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:O=C1C=2C=CC=C(OC)C2C(=O)C=3C(O)=C4C(=C(O)C13)CC(O)(CC4OC5OC(C)C(O)C(N)C5)C(O)CO
- 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