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]

References

↑ 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.

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vinflunine^§ Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine^#) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

I	Camptotheca (Camptothecin Cositecan^† Belotecan Gimatecan Exatecan Irinotecan Lurtotecan^‡ Silatecan^§ Topotecan Rubitecan^‡)

II	Podophyllum (Etoposide^# Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin^# Doxorubicin^# Epirubicin Idarubicin Amrubicin^† Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide^# (Ifosfamide Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Alvocidib^† Seliciclib^† Palbociclib) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Belinostat Panobinostat Romidepsin Vorinostat) PIKI (Idelalisib)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Celecoxib Demecolcine Elesclomol^§ Elsamitrucin Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

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