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9. Contact - got a question about Doxorubicin, or want to leave a comment then check out the sites contact page. Reputable companies have them and respond.
10. Payment - ready to pay for your Doxorubicin, then use your credit card or PayPal! Be aware of companies that don't accept them, there may be genuine reasons but given the huge amount of choice you have when buying online there is no reason at all not to buy via credit card or PayPal.
{{Drugbox| IUPAC_name = (8S
,10S
)-10-(4-amino-5-hydroxy-6-methyl-tetrahydro-2H
-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione| image = Doxorubicin.svg| image2=Doxorubicin-3d-sticks.png| CAS_number = 23214-92-8| ATC_prefix = L01| ATC_suffix =DB01| PubChem = 31703| DrugBank = APRD00185| chemical_formula =| C = 27 |H = 29 |N = 1 |O = 11| molecular_weight = 543.52 Gram/Mole (unit)| bioavailability = 5% (Oral)| protein_bound =| metabolism = CYP3A4, [2005. Vol. 11 (19). Retrieved on April 19, 2007.]-->Doxorubicin' (trade name
Adriamycin) or
hydroxyldaunorubicin is a
DNA-interacting
pharmaceutical widely used in chemotherapy. It is an anthracycline
antibiotic and structurely closely related to
daunomycin, and also intercalation (chemistry) DNA. It is commonly used in the treatment of a wide range of
cancers.
The drug is administered by injection, and may be sold under the brand names
Adriamycin PFS,
Adriamycin RDF, or
Rubex." Doxorubicin (Systemic)."
Mayo Clinic. Last updated on:
June 15,
1999. Retrieved on
April 19,
2007.
Doxil is a
liposome-encapsulated dosage form of doxorubicin made by Ben Venue Laboratories for
Johnson & Johnson. The main benefits of this form are a reduction in cardiotoxicity.
History
The history of doxorubicin can be traced back to the 1950s, when an
Italy research company,
Farmitalia Research Laboratories, began an organized effort to find anticancer compounds from soil-based
microbes. A soil sample was isolated from the area surrounding the
Castel del Monte, a 13th century castle. A new strain of
Streptomyces which produced a bright red pigment was isolated, and an antibiotic was produced from this bacterium that was found to have good activity against Murinaes. Since a group of
France researchers discovered the same compound at about the same time, the two teams named the compound daunorubicin, combining the name
List of Illyrian tribes, a pre-Roman tribe that occupied the area of Italy where the compound was isolated, with the French word for ruby,
rubis, describing the color.Weiss, Raymond B. "The Anthracyclines: Will We Ever Find a Better Doxorubicin?" Seminars in Oncology. Vol. 19, No. 6. December 1992. pp. 670–686. PMID 1462166. Clinical trials began in the 1960s, and the drug saw success in treating acute leukemia and lymphoma. However, by 1967, it was recognized that daunorubicin could produce fatal cardiac toxicity.Tan, C.; Tasaka, H.; Kou-Ping, Y.; et al. Daunomycin, An Antitumor Antibiotic, In the Treatment of Neoplastic Disease. Clinical Evaluation with Special Reference to Childhood Leukemia. 1967,
Cancer, 20, 333 – 353. PMID 4290058.
Researchers at Farmitalia soon discovered that changes in biological activity could be made by minor changes in the structure of the compound. A strain of
Streptomyces was mutated using N-nitroso-N-methyl urethane and this new strain produced a different, red-colored antibiotic. They named this new compound Adriamycin, after the
Adriatic Sea, and the name was later changed to doxorubicin to conform to the established naming convention.Arcamone, F.; Cassinelli, G.; Fantini, G.; et al. Adriamycin, 14-hydroxydaunomycin, A New Antitumor Antibiotic from S. peucetius var. caesius. 1969,
Biotechnol. Bioeng., 11, 1101 – 1110. PMID 5365804. Doxorubicin showed better activity than daunorubicin against murine tumors, and especially solid tumors. It also showed a relatively higher therapeutic index, yet the
cardiotoxicity remained.Di Marco, A.; Gaetani, M.; Scarpinato, B. Adriamycin (NSC-123,127): A New Antibiotic with Antitumor Activity. 1969,
Cancer Chemotherapy Reports, 53, 33 – 37. PMID 5772652.
Doxorubicin and daunorubicin together can be thought of as prototype compounds for the anthracyclines. Subsequent research by many investigators throughout the world has led to many other anthracycline antibiotics, or analogs, and today, it is estimated that there are over 2,000 known analogs of doxorubicin. By 1991, 553 of them have been evaluated in the screening program at the National Cancer Institute (NCI).
Biosynthesis
Doxorubicin (DXR) is a 14-hydroxylated version of daunorubicin, the immediate precursor of DXR in its
Biosynthesis pathway. Daunorubicin is more abundantly found as a natural product because it is produced by a number of different
wild type Strain (biology)s of
streptomyces. In contrast, only one known non-wild type species,
streptomyces peucetius subspecies
cesius ATCC 27952, was initially found to be capable of producing the more widely used doxorubicin. This strain was created by Arcamone et. al in 1969 by
mutation a
Strain (biology) producing daunorubicin, but not DXR, at least in detectable quantities. Subsequently, Hutchinson's group showed that under special environmental conditions, or by the introduction of
Modifications (genetics), other strains of
streptomyces can produce doxorubicin. His group has also
cloned many of the
genes required for DXR production, although not all of them have been fully characterized. In 1996, Strohl's group discovered, isolated and characterized dox A, the gene encoding the enzyme that converts daunorubicin into DXR. By 1999, they produced recombinant Dox A, a
Cytochrome P450 oxidase, and found that it catalyzes multiple steps in DXR biosynthesis, including steps leading to daunorubicin. This was significant because it became clear that all daunorubicin producing strains have the necessary
genes to produce DXR, the much more therapeutically important of the two. Hutchinson's group went on to develop methods to improve the yield of DXR, from the
Industrial fermentation process used in its commercial production, not only by introducing Dox A encoding plasmids, but also by introducing mutations to deactivate
enzymes that shunt DXR precursors to less useful products, for example baumycin-like glycosides. Some triple mutants, that also gene expression Dox A, were able to double the yield of DXR. This is of more than academic interest because at that time DXR cost about $1.37 million per kg and current production in 1999 was 225 kg per annum. More efficient production techniques have brought the price down to $1.1 million per kg for the non-liposomal formulation. Although DXR can be produced semisynthesis from daunorubicin, the process involves electrophilic bromination and multiple steps and the yield is poor. Since daunorubicin is produced by Fermentation (biochemistry), it would be ideal if the
bacteria could complete DXR synthesis more effectively.
Mechanism of action
The exact mechanism of action of doxorubicin is complex and still somewhat unclear, though it is thought to interact with
DNA by intercalation.Fornari, F.A.; Randolph, J.K.; Yalowich, J.C.; Ritke, M.K.; Gewirtz, D.A. Interference by Doxorubicin with DNA Unwinding in MCF-7 Breast Tumor Cells. 1994,
Molecular Pharmacology,
45, 649 – 656. PMID 8183243. Doxorubicin is known to interact with DNA by
Intercalation (disambiguation) and inhibition of macromolecular
biosynthesis.Momparler, R.L.; Karon, M.; Siegel, S.E.; Avila, F. Effect of Adriamycin on DNA, RNA and Protein Synthesis in Cell-Free Systems and Intact Cells. 1976,
Cancer Research,
36, 2891 – 2895. PMID 1277199. Free full text This inhibits the progression of the enzyme
topoisomerase II, which unwinds DNA for Transcription (genetics). Doxorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of
DNA replication.
The planar aromatic chromophore portion of the molecule intercalates between two base pairs of the DNA, while the six-membered daunosamine sugar sits in the minor groove and interacts with flanking base pairs immediately adjacent to the intercalation site, as evidenced by several crystal structures.Frederick, C.A.; Williams, L.D.; Ughetto, G.; van der Marel, G.A.; van Boom, J.H.; Rich, A.; Wang, A.H. Structural Comparison of Anticancer Drug-DNA Complexes: Adriamycin and Daunomycin. 1990,
Biochemistry,
29, 2538 – 2549. PMID 2334681. Crystal structure is available for download as a PDB file.Pigram, W.J.; Fuller, W.; Hamilton, L.D. Stereochemistry of Intercalation: Interaction of Daunomycin with DNA. 1972,
Nature New Biology,
235, 17 – 19. PMID 4502404.
Clinical use
Doxorubicin is commonly used to treat some leukemias, Hodgkin's lymphoma, as well as cancers of the bladder cancer, breast cancer,
stomach cancer,
lung cancer,
ovarian cancer,
thyroid cancer, soft tissue sarcoma,
multiple myeloma, and others. Commonly used doxorubicin-containing chemotherapy regimen are CA (cyclophosphamide, Adriamycin), TAC (Taxotere, CA),
ABVD (Adriamycin,
Bleomycin,
Vinblastine,
Dacarbazine), CHOP (Cyclophosphamide, Adriamycin,
Vincristine, Prednisone) and FAC (5-Fluorouracil, Adriamycin, Cyclophosphamide). Doxil is used primarily for the treatment of ovarian cancer where the disease has progressed or recurred after
platinum-based chemotherapy, or for the treatment of AIDS-related Kaposi's sarcoma." DOXIL Product Information."
Ortho Biotech Products, L.P. Retrieved on April 19, 2007.
Experimental therapy
Combination therapy experiments with sirolimus (rapamycin) and doxorubicin have shown promise in treating Akt-positive
lymphomas in mice.
Recent animal research coupling a Murinae monoclonal antibody with doxorubicin has created an
immunoconjugate that was able to eliminate HIV infection in mice. Current treatment with
antiretroviral drug (ART) still leaves pockets of HIV within the host. The immunoconjugate could potentially provide a complimentary treatment to ART to eradicate antigen-expressing
T cells.
Side effects
Acute side-effects of doxorubicin can include nausea, vomiting, and heart arrhythmias. It can also cause
neutropenia (a decrease in
white blood cells), as well as complete
alopecia (hair loss). When the cumulative dose of doxorubicin reaches 550 mg/m², the risks of developing cardiac side effects, including congestive heart failure, dilated
cardiomyopathy, and death, dramatically increase. Doxorubicin cardiotoxicity is characterized by a dose-dependent decline in
mitochondrial oxidative phosphorylation. Reactive oxygen species, generated by the interaction of doxorubicin with iron, can then damage the myocytes (heart cells), causing myofibrillar loss and cytoplasmic vacuolization. Additionally, some patients may develop Palmar plantar erythrodysesthesia, or, "Hand-Foot Syndrome," characterized by skin eruptions on the palms of the hand or soles of the feet, characterized by swelling, pain and erythema.
Due to these side effects and its red color, doxorubicin has earned the nickname "red devil."
See also
References
External links
-
- Overview at BC Cancer Agency
- Doxil Site
- Adriamycin Solution / Doxorubicin hydrochloride Virtual Cancer Centre
{{Drugbox| IUPAC_name = (8S
,10S
)-10-(4-amino-5-hydroxy-6-methyl-tetrahydro-2H
-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione| image = Doxorubicin.svg| image2=Doxorubicin-3d-sticks.png| CAS_number = 23214-92-8| ATC_prefix = L01| ATC_suffix =DB01| PubChem = 31703| DrugBank = APRD00185| chemical_formula =| C = 27 |H = 29 |N = 1 |O = 11| molecular_weight = 543.52 Gram/Mole (unit)| bioavailability = 5% (Oral)| protein_bound =| metabolism = CYP3A4, [2005. Vol. 11 (19). Retrieved on April 19, 2007.]-->Doxorubicin' (trade name
Adriamycin) or
hydroxyldaunorubicin is a DNA-interacting
pharmaceutical widely used in
chemotherapy. It is an
anthracycline antibiotic and structurely closely related to daunomycin, and also
intercalation (chemistry) DNA. It is commonly used in the treatment of a wide range of
cancers.
The drug is administered by injection, and may be sold under the brand names
Adriamycin PFS,
Adriamycin RDF, or
Rubex." Doxorubicin (Systemic)."
Mayo Clinic. Last updated on: June 15, 1999. Retrieved on April 19, 2007.
Doxil is a liposome-encapsulated dosage form of doxorubicin made by Ben Venue Laboratories for
Johnson & Johnson. The main benefits of this form are a reduction in cardiotoxicity.
History
The history of doxorubicin can be traced back to the 1950s, when an
Italy research company, Farmitalia Research Laboratories, began an organized effort to find anticancer compounds from soil-based
microbes. A soil sample was isolated from the area surrounding the Castel del Monte, a 13th century castle. A new strain of
Streptomyces which produced a bright red pigment was isolated, and an antibiotic was produced from this bacterium that was found to have good activity against Murinaes. Since a group of
France researchers discovered the same compound at about the same time, the two teams named the compound daunorubicin, combining the name
List of Illyrian tribes, a pre-Roman tribe that occupied the area of Italy where the compound was isolated, with the French word for ruby,
rubis, describing the color.Weiss, Raymond B. "The Anthracyclines: Will We Ever Find a Better Doxorubicin?" Seminars in Oncology. Vol. 19, No. 6. December 1992. pp. 670–686. PMID 1462166. Clinical trials began in the 1960s, and the drug saw success in treating acute leukemia and lymphoma. However, by 1967, it was recognized that daunorubicin could produce fatal cardiac toxicity.Tan, C.; Tasaka, H.; Kou-Ping, Y.; et al. Daunomycin, An Antitumor Antibiotic, In the Treatment of Neoplastic Disease. Clinical Evaluation with Special Reference to Childhood Leukemia. 1967,
Cancer, 20, 333 – 353. PMID 4290058.
Researchers at Farmitalia soon discovered that changes in biological activity could be made by minor changes in the structure of the compound. A strain of
Streptomyces was mutated using N-nitroso-N-methyl urethane and this new strain produced a different, red-colored antibiotic. They named this new compound Adriamycin, after the Adriatic Sea, and the name was later changed to doxorubicin to conform to the established naming convention.Arcamone, F.; Cassinelli, G.; Fantini, G.; et al. Adriamycin, 14-hydroxydaunomycin, A New Antitumor Antibiotic from S. peucetius var. caesius. 1969,
Biotechnol. Bioeng., 11, 1101 – 1110. PMID 5365804. Doxorubicin showed better activity than daunorubicin against murine tumors, and especially solid tumors. It also showed a relatively higher therapeutic index, yet the cardiotoxicity remained.Di Marco, A.; Gaetani, M.; Scarpinato, B. Adriamycin (NSC-123,127): A New Antibiotic with Antitumor Activity. 1969,
Cancer Chemotherapy Reports, 53, 33 – 37. PMID 5772652.
Doxorubicin and daunorubicin together can be thought of as
prototype compounds for the anthracyclines. Subsequent research by many investigators throughout the world has led to many other anthracycline antibiotics, or analogs, and today, it is estimated that there are over 2,000 known analogs of doxorubicin. By 1991, 553 of them have been evaluated in the screening program at the
National Cancer Institute (NCI).
Biosynthesis
Doxorubicin (DXR) is a 14-
hydroxylated version of daunorubicin, the immediate precursor of DXR in its
Biosynthesis pathway. Daunorubicin is more abundantly found as a
natural product because it is produced by a number of different
wild type Strain (biology)s of
streptomyces. In contrast, only one known non-
wild type species,
streptomyces peucetius subspecies cesius ATCC 27952, was initially found to be capable of producing the more widely used doxorubicin. This strain was created by Arcamone et. al in 1969 by mutation a Strain (biology) producing daunorubicin, but not DXR, at least in detectable quantities. Subsequently, Hutchinson's group showed that under special environmental conditions, or by the introduction of
Modifications (genetics), other strains of
streptomyces can produce doxorubicin. His group has also
cloned many of the
genes required for DXR production, although not all of them have been fully characterized. In 1996, Strohl's group discovered, isolated and characterized dox A, the
gene encoding the
enzyme that converts daunorubicin into DXR. By 1999, they produced recombinant Dox A, a Cytochrome P450 oxidase, and found that it
catalyzes multiple steps in DXR biosynthesis, including steps leading to daunorubicin. This was significant because it became clear that all daunorubicin producing strains have the necessary genes to produce DXR, the much more therapeutically important of the two. Hutchinson's group went on to develop methods to improve the yield of DXR, from the Industrial fermentation process used in its commercial production, not only by introducing Dox A encoding plasmids, but also by introducing mutations to deactivate
enzymes that shunt DXR precursors to less useful products, for example baumycin-like
glycosides. Some triple mutants, that also
gene expression Dox A, were able to double the yield of DXR. This is of more than academic interest because at that time DXR cost about $1.37 million per kg and current production in 1999 was 225 kg per annum. More efficient production techniques have brought the price down to $1.1 million per kg for the non-liposomal formulation. Although DXR can be produced
semisynthesis from daunorubicin, the process involves electrophilic
bromination and multiple steps and the yield is poor. Since daunorubicin is produced by
Fermentation (biochemistry), it would be ideal if the
bacteria could complete DXR synthesis more effectively.
Mechanism of action
The exact mechanism of action of doxorubicin is complex and still somewhat unclear, though it is thought to interact with DNA by intercalation.Fornari, F.A.; Randolph, J.K.; Yalowich, J.C.; Ritke, M.K.; Gewirtz, D.A. Interference by Doxorubicin with DNA Unwinding in MCF-7 Breast Tumor Cells. 1994,
Molecular Pharmacology,
45, 649 – 656. PMID 8183243. Doxorubicin is known to interact with DNA by
Intercalation (disambiguation) and inhibition of macromolecular
biosynthesis.Momparler, R.L.; Karon, M.; Siegel, S.E.; Avila, F. Effect of Adriamycin on DNA, RNA and Protein Synthesis in Cell-Free Systems and Intact Cells. 1976,
Cancer Research,
36, 2891 – 2895. PMID 1277199. Free full text This inhibits the progression of the enzyme
topoisomerase II, which unwinds DNA for Transcription (genetics). Doxorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of DNA replication.
The planar aromatic chromophore portion of the molecule intercalates between two base pairs of the DNA, while the six-membered daunosamine sugar sits in the minor groove and interacts with flanking base pairs immediately adjacent to the intercalation site, as evidenced by several crystal structures.Frederick, C.A.; Williams, L.D.; Ughetto, G.; van der Marel, G.A.; van Boom, J.H.; Rich, A.; Wang, A.H. Structural Comparison of Anticancer Drug-DNA Complexes: Adriamycin and Daunomycin. 1990,
Biochemistry,
29, 2538 – 2549. PMID 2334681. Crystal structure is available for download as a PDB file.Pigram, W.J.; Fuller, W.; Hamilton, L.D. Stereochemistry of Intercalation: Interaction of Daunomycin with DNA. 1972,
Nature New Biology,
235, 17 – 19. PMID 4502404.
Clinical use
Doxorubicin is commonly used to treat some
leukemias,
Hodgkin's lymphoma, as well as cancers of the bladder cancer, breast cancer,
stomach cancer,
lung cancer,
ovarian cancer, thyroid cancer,
soft tissue sarcoma, multiple myeloma, and others. Commonly used doxorubicin-containing
chemotherapy regimen are CA (cyclophosphamide, Adriamycin), TAC (Taxotere, CA), ABVD (Adriamycin,
Bleomycin,
Vinblastine,
Dacarbazine), CHOP (
Cyclophosphamide, Adriamycin,
Vincristine, Prednisone) and FAC (5-Fluorouracil, Adriamycin, Cyclophosphamide). Doxil is used primarily for the treatment of ovarian cancer where the disease has progressed or recurred after
platinum-based chemotherapy, or for the treatment of AIDS-related Kaposi's sarcoma." DOXIL Product Information."
Ortho Biotech Products, L.P. Retrieved on
April 19, 2007.
Experimental therapy
Combination therapy experiments with
sirolimus (rapamycin) and doxorubicin have shown promise in treating
Akt-positive lymphomas in mice.
Recent animal research coupling a
Murinae monoclonal antibody with doxorubicin has created an immunoconjugate that was able to eliminate HIV infection in mice. Current treatment with
antiretroviral drug (ART) still leaves pockets of HIV within the host. The immunoconjugate could potentially provide a complimentary treatment to ART to eradicate antigen-expressing
T cells.
Side effects
Acute side-effects of doxorubicin can include nausea, vomiting, and heart arrhythmias. It can also cause neutropenia (a decrease in white blood cells), as well as complete
alopecia (hair loss). When the cumulative dose of doxorubicin reaches 550 mg/m², the risks of developing cardiac side effects, including
congestive heart failure, dilated
cardiomyopathy, and death, dramatically increase. Doxorubicin cardiotoxicity is characterized by a dose-dependent decline in mitochondrial oxidative phosphorylation. Reactive oxygen species, generated by the interaction of doxorubicin with iron, can then damage the myocytes (heart cells), causing myofibrillar loss and cytoplasmic vacuolization. Additionally, some patients may develop Palmar plantar erythrodysesthesia, or, "Hand-Foot Syndrome," characterized by skin eruptions on the palms of the hand or soles of the feet, characterized by swelling, pain and erythema.
Due to these side effects and its red color, doxorubicin has earned the nickname "red devil."
See also
- Anthracycline
- Chemotherapy regimen
- History of cancer chemotherapy
- ABVD
- CHOP
References
External links
-
- Overview at BC Cancer Agency
- Doxil Site
- Adriamycin Solution / Doxorubicin hydrochloride Virtual Cancer Centre
Doxorubicin : Cancerbackup
Doxorubicin is a chemotherapy drug that is given as a treatment for many different types of cancer. This section describes how it is given and some of its possible side effects.
Liposomal doxorubicin (Caelyx®, Myocet®) : Cancerbackup
Liposomal doxorubicin (Caelyx®, Myocet®) is a chemotherapy drug that is given as a treatment for some types of cancer. It is most commonly used to treat ovarian cancer and Kaposi ...
Cancer Research UK | CancerHelp UK | Doxorubicin
This page tells you about the possible side effects of doxorubicin. There aresections onWhat doxorubicin isCommon side effectsOccasional side effectsHigh dose side effectsImportant ...
Doxorubicin - Wikipedia, the free encyclopedia
Doxorubicin (trade name Adriamycin) or hydroxyldaunorubicin is a drug widely used in cancer chemotherapy. It is an anthracycline antibiotic and structurally closely related to ...
The electronic Medicines Compendium
This is the official professional web site of the Electronic Medicines Compendium ... Below are a number of possible matches for 'Doxorubicin'. We have looked for this term in the ...
Definition: doxorubicin from Online Medical Dictionary
The Online Medical Dictionary is a searchable dictionary of definitions from medicine, science and technology.
MedlinePlus Drug Information: Doxorubicin
Provides description of drug, list of cancers medicine is used for, precautions, side effects, and common brand names.
Doxorubicin Hydrochloride - National Cancer Institute
This page contains brief information about doxorubicin hydrochloride and a collection of links to more information from the National Cancer Institute (NCI), the Food and Drug ...
Doxorubicin : BC Cancer Agency
The BC Cancer Agency is a part of the Provincial Health Services Authority.
Ovarian cancer (advanced) - paclitaxel, pegylated liposomal ...
The summary for the published technology appraisal on using topotecan, pegylated liposomal doxorubicin hydrochloride and paclitaxel for the treatment of advanced ovarian cancer.
