LKT Labs

Biochemicals for Life Science Research

Pirarubicin

Pirarubicin

Product ID P3568
Cas No. 72496-41-4
Purity ≥90%
Product Unit SizeCostQuantityStock
5 mg $90.80 In stock
10 mg $132.40 Please Inquire
25 mg $478.90 Please Inquire
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Description

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).

Product Info

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

Shipping and Storage

Store Temp

Ambient
Ship Temp

Ambient

Downloads

MSDS

P3568 MSDS PDF
Info Sheet

P3568 Info Sheet PDF

References

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.

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