Adriamycin
- CAS No.
- 23214-92-8
- Chemical Name:
- Adriamycin
- Synonyms
- DOXORUBICIN;Doxil;Rubex;Adriamycin PFS;HydroxydaunoMycin;Doxorubicin hydrohloride;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;(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
- CBNumber:
- CB1170865
- Molecular Formula:
- C27H29NO11
- Molecular Weight:
- 543.53
- MOL File:
- 23214-92-8.mol
- Modify Date:
- 2024/8/21 22:41:43
| Melting point | 205°C |
|---|---|
| Boiling point | 617.77°C (rough estimate) |
| Density | 1.3783 (rough estimate) |
| refractive index | 1.6400 (estimate) |
| storage temp. | Keep in dark place,Sealed in dry,2-8°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 | Doxorubicin (23214-92-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|---|---|
| Signal word | Danger |
| Hazard statements | H302-H315-H319-H335-H350-H362 |
| Precautionary statements | P260-P263-P280 |
| HS Code | 2941900000 |
| 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. |
Adriamycin Chemical Properties,Uses,Production
Chemical Properties
Adriamycin is an orange to red cake-like or needle-like crystalline solid.
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.
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.
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.
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
Potential Exposure
An antibiotic product from streptomyces, used as anticancer drug
Carcinogenicity
Adriamycin is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
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
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.
Adriamycin Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| AVD pharmaceuticals Pvt Ltd | +919860835260 | Pune, India | 102 | 58 | Inquiry |
| Aspen Biopharma Labs Pvt Ltd | +91-9248058660 +91-9248058662 | Telangana, India | 234 | 58 | Inquiry |
| Ajitha Prodrug India Pvt Ltd | +91-9845915533 +91-9845915533 | Karnataka, India | 17 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Hardik Onco Care | 08047642620 | Ahmedabad, India | 7 | 58 | Inquiry |
| Micro Labs Ltd | 08048372692Ext 280 | Karnataka, India | 16 | 58 | Inquiry |
| Shaanxi Dideu Medichem Co. Ltd | +86-29-81148696 +86-15536356810 | China | 3320 | 58 | Inquiry |
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