Doxorubicin hydrochloride, Thermo Scientific Chemicals

Description

Doxorubicin hydrochloride, CAS # 25316-40-9, is the hydrochloride salt of doxorubicin, isolated from the bacterium Streptomyces peucetius, and is considered to be an anthracycline antibiotic with antineoplastic activity.

Antitumor antibiotic agent that inhibits DNA topoisomerase II.Doxorubicin hydrochloride is used as an antineoplastic, antibiotic agent that inhibits DNA topoisomerase. It also inhibits nucleic acid synthesis and induces apoptosis. It posses fluorescent property, which enable it for the measurement of drug efflux pump activities and the role of subcellular organelles (golgi and lysosome) in the sequestration of drugs.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

General Description

• Doxorubicin hydrochloride, isolated from the bacterium Streptomyces peucetius, is an anthracycline antibiotic with antineoplastic activity and is related to daunorubicin
• It can intercalate between base pairs in the DNA helix preventing DNA replication
• It also inhibits the nucleic acid synthesis and can induce apoptosis
• It can inhibit DNA topoisomerase II, resulting in an increased and stabilized cleavable enzyme-DNA linked complex during DNA replication, and prevents nucleotide strand ligation after double-strand breakage
• Doxorubicin hydrochloride forms oxygen free radicals that result in cytotoxicity and lead to the lipid peroxidation of cell membrane lipids

Application

• This compound displays a fluorescent property allowing the measurement of drug efflux pump activity and examining the role of subcellular organelles (Golgi complex and lysosome) in the sequestration of drugs
• It has been used in cell viability assays
• It is used as a drug in polymeric PLGA-based microparticulate drug delivery and to develop in vitro doxorubicin-resistant HepG2 cells (HepG2-DR) and K562 cells (K562-DR)
• It is a substrate of the MRP1 transporter

Specifications

Chemical Identifiers

• CAS: 25316-40-9
• Molecular Formula: C27H30ClNO11
• Molecular Weight (g/mol): 579.98
• MDL Number: MFCD00077757,MFCD00077757,MFCD00941448
• InChI Key: MWWSFMDVAYGXBV-FGBJBKNOSA-N
• Synonym: doxorubicin hydrochloride, adriamycin, doxorubicin hcl, adriacin, adriblastina, rubex, adriamycin hydrochloride, adriblastin, adriamycin pfs
• PubChem CID: 129626538
• IUPAC Name: hydrogen (8S,10S)-10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione chloride
• SMILES: [H+].[Cl-].COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3OC3CC(N)C(O)C(C)O3)C(=O)CO)C(O)=C1C2=O

• Melting Point: 216°C (decomposition)
• Color: Orange-Red
• Quantity: 10 mg
• Beilstein: 4229251
• Merck Index: 14,3439
• Solubility Information: Soluble in water.
• Formula Weight: 579.99
• Physical Form: Solid
• Chemical Name or Material: Doxorubicin hydrochloride

Safety and Handling

Hazard Category	H302-H315-H318-H335-H340-H350-H361fd
Hazard Statement	GHS H Statement H350-H302 May cause cancer. Harmful if swallowed.
Precautionary Statement	P201-P202-P261-P264b-P270-P271-P281-P301+P312-P302+P352-P304+P340-P305+P351+P338-P308+P313-P310-P330-P332+P313-P362-P501c
EINECSNumber	246-818-3
RTECSNumber	QI9295900
TSCA	No
Recommended Storage	Ambient temperatures

SDS

RUO – Research Use Only