Lurtotecan

Lurtotecan
Names

Preferred IUPAC name (8S)-8-Ethyl-8-hydroxy-15-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydro-11H-[1,4]dioxino[2,3-g]pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-9,12(8H,14H)-dione
Identifiers
CAS Number	149882-10-0^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL305666^Y
ChemSpider	54919^Y
PubChem CID	60956
UNII	4J1L80T08I^Y
CompTox Dashboard (EPA)	DTXSID30164422
InChI InChI=1S/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1^Y Key: RVFGKBWWUQOIOU-NDEPHWFRSA-N^Y InChI=1/C28H30N4O6/c1-3-28(35)20-11-22-25-18(14-32(22)26(33)19(20)15-38-27(28)34)17(13-31-6-4-30(2)5-7-31)16-10-23-24(12-21(16)29-25)37-9-8-36-23/h10-12,35H,3-9,13-15H2,1-2H3/t28-/m0/s1 Key: RVFGKBWWUQOIOU-NDEPHWFRBI
SMILES O=C2OCC=1C(=O)N6/C(=C\C=1[C@@]2(O)CC)c5nc4cc3OCCOc3cc4c(c5C6)CN7CCN(C)CC7
Properties
Chemical formula	C₂₈H₃₀N₄O₆
Molar mass	518.561 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Lurtotecan is a semi-synthetic analog of camptothecin with antineoplastic activity. Liposomal lurtotecan was in clinical trials as a treatment for topotecan-resistant ovarian cancer,^[1] but was discontinued.^[2]

Synthesis

References

^ Seiden, MV; Muggia, F; Astrow, A; Matulonis, U; Campos, S; Roche, M; Sivret, J; Rusk, J; Barrett, E (April 2004). "A Phase II Study of Liposomal Lurtotecan (OSI-211) in Patients with Topotecan Resistant Ovarian Cancer". Gynecologic Oncology. 93 (1): 229–32. doi:10.1016/j.ygyno.2003.12.037. PMID 15047241.
^ "Liposomal lurtotecan (OSI 211) on AdisInsight". Adis Insight. Springer International Publishing AG. Retrieved 15 July 2016.
^ Fang, F. G.; Bankston, D. D.; Huie, E. M.; Ross Johnson, M.; Kang, M. C.; Lehoullier, C. S.; Lewis, G. C.; Lovelace, T. C.; Lowery, M. W.; McDougald, D. L.; Meerholz, C. A.; Partridge, J. J.; Sharp, M. J.; Xie, S. (1997). "Convergent catalytic asymmetric synthesis of camptothecin analog GI147211C". Tetrahedron. 53 (32): 10953. doi:10.1016/S0040-4020(97)00357-8.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule 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 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 (Mitoxantrone Losoxantrone 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^# Mitomycins Plicamycin)

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 (Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Umbralisib^‡)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Elesclomol^§ Elsamitrucin Enasidenib Epacadostat Eribulin Estramustine phosphate Glasdegib Idecabtagene vicleucel Ivosidenib Lifileucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib 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

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

Synthesis

References

Navigation menu

Search