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 1.06678079E12
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 1.06678079E12

PubMed

Title	Date	PubMed
Simple and sensitive determination of the new antitumor drug CKD-602 in human plasma by liquid chromatography.	2003 Jan 25	12504179
Evaluation of the toxic potentials of a new camptothecin anticancer agent CKD-602 on fertility and early embryonic development in rats.	2006 Aug	16814440
Reproductive toxicity evaluation of a new camptothecin anticancer agent, CKD-602, in pregnant/lactating female rats and their offspring.	2007 Feb	16896929
Involvement of P-glycoprotein, multidrug resistance protein 2 and breast cancer resistance protein in the transport of belotecan and topotecan in Caco-2 and MDCKII cells.	2008 Nov	18654741
Phase I/IIa study of combination chemotherapy with CKD-602 and cisplatin in patients with recurrent epithelial ovarian cancer.	2009 Aug	19723113
Chemosensitivity of uterine cervical cancer demonstrated by the histoculture drug response assay.	2009 Dec	19966525
Phase I and pharmacokinetic study of pegylated liposomal CKD-602 in patients with advanced malignancies.	2009 Feb 15	19190127
Apoptotic effect of CKD-602 (Camtobell) on oral squamous cell carcinoma cell lines.	2009 Mar	18715816
A multicenter phase II study of belotecan, new camptothecin analogue, in patients with previously untreated extensive stage disease small cell lung cancer.	2010 Jun	19683359
Durable response after just one cycle of belotecan-based chemotherapy in a patient with relapsed primary peritoneal serous carcinoma.	2014 Jan	24102892

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 UTC 2023` Edited by `admin` on `Fri Dec 15 16:03:05 UTC 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