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| | Daunorubicin Basic information |
| Product Name: | Daunorubicin | | 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;DAUNORUBICIN;DAUNORUBICINE HYDROCHLORIDE;DAUNOMYCIN;DAUNOMYCIN HYDROCHLORIDE;LEUKAEMOMYCIN C HYDROCHLORIDE;(8s-cis)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyrannosyl)oxy];3-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naph | | CAS: | 20830-81-3 | | MF: | C27H29NO10 | | MW: | 527.52 | | EINECS: | 244-069-7 | | Product Categories: | | | Mol File: | 20830-81-3.mol |  |
| | Daunorubicin Chemical Properties |
| Melting point | 155 °C | | Boiling point | 608.13°C (rough estimate) | | density | 1.3522 (rough estimate) | | refractive index | 1.6400 (estimate) | | storage temp. | Store at -20°C, protect from light | | solubility | ≥83.33 mg/mL in DMSO | | pka | pKa 4.92±0.16(H2O t=25±0.5 I=0.03) (Uncertain) | | form | Powder | | Stability: | Light Sensitive | | CAS DataBase Reference | 20830-81-3 | | IARC | 2B (Vol. 10, Sup 7) 1987 | | EPA Substance Registry System | Daunomycin (20830-81-3) |
| | Daunorubicin Usage And Synthesis |
| Chemical Properties | Daunomycin is a thin red, needle-shaped
material. | | Originator | Cerubidine,Specia,France,1968 | | Uses | Daunorubicin hydrochloride USP (Cerubidine) is used to traet acute lymphocytic and granulocytic leukemia; lymphomas. | | Uses | antineoplastic | | Uses | Oncology | | Definition | ChEBI: A natural product found in Actinomadura roseola. | | Indications | Daunorubicin (Cerubidine)
is used to treat acute leukemias, while its structural analogue,
doxorubicin (Adriamycin) is extensively employed
against a broad spectrum of cancers. Although
the two drugs have similar pharmacological and toxicological
properties, doxorubicin is more potent against
most animal and human tumors and will be discussed in
greater detail. | | Manufacturing Process | Two 300 ml Erlenmeyer flasks are prepared, each of them containing 60 ml of
the following vegetative medium in tap water: 0.6% peptone, 0.3% dry yeast
and 0.05% calcium nitrate. The pH after sterilization by heating in an
autoclave to 120°C for 20 minutes is 7.2.
Each flask was inoculated with mycelium of Streptomyces F.I. 1762 whose
quantity corresponds to one-fifth of a suspension in sterile water of the
mycelium of a 10 day old culture growth in a test tube containing the
following ingredients dissolved in tap water.
Percent
Saccharose
2
Dry yeast
0.1
Potassium hydrogen phosphate
0.2
Percent
Sodium nitrate
0.2
Magnesium sulfate
0.2
Agar
2
The flasks are incubated at 28°C for 48 hours on a rotary shaker with a stroke
of 60 mm at 220 rpm. 2 ml of a vegetative medium thus grown are used to
inoculate 300 ml Erlenmeyer flasks containing 60 ml of the following
productive medium in tap water at pH 7.0.
Percent
Glucose 4
Dry yeast 1.5
Sodium chloride 0.2
Potassium hydrogen phosphate 0.1
Calcium carbonate 0.1
Calcium carbonate 0.1
Iron sulfate 0.001
Zinc sulfate 0.001
Copper sulfate 0.001
(The medium had been sterilized at 120°C for 20 minutes, the glucose being
previously sterilized separately at 110°C for 20 minutes.) It is incubated at
28°C under the conditions described for the vegetative media. After 120 hours
of fermentation a maximum activity corresponding to a concentration of 60
micrograms/ml is achieved.
| | Brand name | Cerubidine (Bedford); Cerubidine (Sanofi Aventis); Cerubidine (Wyeth). | | Therapeutic Function | Cancer chemotherapy | | General Description | Anthracycline antibiotic. An anticancer agent. | | Biological Activity | daunorubicin is an inhibitor of dna topoisomerase ii [1].daunorubicin is an anthracycline antibiotic. it is also used as an effective chemotherapeutic agent against tumors especially acute myeloid leukaemia and acute lymphocytic leukaemia. daunorubicin can affect the metabolism and synthesis of dna and rna. in the in vitro assay, daunorubicin inhibits the incorporation of thymidine and uridine into l1210 cells. it also inhibits the incorporation of labeled precursors into the isolated dna and rna from incubated cells. when treated with leukemic cells isolated from acute lymphocytic leukemia patients, daunorubicin significantly inhibits the biosynthesis of the dna and rna macromolecules [2, 3]. | | Clinical Use | Antineoplastic agent:
Acute leukaemias
HIV-related Kaposi’s Sarcoma | | Safety Profile | Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data.
Human poison by ingestion. Experimental
poison by subcutaneous, intravenous, and
intraperitoneal routes. Experimental
teratogenic and reproductive effects. Human
mutation data reported. When heated to
decomposition it emits toxic fumes of NOx.
See also DAUNOMYCIN
HYDROCHLORIDE. | | Potential Exposure | An antibiotic. It is used as a medicine
for treating cancer. | | Drug interactions | Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine due to risk of
agranulocytosis.
Cytotoxics: possible increased cardiotoxicity with
trastuzumab - avoid for up to 28 weeks after
stopping trastuzumab.
Avoid with live vaccines. | | Metabolism | Daunorubicin is rapidly taken up by the tissues, especially
by the kidneys, liver, spleen and heart. Subsequent release
of drug and metabolites is slow (half-life ~55 hours). It is
rapidly metabolised in the liver and the major metabolite,
daunorubicinol is also active.
It is excreted slowly in the urine, mainly as metabolites
with 25% excreted within 5 days. Biliary excretion
accounts for 40-50% elimination | | Shipping | UN3249 Medicine, solid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxic
solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-
Poisonous materials, Technical Name Required. | | Waste Disposal | It is inappropriate and possi-
bly dangerous to the environment to dispose of expired or
waste drugs and pharmaceuticals by flushing them down
the toilet or discarding them to the trash. Household quanti-
ties of expired or waste pharmaceuticals may be mixed with
wet cat litter or coffee grounds, double-bagged in plastic,
discard in trash. Larger quantities shall carefully take into
consideration applicable DEA, EPA, and FDA regulations. If
possible return the pharmaceutical to the manufacturer for
proper disposal being careful to properly label and securely
package the material. Alternatively, the waste pharmaceuti-
cal shall be labeled, securely packaged and transported by a
state licensed medical waste contractor to dispose by burial
in a licensed hazardous or toxic waste landfill or incinerator.
Consult with environmental regulatory agencies for guidance
on acceptable disposal practices. Generators of waste con-
taining this contaminant (≥100 kg/mo) must conform with
EPA regulations governing storage, transportation, treatment,
and waste disposal. | | references | [1] hande k r. etoposide: four decades of development of a topoisomerase ii inhibitor. european journal of cancer, 1998, 34(10): 1514-1521.
[2] momparler r l, karon m, siegel s e, et al. effect of adriamycin on dna, rna, and protein synthesis in cell-free systems and intact cells. cancer research, 1976, 36(8): 2891-2895.
[3] meriwether w d, bachur n r. inhibition of dna and rna metabolism by daunorubicin and adriamycin in l1210 mouse leukemia. cancer research, 1972, 32(6): 1137-1142. |
| | Daunorubicin Preparation Products And Raw materials |
| Raw materials | Erythromycin-->streptomyces avermifilis-->D-Glucose monohydrate-->l-LEUCYL DAUNORUBICIN -->DAUNOMYCINONE-->7-DEOXYDAUNOMYCINONE-->Epirubicin-->5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S,10R)--->Daunorubicin hydrochloride | | Preparation Products | Doxorubicin hydrochloride-->carminomycinone |
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