PRODUCT IDENTIFICATION
25316-40-9 (hydrochloride)
C27H29NO11·HCl
H.S. CODE
TOXICITY
CLASSIFICATION
Antineoplastic, Anthracycline
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2 c(c4c(c3O) C(=O) c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N)O.Cl
Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of daunorubicin.
Overall Carcinogenic Evaluation: Group 2A
PHYSICAL AND CHEMICAL PROPERTIES
SOLVENT SOLUBILITY
Soluble in normal saline, methanol, acetonitrile, THF. Practically insoluble in acetone, benzene, chloroform, ethyl ether and petroleum ether.
REFRACTIVE INDEX
NFPA RATINGS
Health hazard: 2, Fire: 0, Reactivity Hazard: 0
AUTOIGNITION
FLASH POINT
EXTERNAL LINKS & GENERAL DESCRIPTION
Wikipedia Linking - Doxorubicin
Google Scholar Search - Doxorubicin
Drug Information Portal (U.S. National Library of Medicine) - Doxorubicin
PubChem Compound Summary - Doxorubicin HCl
Drug Bank - Doxorubicin
KEGG (Kyoto Encyclopedia of Genes and Genomes) - Doxorubicin
http://www.ebi.ac.uk/ - Doxorubicin
http://www.ncbi.nlm.nih.gov/ - Doxorubicin
http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank - Doxorubicin
http://www.sigmaaldrich.com/
Naturally fluorescent anthracycline antibiotic, anticancer drug. Doxorubicin is a substrate of MRP1 which was first cloned from a DOX-resistant lung cancer cell line. Fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles (Golgi and lysosome) in the sequestration of drugs and its implication in drug resistant phenotypes.
Local:
Anthracycline: a class of chemotherapy drugs that are also antibiotics having a four-ring nucleus (tetrahydrotetrahydrotetracenedione.) to which is attached by aminoglycoside linkage including daunosamine (CAS 26548-47-0), isolated from the fungus Streptomyces peucetius or S. coeruleorubidus. The molecule is amphoteric. The ring-system nucleus is lipophilic, but abundant hydroxyl groups at the saturated end of the ring system is hydrophilic. The molecule contains acidic function in the ring phenolic groups as well as a basic function in the amino group in glycoside. Anthracyclines act to terminate cancer cells function by DNA intercalation, metal ion chelation, and the generation of free radicals. They are used to treat a wide range of cancers including leukemia and other neoplasms. Doxorubicin is a hydroxyl form of daunomycin in structure for the reduction in cardiotoxicity. Doxorubicin hydrochloride form of red-orange powder. It is an inhibitor of reverse transcriptase and RNA polymerase. The fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles in the sequestration of drugs and its implication in drug resistant phenotypes The IUPAC name is (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11 -trihydroxy-9-(2- hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione.
Anthracycline |
CAS RN. |
|
eta-Isorhodomycinone |
477-53-2 |
| Rhodomycin | 1401-16-7 |
| Nogalamycin | 1404-15-5 |
| Retamycin | 11130-68-0 |
| Beromycin, anthracycline | 12674-15-6 |
| Requinomycin | 12770-40-0 |
| Daunorubicin | 20830-81-3 |
| Rhodomycinone | 21288-60-8 |
| Doxorubicin | 23214-92-8 |
| Doxorubicin hydrochloride | 25316-40-9 |
| Daunosamine | 26548-47-0 |
| Pillaromycin A | 30361-37-6 |
| Carminomycin | 39472-31-6 |
| Carubicin | 50935-04-1 |
| Cosmomycin C | 55945-22-7 |
| Epirubicin | 56420-45-2 |
| Aclarubicin | 57576-44-0 |
| Idarubicin | 58957-92-9 |
| Bohemic acid complex | 64296-23-7 |
| Menogaril | 71628-96-1 |
| Pirarubicin | 72496-41-4 |
| Iremycin | 75634-51-4 |
| Cosmomycin B | 77517-27-2 |
| Sulfurmycinone | 78173-88-3 |
| Auramycinone | 78173-89-4 |
| Sulfurmycin A | 78173-90-7 |
| Auramycin B | 78173-91-8 |
| Auramycin A | 78173-92-9 |
| Sulfurmycin B | 78193-30-3 |
| Rubeomycin B | 78366-46-8 |
| 2-Hydroxyaklavinone | 79008-78-9 |
| Roseorubicins | 79392-32-8 |
| Taurimycin | 79819-02-6 |
| 2-Hydroxyaclacinomycin B | 85819-82-5 |
| Anthrapyrazole | 91440-30-1 |
| Annamycin | 92689-49-1 |
| Cosmomycin B' | 103470-57-1 |
| Cosmomycin A' | 103470-58-2 |
| Oxaunomycin | 105615-58-5 |
| Viriplanin A | 106153-36-0 |
| Moflomycin | 107430-03-5 |
| Barminomycin II | 108089-33-4 |
| Barminomycin I | 108147-17-7 |
| Nemorubicin | 108852-90-0 |
| Amrubicin hydrochloride | 110311-30-3 |
| 2-Pyrrolinodoxorubicin | 175795-76-3 |
| |
APPEARANCE
IDENTIFICATION
positive (Test IR)
ASSAY
98.5 - 100.5%
2.0% max
HEAVY METALS
10ppm max
0.1% max
4.5 - 5.0
Not regulated
HAZARD OVERVIEW
OSHA Hazards: Target Organ Effect, Harmful by ingestion., Irritant, Carcinogen. Target Organs: Heart, Bone marrow, Blood, LiverHeart, Bone marrow, Blood, Liver. Harmful if swallowed. May cause cancer.
GHS
Danger
PICTOGRAMS
HAZARD STATEMENTS
H302-H350
P STATEMENTS
P201-P308 + P313
Toxic
RIS PHRASES
45-46-22-37/38-41-62-63
SAFETY PHRASES
53-26-36/37/39-45