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Zorubicin

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Chemical compound

Pharmaceutical compound

Zorubicin
Clinical data

Trade names	rubidazon, rubidazone
Routes of administration	i.v.
ATC code	L01DB05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (E)-N'-(1-((2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl)ethylidene)benzohydrazide
CAS Number	54083-22-6
PubChemCID	9595290
DrugBank	DB11618^Y
ChemSpider	7869436
UNII	V25F9362OP
CompTox Dashboard(EPA)	DTXSID4043852
Chemical and physical data
Formula	C₃₄H₃₅N₃O₁₀
Molar mass	645.665 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC1=C(C(C4=C(C=CC=C4OC)C3=O)=O)C3=C(O)C2=C1[C@@H](O[C@]5([H])O[C@@H](C)[C@@H](O)[C@@H](N)C5)C[C@@](/[C@@](C)=N/NC(C6=CC=CC=C6)=O)(O)C2
InChI InChI=1S/C34H35N3O10/c1-15-28(38)20(35)12-23(46-15)47-22-14-34(44,16(2)36-37-33(43)17-8-5-4-6-9-17)13-19-25(22)32(42)27-26(30(19)40)29(39)18-10-7-11-21(45-3)24(18)31(27)41/h4-11,15,20,22-23,28,38,40,42,44H,12-14,35H2,1-3H3,(H,37,43)/b36-16+/t15-,20-,22-,23-,28+,34-/m0/s1 Key:FBTUMDXHSRTGRV-ALTNURHMSA-N
(verify)

Zorubicin (INN) is abenzoyl hydrazone derivative of theanthracycline antineoplastic antibioticdaunorubicin. Zorubicin intercalates into DNA; it as well interacts withtopoisomerase II and inhibits DNA polymerases and therefore is used to treatcancer.^[1]^[2]

References

[edit]

^"NCATS Inxight Drugs — ZORUBICIN".drugs.ncats.io.
^Li X, Xu S, Tan Y, Chen J (June 2015)."The effects of idarubicin versus other anthracyclines for induction therapy of patients with newly diagnosed leukaemia".The Cochrane Database of Systematic Reviews.2015 (6) CD010432.doi:10.1002/14651858.CD010432.pub2.PMC 11218035.PMID 26037486.

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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