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Losoxantrone

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Chemical compound

Pharmaceutical compound

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
PubChemCID	72116
ChemSpider	65094^Y
UNII	47KPH00809
CompTox Dashboard(EPA)	DTXSID60236949
Chemical and physical data
Formula	C₂₂H₂₇N₅O₄
Molar mass	425.489 g·mol⁻¹
3D model (JSmol)	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 ananthroquinone anthrapyrazole antineoplastic agent andanalog ofmitoxantrone.^[1]^[2] It is also sometimes known asDuP 941.^[3]

References

[edit]

^Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, et al. (January 1987). "Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias".Journal of Medicinal Chemistry.30 (1):121–31.doi:10.1021/jm00384a021.PMID 3806589.
^Beylin VG, Colbry NL, Goel OP, Haky JE, Johnson DR, Johnson JL, Kanter GD, Leeds RL, Leja B, Lewis EP, Rithner CD (1989). "Anticancer anthrapyrazoles. Improved syntheses of clinical agents CI-937, CI-941, and piroxantrone hydrochloride".Journal of Heterocyclic Chemistry.26:85–96.doi:10.1002/jhet.5570260117.
^Leteurtre F, Kohlhagen G, Paull KD, Pommier Y (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".Journal of the National Cancer Institute.86 (16):1239–44.doi:10.1093/jnci/86.16.1239.PMID 8040892.

Intracellularchemotherapeutic agents /antineoplastic agents (L01)

SPs/MIs
(M phase)

Blockmicrotubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ 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 (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine^# Clofarabine Fludarabine^#) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^#+daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards:Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas:Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates:Busulfan (Mannosulfan Treosulfan) Aziridines:Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# (Pingyangmycin) Ixabepilone Mitomycin Plicamycin Utidelone)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib^# Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib^‡ Duvelisib Idelalisib Inavolisib Umbralisib^‡) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide^# (Realgar/Indigo naturalis^#) Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Calaspargase pegol Celecoxib Ciltacabtagene autoleucel Darinaparsin Demecolcine Denileukin diftitox Eflornithine Elesclomol^§ Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Idroxioleic acid Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Nirogacestat Obecabtagene autoleucel Oblimersen^† Omacetaxine mepesuccinate Para-toluenesulfonamide Pelabresib Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tabelecleucel Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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