Doxorubicin hydrochloride, Thermo Scientific™

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.

Brand:  Thermo Scientific Alfa Aesar J64000.MF

Product Code. 15486139

Description

This Thermo Scientific 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.

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

Chemical Identifiers

• CAS: 25316-40-9
• Molecular Weight (g/mol): 579.98
• InChI Key: MWWSFMDVAYGXBV-FGBJBKNOSA-N
• PubChem CID: 129626538
• 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

• Molecular Formula: C27H30ClNO11
• MDL Number: MFCD00077757,MFCD00077757,MFCD00941448
• Synonym: doxorubicin hydrochloride, adriamycin, doxorubicin hcl, adriacin, adriblastina, rubex, adriamycin hydrochloride, adriblastin, adriamycin pfs
• 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

Specifications

• CAS: 25316-40-9
• MDL Number: MFCD00077757,MFCD00077757,MFCD00941448
• Beilstein: 4229251
• Synonym: doxorubicin hydrochloride, adriamycin, doxorubicin hcl, adriacin, adriblastina, rubex, adriamycin hydrochloride, adriblastin, adriamycin pfs
• InChI Key: MWWSFMDVAYGXBV-FGBJBKNOSA-N
• 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
• PubChem CID: 129626538
• Chemical Name or Material: Doxorubicin hydrochloride

• Molecular Formula: C27H30ClNO11
• Quantity: 50mg
• Merck Index: 14,3439
• Solubility Information: Soluble in water.
• 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
• Molecular Weight (g/mol): 579.98
• Formula Weight: 579.99

Safety and Handling

Product Identifier

• Doxorubicin hydrochloride

Signal Word

• Danger

Hazard Category

• Acute toxicity Category 4
• Serious eye damage/eye irritation Category 1
• Germ cell mutagenicity Category 1A
• Reproductive toxicity Category 2
• Skin corrosion/irritation Category 2
• Specific target organ toxicity Category 3

Hazard Statement

• H302-Harmful if swallowed.
• H315-Causes skin irritation.
• H318-Causes serious eye damage.
• H335-May cause respiratory irritation.
• H340-May cause genetic defects.
• H361fd-Suspected of damaging fertility. Suspected of damaging the unborn child.

Precautionary Statement

• P280-Wear protective gloves/protective clothing/eye protection/face protection.
• P301+P330+P331-IF SWALLOWED: rinse mouth. Do NOT induce vomiting.
• P302+P352-IF ON SKIN: Wash with plenty of water/soap.
• P304+P340-IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338-IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
• P310-Immediately call a POISON CENTER/doctor/.
• P332+P313-If skin irritation occurs: Get medical advice/attention.

Supplemental information

• MIXTURE LIST-Contains : Doxorubicin hydrochloride