BELOTECAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H27N3O4
Molecular Weight	433.4996
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=C(CCNC(C)C)C5=CC=CC=C5N=C34)C2=O

InChI

InChIKey=LNHWXBUNXOXMRL-VWLOTQADSA-N

InChI=1S/C25H27N3O4/c1-4-25(31)19-11-21-22-17(12-28(21)23(29)18(19)13-32-24(25)30)15(9-10-26-14(2)3)16-7-5-6-8-20(16)27-22/h5-8,11,14,26,31H,4,9-10,12-13H2,1-3H3/t25-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H27N3O4
Molecular Weight	433.4996
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9875499

Belotecan is a semisynthetic analogue of camptothecin containing a 2-(N-isopropylamino) ethyl group linkage at position C-7 of the camptothecin ring. It stabilizes the complex formed between topoisomerase I and DNA, thereby preventing the religation of DNA breaks. This leads to an inhibition of DNA replication and triggers apoptotic cell death. Belotecan was approved in Korea under the name Camtobell for the treatment of patients with ovarian and small cell lung cancers.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase 1 16 Target ID: P11387\|\|\|Q9UJN0 Gene ID: 7150.0 Gene Symbol: TOP1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9875499	Inhibitor 8297		0.275 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ovarian cancer 157 Sources: http://www.kpbma.or.kr/attach/2016%20%EC%A0%9C%EC%95%BD%ED%98%91%ED%9A%8C%20%EC%98%81%EB%AC%B8%EB%94%94%EB%A0%89%ED%86%A0%EB%A6%AC_%EB%82%B4%EC%A7%80%EC%B5%9C%EC%A2%85.pdf	Primary		Approved 8429	CAMTOBELL Approved Use Ovarian cancer, SCLC Launch Date 2003
Small-cell lung cancer 41 Sources: http://www.kpbma.or.kr/attach/2016%20%EC%A0%9C%EC%95%BD%ED%98%91%ED%9A%8C%20%EC%98%81%EB%AC%B8%EB%94%94%EB%A0%89%ED%86%A0%EB%A6%AC_%EB%82%B4%EC%A7%80%EC%B5%9C%EC%A2%85.pdf	Primary		Approved 8429	CAMTOBELL Approved Use Ovarian cancer, SCLC Launch Date 2003

PubMed

Title	Date	PubMed
4-Week repeated intravenous dose toxicity study of a new camptothecin anticancer agent CKD-602 in dogs.	2005 May	15778009
Reproductive toxicity evaluation of a new camptothecin anticancer agent, CKD-602, in pregnant/lactating female rats and their offspring.	2007 Feb	16896929
Effect of probenecid on the biliary excretion of belotecan.	2007 Nov	18087819
A phase I and pharmacologic study of belotecan in combination with cisplatin in patients with previously untreated extensive-stage disease small cell lung cancer.	2007 Oct 15	17947485
Phase II evaluation of CKD-602, a camptothecin analog, administered on a 5-day schedule to patients with platinum-sensitive or -resistant ovarian cancer.	2008 Jun	18405948
CKD-602, a camptothecin derivative, inhibits proliferation and induces apoptosis in glioma cell lines.	2009 Jun	19424618
The efficacy and toxicity of belotecan (CKD-602), a camptothericin analogue topoisomerase I inhibitor, in patients with recurrent or refractory epithelial ovarian cancer.	2010 Jun	20566426
Efficacy and toxicity of belotecan with and without cisplatin in patients with recurrent ovarian cancer.	2010 Jun	19745693
Belotecan for relapsing small-cell lung cancer patients initially treated with an irinotecan-containing chemotherapy: a phase II trial.	2010 Oct	20138389

Patents

Sample Use Guides

In Vivo Use Guide

Small cell lung cancer: 0.5mg/m2/day for day 1 to 4. Ovarian cancer: 0.5mg/m2 IV days 1, 2, 3, 4, 5 of each 21 day cycle until 6 cycle or disease progression.

Route of Administration: Intravenous

In Vitro Use Guide

In a cell viability assay, human glioblastoma cell lines (U87 MG, U251 MG, U343 MG, LN229) were plated in 96-well plates at a density of 2x10(3) cells/well (100 ul). In each experimental set, cells were plated in quadruplicate and were treated with different concentrations (0.05, 0.1, 0.2, 0.5, 1, 2, 5 uM) of belotecan for 24, 48 and 72 h. The IC50 values were 84.66 nM for U87 MG cells, 29.13 nM for U343 MG, 14.57 nM for U251 MG cells and 9.07 nM for LN229 cells at 48 h after treatment.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:03:05 GMT 2023` Edited by `admin` on `Fri Dec 15 16:03:05 GMT 2023`
Record UNII	27Z82M2G1N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BELOTECAN

Official Name

English

1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 4-ETHYL-4-HYDROXY-11-(2-((1-METHYLETHYL)AMINO)ETHYL)-, (4S)-

Systematic Name

English

BELOTECAN [MART.]

Common Name

English

BELOTECAN [MI]

Common Name

English

(4S)-4-ETHYL-4-HYDROXY-11-(2-((1-METHYLETHYL)AMINO)ETHYL)-1,12-DIHYDRO-14H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H)-DIONE

Systematic Name

English

Belotecan [WHO-DD]

Common Name

English

belotecan [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2843