Erbulozole

Erbulozole
Identifiers

Synonyms	Erbuzole
CAS Number	124784-31-2
PubChem CID	9934372
ChemSpider	8110000
Chemical and physical data
Formula	C₂₄H₂₇N₃O₅S
Molar mass	469.55g/mol
3D model (JSmol)	Interactive image
SMILES CCOC(=O)NC1=CC=C(C=C1)SC[C@H]2CO[C@](O2)(CN3C=CN=C3)C4=CC=C(C=C4)OC
InChI InChI=1S/C24H27N3O5S/c1-3-30-23(28)26-19-6-10-22(11-7-19)33-15-21-14-31-24(32-21,16-27-13-12-25-17-27)18-4-8-20(29-2)9-5-18/h4-13,17,21H,3,14-16H2,1-2H3,(H,26,28)/t21-,24+/m1/s1 Key:KLEPCGBEXOCIGS-QPPBQGQZSA-N
(verify)

Erbulozole (R55104) is a congener of the microtubule inhibitor tubulozole. It is undergoing phase I clinical trials as a chemotherapeutic agent.^[1]

Synthesis

Erbulozole synthesis: Lednicer book 6 (Drugs of the Future citation).

↑ Van Belle, SJ; Distelmans, W; Vandebroek, J; Bruynseels, J; Van Ginckel, R; Storme, GA (1993). "Phase I trial of erbulozole (R55104)". Anticancer research. 13 (6B): 2389–91. PMID 8135472.

Distelmans, W.; VanGinckel, P.; Heeres, J.; Van der Veken, L. J. E. (1991). "Erbulozole. Antineoplastic, Microtubule inhibitor". Drugs Future. 16 (6): 577.

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 Doxifluridine 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 phosphate 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^# Mitomycins Plicamycin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Niraparib Olaparib Rucaparib) 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

Receptor tyrosine kinase	ErbB: HER1/EGFR (Cetuximab Panitumumab) HER2/neu (Trastuzumab Trastuzumab emtansine)
Others for solid tumors	EpCAM (Catumaxomab Edrecolomab) VEGF-A (Bevacizumab)
Leukemia/lymphoma	lymphoid: CD20 (Ibritumomab Ofatumumab Rituximab Tositumomab), CD30 (Brentuximab), CD52 (Alemtuzumab) myeloid: CD33 (Gemtuzumab)

RET inhibitors: Vandetanib (also VEGFR and EGFR). Entrectinib (ALK, ROS1, NTRK). c-MET inhibitor: Cabozantinib (also VEGFR2).

Other

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