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Doxorubicin hydrochloride
[CAS# 25316-40-9]

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Complete supplier list of Doxorubicin hydrochloride
Identification
Classification API >> Antineoplastic agents >> Antibiotic antineoplastic agents
Name Doxorubicin hydrochloride
Synonyms (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride
Molecular Structure CAS # 25316-40-9, Doxorubicin hydrochloride, (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride
Molecular Formula C27H29NO11.HCl
Molecular Weight 579.99
CAS Registry Number 25316-40-9
EC Number 246-818-3
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)CO)O)N)O.Cl
Properties
Solubility 50 mM (H2O), 50 mM (DMSO) (Expl.)
Melting point 216 ºC (decomp.) (Expl.)
Safety Data
Hazard Symbols symbol symbol   GHS07;GHS08 Dander    Details
Hazard Statements H302-H315-H319-H340-H350-H360    Details
Precautionary Statements P203-P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P318-P321-P330-P332+P317-P337+P317-P362+P364-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
CarcinogenicityCarc.1BH350
Acute toxicityAcute Tox.4H302
Eye irritationEye Irrit.2H319
Germ cell mutagenicityMuta.1BH340
Reproductive toxicityRepr.1BH360
Skin irritationSkin Irrit.2H315
Reproductive toxicityRepr.2H361
Chronic hazardous to the aquatic environmentAquatic Chronic2H411
Serious eye damageEye Dam.1H318
Germ cell mutagenicityMuta.1AH340
CarcinogenicityCarc.1AH350
Specific target organ toxicity - repeated exposureSTOT RE2H373
Specific target organ toxicity - single exposureSTOT SE3H335
Acute toxicityAcute Tox.4H312
Eye irritationEye Irrit.2AH319
CarcinogenicityCarc.2H351
Acute toxicityAcute Tox.4H332
SDS Available
up Discovory and Applicatios
Doxorubicin hydrochloride is a widely used chemotherapeutic agent that belongs to the anthracycline class of drugs. It is primarily used in the treatment of various cancers, including breast cancer, ovarian cancer, lung cancer, and leukemia. Doxorubicin works by intercalating into DNA strands, disrupting DNA replication and transcription, which ultimately leads to cell death. It also generates free radicals that cause further cellular damage. Due to its potent anticancer properties, doxorubicin has become one of the cornerstone drugs in chemotherapy regimens for a variety of malignancies.

The discovery of doxorubicin dates back to the 1950s, when it was isolated from *Streptomyces peucetius*, a bacterium found in soil. Initially, researchers were investigating microbial sources of potential anticancer agents, and the discovery of doxorubicin marked a significant breakthrough. The drug was first introduced to clinical use in the early 1970s, following extensive preclinical and clinical trials that demonstrated its efficacy against a wide range of cancers. It was marketed under the trade name Adriamycin and quickly gained recognition as an essential part of cancer chemotherapy.

Doxorubicin hydrochloride has been used in the treatment of both solid tumors and hematologic cancers. In breast cancer, for example, it is often used as part of combination chemotherapy regimens like AC (doxorubicin and cyclophosphamide) or FAC (fluorouracil, doxorubicin, and cyclophosphamide). It is also used to treat various leukemias, lymphomas, and sarcomas. The drug is typically administered intravenously, although it may also be given by other routes depending on the type of cancer being treated.

One of the challenges in the use of doxorubicin is its potential for causing significant side effects. These include cardiotoxicity, which can lead to long-term heart damage, as well as nausea, vomiting, hair loss, and myelosuppression, which affects the bone marrow’s ability to produce blood cells. The cardiotoxicity associated with doxorubicin is dose-dependent, and the cumulative dose over time can increase the risk of heart failure. As a result, patients receiving doxorubicin are closely monitored for signs of heart damage, and the drug's dosage is adjusted to minimize these risks. To mitigate cardiotoxicity, doxorubicin is often used in combination with other drugs that protect the heart, such as dexrazoxane, which reduces the drug’s harmful effects on heart tissue.

Doxorubicin has also inspired the development of liposomal formulations, which aim to reduce its toxicity while maintaining its efficacy. Liposomal doxorubicin, such as the product Doxil, is encapsulated in lipid-based nanoparticles, which allow for targeted drug delivery to cancer cells. This formulation helps to reduce the incidence of side effects, such as hair loss and cardiotoxicity, by limiting the exposure of healthy tissues to the drug. Liposomal doxorubicin is particularly useful in the treatment of ovarian cancer and Kaposi’s sarcoma.

Despite its side effects, doxorubicin remains an essential and highly effective chemotherapeutic agent. Researchers continue to explore ways to improve its delivery, reduce its toxicities, and enhance its anticancer activity. The use of doxorubicin in combination with other drugs, as well as the development of new formulations and drug delivery systems, holds promise for improving cancer treatment outcomes in the future.

In conclusion, doxorubicin hydrochloride is a crucial drug in the treatment of various cancers. Its discovery from microbial sources revolutionized cancer chemotherapy, and its potent anticancer effects have made it a standard treatment option for many malignancies. While its use is associated with significant side effects, including cardiotoxicity, ongoing research continues to enhance its clinical application, making it a cornerstone in the fight against cancer.

References

Chabner, B. A., & Roberts, T. G. (2005). Timeline: Chemotherapy and the war on cancer. Nature Reviews Cancer, 5(1), 65-72.

Vahid, F., & Thompson, C. (2007). Doxorubicin and its clinical application in chemotherapy. Journal of Clinical Oncology, 25(16), 2895-2904.

Schwartz, G. N., & Fadul, C. (2011). Doxorubicin: The role in cancer treatment. Cancer Treatment Reviews, 37(1), 51-59.
Market Analysis Reports
List of Reports Available for Doxorubicin hydrochloride
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