Pirarubicin

• CAT Number: A000632
• CAS Number: 72496-41-4
• Molecular Formula: C32H37NO12
• Molecular Weight: 627.64
• Purity: ≥95%
• Synonyms: 72496-41-4; MFCD00869742; Theprubicin; THP-doxorubicin; C32H37NO12
• Target: Topoisomerase
• Solubility: >7.65mg/mL in DMSO
• Storage: -20°C
• IUPAC Name: (7S,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
• InChI: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1
• InChIKey: KMSKQZKKOZQFFG-YXRRJAAWSA-N
• SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6

Pirarubicin（Cat No.:A000632）is an anthracycline anticancer agent used in the treatment of various solid tumors, including breast cancer and bladder cancer. It works by intercalating into DNA, thereby inhibiting topoisomerase II, which prevents DNA replication and transcription, ultimately leading to cell death. Pirarubicin is a derivative of doxorubicin, but with reduced cardiotoxicity, making it a safer option in chemotherapy regimens. Its efficacy in inhibiting tumor growth, along with its relatively lower risk of heart-related side effects, makes it valuable in oncology for both research and clinical applications.

Reference

1: Miyamoto K, Ito A, Wakabayashi M, Eba J, Arai Y, Nishiyama H, Sugimoto M,
Yamashita R, Kakehi Y; Urologic Oncology Study Group of the Japan Clinical
Oncology Group. A Phase III trial of a single early intravesical instillation of
pirarubicin to prevent bladder recurrence after radical nephroureterectomy for
upper tract urothelial carcinoma (JCOG1403, UTUC THP Phase III). Jpn J Clin
Oncol. 2017 Nov 9:1-4. doi: 10.1093/jjco/hyx158. [Epub ahead of print] PubMed
PMID: 29136187.

2: Islam W, Fang J, Etrych T, Chytil P, Ulbrich K, Sakoguchi A, Kusakabe K, Maeda
H. HPMA Copolymer Conjugate with Pirarubicin: In Vitro and Ex Vivo Stability and
Drug Release study. Int J Pharm. 2017 Nov 10. pii: S0378-5173(17)31055-4. doi:
10.1016/j.ijpharm.2017.11.011. [Epub ahead of print] PubMed PMID: 29133205.

3: Wang YD, Zhang Y, Sun B, Leng XW, Li YJ, Ren LQ. Cardioprotective effects of
rutin in rats exposed to pirarubicin toxicity. J Asian Nat Prod Res. 2017 Oct
27:1-13. doi: 10.1080/10286020.2017.1394292. [Epub ahead of print] PubMed PMID:
29078725.

4: Mizutani H, Hotta S, Nishimoto A, Ikemura K, Miyazawa D, Ikeda Y, Maeda T,
Yoshikawa M, Hiraku Y, Kawanishi S. Pirarubicin, an Anthracycline Anticancer
Agent, Induces Apoptosis Through Generation of Hydrogen Peroxide. Anticancer Res.
2017 Nov;37(11):6063-6069. PubMed PMID: 29061786.

5: Jiang B, Dong Y, He H, Han C. Application of pirarubicin photosensitizer
fluorescence cystoscopy in early detection of bladder cancer. Oncol Lett. 2017
Sep;14(3):3309-3312. doi: 10.3892/ol.2017.6570. Epub 2017 Jul 12. PubMed PMID:
28927081; PubMed Central PMCID: PMC5588036.

6: Fang Z, Wang Y, Li H, Yu S, Liu Z, Fan Z, Chen X, Wu Y, Pan X, Li X, Wang C.
Combination Treatment of Citral Potentiates the Efficacy of Hyperthermic
Intraperitoneal Chemoperfusion with Pirarubicin for Colorectal Cancer. Mol Pharm.
2017 Oct 2;14(10):3588-3597. doi: 10.1021/acs.molpharmaceut.7b00652. Epub 2017
Sep 6. PubMed PMID: 28841022.

7: Etrych T, Tsukigawa K, Nakamura H, Chytil P, Fang J, Ulbrich K, Otagiri M,
Maeda H. Comparison of the pharmacological and biological properties of HPMA
copolymer-pirarubicin conjugates: A single-chain copolymer conjugate and its
biodegradable tandem-diblock copolymer conjugate. Eur J Pharm Sci. 2017 Aug
30;106:10-19. doi: 10.1016/j.ejps.2017.05.031. Epub 2017 May 18. PubMed PMID:
28528285.

8: Wang Y, Zhang Y, Sun B, Tong Q, Ren L. Rutin Protects against
Pirarubicin-Induced Cardiotoxicity through TGF-β1-p38 MAPK Signaling Pathway.
Evid Based Complement Alternat Med. 2017;2017:1759385. doi: 10.1155/2017/1759385.
Epub 2017 Mar 6. PubMed PMID: 28367221; PubMed Central PMCID: PMC5358477.

9: Deng C, Jia M, Wei G, Tan T, Fu Y, Gao H, Sun X, Zhang Q, Gong T, Zhang Z.
Inducing Optimal Antitumor Immune Response through Coadministering iRGD with
Pirarubicin Loaded Nanostructured Lipid Carriers for Breast Cancer Therapy. Mol
Pharm. 2017 Jan 3;14(1):296-309. doi: 10.1021/acs.molpharmaceut.6b00932. Epub
2016 Dec 12. PubMed PMID: 27936775.

10: Nakamura H, Koziolová E, Chytil P, Tsukigawa K, Fang J, Haratake M, Ulbrich
K, Etrych T, Maeda H. Pronounced Cellular Uptake of Pirarubicin versus That of
Other Anthracyclines: Comparison of HPMA Copolymer Conjugates of Pirarubicin and
Doxorubicin. Mol Pharm. 2016 Dec 5;13(12):4106-4115. Epub 2016 Nov 21. PubMed
PMID: 27934482.