ChemicalBook
Chinese Japanese Germany Korea

DEGARELIX

DEGARELIX
DEGARELIX structure
CAS No.
214766-78-6
Chemical Name:
DEGARELIX
Synonyms
FirMagon;DEGARELIX;Degarelix acetate;Degarelix impurity;DEGARELIX USP/EP/BP;Degarelix acetate salt;Degarelix, Degarelix acetate;Degarelix acetate(FE-200486,Degarelix);N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-4-[2,6-dioxohexahydropyrimidin-4(S)-ylcarboxamido]-L-phenylalanyl-4-ureido-D-phenylalanyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide acetate;D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-[[[(4S)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-L-phenylalanyl-4-[(aminocarbonyl)amino]-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-ly
CBNumber:
CB52448443
Molecular Formula:
C82H103ClN18O16
Formula Weight:
1632.26
MOL File:
214766-78-6.mol

DEGARELIX Properties

Density 
1.325±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
pka
10.38±0.40(Predicted)
FDA UNII
SX0XJI3A11
NCI Dictionary of Cancer Terms
degarelix acetate; Firmagon
NCI Drug Dictionary
degarelix
ATC code
L02BX02

DEGARELIX Chemical Properties,Uses,Production

Description

Antagonists of GnRH have proven to be an effective therapy for hormonally regulated cancers, such as prostate and some types of breast. As analogs of GnRH, they bind competitively and reversibly to GnRH receptors in the pituitary gland, thereby blocking the release of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). In men, the reduction of LH triggers the ablation of testosterone secretion from the testes, and these castration-like levels have been essential in the effective management of advanced prostate cancer. In comparison to GnRH agonists, antagonists do not suffer from a potential flare of the disease as a result of an initial stimulation of the hypothalamic-pituitary-gonadal axis prior to down-regulation of the GnRH receptor. Moreover, GnRH antagonists provide beneficial effects more rapidly postdosing and result in a more efficient suppression of gonadotropin levels. With this in mind, degarelix acetate has been launched as a third-generation GnRH antagonist for the treatment of prostate cancer, and it joins other third-generation agents, ganirelix and cetronelix, on the market.

Originator

Ferring Pharmaceutical (Switzerland)

Uses

Advanced hormone-dependent prostate carcinoma

brand name

Firmagon

Clinical Use

Ferring launched degarelix acetate, a gonadotrophin-releasing hormone (GnRH) antagonist, in 2009 in the U.S. for the treatment of prostate cancer. The compound has been approved by the E.U. for the same indication, and in the same year it was launched in the UK and Germany. Degarelix has been developed as a one-month or three-month sustained-release injectable formulation. Compared to other GnRH antagonists, degarelix displays improved aqueous solubility, longer acting effects and weaker histamine-releasing properties.

Side effects

The most common adverse events included injection site reactions (pain, erythema, swelling, or induration), hot flashes, increased weight, and increases in serum levels of transaminases and gamma-glutamyltransferase. In addition to being contraindicated in patients with a previous hypersensitivity to degarelix, it should not be administered to women who are or may become pregnant as fetal harm can occur. Since long-term androgen deprivation therapy prolongs the QT interval, physicians should consider whether the benefits of degarelix outweigh the potential risks in patients with congenital long QT syndrome, electrolyte abnormalities, or congestive heart failure or in patients taking antiarrhythmic medications.

Chemical Synthesis

The synthesis of degarelix acetate employed iterative peptide coupling and protection/de-protection sequences in high yields (85–99%), and this sequence is described in the scheme. Boc-D-alanine (21) was immobilized via MBHA resin (Bachem) by reaction with diisopropyl carbodiimide (DIC) and 1-hydroxybenzotriazole (HOBT). The resulting product was treated with trifluoroacetic acid (TFA) to remove the N-Boc protecting group to reveal amine 22. The N-terminus of 22 was then subjected to sequential coupling and de-protection cycles with the following protected amino acids: N-Boc-L-proline, N-a- Boc-N6-isopropyl-N6-carbobenzoxy-L-lysine and N-Boc-L-leucine to give 23 and 24, respectively. The N-terminus of 24 was coupled with N-a-Boc-D-4-(Fmoc-amino)phenylalanine, followed by removal of the Fmoc group with piperidine in DMF to give the corresponding free aniline. The free aniline resin was then reacted with t-butyl isocyanate to generate the corresponding t-butyl urea followed by reaction with TFA to remove the Boc group to give the t-butyl urea amine 25. The N-terminus of 25 was coupled with N-a-Boc-L-4-(Fmoc-amino)phenylalanine, followed by removal of the Fmoc group with piperidine in DMF to generate the corresponding free aniline. The free aniline was reacted with L-hydroorotic acid, followed by reaction with TFA to liberate amine 26. Amine 26 was then coupled with O-benzylated-N-Boc-serine, followed by removal of the Boc group with TFA and reacting the resulting amine with N-a-Boc-D-(3-pyridyl)alanine and subsequent removal of the Boc group with TFA gave amine 27. Amine 27 was coupled with N-Boc-D-(4-chlorophenyl)alanine, followed by removal of the Boc group with TFA, and the resulting amine was then coupled with N-Boc-D-(2-naphthyl)alanine, followed by removal of its Boc group with TFA to give 28. Acylation of 28 with acetic anhydride followed by sequential treatment with HF and TFA resulted in cleavage from the resin, removal of the O-benzyl group, and conversion of the t-butyl urea to the corresponding NH2-urea, resulting in free degarelix. Finally, treatment with acetic acid provided degarelix acetate (V).

DEGARELIX Preparation Products And Raw materials

Raw materials

Preparation Products


DEGARELIX Suppliers

Global( 134)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
AFINE CHEMICALS LIMITED
008657185134551
008657185134895 info@afinechem.com CHINA 15559 58
Alpha Biopharmaceuticals Co., Ltd
0086-411-39042497
0086-411-39042693 sales@alphabiopharm.com China 896 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 914 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Shanghai Longyu Biotechnology Co., Ltd.
+8615821988213
+86 15821988213 info@longyupharma.com China 2471 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58

View Lastest Price from DEGARELIX manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-22 Degarelix
214766-78-6
US $75.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biological Technology Co., Ltd
2021-10-21 Degarelix
214766-78-6
US $50.00-100.00 / g 0.5KG >99% 20tons Anhui Rencheng Technology Co., Ltd
2021-08-13 DEGARELIX
214766-78-6
US $32.00 / KG 1g 99.9% 500000kgs Shijiazhuang tongyang Import and Export Co., LTD

214766-78-6(DEGARELIX)Related Search:


  • DEGARELIX
  • Degarelix acetate
  • N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-4-[2,6-dioxohexahydropyrimidin-4(S)-ylcarboxamido]-L-phenylalanyl-4-ureido-D-phenylalanyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide acetate
  • Degarelix acetate salt
  • D-Alaninamide, N-acetyl-3-(naphtalen-2-yl)-D-alanyl-4-chloro-D-phenylalanyl-3-(pyridin-3-yl)-D-alanyl-L-seryl-4-((((4S)-2,6-dioxohexahydropyrimidin-4-yl)carbonyl)amino)-L-phenylalanyl-4-(carbamoylamino)-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-
  • Degarelix acetate(FE-200486,Degarelix)
  • FirMagon
  • Degarelix, Degarelix acetate
  • D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-[[[(4S)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-L-phenylalanyl-4-[(aminocarbonyl)amino]-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-ly
  • D-Alaninamide, N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-4-[[[(4S)-hexahydro-2,6-dioxo-4-pyrimidinyl]carbonyl]amino]-L-phenylalanyl-4-[(aminocarbonyl)amino]-D-phenylalanyl-L-leucyl-N6-(1-methylethyl)-L-lysyl-L-prolyl-
  • Degarelix impurity
  • DEGARELIX USP/EP/BP
  • 214766-78-6
  • 217466-78-6
  • C82H103ClN18O16C2H4O2
  • C82H103N18O16Cl
  • C82H103ClN18O16
  • API
Copyright 2017 © ChemicalBook. All rights reserved