Details of the Drug

General Information of Drug (ID: DMAYO46)

Drug Name
AEZS-108
Synonyms
Zoptarelin doxorubicin; AEZS-108; AN-152; UNII-27844X2J29; ZEN-008; 27844X2J29; Zoptrex; Zoptarelin doxorubicin [INN]; Zoptarelin doxorubicin [USAN]; AEZS 108; CHEMBL3544954; AN 152; Luteinizing hormone-releasing factor (pig), 6-(N6-(5-(2-(4-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl)-2-oxoethoxy)-1,5-dioxopentyl)-D-lysine)-, (2S-cis)-
Indication
Disease Entry ICD 11 Status REF
Acute lymphoblastic leukaemia 2A85 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 1893
Logarithm of the Partition Coefficient (xlogp) -0.4
Rotatable Bond Count (rotbonds) 48
Hydrogen Bond Donor Count (hbonddonor) 23
Hydrogen Bond Acceptor Count (hbondacc) 29
Chemical Identifiers
Formula
C91H117N19O26
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
Canonical SMILES
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)COC(=O)CCCC(=O)NCCCC[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N6CCC[C@H]6C(=O)NCC(=O)N)NC(=O)[C@H](CC7=CC=C(C=C7)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC8=CNC9=CC=CC=C98)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@@H]1CCC(=O)N1)O)N)O
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
InChIKey
OOUACICUAVTCEC-LZHWUUGESA-N
Cross-matching ID
PubChem CID
16134409
CAS Number
139570-93-7
TTD ID
D02HBB

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Gonadotropin-releasing hormone receptor (GNRHR) TT8R70G GNRHR_HUMAN Modulator [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT01767155) Study Comparing AEZS-108/ZoptEC (Zoptarelin Doxorubicin in Endometrial Cancer) to Doxorubicin as a Second Line Therapy of Endometrial Cancer. U.S. National Institutesof Health.
2 Stability of cytotoxic luteinizing hormone-releasing hormone conjugate (AN-152) containing doxorubicin 14-O-hemiglutarate in mouse and human serum in vitro: implications for the design of preclinicalstudies. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):829-34.