Degarelix

DCTPepD ID  DCTPepD0007

Active Ingredients   Degarelix

Description  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. Chemically, Degarelix is a synthetic linear decapeptide amide with seven unnatural amino acids, five of which are D-amino acids.

Synonyms  FE200486; Firmagon; 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-D-alaninamide; Degarelix

Disease  Prostate cancer

Classification

  

GnRH antagonist Peptide and derivative

Structure Information


Molecular Formula  C82H103ClN18O16

Molecular Weight  1632.286

Active Sequence  xxxSXxLXPa

Sequence Length  10

Modification  x(1)=D-2Nal, x(2)=D-Phe(4-Cl), x(3)=D-3Pal, X(5)=Phe(4-S-dihydroorotamido), x(6)=D-Phe(4-ureido), X(8)=Lys(iPr), C-terminal Ac, N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (4S)-N-{4-[(2S)-2-{[(1R)-2-[4-(carbamoylamino)phenyl]-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-6-[(propan-2-yl)amino]hexan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}ethyl]carbamoyl}-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]ethyl]phenyl}-2,6-dioxo-1,3-diazinane-4-carboxamide

InChI  InChI=1S/C82H103ClN18O16/c1-45(2)35-60(72(107)92-59(16-9-10-33-87-46(3)4)80(115)101-34-12-17-68(101)79(114)88-47(5)70(84)105)93-74(109)63(38-51-23-30-58(31-24-51)91-81(85)116)95-76(111)64(39-50-21-28-57(29-22-50)90-71(106)66-42-69(104)100-82(117)99-66)97-78(113)67(44-102)98-77(112)65(41-53-13-11-32-86-43-53)96-75(110)62(37-49-19-26-56(83)27-20-49)94-73(108)61(89-48(6)103)40-52-18-25-54-14-7-8-15-55(54)36-52/h7-8,11,13-15,18-32,36,43,45-47,59-68,87,102H,9-10,12,16-17,33-35,37-42,44H2,1-6H3,(H2,84,105)(H,88,114)(H,89,103)(H,90,106)(H,92,107)(H,93,109)(H,94,108)(H,95,111)(H,96,110)(H,97,113)(H,98,112)(H3,85,91,116)(H2,99,100,104,117)/t47?,59-,60-,61+,62+,63+,64-,65?,66?,67-,68-/m0/s1

InChI_Key MEUCPCLKGZSHTA-CTZYXKPMSA-N

SMILES  CC(NCCCC[C@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H](NC(C(NC([C@H](NC([C@H](NC(C)=O)CC1=CC=C2C=CC=CC2=C1)=O)CC3=CC=C(Cl)C=C3)=O)CC4=CN=CC=C4)=O)CO)=O)CC5=CC=C(NC(C(NC(N6)=O)CC6=O)=O)C=C5)=O)CC7=CC=C(NC(N)=O)C=C7)=O)CC(C)C)=O)C(N8CCC[C@@]8([H])C(NC(C)C(N)=O)=O)=O)C

External Codes


PubChem CID  16136245

DrugBank Accession Number  DB06699

NCI Thesaurus Code  C48385  

UNII  SX0XJI3A11   GSRS

CAS  214766-78-6



Drug approval


Drug indication
    Degaralix is used for the treat of advanced prostate cancer and is also being studied in the treatment of benign prostatic hyperplasia.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Firmagon eq 80mg base/vial; eq 120mg base/vial Powder; Subcutaneous Ferring Prescription NDA: 022201 2008
Firmagon eq 120mg base/vial Powder; Subcutaneous Ferring Prescription NDA: 022202 2008
Firmagon 80 mg/vial Powder; Subcutaneous Ferring Inc Prescription DIN: 02337029 2009
Firmagon 120 mg/vial Powder; Subcutaneous Ferring Inc Prescription DIN: 02337037 2009
Firmagon 80 mg/vial; 120 mg/vial Powder; Subcutaneous Ferring Pharmaceuticals Prescription EMEA/H/C/000986 2009

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT03069937 A Phase II Study of Docetaxel Before Medical Castration With Degarelix in Patients With Newly Diagnosed Metastatic Prostatic Adenocarcinoma. Metastatic Prostatic Adenocarcinoma Phase 2 Treatment
NCT02475057 A Pilot Study on Endothelial Function and Cardiovascular Biomarkers in Prostate Cancer (PCa) Patients, With Pre-existing Cardiovascular Disease, Treated With Degarelix vs. Luteinizing Hormone-Releasing Hormone (LHRH) Agonists Prostatic Neoplasms; Cardiovascular Diseases Phase 4 Treatment
NCT01512472 Randomized, Multicentre Efficacy and Safety Study Comparing 10 Mons vs 4 Mons Degarelix Therapy in Prolonging the Off Treatment Interval in Men With Localized Prostate Cancer Receiving Intermittent ADT for Biochemical Recurrence Following Radical Local Therapy Prostate Cancer Recurrent Phase 4 Treatment
NCT02015871 An Extension Long-Term Safety and Tolerability Trial of Degarelix, Following a 1-year Open-Label, Multi-Centre, Randomised, Parallel-group Trial in Which the Efficacy and Safety of Degarelix One-month Dosing Regimen Was Compared With Goserelin in Chinese Patients With Prostate Cancer Requiring Androgen Ablation Therapy Prostate Cancer Phase 3 Treatment
NCT01994239 A Multicenter Randomised Phase II Study Comparing the Efficiency of a HT Concomitant With RT vs RT Alone in the Salvage of Patients With a Detectable PSA After Prostatectomy Adenocarcinoma of Prostate Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DCTPep is developed by Dr.Zheng's team.