Pirarubicin
Pirarubicin is an anthracycline derivative of adriamycin that is clinically co-administered with other anticancer chemotherapeutics in the treatment of a variety of cancers. Pirarubicin is a DNA intercalator that inhibits topoisomerase II and DNA polymerase, inhibiting synthesis of DNA in vitro and in vivo. Pirarubicin induces G2 phase cell cycle arrest, inhibiting tumor growth and increasing survival rates in animal models of colon cancer. Additionally, pirarubicin induces endothelium-dependent relaxation of aortic tissue, likely due to modulation of signaling by endothelium-derived relaxing factor (EDRF).
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18954702
| Cas No. |
72496-41-4 |
|---|---|
| Purity |
≥90% |
| Formula |
C32H37NO12 |
| Formula Wt. |
627.64 |
| Chemical Name |
(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione |
| IUPAC Name |
(9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione |
| Synonym |
THP |
| Melting Point |
188-192°C (dec.) |
| Appearance |
Orange red crystalline powder |
Hiyama E, Ueda Y, Onitake Y, et al. A cisplatin plus pirarubicin-based JPLT2 chemotherapy for hepatoblastoma: experience and future of the Japanese Study Group for Pediatric Liver Tumor (JPLT). Pediatr Surg Int. 2013 Oct;29(10):1071-5. PMID: 24026876.
Kataoka K, Naomoto Y, Muro M, et al. Antitumor effect of pirarubicin (THP) against human colon cancer transplanted into nude mice and the mechanism of cell cycle progression. Gan To Kagaku Ryoho. 1992 Mar;19(3):367-71. PMID: 1543363.
Hirano S, Agata N, Hara Y, et al. Pirarubicin-induced endothelium-dependent relaxation in rat isolated aorta. J Pharm Pharmacol. 1991 Dec;43(12):848-54. PMID: 1687584.
Schott B, Robert J. Comparative cytotoxicity, DNA synthesis inhibition and drug incorporation of eight anthracyclines in a model of doxorubicin-sensitive and -resistant rat glioblastoma cells. Biochem Pharmacol. 1989 Jan 1;38(1):167-72. PMID: 2910297.
Tanaka M, Yoshida S, Kimura K. Mechanism of inhibition of DNA polymerases by 4-epiadriamycin and 4-O-tetrahydropyranyladriamycin. Gann. 1983 Dec;74(6):829-36. PMID: 6365674.
