Bisantrene HCl
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MedKoo CAT#: 206518

CAS#: 71439-68-4 (2HCl)

Description: Bisantrene, aslo known as CL-216942 and NSC 337766, is topoisomerase II poisons and DNA intercalators. It may be used as model compounds to study P-glycoprotein-mediated multiple drug resistance (MDR1). Bisantrene may be used as a Rac1 inhibitor. Bisantrene intercalates with and disrupts the configuration of DNA, resulting in DNA single-strand breaks, DNA-protein crosslinking, and inhibition of DNA replication. This agent is similar to doxorubicin in activity, but unlike doxorubicin, does not exhibit cardiotoxicity.


Chemical Structure

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Bisantrene HCl
CAS# 71439-68-4 (2HCl)

Theoretical Analysis

MedKoo Cat#: 206518
Name: Bisantrene HCl
CAS#: 71439-68-4 (2HCl)
Chemical Formula: C22H24Cl2N8
Exact Mass: 0.00
Molecular Weight: 471.390
Elemental Analysis: C, 56.06; H, 5.13; Cl, 15.04; N, 23.77

Price and Availability

Size Price Availability Quantity
50mg USD 350 2 Weeks
100mg USD 550 2 weeks
200mg USD 950 2 weeks
500mg USD 1950 2 weeks
1g USD 2950 2 weeks
2g USD 5250 2 weeks
5g USD 7650 2 weeks
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Related CAS #: 71439-68-4 (2HCl)   97910-18-4 (4HCl)   97910-19-5 (nitrate)   97910-20-8 (sulfate)   101218-44-4 (acetate)   78186-34-2 (free base)    

Synonym: CL-216942; CL216942; CL 216942; NSC-337766; Bisantrene HCl

IUPAC/Chemical Name: 9,10-bis((Z)-(2-(4,5-dihydro-1H-imidazol-2-yl)hydrazono)methyl)anthracene dihydrochloride

InChi Key: KINULKKPVJYRON-VCZQZRGZSA-N

InChi Code: InChI=1S/C22H22N8.2ClH/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22;;/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30);2*1H/b27-13-,28-14-;;

SMILES Code: [H]Cl.[H]Cl.C12=CC=CC=C1C(/C=N\NC3=NCCN3)=C4C=CC=CC4=C2/C=N\NC5=NCCN5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related: 78186-34-2 (Bisantrene 2HCl) 78186-34-2 (Bisantrene free base).

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 471.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Folini M, Pivetta C, Zagotto G, De Marco C, Palumbo M, Zaffaroni N, Sissi C. Remarkable interference with telomeric function by a G-quadruplex selective bisantrene regioisomer. Biochem Pharmacol. 2010 Jun 15;79(12):1781-90. doi: 10.1016/j.bcp.2010.02.018. Epub 2010 Mar 3. PubMed PMID: 20206144.

2: Zagotto G, Oliva A, Guano F, Menta E, Capranico G, Palumbo M. Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues. Bioorg Med Chem Lett. 1998 Jan 20;8(2):121-6. PubMed PMID: 9871638.

3: Sissi C, Bolgan L, Moro S, Zagotto G, Bailly C, Menta E, Capranico G, Palumbo M. DNA-binding preferences of bisantrene analogues: relevance to the sequence specificity of drug-mediated topoisomerase II poisoning. Mol Pharmacol. 1998 Dec;54(6):1036-45. PubMed PMID: 9855632.

4: Capranico G, Guano F, Moro S, Zagotto G, Sissi C, Gatto B, Zunino F, Menta E, Palumbo M. Mapping drug interactions at the covalent topoisomerase II-DNA complex by bisantrene/amsacrine congeners. J Biol Chem. 1998 May 22;273(21):12732-9. PubMed PMID: 9582297.

5: Aksentijevich I, Cardarelli CO, Pastan I, Gottesman MM. Retroviral transfer of the human MDR1 gene confers resistance to bisantrene-specific hematotoxicity. Clin Cancer Res. 1996 Jun;2(6):973-80. PubMed PMID: 9816258.

6: Yao S, Wilson WD. 1D and 2D 1H NMR studies on bisantrene complexes with short DNA oligomers. Sci China B. 1995 Dec;38(12):1462-72. PubMed PMID: 8745574.

7: Leblanc T, Deméocq F, Leverger G, Baruchel A, Lemerle S, Vannier JP, Nelken B, Guillot T, Schaison G. Treatment of relapsed or refractory acute leukemia in childhood with bisantrene combined with high dose aracytine. Med Pediatr Oncol. 1994;22(2):119-24. PubMed PMID: 8259097.

8: Zhang XP, Ritke MK, Yalowich JC, Slovak ML, Ho JP, Collins KI, Annable T, Arceci RJ, Durr FE, Greenberger LM. P-glycoprotein mediates profound resistance to bisantrene. Oncol Res. 1994;6(7):291-301. PubMed PMID: 7865904.

9: Murdock KC, Lee VJ, Citarella RV, Durr FE, Nicolau G, Kohlbrenner M. N-phosphoryl derivatives of bisantrene. Antitumor prodrugs with enhanced solubility and reduced potential for toxicity. J Med Chem. 1993 Jul 23;36(15):2098-101. PubMed PMID: 8340913.

10: Spadea A, Petti MC, Aloespiriti MA, Avvisati G, De Gregoris C, Fazi P, Latagliata R, Amadori S, Mandelli F. Bisantrene in relapsed and refractory acute myelogenous leukemia. Leuk Lymphoma. 1993 Feb;9(3):217-20. PubMed PMID: 8471980.

11: Herman TS, Teicher BA, Varshney A, Khandekar V, Brann T. Effect of hypoxia and acidosis on the cytotoxicity of mitoxantrone, bisantrene and amsacrine and their platinum complexes at normal and hyperthermic temperatures. Anticancer Res. 1992 May-Jun;12(3):827-36. PubMed PMID: 1622142.

12: Durie BG, Crowley J, Coltman CA Jr, Chapman RA, Balcerzk SP, Bonnet JD, Lipschitz DA, Stephens RL, Cheson BD. Phase II evaluation of bisantrene in refractory multiple myeloma. A Southwest Oncology Group study. Invest New Drugs. 1991 Nov;9(4):329-31. PubMed PMID: 1804807.

13: Cowan JD, Neidhart J, McClure S, Coltman CA Jr, Gumbart C, Martino S, Hutchins LF, Stephens RL, Vaughan CB, Osborne CK. Randomized trial of doxorubicin, bisantrene, and mitoxantrone in advanced breast cancer: a Southwest Oncology Group study. J Natl Cancer Inst. 1991 Aug 7;83(15):1077-84. PubMed PMID: 1875415.

14: Stiff PJ, Sweet D, Kilton LJ, Johnson CM, Muntean B, Blough RR. Phase II trial of Bisantrene for metastatic melanoma: an Illinois cancer council study. Med Pediatr Oncol. 1991;19(2):126-8. PubMed PMID: 2011097.

15: Visani G, Rizzi S, Tosi P, Cenacchi A, Gamberi B, Lemoli RM, Papadopulu P, Tura S. In vitro effects of bisantrene on fresh clonogenic leukemia cells: a preliminary study on 15 cases. Haematologica. 1990 Nov-Dec;75(6):527-31. PubMed PMID: 2098293.

16: Vogelzang NJ, Lanzotti VJ, Muntean B, Blough RR. Bisantrene in advanced, hormone-resistant carcinoma of the prostate: an Illinois Cancer Council phase II study. Invest New Drugs. 1990 Aug;8(3):313-5. PubMed PMID: 2272771.

17: Salianov VI, Evdokimov IuM, Palumbo M. [Study of the properties of condensed forms of the complexes of linear and supercoiled DNA with mitoxantrone and bisantrene]. Antibiot Khimioter. 1990 Jan;35(1):19-22. Russian. PubMed PMID: 2334240.

18: Mills GM, Dahlberg S, Cowan J, Neilan BA, Gumbart CH, Hussein K, Coltman CA Jr. Phase II evaluation of bisantrene in acute leukemia. A Southwest Oncology Group Study. Am J Clin Oncol. 1989 Dec;12(6):507-10. PubMed PMID: 2589232.

19: Tosi P, Visani G, Colombini R, Verlicchi F, Benfenati D, Cenacchi A, Russo D, Zuffa E, Papadopulu P, Tura S. Phase II study of bisantrene in relapsed/refractory acute non lymphoid leukemias (ANLL). Haematologica. 1989 Nov-Dec;74(6):555-8. PubMed PMID: 2628237.

20: Elliott JA, Wilson WD, Shea RG, Hartley JA, Reszka K, Lown JW. Interaction of bisantrene anti-cancer agents with DNA: footprinting, structural requirements for DNA unwinding, kinetics and mechanism of binding and correlation of structural and kinetic parameters with anti-cancer activity. Anticancer Drug Des. 1989 Mar;3(4):271-82. PubMed PMID: 2539168.