A water-soluble antineoplastic antibiotic
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Becatecarin

Item No. 15576

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,11-dichloro-6-[2-(diethylamino)ethyl]-12,13-dihydro-12-(4-O-methyl-b-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
CAS Number
119673-08-4
Synonyms
  • BMS 181176
  • BMY 27557
  • NSC 655649
  • XL 119
Molecular Formula
C33H34Cl2N4O7
Formula Weight
669.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleWater: Soluble
SMILES
O=C(N(CCN(CC)CC)C1=O)C2=C1C(C(C=CC=C3Cl)=C3N4[C@@H]5O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]5O)=C4C6=C2C7=C(C(Cl)=CC=C7)N6
InChi Code
InChI=1S/C33H34Cl2N4O7/c1-4-37(5-2)12-13-38-31(43)22-20-15-8-6-10-17(34)24(15)36-25(20)27-21(23(22)32(38)44)16-9-7-11-18(35)26(16)39(27)33-29(42)28(41)30(45-3)19(14-40)46-33/h6-11,19,28-30,33,36,40-42H,4-5,12-14H2,1-3H3/t19-,28-,29-,30-,33-/m1/s1
InChi Key
JSKFWUPVIZYJMR-UDOAKELVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 µg

    $236

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    1 mg

    $655

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    Cayman Chemical
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    Product Description

    Becatecarin is a water-soluble, diethylaminoethyl analog of the antineoplastic antibiotic rebeccamycin.1 It intercalates into DNA, stabilizing the DNA-topoisomerase complex.2 This results in the potent catalytic inhibition of both topoisomerases I and II, initiating DNA cleavage and apoptosis.2 Becatecarin, alone or in combination with other compounds, has anti-cancer as well as myelosuppressive effects in vivo.3,4 It is also a transport substrate of the ATP-binding cassette (ABC) transporter ABCG2.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kaneko, T., Wong, H., Utzig, J., et al. Water soluble derivatives of rebeccamycin. J. Antibiot. (Tokyo) 43(1), 125-127 (1990).

    2. Long, B.H., Rose, W.C., Vyas, D.M., et al. Discovery of antitumor indolocarbazoles: Rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Curr. Med. Chem. Anticancer Agents 2(2), 255-266 (2002).

    3. Ricart, A.D., Hammond, L.A., Kuhn, J.G., et al. Phase I and pharmacokinetic study of sequences of the rebeccamycin analogue NSC 655649 and cisplatin in patients with advanced solid tumors. Clin. Cancer Res. 11(24 Pt 1), 8728-8736 (2005).

    4. Schwandt, A., Mekhail, T., Halmos, B., et al. Brief report: Phase II trial of rebeccamycin analogue, a dual topoisomerase I and II inhibitor, in relapsed "sensitive" small cell lung cancer. J. Thorac. Oncol. 7(1), 751-754 (2012).

    5. Robey, R.W., Obrzut, T., Shukla, S., et al. Becatecarin (rebeccamycin analog, NSC 655649) is a transport substrate and induces expression of the ATP-binding cassette transporter, ABCG2, in lung carcinoma cells. Cancer Chemother. Pharmacol. 64(3), 575-583 (2009).