WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206028
Description: Losoxantrone is a DNA intercalator that was developed with the potential to replace anthracyclines. Losoxantrone is also a bioreductive drugs. In phase II trials, losoxantrone demonstrated a partial biochemical response rate of 25%, response in measurable disease sites in 22%, and improvement in clinical symptoms in one-third of patients.
MedKoo Cat#: 206028
Chemical Formula: C22H27N5O4
Exact Mass: 425.2063
Molecular Weight: 425.48088
Elemental Analysis: C, 62.10; H, 6.40; N, 16.46; O, 15.04
Synonym: Losoxantrone; Biantrazole; CI941; DuP941.
IUPAC/Chemical Name: 7-Hydroxy-2-[2-(2-hydroxyethylamino)ethyl]-5-[2-(2-hydroxyethylamino)ethylamino]anthra[1,9-cd]pyrazol-6(2H)-one
InChi Key: YROQEQPFUCPDCP-UHFFFAOYSA-N
InChi Code: InChI=1S/C22H27N5O4/c28-12-9-23-6-7-25-15-4-5-16-20-19(15)22(31)18-14(2-1-3-17(18)30)21(20)26-27(16)11-8-24-10-13-29/h1-5,23-25,28-30H,6-13H2
SMILES Code: O=C1C2=C3C(N(CCNCCO)N=C3C4=C1C(O)=CC=C4)=CC=C2NCCNCCO
Appearance: Solid powder
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: >5 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
The following data is based on the product molecular weight 425.48088 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.
|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|
1: Liang H, Wu X, Guziec LJ, Guziec FS Jr, Larson KK, Lang J, Yalowich JC, Hasinoff BB. A structure-based 3D-QSAR study of anthrapyrazole analogues of the anticancer agents losoxantrone and piroxantrone. J Chem Inf Model. 2006 Jul-Aug;46(4):1827-35. PubMed PMID: 16859314.
2: Renner UD, Piperopoulos G, Gebhardt R, Ehninger G, Zeller KP. The oxidative biotransformation of losoxantrone (CI-941). Drug Metab Dispos. 2002 Apr;30(4):464-78. PubMed PMID: 11901102.
3: Goh BC, Vokes EE, Joshi A, Ratain MJ. Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours. Br J Cancer. 2002 Feb 12;86(4):534-9. PubMed PMID: 11870533; PubMed Central PMCID: PMC2375276.
4: Joshi AS, Pieniaszek HJ Jr, Vokes EE, Vogelzang NJ, Davidson AF, Richards LE, Chai MF, Finizio M, Ratain MJ. Elimination pathways of [14C]losoxantrone in four cancer patients. Drug Metab Dispos. 2001 Feb;29(2):96-9. PubMed PMID: 11159796.
5: Huan SD, Natale RB, Stewart DJ, Sartiano GP, Stella PJ, Roberts JD, Symes AL, Finizio M. A multicenter phase II trial of losoxantrone (DuP-941) in hormone-refractory metastatic prostate cancer. Clin Cancer Res. 2000 Apr;6(4):1333-6. PubMed PMID: 10778959.
6: Hasinoff BB, Tran KT. The displacement of iron(III) from its complexes with the anticancer drugs piroxantrone and losoxantrone by the hydrolyzed form of the cardioprotective agent dexrazoxane. J Inorg Biochem. 1999 Nov-Dec;77(3-4):257-9. PubMed PMID: 10643663.
7: Diab SG, Baker SD, Joshi A, Burris HA, Cobb PW, Villalona-Calero MA, Eckhardt SG, Weiss GR, Rodriguez GI, Drengler R, Kraynak M, Hammond L, Finizio M, Von Hoff DD, Rowinsky EK. A phase I and pharmacokinetic study of losoxantrone and paclitaxel in patients with advanced solid tumors. Clin Cancer Res. 1999 Feb;5(2):299-308. PubMed PMID: 10037178.
8: Herman EH, Zhang J, Hasinoff BB, Tran KT, Chadwick DP, Clark JR Jr, Ferrans VJ. Comparison of the chronic toxicity of piroxantrone, losoxantrone and doxorubicin in spontaneously hypertensive rats. Toxicology. 1998 Jun 26;128(1):35-52. PubMed PMID: 9704904.
9: Shea JA, Shamrock WF, Abboud CA, Woodeshick RW, Nguyen LQ, Rubino JT, Segretario J. Validation of cleaning procedures for highly potent drugs. I. Losoxantrone. Pharm Dev Technol. 1996 Apr;1(1):69-75. PubMed PMID: 9552333.
10: Richards LE, Sun JH. Identification of two regioisomeric monocarboxylic acid metabolites of losoxantrone (DuP 941; Biantrazole) excreted in human urine. Drug Metab Dispos. 1995 May;23(5):600-2. PubMed PMID: 7587938.
11: Leteurtre F, Kohlhagen G, Paull KD, Pommier Y. Topoisomerase II inhibition and cytotoxicity of the anthrapyrazoles DuP 937 and DuP 941 (Losoxantrone) in the National Cancer Institute preclinical antitumor drug discovery screen. J Natl Cancer Inst. 1994 Aug 17;86(16):1239-44. PubMed PMID: 8040892.