INNO-206 - CAS 1361644-26-9
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INNO-206 - CAS 1361644-26-9 Catalog number: BADC-00027

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INNO-206 (Aldoxorubicin) is the 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity.

Category
ADCs Cytotoxin
Product Name
INNO-206
CAS
1361644-26-9
Catalog Number
BADC-00027
Molecular Formula
C37H42N4O13
Molecular Weight
750.75
INNO-206

Ordering Information

Catalog Number Size Price Quantity
BADC-00027 -- $--
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Description
INNO-206 (Aldoxorubicin) is the 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity.
Synonyms
Doxorubicin-hydrazone-caproyl-maleimide; Aldoxorubicin; 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-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; 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, (2E)-2-[1-[(2S,4S)-4-[(3-amino-2,3,6-trideoxy-α-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
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
Canonical SMILES
CC1C(C(CC(O1)OC2CC(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)/b39-23+/t17-,20-,22-,27-,32+,37-/m0/s1
InChIKey
OBMJQRLIQQTJLR-USGQOSEYSA-N
Density
1.60±0.1 g/cm3
Solubility
Soluble in DMSO
Index Of Refraction
1.708
LogP
3.08
PSA
271.33000
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.
In Vitro
Aldoxorubicin (INNO-206) inhibited blood vessel formation and reduced multiple myeloma cell growth in a pH-dependent fashion. INNO-206 alone produced marked anti-multiple myeloma effects in vivo at doses that doxorubicin was toxic, and the combination of INNO-206 plus bortezomib produced increased anti-multiple myeloma effects compared with either agent alone. In contrast, all mice receiving bortezomib with doxorubicin or PLD died.
In Vivo
INNO-206 inhibited blood vessel formation and reduced multiple myeloma cell growth in a pH-dependent fashion. INNO-206 alone produced marked anti-multiple myeloma effects in vivo at doses that doxorubicin was toxic, and the combination of INNO-206 plus bortezomib produced increased anti-multiple myeloma effects compared with either agent alone. In contrast, all mice receiving bortezomib with doxorubicin or PLD died.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT01580397Pancreatic Ductal AdenocarcinomaPhase 22013-06-28CytRxCompleted
NCT02014844GlioblastomaPhase 22017-01-06CytRxCompleted
NCT01706835Advanced Solid TumorsPhase 12014-12-17CytRxCompleted
NCT02235688Metastatic Solid TumorsPhase 12017-06-07CytRxCompleted
NCT01337505Malignant Solid TumourPhase 12013-02-13CytRxCompleted
Application
ADCs Cytotoxin-Linker
Appearance
Solid Power
Purity
>98%
Shelf Life
≥360 days if stored properly
Shipping
Room temperature, or blue ice upon request.
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Pictograms
Health Hazard
Signal Word
Danger
1.Anti-myeloma effects of the novel anthracycline derivative INNO-206.
Sanchez E1, Li M, Wang C, Nichols CM, Li J, Chen H, Berenson JR. Clin Cancer Res. 2012 Jul 15;18(14):3856-67. doi: 10.1158/1078-0432.CCR-11-3130. Epub 2012 May 22.
PURPOSE: Doxorubicin has shown efficacy especially in combination treatment for the treatment of multiple myeloma; however, its side effects limit its use. INNO-206 is an albumin-binding prodrug of doxorubicin, which is released from albumin under acidic conditions. Because INNO-206 has not been previously evaluated in any hematologic malignancy, we determined its anti-multiple myeloma effects.
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Historical Records: 2,5-dioxopyrrolidin-1-yl 4-formylbenzoate | INNO-206
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