Zoptarelin doxorubicin
DRACPC ID DRACPC0086
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
Type Small Molecule
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
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.
