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 Date1.06678079E12 |
|||
| Primary | CAMTOBELL Approved UseOvarian cancer, SCLC Launch Date1.06678079E12 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Preformulation studies of a novel camptothecin anticancer agent, CKD-602: physicochemical characterization and hydrolytic equilibrium kinetics. | 2002 Jun 4 |
|
| In vitro pharmacodynamics of CKD-602 in HT-29 cells. | 2002 Oct |
|
| Safety pharmacology of CKD-602, a novel anticancer agent. | 2003 |
|
| CKD-602. Chong Kun Dang. | 2003 Dec |
|
| Simple and sensitive determination of the new antitumor drug CKD-602 in human plasma by liquid chromatography. | 2003 Jan 25 |
|
| Subacute toxicity evaluation of a new camptothecin anticancer agent CKD-602 administered by intravenous injection to rats. | 2004 Dec |
|
| Effects of CKD-602, a new camptothecin anticancer agent, on pregnant does and embryo-fetal development in rabbits. | 2005 |
|
| 4-Week repeated intravenous dose toxicity study of a new camptothecin anticancer agent CKD-602 in dogs. | 2005 May |
|
| Embryotoxic effects of CKD-602, a new camptothecin anticancer agent, in rats. | 2005 May-Jun |
|
| The synergism between Belotecan and cisplatin in gastric cancer. | 2006 |
|
| Evaluation of the toxic potentials of a new camptothecin anticancer agent CKD-602 on fertility and early embryonic development in rats. | 2006 Aug |
|
| 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 |
|
| Reproductive toxicity evaluation of a new camptothecin anticancer agent, CKD-602, in pregnant/lactating female rats and their offspring. | 2007 Feb |
|
| STEALTH liposomal CKD-602, a topoisomerase I inhibitor, improves the therapeutic index in human tumor xenograft models. | 2007 Jul-Aug |
|
| Effect of probenecid on the biliary excretion of belotecan. | 2007 Nov |
|
| 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 |
|
| 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 |
|
| Phase I/IIa study of combination chemotherapy with CKD-602 and cisplatin in patients with recurrent epithelial ovarian cancer. | 2009 Aug |
|
| Chemosensitivity of uterine cervical cancer demonstrated by the histoculture drug response assay. | 2009 Dec |
|
| Phase I and pharmacokinetic study of pegylated liposomal CKD-602 in patients with advanced malignancies. | 2009 Feb 15 |
|
| 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 |
|
| Pharmacokinetic study of pegylated liposomal CKD-602 (S-CKD602) in patients with advanced malignancies. | 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 |
|
| Decreased urinary secretion of belotecan in folic acid-induced acute renal failure rats due to down-regulation of Oat1 and Bcrp. | 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 |
|
| Efficacy and toxicity of belotecan with and without cisplatin in patients with recurrent ovarian cancer. | 2010 Jun |
|
| A multicenter phase II study of belotecan, new camptothecin analogue, in patients with previously untreated extensive stage disease small cell lung 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 |
|
| Belotecan for relapsing small-cell lung cancer patients initially treated with an irinotecan-containing chemotherapy: a phase II trial. | 2010 Oct |
|
| 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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| Record UNII |
01DZ4127G7
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C2843
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