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MedKoo Cat#: 206028 | Name: Losoxantrone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Losoxantrone
Losoxantrone
CAS#88303-60-0

Theoretical Analysis

MedKoo Cat#: 206028

Name: Losoxantrone

CAS#: 88303-60-0

Chemical Formula: C22H27N5O4

Exact Mass: 425.2063

Molecular Weight: 425.48

Elemental Analysis: C, 62.10; H, 6.40; N, 16.46; O, 15.04

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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
Purity
>98%
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
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Preparing Stock Solutions

The following data is based on the product molecular weight 425.48 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
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.

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