CAS 20830-81-3

Daunorubicin

Description:

Daunorubicin is an anthracycline antibiotic that is primarily used in cancer chemotherapy, particularly for treating certain types of leukemia, such as acute myeloid leukemia (AML) and acute lymphoblastic leukemia (ALL). It is derived from the bacterium Streptomyces peucetius and functions by intercalating into DNA, thereby inhibiting DNA and RNA synthesis, which ultimately leads to cell death. Daunorubicin is characterized by its red color, which is indicative of its anthracycline structure. The compound has a complex molecular structure that includes a tetracyclic ring system, which is essential for its biological activity. It is typically administered intravenously and can exhibit side effects such as cardiotoxicity, myelosuppression, and nausea. Due to its potent effects, daunorubicin is often used in combination with other chemotherapeutic agents to enhance therapeutic efficacy while managing potential resistance. Its use is carefully monitored, and dosing is adjusted based on patient response and tolerance.

Formula: C₂₇H₂₉NO₁₀

InChI: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1

InChI key: InChIKey=STQGQHZAVUOBTE-VGBVRHCVSA-N

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

Synonyms:

• (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
• (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside hydrochloride (1:1)
• (7S,9S)-9-Acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,l 1-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• (7S,9S)-9-acetyl-6,9,11-trihydroxy-4-methoxy-7-tetrahydropyran-2-yloxy-8,10-dihydro-7H-tetracene-5,12-dione
• (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• (8S-Cis)-8-Acetyl-10-((3-Amino-2,3,6-Trideoxy-Alpha-L-Lyxo-Hexopyranosyl)Oxy)-7,8,9,10-Tetrahydro-6,8,11-Trihydroxy-1-Methoxy-5,12-Naphthacenedione Hydrochloride
• (8S-Cis)-8-Acetyl-10-[(3-Amino-2,3,6-Trideoxy-Alpha-L-Lyxo-Hexopyrannosyl)Oxy]
• (8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-l-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• 3-Acetyl-1,2,3,4,6,11-Hexahydro-3,5,12-Trihydroxy-10-Methoxy-6,11-Dioxo-1-Naph
• 3-Acetyl-3,5,12-Trihydroxy-10-Methoxy-6,11-Dioxo-1,2,3,4,6,11-Hexahydrotetracen-1-Yl 3-Amino-2,3,6-Trideoxyhexopyranoside
• 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
• 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
• 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
• 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
• 5,12-Naphthacenedione, 8-acetyl-10-[3-amino,2,3,6-trideoxy-α-L-lyoxohexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)
• Acetyladriamycin
• Ammonia
• Cerubidin
• D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)carbonyl]amino]-
• DaunoXome
• Daunoblastina
• Daunomycin Hydrochloride
• Daunomycine
• Daunorrubicina
• Daunorubicin
• Daunorubicine
• Daunorubicine Hydrochloride
• Fsl 0507
• Hydrate
• Hydrochloride
• Leukaemomycin C
• Leukaemomycin C Hydrochloride
• Methane
• Molecular Hydrogen
• Nsc 82151
• Nsc 83142
• Rp 13057
• Rubidomycin
• Rubomycin C
• (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione

Daunorubicin Hydrochloride

CAS: 20830-81-3, 23541-50-6

Formula: C₂₇H₂₉NO₁₀·HCl

Purity: >98.0%(N)

Color and Shape: Orange to Red powder to crystal

Molecular weight: 563.98

Ref: 3B-D4532

Daunorubicin-13C-d3 Trifluoroacetate (Epirubicin EP Impurity D-13C-d3 Trifluoroacetate)

CAS: 20830-81-3

Formula: C₂₆₁₃CH₂₆D₃NO₁₀·C₂HF₃O₂

Molecular weight: 531.54 114.02

Ref: 4Z-D-4810

Daunorubicin

CAS: 20830-81-3

Daunorubicin is an anthracycline antibiotic and topoisomerase II inhibitor with anticancer activity, inhibiting DNA and RNA synthesis, leukaemia (AML)(ALL).

Formula: C₂₇H₂₉NO₁₀

Purity: 97.84%

Color and Shape: Reddish Needles

Molecular weight: 527.52

Ref: TM-T1511L

Daunorubicin-13C,d3 (>85%)

Controlled Product

CAS: 20830-81-3

Formula: CC₂₆D₃H₂₆NO₁₀

Purity: >85%

Color and Shape: Neat

Molecular weight: 531.53

Ref: TR-D194502

Daunorubicin

CAS: 20830-81-3

Anthracycline antibiotic with potent anti-tumoral activity. The compound interferes with DNA replication and RNA transcription since it intercalates between the base pairs of nucleic acids. It also inhibits the topoisomerase II, proteasome and generates free radicals, which leads to cell death of treated cells. Moreover, daunorubicin triggers apoptosis trough the stimulation of ceramide synthesis. It has been used as chemotherapy agent for the treatment of myeloid leukaemia (AML) and acute lymphocytic leukaemia (ALL).

Formula: C₂₇H₂₉NO₁₀

Purity: Min. 95%

Molecular weight: 527.52 g/mol

Ref: 3D-MD32002