Daunorubicin hydrochloride
[CAS# 23541-50-6]

Identification

• Classification: API >> Antineoplastic agents >> Antibiotic antineoplastic agents
• Name: Daunorubicin hydrochloride
• Synonyms: (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
• Molecular Formula: C₂₇H₂₉NO₁₀.HCl
• Molecular Weight: 563.99
• CAS Registry Number: 23541-50-6
• EC Number: 245-723-4
• 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(=O)C)O)N)O.Cl

Properties

• Solubility: 113 mg/mL (DMSO, water)
• Melting point: 188-190 °C (dec.)

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08 Danger
• Risk Statements: H301-H302-H334-H341-H351-H360
• Safety Statements: P203-P233-P260-P264-P270-P271-P280-P284-P301+P316-P301+P317-P304+P340-P318-P321-P330-P342+P316-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Carcinogenicity	Carc.	2	H351
Acute toxicity	Acute Tox.	3	H301
Respiratory sensitization	Resp. Sens.	1	H334
Reproductive toxicity	Repr.	1B	H360
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H302
Germ cell mutagenicity	Muta.	1B	H340
Skin sensitization	Skin Sens.	1	H317
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	1B	H350
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 2811

Discovery and Applications

Daunorubicin hydrochloride is a chemotherapy medication derived from the natural product daunomycin, which was first isolated from the bacterium Streptomyces peucetius in the 1960s. Its discovery was a result of screening microbial extracts for compounds with anticancer activity. Daunorubicin hydrochloride was identified for its potent cytotoxic effects against cancer cells and has since become a cornerstone of cancer chemotherapy.

Daunorubicin hydrochloride is used in the treatment of various types of cancer, including acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), and certain types of lymphoma. It works by intercalating into DNA strands, inhibiting DNA and RNA synthesis, and inducing apoptosis in rapidly dividing cancer cells. Daunorubicin hydrochloride is administered intravenously and is often used in combination with other chemotherapy drugs to maximize efficacy and reduce the risk of drug resistance. Despite its efficacy, daunorubicin hydrochloride is associated with significant side effects, including bone marrow suppression and cardiotoxicity. Therefore, careful monitoring and dose adjustment are necessary to optimize treatment outcomes while minimizing adverse effects.

References

2024. The first example of a ring closing metathesis in a series of anthracycline antibiotics. *Russian Chemical Bulletin*, 73(10).
DOI: 10.1007/s11172-024-4430-4

2022. Daunorubicin glycoconjugates with natural galectin ligands. *Russian Chemical Bulletin*, 71(3).
DOI: 10.1007/s11172-022-3450-1

1979. Interaction between daunorubicin and chromatin from Ehrlich ascites tumor cells. *Biochemical and Biophysical Research Communications*, 88(2).
DOI: 10.1016/0006-291x(79)92107-7