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Aldoxorubicin

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Also known as: Inno-206, 1361644-26-9, Doxorubicin-emch, Doxo-emch, Aldoxorubicin [usan], N-[(e)-[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

Molecular Formula

C₃₇H₄₂N₄O₁₃

Molecular Weight

750.7 g/mol

InChI Key

OBMJQRLIQQTJLR-USGQOSEYSA-N

FDA UNII

C28MV4IM0B

Aldoxorubicin is a 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity. Following intravenous administration, aldoxorubicin binds selectively to the cysteine-34 position of albumin via its maleimide moiety. Doxorubicin is released from the albumin carrier after cleavage of the acid-sensitive hydrazone linker within the acidic environment of tumors and, once located intracellularly, intercalates DNA, inhibits DNA synthesis, and induces apoptosis. Albumin tends to accumulate in solid tumors as a result of high metabolic turnover, rapid angiogenesis, hypervasculature, and impaired lymphatic drainage. Because of passive accumulation within tumors, this agent may improve the therapeutic effects of doxorubicin while minimizing systemic toxicity.

1 2D Structure

Aldoxorubicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(E)-[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

2.1.2 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)/b39-23+/t17-,20-,22-,27-,32+,37-/m0/s1

2.1.3 InChI Key

OBMJQRLIQQTJLR-USGQOSEYSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=NNC(=O)CCCCCN6C(=O)C=CC6=O)CO)O)N)O

2.1.5 Isomeric 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(=N/NC(=O)CCCCCN6C(=O)C=CC6=O)/CO)O)N)O

2.2 Other Identifiers

2.2.1 UNII

C28MV4IM0B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aldoxo

2. Doxo-emch

3. Inno-206

2.3.2 Depositor-Supplied Synonyms

1. Inno-206

2. 1361644-26-9

3. Doxorubicin-emch

4. Doxo-emch

5. Aldoxorubicin [usan]

6. N-[(e)-[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

7. Aldoxorubicin (usan)

8. 151038-96-9

9. C28mv4im0b

10. Aldoxorubicin [inn]

11. Aldoxorubicin [who-dd]

12. Chembl2107818

13. Schembl15221892

14. Dtxsid001098062

15. Ex-a3971

16. Aldoxorubicin;inno 206;inno206

17. Nsc784722

18. Zinc163337436

19. Cs-1186

20. Db06013

21. Nsc-784722

22. Hy-16261

23. D10383

24. (6-maleimidocaproyl)hydrazone Of Doxorubicin

25. (8s)-1-methoxy-6,8alpha,11-trihydroxy-8-[1-[2-[6-(2,5-dioxo-3-pyrroline-1-yl)hexanoyl]hydrazono]-2-hydroxyethyl]-10alpha-(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyloxy)-7,8,9,10-tetrahydronaphthacene-5,12-dione

26. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (1-((2s,4s)-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-hydroxyethylidene)hydrazide

27. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (1-(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-hydroxyethylidene)hydrazide, (2s-cis)-

28. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (2e)-2-(1-((2s,4s)-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-hydroxyethylidene)hydrazide

29. 1h-pyrrole-1-hexanoic Acid, 2,5-dihydro-2,5-dioxo-, (2e)-2-[1-[(2s,4s)-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-hydroxyethylidene]hydrazide

30. N'-((1e)-1-((2s,4s)-4-((3-amino-2,3,6-trideoxy-.alpha.-l-lyxohexopyranosyl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl(-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)hexanohydrazide

31. N'-((e)-1-((2s,4s)-4-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)-2-hydroxyethylidene)-6-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)hexanehydrazide

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₂N₄O₁₃
Molecular Weight	750.7 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	12
Exact Mass	750.27483741 g/mol
Monoisotopic Mass	750.27483741 g/mol
Topological Polar Surface Area	268 Å²
Heavy Atom Count	54
Formal Charge	0
Complexity	1510
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in solid tumors.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

INNO-206 is the (6-Maleimidocaproyl) hydrazone of doxorubicin. INNO-206 is a prodrug of doxorubicin that binds endogenous albumin after administration. The bound doxorubicin is released in the acidic environment of the tumor cell through cleavage of an acid sensitive linker. In preclinical models, INNO-206 was superior to doxorubicin with regard to antitumor efficacy and toxicity.