Drug Libraray

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

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

PubChem CID 16134409

DrugBank Accession Number DB12755

NCI Thesaurus Code C74025

UNII 27844X2J29 GSRS

CAS 139570-93-7

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.