Doxorubicin

  • Hydroxyldaunorubicin
  • Adriamycin
  • ( 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 ( IUPAC)
  • C27H29NO11 (doxorubicin )
  • C27H29NO11 · HCl (doxorubicin · hydrochloride)
  • 23214-92-8
  • 25316-40-9 (hydrochloride)

L01DB01

Cytostatic

Intercalation

  • 543.52 g · mol -1 ( doxorubicin)
  • 579.98 g.mol -1 (doxorubicin · hydrochloride)

205 ° C ( decomposition) (doxorubicin · hydrochloride)

Readily soluble in water, methanol, acetonitrile, and tetrahydrofuran (doxorubicin · hydrochloride)

Hydrochloride

Risk

570 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Doxorubicin is the hydroxy derivative of daunorubicin and belongs to the group of anthracyclines. It is used as a stereochemically pure drug in chemotherapy ( cytostatic ). Doxorubicin belongs to the group of drugs called intercalating. The effect is due to the intercalation into the DNA. Side effects are, inter alia cardiotoxicity.

Properties

Doxorubicin acts as Interkalans to planar compounds in DNA and RNA. DNA synthesis is disrupted, topoisomerase II is inhibited and there is a free-radical formation.

Doxorubicin has fluorescent properties which can be used to inspect the ejection of doxorubicin from the cell. A involviertes in such processes protein is the first of a doxorubicin -resistant lung cancer cell line cloned MRP1 from the family of ABC transporters. Further doxorubicin can also be used in order to clarify the location of the proteins involved in the multiple drug resistance and the role of organelles such as the Golgi apparatus and the lysosomes.

Applications

Doxorubicin is used as a cytostatic drug application in the treatment of tumors such as Breast cancer, lung cancer and lymphoma. The drug is administered intravenously in these indications. For the treatment especially of hepatocellular carcinoma (HCC ) is (TACE ) applied intra-arterially in the transarterial chemoembolization. For this purpose it is applied either in an emulsion with an oily contrast medium ( Lipiodol ) or bound to drug-eluting particles.

The most important side effects include bone marrow suppression, nephrotoxicity, cardiotoxicity, ulcerations and dermatotoxische effects. It can take place an accumulation in tumor tissue as independent as the heart, is counteracted by a PEGylation, to concentrate the levels in plasma and tumor tissue.

Trade names

Monopreparations: Adriblastin (D, A, CH), Adrimedac (D), Doxil (D, A, CH), Myocet (D, A), Ribodoxo (D ), various generics (D, A, CH) Farmorubicin (active ingredient: epirubicin )

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Intercalation (chemistry) Dangerous Substances Directive (67/548/EEC) Fluorescence ATP-binding cassette transporter Digital Object Identifier
31286
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