Losoxantrone

Losoxantrone

Identifiers

IUPAC name

7-Hydroxy-2-{2-[(2-hydroxyethyl)amino]ethyl}-5-({2-[(2-hydroxyethyl)amino]ethyl}amino)dibenzo[cd,g]indazol-6(2H)-one

CAS Number
88303-60-0 Y

PubChem (CID)
72116

ChemSpider
65094 Y

Chemical and physical data

Formula
C22H27N5O4

Molar mass
425.48088 g/mol

3D model (Jmol)
Interactive image

SMILES

c1cc-2c(c(c1)O)C(=O)c3c(ccc4c3c2nn4CCNCCO)NCCNCCO

InChI

InChI=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 Y

Key:YROQEQPFUCPDCP-UHFFFAOYSA-N Y

Losoxantrone (biantrazole) is a anthroquinone anthrapyrazole antineoplastic agent and analog of mitoxantrone.[1][2] It is also sometimes known as DuP 941.[3]
See also[edit]

Mitoxantrone
Piroxantrone

References[edit]

^ Showalter, H. D. H.; Johnson, J. L.; Hoftiezer, J. M.; Turner, W. R.; Werbel, L. M.; Leopold, W. R.; Shillis, J. L.; Jackson, R. C.; Elslager, E. F. (1987). “Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias”. Journal of Medicinal Chemistry. 30: 121. doi:10.1021/jm00384a021. 
^ Beylin, V. G.; Colbry, N. L.; Goel, O. P.; Haky, J. E.; Johnson, D. R.; Johnson, J. L.; Kanter, G. D.; Leeds, R. L.; Leja, B.; Lewis, E. P.; Rithner, C. D.; Showalter, H. D. H.; Sercel, A. D.; Turner, W. R.; Uhlendorf, S. E. (1989). “Anticancer anthrapyrazoles. Improved syntheses of clinical agents CI-937, CI-941, and piroxantrone hydrochloride”. Journal of Heterocyclic Chemistry. 26: 85. doi:10.1002/jhet.5570260117. 
^ Leteurtre, F.; Kohlhagen, G.; Paull, K. D.; Pommier, Y. (17 August 1994). “Topoisomerase II Inhibition and Cytotoxicity of the Anthrapyrazoles DuP 937 and DuP 941 (Losoxantrone) in the National Cancer Institute Preclinical Antitumor Drug Discovery Screen”. JNCI Journal of the National Cancer Institute. 86 (16): 1239–1244. doi:10.1093/jnci/86.16.1239. 

v
t
e

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine#
Vincristine#
Vinflunine§
Vindesine
Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel
Docetaxel#
Larotaxel
Ortataxel†
Paclitaxel#
Tesetaxel)
Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid

Dihydrofolate reductase inhibitor (