Ozarelix

DRACPC ID  DRACPC0071

Active Ingredients   Ozarelix

Description  A highly modified, fourth generation linear decapeptide with gonadotropin-releasing hormone (GnRH or LHRH) antagonizing properties. Ozarelix 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 hormonally dependent disease states such as hormone-dependent prostate cancer.

Synonyms  SPI-153; D 63153; D-63 153; D63 153; D63153; LHRH antagonist SPI-153; Ozarelix

Type  Small Molecule

Disease  Prostate Cancer, Benign Prostatic Hypertrophy, Benign Prostatic Hyperplasia

Classification

  

GnRH/LHRH antagonist Peptide and derivative

Structure Information


Molecular Formula  C72H96ClN17O14

Molecular Weight  1459.1

Active Sequence  xxxSXxXRPa

Sequence Length  10

Modification  x(1)=D-2Nal, x(2)=D-Phe(4-Cl), x(3)=D-3Pal, X(5)=N(Me)Tyr, x(6)=D-hCit, X(7)=Nle, C-terminal Ac, N-terminal NH2

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  (2S)-1-[(2S)-2-[[(2S)-2-[[(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]-6-(carbamoylamino)hexanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

InChI  InChI=1S/C72H96ClN17O14/c1-5-6-17-52(63(96)85-54(19-12-33-79-71(75)76)70(103)90-34-13-20-59(90)67(100)81-42(2)61(74)94)83-62(95)53(18-9-10-32-80-72(77)104)84-68(101)60(39-45-24-29-51(93)30-25-45)89(4)69(102)58(41-91)88-66(99)57(38-47-14-11-31-78-40-47)87-65(98)56(36-44-22-27-50(73)28-23-44)86-64(97)55(82-43(3)92)37-46-21-26-48-15-7-8-16-49(48)35-46/h7-8,11,14-16,21-31,35,40,42,52-60,91,93H,5-6,9-10,12-13,17-20,32-34,36-39,41H2,1-4H3,(H2,74,94)(H,81,100)(H,82,92)(H,83,95)(H,84,101)(H,85,96)(H,86,97)(H,87,98)(H,88,99)(H4,75,76,79)(H3,77,80,104)/t42-,52+,53-,54+,55-,56-,57-,58+,59+,60+/m1/s1

InChI_Key KATZUZNTRINHDT-HALMFYTRSA-N

SMILES  [H]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)[H])=O)=O)CCCNC(N)=N)=O)CCCC)=O)CCCCNC(N)=O)=O)CC2=CC=C(C=C2)O)C)=O)CO)C([C@H](NC([C@H](NC([C@H](NC(C)=O)CC3=CC4=CC=CC=C4C=C3)=O)CC5=CC=C(C=C5)Cl)=O)CC6=CN=CC=C6)=O

External Codes


PubChem CID  25080293

DrugBank Accession Number  DB12581

NCI Thesaurus Code  C95214  

UNII  Q1IF8M2YL3   GSRS

CAS  295350-45-7



Drug approval


Drug indication
    Ozarelix has been used in trials studying the treatment of Prostate Cancer, Benign Prostatic Hypertrophy, and Benign Prostatic Hyperplasia (BPH).

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT00427219 A Randomized, Double-Blind, Placebo-Controlled Trial of the Safety and Efficacy of Ozarelix, in Patients With Lower Urinary Tract Symptoms(LUTS) Due to Benign Prostatic Hypertrophy (BPH) Benign Prostatic Hypertrophy Phase 2 Treatment
NCT01252693 Phase 2 Study Assessing the Safety and Efficacy of a Monthly Dosing Regimen of Ozarelix Versus Goserelin Depot (Zoladex®) in Men With Prostate Cancer Prostate Cancer Phase 2 Treatment
NCT00743184 A Multi-Center, Randomized, Double-Blind, Placebo-Controlled Trial of the Safety and Efficacy of Ozarelix, in Patients With Lower Urinary Tract Symptoms (LUTS) Due to Benign Prostatic Hyperplasia (BPH) Benign Prostatic Hyperplasia (BPH); Lower Urinary Tract Symptoms (LUTS) Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DRACP is developed by Dr.Zheng's team.