EPIRUBICIN HYDROCHLORIDE

PRODUCT IDENTIFICATION
CAS NO. 56420-45-2
57918-25-9 (parent)
56390-09-1 (hydrochloride)

EPIRUBICIN HYDROCHLORIDE

EINECS NO. 260-145-2
FORMULA C27H29NO11·HCl
MOL WT. 579.15

H.S. CODE

 2932.99.6100

TOXICITY

  
SYNONYMS Farmorubicin; Ellence;
(1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12- trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside hydrochloride; 4'-Epidoxorubicin hydrochloride; 4'-epi-Adriamycin hydrochloride; Epidoxorubicin hydrochloride; Epirubicin HCl; Epirubicin hydrochloride; Farmorubicin; Pharmorubicin; (8S-cis)-10-((3-Amino-2,3,6-trideoxy-alpha-L- arabino-hexopyranosyl)oxy)- 7,8,9,10-tetrahydro- 6,8,11-trihydroxy-8-(hydroxyacetyl)- 1-methoxyn aphthacene-5,12-dione hydrochloride; (8S-cis)-10-((3-Amino-2,3,6- trideoxy-alpha- L-arabino- hexopyranosyl) oxy)-7,8,9,10- tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1- methoxy-5,12- naphthacenedione hydrochloride; Farmorubicina;
SMILES

O1[C@@H](C)[C@@H]([C@H](C[C@@H]1O[C@@H]1c2c(c (c3C(c4 cccc (c4 C (c3c2O)=O)OC)=O)O)C[C@](C(CO)=O) (O)C1)N)O.Cl

CLASSIFICATION 

Anthracycline, Topoisomerase II Inhibitor, Antibiotics, Antineoplastic

EXTRA NOTES

An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE orange to red crystals
MELTING POINT 185 C (Decomposes)
BOILING POINT

 

RELATIVE DENSITY  
SOLUBILITY IN WATER  
pH  
VAPOR DENSITY

 

REFRACTIVE INDEX

 

NFPA RATINGS

 Health hazard: 1, Fire: 0, Reactivity Hazard: 0

AUTOIGNITION

 

FLASH POINT

 

STABILITY Stable under normal conditions. Light sensitive

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Epirubicin

Google Scholar Search - Epirubicin

Drug Information Portal (U.S. National Library of Medicine) - Epirubicin

PubChem Compound Summary - Epirubicin HCl

Drug Bank -  Epirubicin

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Epirubicin

http://www.ebi.ac.uk/ - Epirubicin

http://www.ncbi.nlm.nih.gov/ - Epirubicin

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank - Epirubicin

http://www.sigmaaldrich.com/
Epirubicin is antimitotic and cytotoxic. It inhibits nucleic acid and protein synthesis. Epirubicin may do so by forming complexes with DNA and intercalation between base pairs, by inhibiting topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, and by preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It inhibits DNA helicase activity.

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.

Epirubicin, an anthracycline cytotoxic agent, is the 4'-epi-isomer of doxorubicin, It has the same actions as doxorubicin, but has different spatial orientation of the hydroxyl group at the 4' carbon of the sugar, which features fewer side-effects and lower toxicity. The IUPAC name is (7S,9S)-7-[(2S,4S,5R,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
SALES SPECIFICATION

APPEARANCE

 orange to red crystals

IDENTIFICATION

positive (Test IR)

ASSAY

97.0 - 102.0%

SPECIFIC ROTATION +272° ~ +276° (c=0.01 in MeOH)

HEAVY METALS

10ppm max

RESIDUE ON IGNITION

0.1% max

pH

4.0 - 5.5

TRANSPORTATION
PACKING
 
HAZARD CLASS  
UN NO.

Not regulated

SAFETY INFORMATION

HAZARD OVERVIEW

May be harmful if inhaled. May cause respiratory tract irritation. Skin Harmful if absorbed through skin. May cause skin irritation. May cause eye irritation. Harmful if swallowed.

GHS

 

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H302

P STATEMENTS

P201-P308 + P313

EC DIRECTIVES

 

HAZARD CODES

Xn

RIS PHRASES

22

SAFETY PHRASES