20830-81-3 Usage
Uses
Used in Oncology:
Daunorubicin is used as an antineoplastic agent for the treatment of various types of cancer. It is particularly effective against acute lymphocytic and granulocytic leukemia, as well as lymphomas. The drug works by intercalating into DNA, inhibiting topoisomerase II, and generating free radicals, which ultimately leads to the disruption of cellular processes and the induction of apoptosis in cancer cells.
Used in Pharmaceutical Industry:
Daunorubicin is used as a key component in the development of cancer treatment regimens. Its brand names include Cerubidine (Bedford), Cerubidine (Sanofi Aventis), and Cerubidine (Wyeth). The drug is often combined with other chemotherapeutic agents to enhance the treatment's effectiveness and overcome drug resistance in cancer cells.
Originator
Cerubidine,Specia,France,1968
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.PercentSaccharose 2Dry yeast 0.1Potassium hydrogen phosphate 0.2 PercentSodium nitrate 0.2Magnesium sulfate 0.2Agar 2The 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.PercentGlucose 4Dry yeast 1.5Sodium chloride 0.2Potassium hydrogen phosphate 0.1Calcium carbonate 0.1Calcium carbonate 0.1Iron sulfate 0.001Zinc 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.
Therapeutic Function
Cancer chemotherapy
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 leukaemiasHIV-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 drugsAntipsychotics: 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.
Check Digit Verification of cas no
The CAS Registry Mumber 20830-81-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,8,3 and 0 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 20830-81:
(7*2)+(6*0)+(5*8)+(4*3)+(3*0)+(2*8)+(1*1)=83
83 % 10 = 3
So 20830-81-3 is a valid CAS Registry Number.
InChI:InChI=1/C26H26O9.CH4.ClH.H3N.H2O.H2/c1-12(27)26(32)10-14-19(16(11-26)35-17-8-3-4-9-34-17)25(31)21-20(23(14)29)22(28)13-6-5-7-15(33-2)18(13)24(21)30;;;;;/h5-7,16-17,29,31-32H,3-4,8-11H2,1-2H3;1H4;1H;1H3;1H2;1H/t16-,17?,26-;;;;;/m0...../s1
20830-81-3Relevant articles and documents
1H NMR structural and thermodynamical analysis of the hetero-association of daunomycin and novatrone in aqueous solution
Veselkov,Evstigneev,Rozvadovskaya,Hernandez Santiago,Zubchenok,Djimant,Davies
, p. 31 - 37 (2004)
The complexation of antitumour antibiotics novatrone (NOV) and daunomycin (DAU) in aqueous solution has been studied by one- and two-dimensional 1H-NMR spectroscopy (500 MHz) in order to elucidate the probable molecular mechanism of the action
Synthesis of new maleimide derivatives of daunorubicin and biological activity of acid labile transferrin conjugates
Kratz, Felix,Beyer, Ulrich,Schumacher, Peter,Krueger, Michael,Zahn, Heike,Roth, Thomas,Fiebig, Heinz H.,Unger, Clemens
, p. 617 - 622 (1997)
Maleimide groups were bound to the 3'-amino position of daunorubicin through a benzamide bond or to the 13-keto position through a benzoyl hydrazone or phenylacetyl hydrazone bond. The acid labile transferrin conjugates prepared with the latter two derivatives exhibited high activity in human melanoma cells (MEXF 989) using a clonogenic cell assay comparable to or exceeding that of daunorubicin.
Synthesis and Antiproliferative Activity of Conjugates of Anthracycline Antibiotics with Sesquiterpene Lactones of the Elecampane
Semakov,Anikina,Afanasyeva,Pukhov,Klochkov
, p. 538 - 546 (2018/10/24)
The daunorubicin and doxorubicin anthracycline antibiotics were modified with the Inula helenium L. sesquiterpene lactones (alantolactone, isoalantolactone, and alloalantolactone) and with their epoxy derivatives. Antiproliferative properties of these conjugates were studied on tumor and normal cell lines. The daunorubicin conjugates with the sesquiterpene lactones (isoalantolactone, allantolactone, and alloalantolactone) and with their epoxy derivatives were found to exhibit the higher activity against human tumor cell lines than the corresponding doxorubicin conjugates. The daunorubicin conjugate with epoxyisoalantolactone proved to be the most effective compound, because it was more cytotoxic than daunorubicin towards a number of cell lines, including those daunorubicin-resistant, and did not affect normal human cells.
Block copolymers for stable micelles
-
Page/Page column, (2013/11/19)
The present invention relates to the field of polymer chemistry and more particularly to multiblock copolymers and micelles comprising the same. Compositions herein are useful for drug-delivery applications.
THERAPEUTIC FOR HEPATIC CANCER
-
, (2011/02/18)
A novel pharmaceutical composition for treating or preventing hepatocellular carcinoma and a method of treatment are provided. A pharmaceutical composition for treating or preventing liver cancer is obtained by combining a chemotherapeutic agent with an anti-glypican 3 antibody. Also disclosed is a pharmaceutical composition for treating or preventing liver cancer which comprises as an active ingredient an anti-glypican 3 antibody for use in combination with a chemotherapeutic agent, or which comprises as an active ingredient a chemotherapeutic agent for use in combination with an anti-glypican 3 antibody. Using the chemotherapeutic agent and the anti-glypican 3 antibody in combination yields better therapeutic effects than using the chemotherapeutic agent alone, and mitigates side effects that arise from liver cancer treatment with the chemotherapeutic agent.
METHOD OF DERIVATISING AN ANALYTE FOR SUBSEQUENT DETECTION THROUGH A NUCLEIC ACID BASED SENSOR
-
, (2010/04/30)
A method of derivatising an analyte for subsequent detection through a nucleic acid based sensor and a sensor based thereon.
Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same
-
, (2010/05/13)
Monoclonal antibodies that bind specifically to Claudin 3 expressed on cell surface are provided. The antibodies of the present invention are useful for diagnosis of cancers that have enhanced expression of Claudin 3, such as ovarian cancer, prostate cancer, breast cancer, uterine cancer, liver cancer, lung cancer, pancreatic cancer, stomach cancer, bladder cancer, and colon cancer. The present invention provides monoclonal antibodies showing cytotoxic effects against cells of these cancers. Methods for inducing cell injury in Claudin 3-expressing cells and methods for suppressing proliferation of Claudin 3-expressing cells by contacting Claudin 3-expressing cells with a Claudin 3-binding antibody are disclosed. The present application also discloses methods for diagnosis or treatment of cancers.
Immune Modulating Oligonucleotides in Connection with Chemotherapeutic Measures
-
, (2009/07/02)
The invention relates to the use of immune modulators on the basis of DNA in the form of covalently closed nucleic acid molecules comprising immune stimulatory sequence motifs, for the production of a pharmaceutical for the therapeutic treatment of tumor diseases in combination with chemotherapeutic drugs.
TARGETED DRUG DELIVERY USING SULFONAMIDE DERIVATIVES
-
, (2008/06/13)
The present invention relates to Glutathione S-transferase (GST)/Reduced Glutathione (GSH) as a means for the in-vivo release of a drug that has been conjugated to specific electrophilic moieties via a sulfonamide bond. The drug may be an anticancer agent (or one with other therapeutic properties) carrying a free —NH— which has been derivatized by the attachment of an electrophile containing a moiety, such as p-CN— or p-NO 2-pyridinylsulfonyl groups, or p-NO 2- or 2,4 dinitrophenylsulfonyl groups, or suitable derivatives thereof, to make a prodrug. Optionally, the sulfonamide moiety may have attached to it a targeting molecule. The present invention also provides Glutathione S-transferase (GST)/Reduced Gluthathione (GSH) as a means for the release of a protected amino derivative that has been conjugated to specific electrophilic moieties via a sulfonamide bond. The precursor is a synthetic intermediate carrying a free —NH— which has been derivatized by the attachment of an electrophile via a sulfonamide bond.
13-dihydro-3′ aziridino anthracyclines
-
, (2008/06/13)
The present invention relates to anthracycline glycosides, to a process for their preparation and to pharmaceutical compositions containing the same.
