Degarelix | 214766-78-6

Degarelix Properties

Density	1.325±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility	DMSO:10.0(Max Conc. mg/mL);6.13(Max Conc. mM) H2O:25.0(Max Conc. mg/mL);15.32(Max Conc. mM)
pka	10.38±0.40(Predicted)
Sequence	Ac-D-2-Nal-D-4-Cl-Phe-D-3-Pal-Ser-4-Aph(Hor)-4-D-Aph(Cbm)-Leu-Lys(ipr)-Pro-D-Ala-NH2
InChIKey	MEUCPCLKGZSHTA-XYAYPHGZSA-N
NCI Dictionary of Cancer Terms	degarelix acetate; Firmagon
FDA UNII	SX0XJI3A11
NCI Drug Dictionary	degarelix
ATC code	L02BX02

Pharmacokinetic data

Protein binding	90%
Excreted unchanged in urine	20-30%
Volume of distribution	1(L/kg)
Biological half-life	43-53 days (28 after 80 mg maintenance dose) / -

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08
Signal word	Danger
Hazard statements	H360

Degarelix price

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
TRC	D495465	Degarelix	214766-78-6	1mg	$115	2021-12-16	Buy
TRC	D495465	Degarelix	214766-78-6	2.5mg	$250	2021-12-16	Buy
ChemScene	CS-5350	Degarelix 99.92%	214766-78-6	10mg	$300	2021-12-16	Buy
Biosynth Carbosynth	FD110099	Degarelix acetate salt	214766-78-6	5mg	$300	2021-12-16	Buy
Biosynth Carbosynth	FD110099	Degarelix acetate salt	214766-78-6	1mg	$150	2021-12-16	Buy

Product number	Packaging	Price	Buy
D495465	1mg	$115	Buy
D495465	2.5mg	$250	Buy
CS-5350	10mg	$300	Buy
FD110099	5mg	$300	Buy
FD110099	1mg	$150	Buy

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

Uses

Degarelix, is a competitive and reversible gonadotropin-releasing hormone receptor (GnRHR) antagonist.

Definition

ChEBI: Degarelix is a polypeptide.

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.

Synthesis

The synthesis of degarelix acetate employed iterative peptide coupling and protection/de-protection sequences in high yields (85¨C99%), 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).

Synthesis_214766-78-6

Metabolism

Undergoes peptide hydrolysis in the hepato-biliary system, and is mainly (70-80%) excreted as peptide fragments in the faeces.

Degarelix Preparation Products And Raw materials

Raw materials

Preparation Products

Degarelix Suppliers

Global( 212)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
AFINE CHEMICALS LIMITED	0571-85134551	info@afinechem.com	CHINA	15377	58
Apextide Co Ltd	+undefined15700198315	senjie.hou@sinopep.com	China	71	58
Zibo Hangyu Biotechnology Development Co., Ltd	+86-0533-2185556 +8617865335152	Mandy@hangyubiotech.com	China	11013	58
Henan Bao Enluo International TradeCo.，LTD	+86-17331933971 +86-17331933971	deasea125996@gmail.com	China	2503	58
Anhui Ruihan Technology Co., Ltd	+8617756083858	daisy@anhuiruihan.com	China	994	58
Nantong Guangyuan Chemicl Co,Ltd	+undefined17712220823	admin@guyunchem.com	China	616	58
Alpha Biopharmaceuticals Co., Ltd	+86-411-39042497 +8613921981412	sales@alphabiopharm.com	China	886	58
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	32480	60
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58

Supplier	Advantage
AFINE CHEMICALS LIMITED	58
Apextide Co Ltd	58
Zibo Hangyu Biotechnology Development Co., Ltd	58
Henan Bao Enluo International TradeCo.，LTD	58
Anhui Ruihan Technology Co., Ltd	58
Nantong Guangyuan Chemicl Co,Ltd	58
Alpha Biopharmaceuticals Co., Ltd	58
Henan Tianfu Chemical Co.,Ltd.	55
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58

View Lastest Price from Degarelix manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-04-15	Degarelix 214766-78-6	US $1.00-100.00 / mg	100mg	98.00%	5ton/month	ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD
2024-03-08	Degarelix 214766-78-6	US $10.00 / kg	1kg	99%	1000kg	Nantong Guangyuan Chemicl Co,Ltd
2024-01-08	Degarelix Acetate 214766-78-6	US $50.00-30.00 / kg	1kg	99.60%	50tons	Wuhan Boyuan Import & Export Co., LTD

Degarelix
214766-78-6
US $1.00-100.00 / mg
98.00%
ANHUI SHENGZHIKAI BIOTECHNOLOGY CO.,LTD

Degarelix
214766-78-6
US $10.00 / kg
99%
Nantong Guangyuan Chemicl Co,Ltd

Degarelix Acetate
214766-78-6
US $50.00-30.00 / kg
99.60%
Wuhan Boyuan Import & Export Co., LTD

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Degarelix N-L-phenylalanyl-L-2-amino-1-phenylpropane N-[4-(3-OXO-PROPYL)-PHENYL]-ACETAMIDE

1of4

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-(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) Degarelix, Degarelix acetate Degarelix acetate salt 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 Degarelix-d7 Degarelix acetate FirMagon Dikarek 214766-78-6 217466-78-6 C82H103ClN18O16C2H4O2 C82H103N18O16Cl C82H103ClN18O16 API