CAS 54193-28-1

Doxorubicinol

Description:

Doxorubicinol, with the CAS number 54193-28-1, is a metabolite of the anthracycline antibiotic doxorubicin, which is widely used in cancer therapy. This compound retains some of the pharmacological properties of its parent drug, including antitumor activity, but has a different profile in terms of efficacy and toxicity. Doxorubicinol is characterized by its ability to intercalate DNA, disrupting the replication process and leading to cell death, which is a common mechanism of action among anthracyclines. It is typically less potent than doxorubicin but can contribute to the overall therapeutic effects in patients undergoing treatment. The compound is also known for its potential cardiotoxicity, a side effect associated with doxorubicin, although the extent may vary. In terms of physical properties, doxorubicinol is a red-orange crystalline solid, soluble in water and organic solvents, which facilitates its formulation for clinical use. Its chemical structure includes a tetracyclic ring system, characteristic of anthracyclines, contributing to its biological activity.

Formula: C₂₇H₃₁NO₁₁

InChI: InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1

InChI key: InChIKey=NKZRZOVSJNSBFR-FEMMEMONSA-N

SMILES: OC=1C2=C([C@@H](O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C[C@@]([C@H](CO)O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=O)=C(OC)C=CC5

Synonyms:

• 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, [8S-[8α,8(R*),10α]]-
• 13-Dihydrodoxorubicin
• 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
• (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• Adriamycinol

Doxorubicinol HCl (Mixture of Diastereomers)

CAS: 1242592-26-2, 54193-28-1

Formula: C₂₇H₃₁NO₁₁·HCl

Molecular weight: 545.54 36.46

Ref: 4Z-D-343

Doxorubicinol hydrochloride

CAS: 54193-28-1

Formula: C₂₇H₃₂ClNO₁₁

Purity: ≥ 90.0% (sum of isomers)

Color and Shape: Red to dark red/brown powder

Molecular weight: 582.0

Ref: 7W-GK1667

Doxorubicinol

CAS: 54193-28-1

Doxorubicinol is the major circulating metabolite of doxorubicin with antineoplastic acitivity.

Formula: C₂₇H₃₁NO₁₁

Color and Shape: Solid

Molecular weight: 545.54

Ref: TM-T25349

Doxorubicinol Hydrochloride (>90%)(Mixture of diastereomers)

Controlled Product

CAS: 54193-28-1, 63950-05-0

Applications A metabolite of Doxorubicin as neoplasm inhibitor.
References Smith, T.H.

Formula: C₂₇H₃₁NO₁₁•HCl

Color and Shape: Red

Molecular weight: 545.54 + 36.46

Ref: TR-D558020

Doxorubicinol (>90%)

Controlled Product

CAS: 54193-28-1

Applications Doxorubicinol is a cardiotoxic metabolite of Doxorubicin (D558000). Used as an antineoplastic.
References Freeland, M.M., et. al.: Anti-Cancer Drug, 23, 584 (2012)

Formula: C₂₇H₃₁NO₁₁

Purity: >90%

Color and Shape: Neat

Molecular weight: 545.54

Ref: TR-D558025

Doxorubicinol,mixture of diastereomers

CAS: 54193-28-1

Doxorubicinol, a mixture of diastereomers, is an anthracycline antibiotic that inhibits the growth of cells by binding to DNA and preventing the production of RNA. Doxorubicinol has been shown to be effective in treating breast cancer and solid tumours, including those resistant to doxorubicin. This drug has also been shown to inhibit the production of matrix metalloproteinases that are involved in tumor invasion and metastasis. The concentration-time curve for doxorubicinol can be determined experimentally by blood sampling and measuring its metabolites. The ryanodine receptor is a calcium channel found on the surface membrane of cardiac muscle cells that regulates intracellular calcium levels. Doxorubicinol may bind to this receptor, which could account for its cardiotoxic effects.

Formula: C₂₇H₃₁NO₁₁

Purity: (%) Min. 90%

Molecular weight: 545.54 g/mol

Ref: 3D-FD76789