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Accession NumberDB06699
TypeSmall Molecule

Degarelix is used for the treatment of advanced prostate cancer. Degarelix is a synthetic peptide derivative drug which binds to gonadotropin-releasing hormone (GnRH) receptors in the pituitary gland and blocks interaction with GnRH. This antagonism reduces luteinising hormone (LH) and follicle-stimulating hormone (FSH) which ultimately causes testosterone suppression. Reduction in testosterone is important in treating men with advanced prostate cancer. Chemically, it is a synthetic linear decapeptide amide with seven unnatural amino acids, five of which are D-amino acids. FDA approved on December 24, 2008.

SynonymsNot Available
External Identifiers
  • FE200486
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FirmagonkitFerring Pharmaceuticals Inc.2009-03-02Not applicableUs
Firmagonpowder for solution120 mgsubcutaneousFerring Inc2009-11-24Not applicableCanada
Firmagonpowder for solution80 mgsubcutaneousFerring Inc2009-11-24Not applicableCanada
FirmagonkitFerring Pharmaceuticals Inc.2009-03-02Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Degarelix acetate hydrate
  • Monoisotopic Mass: 1690.769926417
  • Average Mass: 1692.311
CAS number214766-78-6
WeightAverage: 1632.29
Monoisotopic: 1630.748797
Chemical FormulaC82H103ClN18O16
CC(C)C[[email protected]](NC(=O)[C@@H](CC1=CC=C(NC(N)=O)C=C1)NC(=O)[[email protected]](CC1=CC=C(NC(=O)[C@@H]2CC(=O)NC(=O)N2)C=C1)NC(=O)[[email protected]](CO)NC(=O)[C@@H](CC1=CC=CN=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC=C2C=CC=CC2=C1)NC(C)=O)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1CCC[[email protected]]1C(=O)N[[email protected]](C)C(N)=O
DescriptionThis compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
  • Polypeptide
  • Alpha peptide
  • Phenylalanine or derivatives
  • Leucine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alanine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-phenylurea
  • Naphthalene
  • Amphetamine or derivatives
  • Anilide
  • Pyrrolidine-2-carboxamide
  • N-arylamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Chlorobenzene
  • Ureide
  • Halobenzene
  • Pyrimidone
  • Fatty amide
  • 1,3-diazinane
  • Fatty acyl
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • N-acyl-amine
  • Pyrimidine
  • Pyridine
  • Benzenoid
  • Acetamide
  • Tertiary carboxylic acid amide
  • Dicarboximide
  • Heteroaromatic compound
  • Pyrrolidine
  • Carboxamide group
  • Primary carboxylic acid amide
  • Secondary carboxylic acid amide
  • Urea
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Amine
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
IndicationDegaralix is used for the management of advanced prostate cancer.
PharmacodynamicsDegarelix is a synthetic derivative of GnRH decapeptide, the ligand of the GnRH receptor. Gonadotropin and androgen production result from the binding of endogenous GnRH to the GnRH receptor. Degarelix antagonizes the GnRH receptor which in turn blocks the release of LH and FSH from the pituitary. LF and FSH decreases in a concentration-dependent manner. The reduction in LH leads to a decrease in testosterone release from the testes.
Mechanism of actionGnRH antagonists compete with natural GnRH for binding to GnRH receptors in the pituitary gland. This reversible blinding blocks the release of LH and FSH from the pituitary. The reduction in LH subsequently leads to a rapid and sustained suppression of testosterone release from the testes and subsequently reduces the size and growth of the prostate cancer.
Related Articles
AbsorptionDegarelix forms a depot at the site of injection after subcutaneous administration from which the drug slowly released into circulation. After a single bolus dose of 2mg/kg, peak plasma concentrations of degarelix occured within 6 hours at a concentration of 330 ng/mL. Ki = 0.082 ng/mL and 93% of receptors were fully suppressed; MRT = 4.5 days.
Volume of distribution

Central compartment: 8.88 – 11.4 L;
Peripheral compartment: 40.9 L

Protein binding90% of the drug is bound to plasma proteins.

70% - 80% of degarelix is subject to peptide hydrolysis during its passage through the hepatobiliary system and then fecally eliminated. No active or inactive metabolites or involvement of CYP450 isozymes.

Route of eliminationFecal (70% to 80%) and renal (20%-30% of unchanged drug)
Half lifeTerminal half-life: 41.5 - 70.2 days; Absorption half-life: 32.9 hours; Half-life from injection site: 1.17 days.

Following subcutaneous administration of degarelix to prostate cancer patients the clearance is approximately 9 L/hr.

ToxicityThe most commonly observed adverse reactions (> 10%) during degarelix therapy included injection site reactions (e.g., pain, erythema, swelling, or induration), hot flashes, increased weight, and increases in serum levels of transaminases and gamma-glutamyltransferase (GGT).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption+0.8352
Blood Brain Barrier-0.953
Caco-2 permeable-0.7556
P-glycoprotein substrateSubstrate0.8461
P-glycoprotein inhibitor INon-inhibitor0.6672
P-glycoprotein inhibitor IINon-inhibitor0.7791
Renal organic cation transporterNon-inhibitor0.8579
CYP450 2C9 substrateNon-substrate0.7299
CYP450 2D6 substrateNon-substrate0.8156
CYP450 3A4 substrateSubstrate0.6482
CYP450 1A2 substrateNon-inhibitor0.8566
CYP450 2C9 inhibitorNon-inhibitor0.6493
CYP450 2D6 inhibitorNon-inhibitor0.8566
CYP450 2C19 inhibitorNon-inhibitor0.7291
CYP450 3A4 inhibitorNon-inhibitor0.5961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8478
Ames testNon AMES toxic0.652
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7005 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8534
hERG inhibition (predictor II)Inhibitor0.5235
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
ManufacturersNot Available
PackagersNot Available
Dosage forms
Powder for solutionsubcutaneous120 mg
Powder for solutionsubcutaneous80 mg
PricesNot Available
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2286190 No2007-01-092018-04-13Canada
US5925730 No2001-05-182021-05-18Us
Experimental PropertiesNot Available
Predicted Properties
Water Solubility0.0041 mg/mLALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)11.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area512.87 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity431.13 m3·mol-1ChemAxon
Polarizability168.98 Å3ChemAxon
Number of Rings8ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Carin WINDERSTROM, “KIT AND METHOD FOR PREPARATION OF A DEGARELIX SOLUTION.” U.S. Patent US20100286603, issued November 11, 2010.

General References
  1. 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. [PubMed:20110043 ]
  2. Persson BE, Kold Olesen T, Jensen JK: Degarelix: a new approach for the treatment of prostate cancer. Neuroendocrinology. 2009;90(3):235-44. doi: 10.1159/000228832. Epub 2009 Jul 14. [PubMed:19602868 ]
External Links
ATC CodesL02BX02
AHFS Codes
  • 10:00
PDB EntriesNot Available
FDA labelDownload (448 KB)
MSDSDownload (479 KB)
Drug Interactions
CapromabDegarelix may decrease effectiveness of Capromab as a diagnostic agent.
CitalopramDegarelix may increase the QTc-prolonging activities of Citalopram.
DofetilideDegarelix may increase the QTc-prolonging activities of Dofetilide.
GoserelinDegarelix may increase the QTc-prolonging activities of Goserelin.
LeuprolideDegarelix may increase the QTc-prolonging activities of Leuprolide.
MifepristoneMifepristone may increase the QTc-prolonging activities of Degarelix.
Food InteractionsNot Available


Pharmacological action
General Function:
Peptide binding
Specific Function:
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol-calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling.
Gene Name:
Uniprot ID:
Molecular Weight:
37730.355 Da
  1. 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. [PubMed:20110043 ]
  2. Kirby RS, Fitzpatrick JM, Clarke N: Abarelix and other gonadotrophin-releasing hormone antagonists in prostate cancer. BJU Int. 2009 Dec;104(11):1580-4. doi: 10.1111/j.1464-410X.2009.08924.x. [PubMed:20053189 ]
  3. 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. [PubMed:19450172 ]
  4. Samant MP, Miller C, Hong DJ, Koerber SC, Croston G, Rivier CL, Rivier JE: Synthesis and biological activity of GnRH antagonists modified at position 3 with 3-(2-methoxy-5-pyridyl)-alanine. J Pept Res. 2005 Feb;65(2):284-91. [PubMed:15705170 ]
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Drug created on May 06, 2010 10:15 / Updated on August 24, 2016 01:52