Zoptarelin doxorubicin

DCTPepD ID  DCTPepD0086

Active Ingredients   Zoptarelin doxorubicin

Description  A peptide agonist of the gonadotropin releasing hormone-1 receptor (GnRH-1R) that is conjugated to the anthracycline antibiotic doxorubicin with potential antineoplastic activity. Zoptarelin doxorubicin binds to GnRH-1Rs, which may be highly expressed on endometrial and ovarian tumor cell membrane surfaces, and is internalized. Once inside the cell, the doxorubicin moiety of this agent intercalates into DNA and inhibits the topoisomerase II activity, which may result in the inhibition of tumor cell DNA replication and tumor cell proliferation.

Synonyms  AEZS-108; AEZS108; AN 152; AN-152; Doxorubicin-GNRH Agonist Conjugate AEZS-108; ZEN-008; Zoptarelin Doxorubicin

Disease  Breast Cancer, Ovarian Cancer, Prostate Cancer, Endometrial Cancer, Urothelial Carcinoma

Classification

  

GnRH-1R agonist Peptide and derivative Peptide-Drug Conjugates Cancer Targeted Conjugates

Structure Information


Molecular Formula  C91H117N19O26

Molecular Weight  1893

Active Sequence  Not available

Sequence Length  Not available

Modification  Not available

Structure

 

Show IUPAC/InChI/SMILES

IUPAC Name  [2-[(2S,4S)-4-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl] 5-[[(5R)-6-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-carbamimidamido-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-[[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-oxohexyl]amino]-5-oxopentanoate

InChI  InChI=1S/C91H117N19O26/c1-44(2)31-58(83(125)104-57(17-11-29-98-90(94)95)89(131)110-30-12-18-63(110)88(130)100-40-67(93)114)105-81(123)55(16-7-8-28-97-68(115)20-10-21-70(117)134-42-66(113)91(132)36-52-73(65(37-91)136-71-35-53(92)76(118)45(3)135-71)80(122)75-74(78(52)120)77(119)51-14-9-19-64(133-4)72(51)79(75)121)103-84(126)59(32-46-22-24-49(112)25-23-46)106-87(129)62(41-111)109-85(127)60(33-47-38-99-54-15-6-5-13-50(47)54)107-86(128)61(34-48-39-96-43-101-48)108-82(124)56-26-27-69(116)102-56/h5-6,9,13-15,19,22-25,38-39,43-45,53,55-63,65,71,76,99,111-112,118,120,122,132H,7-8,10-12,16-18,20-21,26-37,40-42,92H2,1-4H3,(H2,93,114)(H,96,101)(H,97,115)(H,100,130)(H,102,116)(H,103,126)(H,104,125)(H,105,123)(H,106,129)(H,107,128)(H,108,124)(H,109,127)(H4,94,95,98)/t45-,53-,55+,56-,57-,58-,59-,60-,61-,62-,63-,65-,71-,76+,91-/m0/s1

InChI_Key OOUACICUAVTCEC-LZHWUUGESA-N

SMILES  C[C@@H]1O[C@@H](O[C@@H]2C3=C(C(O)=C(C4=O)C(C(C5=C4C=CC=C5OC)=O)=C3O)C[C@](C(COC(CCCC(NCCCC[C@@H](NC([C@H](CC6=CC=C(O)C=C6)NC([C@H](CO)NC([C@H](CC7=CNC8=CC=CC=C87)NC([C@H](CC9=CN=CN9)NC([C@H]%10NC(CC%10)=O)=O)=O)=O)=O)=O)C(N[C@@H](CC(C)C)C(N[C@@H](CCCNC(N)=N)C(N%11[C@@H](CCC%11)C(NCC(N)=O)=O)=O)=O)=O)=O)=O)=O)(O)C2)C[C@H](N)[C@@H]1O

External Codes


PubChem CID  16134409

DrugBank Accession Number  DB12755

NCI Thesaurus Code  C74025  

UNII  27844X2J29   GSRS

CAS  139570-93-7



Drug approval


Drug indication
    Zoptarelin doxorubicin has been used in trials studying the treatment of Breast Cancer, Ovarian Cancer, Prostate Cancer, Endometrial Cancer, and Urothelial Carcinoma, among others.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT01767155 Randomized Controlled Study Comparing AEZS-108 With Doxorubicin as Second Line Therapy for Locally Advanced, Recurrent or Metastatic Endometrial Cancer. Endometrial Cancer Phase 3 Treatment
NCT01698281 A Randomized Phase 2 Trial of AEZS-108 in Chemotherapy Refractory Triple Negative, LHRH-positive Metastatic Breast Cancer. Breast Cancer Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





DCTPep is developed by Dr.Zheng's team.