub 2014 Mar 1. PMID: 24603064.