23214-92-8
| Name | Adriamycin |
| CAS | 23214-92-8 |
| EINECS(EC#) | 245-495-6 |
| Molecular Formula | C27H29NO11 |
| MDL Number | MFCD00869292 |
| Molecular Weight | 543.52 |
| MOL File | 23214-92-8.mol |
Synonyms
PK 2
PROK2
Rubex
Doxil
Evacet
Rubidox
NSC 123127
ADRIAMYCIN
DOXORUBICIN
Adriblastin
adriamycine
NCI-C-01514
Biotransdox
Doxorubincine
Adriamycin RDF
Adriamycin PFS
Doxorubicin base
HydroxydaunoMycin
ADRIAMYCIN, PHARMA
Protein Bv8 homolog
Prokineticin-2 human
DOXOPINHYDROCHLORIDE
14-Hydroxydaunomycin
ADRIAMYCINSEMIQUINONE
Doxorubicin Free Base
Doxorubicin hydrohloride
Rubex (hydrochloride salt)
Adriacin (hydrochloride salt)
adiblastine (hydrochloride salt)
adriblatina (hydrochloride salt)
adriablatina (hydrochloride salt)
Adriblastina (hydrochloride salt)
adriablastine (hydrochloride salt)
Farmablastina (hydrochloride salt)
Adriamycin RDF (hydrochloride salt)
Adriamycin PFS (hydrochloride salt)
Doxorubicin hydrochloride (hydrochloride salt)
Hydroxydaunomycin hydrochloride (hydrochloride salt)
Hydroxydaunorubicin hydrochloride (hydrochloride salt)
AdriaMycin, 14-HydroxydaunoMycin, FI 106, K 1039, KW 125, NSC 123127
etrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
(85-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-l-lyxohexapyranosyl)oxy]-7,8,9,10- t
(85-Cis)-10-Tetrahydro-6,8,11-Trihydroxy-8-(Hydroxyacetyl)-1-methoxy-5,12-Naphthacenedione
10-((3-AMino-2,3,6-trideoxy-α-L-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-Methoxy-5,12-naphthacenedione
(8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
10-((3-amino-2,3,6-trideoxy-alpha-l-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
(1s,3s)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside
(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-Methoxy-5,12-Naphthacenedione
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
(8S,10S)-10-{[(2R,4S,5S,6S)-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
5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
(8S)-10-((4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
Chemical Properties
| Appearance | Adriamycin is an orange to red cake-like or needle-like crystalline solid. |
| Melting point | 205°C |
| Boiling point | 617.77°C (rough estimate) |
| density | 1.3783 (rough estimate) |
| refractive index | 1.6400 (estimate) |
| storage temp. | -20°C |
| solubility | ≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic |
| form | solid |
| pka | pKa 8.2 (Uncertain) |
| Water Solubility | Soluble |
| CAS DataBase Reference | 23214-92-8 |
| IARC | 2A (Vol. 10, Sup 7) 1987 |
| EPA Substance Registry System | 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-. alpha.-L-lyxo-hexopyranosyl) oxy]-7,8,9,10-tetrahydro6,8,11-trihydroxy-8-(hydroxyacetyl)1-methoxy-, (8S,10S)-(23214-92-8) |
Safety Data
| HS Code | 2941900000 |
| Safety Profile |
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal, subcutaneous, parenteral, and intravenous routes. Human systemic effects by intravenous route: cardiac myopathy including infarction, nausea or vomiting, and effects on the hair. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and HCl
|
| Hazardous Substances Data | 23214-92-8(Hazardous Substances Data) |
| Toxicity |
An anthracycline cytotoxic
antineoplastic that is produced by Streptomyces peucetius. The
LD50 in mice is 9.4 mg/kg, i.v. It is a carcinogen that inhibits
DNA and RNA synthesis by intercalating in double-stranded
DNA with the amino sugar in the minor groove and the 90-OH
group of the anthracycline ring hydrogen-bonded to the adjacent
guanine. It also alters membrane fluidity and ion transport, and
generates free radicals through a cytochrome P450-mediated
reductive process. In humans, it causes alopecia, stomatitis, nausea,
vomiting, diarrhea, cardiotoxicity (manifested by tachycardia),
and potentially fatal congestive heart failure.
|
Hazard Information
Uses
Doxorubicin (adriamycin) is the most extensively studied of a family of highly fluorescent anthracycline antibiotics produced by several Streptomyces species, first reported in 1967 and later approved for human therapeutic use as an antitumour agent for the treatment of a wide range of cancers. Doxorubicin also exhibits anti-HIV and antibacterial activity. The mode of action of doxorubicin is thought to be due to intercalation of DNA and inhibition of nucleic acid synthesis.
Brand name
Adriblastina (Farmitalia, Societa Farmaceutici Italia, Italy).
Potential Exposure
An antibiotic product from streptomyces, used as anticancer drug
First aid
Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involvedand take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides
Chemical Properties
Adriamycin is an orange to red cake-like or needle-like crystalline solid.
Waste Disposal
It is inappropriate and possibly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities 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 pharmaceutical 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.
Originator
Adriblastina,Farmitalia,Italy,1971
Definition
ChEBI: Doxorubicin is a deoxy hexoside, an anthracycline, an anthracycline antibiotic, an aminoglycoside, a member of tetracenequinones, a member of p-quinones, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It has a role as an Escherichia coli metabolite. It is a conjugate base of a doxorubicin(1+). It derives from a hydride of a tetracene.
Indications
Doxorubicin binds tightly to DNA by its ability to
intercalate between base pairs and therefore is preferentially
concentrated in nuclear structures. Intercalation
results in steric hindrance, hence production of
single-strand breaks in DNA and inhibition of DNA
synthesis and DNA-dependent RNA synthesis. The enzyme
topoisomerase II is thought to be involved in the
generation of DNA strand breaks by the anthracyclines.
Cells in S-phase are most sensitive to doxorubicin, although
cytotoxicity also occurs in other phases of the
cell cycle.
Manufacturing Process
Two 300 ml Erlenmeyer flasks, each containing 60 ml of the following culture
medium for the vegetative phase, were prepared: peptone 0.6%; dry yeast
0.3%; hydrated calcium carbonate 0.2%; magnesium sulfate 0.01%; the pH
after sterilization was 7.2. Sterilization has been effected by heating in
autoclave to 120°C for 20 minutes. Each flask was inoculated with a quantity
of mycelium of the mutant F.I.106 (the new strain thus obtained has been
given the code F.I.106 of the Farmitalia microbiological collection and has
been called Streptomycespeucetius var. caesius) corresponding to 1/9 of a
suspension in sterile water of the mycelium of a 10 day old culture grown in a
big test tube on the following medium: saccharose 2%; dry yeast 0.1%;
bipotassium phosphate 0.2%; sodium nitrate 0.2%; magnesium sulfate 0.2%;
agar 2%; tap water up to 100%. The flasks were then incubated at 28°C for
48 hours on a rotary shaker with a stroke of 30 mm at 220 rpm.，
2 ml of a vegetative medium thus grown were used to inoculate 300 ml Erlenmeyer flasks with 60 ml of the following medium for the productive phase: glucose 6%; dry yeast 2.5%; sodium chloride 0.2%; bipotassium phosphate 0.1%; calcium carbonate 0.2%; magnesium sulfate 0.01%; ferrous sulfate 0.001%; zinc sulfate 0.001%; copper sulfate 0.001%; tap water to 100%. The glucose was previously sterilized separately at 110°C for 20 minutes. The resulting pH was 7. This was sterilized at 120°C for 20 minutes and incubated at 28°C under the same conditions by stirring, as for the vegetative media.
The maximum concentration of the antibiotic was reached on the 6th day of fermentation. The quantity of adriamycin produced at this time corresponds to a concentration of 15 μg/ml.
2 ml of a vegetative medium thus grown were used to inoculate 300 ml Erlenmeyer flasks with 60 ml of the following medium for the productive phase: glucose 6%; dry yeast 2.5%; sodium chloride 0.2%; bipotassium phosphate 0.1%; calcium carbonate 0.2%; magnesium sulfate 0.01%; ferrous sulfate 0.001%; zinc sulfate 0.001%; copper sulfate 0.001%; tap water to 100%. The glucose was previously sterilized separately at 110°C for 20 minutes. The resulting pH was 7. This was sterilized at 120°C for 20 minutes and incubated at 28°C under the same conditions by stirring, as for the vegetative media.
The maximum concentration of the antibiotic was reached on the 6th day of fermentation. The quantity of adriamycin produced at this time corresponds to a concentration of 15 μg/ml.
Therapeutic Function
Cancer chemotherapy
Biological Activity
doxorubicin is a semi-synthesized anticancer agent derived from bacterial culture. [1] it is an anthracycline antibiotic. it is been widely used in blood cancers, solid tumors and sarcomas.doxorubicin intercalates into dna double strand and inhibits the progression of dna topoisomerase ii, stopping replication process. [2] doxorubicin also induces histone eviction from open chromatin, causing dna damage and epigenetic deregulation. [3]doxorubicin is administrated intravenously. approximately 75% of doxorubicin and its metabolites bind to plasma protein. doxorubicin does not cross blood brain barrier. 50% of the drug is eliminated unchanged from the body mainly though bile excretion. the remaining undergoes one-electron reduction, two-electron reduction, and deglycosidation. the major metabolite is a potent membrane ion pump inhibitor, which is associated with cardiomyopathy. [4]
Mechanism of action
Doxorubicin is not absorbed orally, and because of
its ability to cause tissue necrosis must not be injected
intramuscularly or subcutaneously. Distribution studies
indicate rapid uptake in all tissues except the CNS.
Extensive tissue binding, primarily intranuclear, accounts
for the prolonged elimination half-life.The drug
is extensively metabolized in the liver to hydroxylated
and conjugated metabolites and to aglycones that are
primarily excreted in the bile.
Clinical Use
Doxorubicin is one of the most effective agents used
in the treatment of carcinomas of the breast, ovary, endometrium,
bladder, and thyroid and in oat cell cancer
of the lung. It is included in several combination regimens
for diffuse lymphomas and Hodgkin’s disease.
Doxorubicin can be used as an alternative to daunorubicin
in acute leukemias and is useful in Ewing’s sarcoma,
osteogenic sarcoma, soft-tissue sarcomas, and
neuroblastoma. Some activity has been reported in
non–oat cell lung cancer, multiple myeloma, and adenocarcinomas
of the stomach, prostate, and testis.
Side effects
The most important toxicities caused by doxorubicin
involve the heart and bone marrow.Acutely, doxorubicin
may cause transient cardiac arrhythmias and
depression of myocardial function. Doxorubicin may
cause radiation recall reactions, with flare-ups of dermatitis,
stomatitis, or esophagitis that had been produced
previously by radiation therapy. Less severe toxicities
include phlebitis and sclerosis of veins used for
injection, hyperpigmentation of nail beds and skin
creases, and conjunctivitis. Because of its intense red
color, doxorubicin will impart a reddish color to the
urine for 1 or 2 days after administration.
Carcinogenicity
Adriamycin is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
storage
Store at -20°C, protect from light
References
[1]brayfield, a, ed. (2013). doxorubicin. martindale: the complete drug reference. pharmaceutical press. retrieved 15 april 2014.
[2]pommier y., et al. (2010). dna topoisomerases and their poisoning by anticancer and antibacterial drugs. chemistry & biology 17 (5): 421–433.
[3]pang, b., et al. (2013). drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin. nature communications 4 (5): 1908
[4]boucek rj., et al. (1987). the major metabolite of doxorubicin is a potent inhibitor of membrane-associated ion pumps. a correlative study of cardiac muscle with isolated membrane fractions. j of biol chem 262: 15851-15856.
[2]pommier y., et al. (2010). dna topoisomerases and their poisoning by anticancer and antibacterial drugs. chemistry & biology 17 (5): 421–433.
[3]pang, b., et al. (2013). drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin. nature communications 4 (5): 1908
[4]boucek rj., et al. (1987). the major metabolite of doxorubicin is a potent inhibitor of membrane-associated ion pumps. a correlative study of cardiac muscle with isolated membrane fractions. j of biol chem 262: 15851-15856.
Questions And Answer
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Antitumor antibiotics
Adriamycin is a kind of anthracycline antitumor antibiotics produced by Streptomyces peucetius sub sp caesius, belonging to cell cycle non-specific drug (CCNSA). Cells of S and M phases are most sensitive to it. Its hydrochloride appears as orange needle crystal. The melting point is 204 ~ 205 ℃. It is easily soluble in water, ethanol and methanol. The aqueous solution is stable and stays constant at 5 ° C for 1 month but is not stable at higher temperatures or in acidic or alkaline solutions. The acidic aqueous solution is orange, neutral orange-red, alkaline (pH> 9) purple-blue. It is insoluble in acetone, benzene, petroleum ether, ether and chloroform. It is an antitumor antibiotic isolated from the actinomycetes culture. The mechanism of action is similar to daunorubicin, which has a broader anti-tumor spectrum and a higher therapeutic index. It is clinically applied for the treatment of acute and chronic lymphocytic leukemia and solid tumor leukemia, lymphoma, breast cancer, ovarian cancer, soft tissue sarcoma, osteogenic sarcoma, rhabdomyosarcoma, Ewing's sarcoma, nephroblastoma, neuroblastoma, gastric cancer, pancreatic cancer, liver cancer, prostate cancer, head and neck squamous cell carcinoma, testicular cancer, lung cancer, bladder cancer, medullary thyroid carcinoma and sarcoma. This product can cause myelosuppression, gastrointestinal reactions and cardiac toxicity. 4'-Epirubicin (4'-epi-adriamycin) is the reverse configuration of the C4 hydroxyl in the glycosyl group of Adriamycin. Its anti-tumor effect is similar to that of Adriamycin, but its cardiotoxicity is low. 4'-deoxyadriamycin (4'-deoxyadriamycin) has a different antitumor spectrum of animal tumors with doxorubicin with lower damage to the heart compared to doxorubicin. ; -
Pharmacological effects
This product belongs to anthracycline antineoplastic drugs, having similar structure to daunorubicin with the only difference being an H-hydroxy substitution in the side chain 14 carbon atoms. It has both fat-soluble anthracene ring ligand and water-soluble daunosamine. It also has acidic phenolic hydroxyl and basic amino group, thus having a strong anticancer pharmacological activity. Adriamycin is obtained from the culture Str. Pe-ucetius var. Caesius. Owing to the quinone-hydroquinone structure on the anthracene ring ligand in the molecule, it has the ability of accepting electrons and providing neutrons, to be inserted between adjacent base pairs of DNA, generating active free radicals, unwinding and breaking DNA double helix. It can further inhibit the activity of the nucleic acid template, interfering with the transcription process to prevent mRNA synthesis. In addition it may cause cell membrane rupture, exhibiting cytotoxicity, belonging to a cell cycle non-specific drug. This product has the function of forming superoxide radicals, and has a special role in the destruction of cell membrane structure and function. It is effective in the targeting all stages of the cells, but being of highest efficient in the treatment of the early S phase cells, followed by M, with the G1 phase being most insensitive to it. It can delay the G1, S and G2 phase. However, the maximum cytotoxicity occurs in S phase and is more sensitive to early S and M phase cells. Adriamycin can cause chromosome aberrations in cells and increase the exchange rate of chromatids.
This product has poor oral absorption, and should be administrated by only intravenous injection. Its plasma protein binding rate is low. It can rapidly disappear from the blood after injection, being widely distributed in the heart, stomach, lung, liver and spleen organizations, but no penetrating through the blood-brain barrier. Plasma attenuation curve is divided into three phases with half-life being 12 minutes, 3.3 hours and 30 hours, respectively. It is mainly subject to liver metabolism with the main metabolite being doxorubicin alcohol, having a considerable anti-cancer activity. Approximately 40% to 50% of the dose is excreted by bile after 7 days of administration, of which 50% is prototype and 23% is active metabolite. 5% to 10% of urine excreted. Upon liver and renal insufficiency, doxorubicin stay in the body for longer with the clear curve exhibiting heterogeneous phases and its three-phase T1 / 2 were 0.5 hours, 3 hours and 40 to 50 hours, respectively. It is clinical mainly for the treatment of acute or chronic leukemia, Hodgkin and non-Hodgkin's lymphoma and malignant lymphoma. Daunorubicin resistant tumors are still sensitive to doxorubicin. It also has certain efficacy in the treatment of Ewing's tumor, osteosarcoma, soft tissue tumor, lung cancer, choriocarcinoma, breast cancer, bladder cancer, thyroid cancer and soft tissue tumors. It combination with cytarabine, vincristine and fluorouracil can increase its efficacy. Tumor cells are resistant to doxorubicin. Drug-resistant cells, compared to the sensitive cells, have lower permeability of the cell membrane, decreased cellular uptake doxorubicin reduction, and can actively discharge doxorubicin. Daunorubicin resistant cells may also be cross-resistant to doxorubicin. ; -
Adverse reactions
A dose of more than 500mg / m2, 25% to 30% can possibly lead to ECG abnormalities, arrhythmia and decreased cardiac function. There are few cases of congestive heart failure, myocardial degeneration, local necrosis, and even death. 60% to 80% may have myelosuppression, manifested as leukopenia, thrombocytopenia and anemia with reaching minimum in 7 to 10 days and recovering at the first 4 weeks. In addition, there may be nausea and vomiting, mouth ulcers. Similar to daunorubicin, side effects of doxorubicin include cardiotoxicity, bone marrow suppression, nausea, vomiting and stomatitis as well as hair loss. Early signs of cardiac toxicity exhibit temporary ECG changes with the majority undergoing self-remission. Late (chronic) cardiotoxicity, also known as delayed cardiomyopathy that is dose related, is irreversible serious myocardial disease with severe cases being lethal. Therefore, heart disease and hypertension patients should use with caution. There are phlebitis, skin pigmentation and liver damage. Cardiotoxicity patients can administrate vitamin E, vitamin C, coenzyme Q10, N-acetyl cysteine and selenium preparations. Heart failure patients may be given digitalis preparations and diuretics. ; -
Medicine interactions
- Cross-resistant to daunorubicin, vincristine and actinomycin D.
- Synergistic effect with cyclophosphamide, fluorouracil, methotrexate, chlorelimide, cisplatin and nitrosoureas.
- Used with caution during live virus vaccination.
- Combination with azathioprine or mercaptopurine can increase doxorubicin liver toxicity.
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