LURTOTECAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H30N4O6
Molecular Weight	518.561
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C3N=C5C=C6OCCOC6=CC5=C4CN7CCN(C)CC7)C2=O

InChI

InChIKey=RVFGKBWWUQOIOU-NDEPHWFRSA-N

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

HIDE SMILES / InChI

Molecular Formula	C28H30N4O6
Molecular Weight	518.561
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800004939 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/lurtotecan

Lurtotecan is a semisynthetic analog of camptothecin with antineoplastic activity. It is an inhibitor of DNA topoisomerase I. Liposomal formulation of lurtotecan was being studied in the treatment of cancer. Lurtotecan development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase I 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9632354 \| https://www.ncbi.nlm.nih.gov/pubmed/9328158	Inhibitor 8297

PubMed

Title	Date	PubMed
Camptothecins: a review of their chemotherapeutic potential.	2002	12269849
Phase II study of OSI-211 (liposomal lurtotecan) in patients with metastatic or loco-regional recurrent squamous cell carcinoma of the head and neck. An EORTC New Drug Development Group study.	2004 Dec	15571957
Gateways to clinical trials.	2004 Jun	15319815
Gateways to clinical trials.	2004 Sep	15538546
Topoisomerase I inhibitors in the treatment of gastrointestinal cancer: from intravenous to oral administration.	2004 Sep	15377400
Gateways to clinical trials.	2005 Dec	16395422
Randomized trial of two intravenous schedules of the topoisomerase I inhibitor liposomal lurtotecan in women with relapsed epithelial ovarian cancer: a trial of the national cancer institute of Canada clinical trials group.	2005 Mar 20	15699482
Stealth liposomes: review of the basic science, rationale, and clinical applications, existing and potential.	2006	17717971
Experimental designs for phase I and phase I/II dose-finding studies.	2006 Mar 13	16434987
Tumour-targeted nanomedicines: principles and practice.	2008 Aug 5	18648371
Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors.	2009 Apr	19139163

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:14:55 GMT 2023` Edited by `admin` on `Sat Dec 16 17:14:55 GMT 2023`
Record UNII	4J1L80T08I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LURTOTECAN

Official Name

English

(8S)-8-ETHYL-2,3-DIHYDRO-8-HYDROXY-15-((4-METHYL-1-PIPERAZINYL)METHYL)-11H-P-DIOXINO(2,3-G)PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-9,12(8H,14H)-DIONE

Common Name

English

11H-1,4-DIOXINO(2,3-G)PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-9,12(8H,14H)-DIONE, 8-ETHYL-2,3-DIHYDRO-8-HYDROXY-15-((4-METHYL-1-PIPERAZINYL)METHYL)-, (S)

Common Name

English

lurtotecan [INN]

Common Name

English

Lurtotecan [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843