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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.

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Aldoxorubicin Manufacturers

A Aldoxorubicin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Aldoxorubicin, including repackagers and relabelers. The FDA regulates Aldoxorubicin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Aldoxorubicin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Aldoxorubicin Suppliers

A Aldoxorubicin supplier is an individual or a company that provides Aldoxorubicin active pharmaceutical ingredient (API) or Aldoxorubicin finished formulations upon request. The Aldoxorubicin suppliers may include Aldoxorubicin API manufacturers, exporters, distributors and traders.

Aldoxorubicin GMP

Aldoxorubicin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Aldoxorubicin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Aldoxorubicin GMP manufacturer or Aldoxorubicin GMP API supplier for your needs.

Aldoxorubicin CoA

A Aldoxorubicin CoA (Certificate of Analysis) is a formal document that attests to Aldoxorubicin's compliance with Aldoxorubicin specifications and serves as a tool for batch-level quality control.

Aldoxorubicin CoA mostly includes findings from lab analyses of a specific batch. For each Aldoxorubicin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Aldoxorubicin may be tested according to a variety of international standards, such as European Pharmacopoeia (Aldoxorubicin EP), Aldoxorubicin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Aldoxorubicin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.