An anthracycline antitumor antibiotic
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Pirarubicin

Item No. 28384

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8S,10S)-10-[[3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranosyl]oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
CAS Number
72496-41-4
Molecular Formula
C32H37NO12
Formula Weight
627.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 10 mg/mlEthanol: 2 mg/ml
λmax
235, 289, 480, 496 nm
SMILES
COC1=C2C(C(C(C(O)=C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O[C@H]5OCCCC5)[C@H](C)O4)C3=C6O)=C6C2=O)=O)=CC=C1
InChi Code
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
InChi Key
KMSKQZKKOZQFFG-YXRRJAAWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $49

    Add

    10 mg

    $93

    Add

    25 mg

    $213

    Add

    100 mg

    $702

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Pirarubicin is an anthracycline that has anticancer activity.1 It interacts with topoisomerase II to inhibit DNA replication. Pirarubicin inhibits the growth of human HeLa and C33A cervical, as well as T-24 bladder cancer cells (IC50s = 29, 52, and 36 ng/ml, respectively).2 It inhibits the growth of human Huh7 and MHCC97H liver cancer cells (IC50s = 0.159 and 0.374 μM, respectively).3 Pirarubicin also inhibits the growth of M5076 mouse ovarian cancer cells in vitro (IC50 = 0.366 μM) and in vivo in a mouse allograft model when administered at a dose of 2 mg/kg for four days.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Monneret, C. Recent developments in the field of antitumour anthracyclines. Eur. J. Med. Chem. 36(6), 483-493 (2001).

    2. Tsuchiya, K.S., Ishii, T., Ikeno, S., et al. Inhibition of anchorage-independent growth of tumor cells by IT-62-B, a new anthracycline. J. Antibiot. (Tokyo) 50(10), 853-859 (1997).

    3. Huang, H., Chen, T., Zhou, Y., et al. RIPK1 inhibition enhances pirarubicin cytotoxic efficacy through AKT-P21-dependent pathway in hepatocellular carcinoma. Int. J. Med. Sci. 15(14), 1648-1657 (2018).

    4. Sugiyama, T., Sadzuka, Y., Nagasawa, K., et al. Membrane transport and antitumor activity of pirarubicin, and comparison with those of doxorubicin. Jpn. J. Cancer Res. 90(7), 775-780 (1999).