Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H27N3O4.ClH |
| Molecular Weight | 469.961 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC[C@@]1(O)C(=O)OCC2=C1C=C3N(CC4=C(CCNC(C)C)C5=CC=CC=C5N=C34)C2=O
InChI
InChIKey=SJKBXKKZBKCHET-UQIIZPHYSA-N
InChI=1S/C25H27N3O4.ClH/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;1H/t25-;/m0./s1
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: P11387|||Q9UJN0 Gene ID: 7150.0 Gene Symbol: TOP1 Target Organism: Homo sapiens (Human) |
0.275 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CAMTOBELL Approved UseOvarian cancer, SCLC Launch Date2003 |
|||
| Primary | CAMTOBELL Approved UseOvarian cancer, SCLC Launch Date2003 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro pharmacodynamics of CKD-602 in HT-29 cells. | 2002 Oct |
|
| Effects of CKD-602, a new camptothecin anticancer agent, on pregnant does and embryo-fetal development in rabbits. | 2005 |
|
| Plasma, tumor, and tissue disposition of STEALTH liposomal CKD-602 (S-CKD602) and nonliposomal CKD-602 in mice bearing A375 human melanoma xenografts. | 2007 Dec 1 |
|
| Belotecan, new camptothecin analogue, is active in patients with small-cell lung cancer: results of a multicenter early phase II study. | 2008 Jan |
|
| 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 |
|
| 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 |
|
| CKD-602, a camptothecin derivative, inhibits proliferation and induces apoptosis in glioma cell lines. | 2009 Jun |
|
| Apoptotic effect of CKD-602 (Camtobell) on oral squamous cell carcinoma cell lines. | 2009 Mar |
|
| Gateways to clinical trials. | 2009 Nov |
|
| Phase II study of combination chemotherapy with etoposide and ifosfamide in patients with heavily pretreated recurrent or persistent epithelial ovarian cancer. | 2009 Oct |
|
| Comparison of the efficacy between topotecan- and belotecan-, a new camptothecin analog, based chemotherapies for recurrent epithelial ovarian cancer: a single institutional experience. | 2010 Feb |
|
| Multicenter phase 2 study of belotecan, a new camptothecin analog, and cisplatin for chemotherapy-naive patients with extensive-disease small cell lung cancer. | 2010 Jan 1 |
|
| 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 |
|
| Toxicity study of a new camptothecin anti-cancer agent CKD-602 in dogs: 4-week continuous intravenous dose by infusion pump and 4-week repeated intravenous dose. | 2010 Nov |
|
| Durable response after just one cycle of belotecan-based chemotherapy in a patient with relapsed primary peritoneal serous carcinoma. | 2014 Jan |
Patents
Sample Use Guides
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 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
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Fri Dec 15 16:05:19 GMT 2023
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| Record UNII |
01DZ4127G7
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Validated (UNII)
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C2843
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