Abarelix

DRACPC ID  DRACPC0006

Active Ingredients   Abarelix

Description  A synthetic decapeptide and antagonist of naturally occurring gonadotropin-releasing hormone (GnRH). Abarelix directly and competitively binds to and blocks the gonadotropin releasing hormone receptor in the anterior pituitary gland, thereby inhibiting the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. As a result, this may relieve symptoms associated with prostate hypertrophy or prostate cancer, since testosterone is required to sustain prostate growth.

Synonyms  Plenaxis; PPI-149; R-3827; Abarelix

Type  Small Molecule

Disease  Prostate cancer

Classification

  

GnRH antagonists Peptide and derivative

Structure Information


Molecular Formula  C72H95ClN14O14

Molecular Weight  1416.1

Active Sequence  xxxSXnLXPa

Sequence Length  10

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

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S)-1-[[(2S)-1-[(2S)-2-[[(2R)-1-amino-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-6-(propan-2-ylamino)hexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]butanediamide

InChI  InChI=1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1

InChI_Key AIWRTTMUVOZGPW-HSPKUQOVSA-N

SMILES  CC(N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@H](C(N([C@H](C(N[C@@H](C(N[C@H](C(N[C@H](C(N1CCC[C@H]1C(N[C@@H](C(N)=O)C)=O)=O)CCCCNC(C)C)=O)CC(C)C)=O)CC(N)=O)=O)CC2=CC=C(C=C2)O)C)=O)CO)=O)CC3=CC=CN=C3)=O)CC4=CC=C(C=C4)Cl)=O)CC5=CC=C6C=CC=CC6=C5)=O

External Codes


PubChem CID  16131215

DrugBank Accession Number  DB00106

NCI Thesaurus Code  C2015  

UNII  W486SJ5824   GSRS

CAS  183552-38-7



Drug approval


Drug indication
    For palliative treatment of advanced prostate cancer.

Drug Name Strength Dosage Form/Route Company Marketing Status Drug ID Approval year
Plenaxis 100 mg/vial Injectable; Intramuscular Speciality European Discontinued NDA: 021320 2003

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00841113 Phase III Study of the Comparison of Abarelix Versus Goserelin Plus Bicalutamide in Patients With Advanced or Metastatic Prostate Cancer. A One Year Randomised, Open Label, Multi-Centre Phase III Trial. Prostate Cancer Phase 3 Treatment
NCT00100243 Phase 2 Study of Abarelix in Androgen-Independent Prostate Cancer Progressing After Agonist Therapy Prostate Cancer Phase 2 Treatment
NCT00103623 Incidence of Immediate Onset Systemic Allergic Reactions in Patients Treated With Plenaxis® Prostate Cancer Phase 4 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DRACP is developed by Dr.Zheng's team.