Aldoxorubicin

Aldoxorubicin

Identifiers
IUPAC name N-[[1-[(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-hydroxyethylidene]amino]-6-(2,5-dioxopyrrol-1-yl)hexanamide
PubChem CID	71300693
ChemSpider	7986464
KEGG	D10383
Chemical and physical data
Formula	C37H42N4O13
Molar mass	750.76 g·mol−1
3D model (Jmol)	Interactive image
SMILES C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)O)N)O
InChI InChI=1S/C37H42N4O13/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43)/t17-,20-,22-,27-,32+,37-/m0/s1 Key:OBMJQRLIQQTJLR-FRTGXRTISA-N

Aldoxorubicin (INNO-206) is a tumor-targeted doxorubicin conjugate in development by CytRx, which maintains the rights to its use. Specifically, it is the (6-maleimidocaproyl) hydrazone of doxorubicin. Essentially, this chemical name describes doxorubicin attached to an acid sensitive linker (N-ε-maleimidocaproic acid hydrazide, or EMCH).

The proposed mechanism of action is as follows:

Five phase I trials for safety characterization have been completed. Several phase II and III trials are underway.

As of January 2017, there are 6 phase II clinical trials in progress:

A phase III trial for patients with relapsed soft tissue sarcoma comparing aldoxorubicin with several other chemotherapeutics is expected to complete in 2018. In November 2016, CytRx announced that preliminary results had been positive.