CAS Number123948-87-8
SynonymsMFCD00866235; 9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate; EINECS 231-595-7
Molecular FormulaC23H23N3O5
Molecular Weight421.45 (anhydrous free base basis)
Purity≥98 (HPLC and enzymatic)%
Density1.5±0.1 g/cm3
Boiling Point782.9±60.0 °C at 760 mmHg
Melting Point−114 °C(lit.)
Appearancepowder
Symbol
Signal WordWarning
Please Login or Create an Account to: See VlP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 123948-87-8 |
| Catalog No. | 2A-9012779 |
| Chinese Name | 拓扑替康 |
| Synonyms | MFCD00866235; 9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate; EINECS 231-595-7 |
| Molecular Formula | C23H23N3O5 |
| Molecular Weight | 421.45 (anhydrous free base basis) |
| Purity | ≥98 (HPLC and enzymatic) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 782.9±60.0 °C at 760 mmHg |
| Melting Point | −114 °C(lit.) |
| Appearance | powder |
| Water Solubility | H2O: soluble |
| Storage Condition | 2-8°C |
| Packaging | II |
| Application | Topotecan (SKF 104864A; NSC 609669) is a topoisomerase I inhibitor. |
| HTC | 2942000000 |
| PubChem ID | 329826724 |
| MDL Number | MFCD00870670 |
| SMILES | [n]21c(cc5c([c]2=O)COC(=O)[C@]5(O)CC)c3nc4c(cc3C1)c(c(cc4)O)CN(C)C |
| InChI | 1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1 |
| InChI Key | UCFGDBYHRUNTLO-QHCPKHFHSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | 8 |
| MSDS | msds/12779_1_123948_87_8.pdf |
| Bioactivity | Topotecan (SKF 104864A; NSC 609669) is a Topoisomerase I inhibitor. The IC50 values of Topotecan at 24 h are 2.73±0.25 μM of U251 cells, 2.95±0.23 μM of U87 cells, 5.46±0.41 μM of GSCs-U251 and 5.95±0.24 μM of GSCs-U87. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Cancer Target Topoisomerase I In Vitro Topotecan (SKF104864) obviously inhibits proliferation of not only human glioma cells but also glioma stem cells (GSCs) in a dose- and time-dependent manner. According to the IC50 values at 24 h, 3 μM of Topotecan (SKF104864) is selected as the optimal administration concentration. In addition, Topotecan (SKF104864) induces cell cycle arrest in G0/G1 and S phases and promoted apoptosis. Results show that the cell viability is inhibited by Topotecan (SKF104864) in a dose-dependent manner. 2, 20 and 40 μM of Topotecan obviously inhibits the cell viability compared with the control groups. The IC50 values of Topotecan (SKF104864) at 24 h are 2.73±0.25 μM of U251 cells, 2.95±0.23 μM of U87 cells, 5.46±0.41 μM of GSCs-U251 and 5.95±0.24 μM of GSCs-U87. Thus 3 μM of Topotecan is selected as the optimal administration concentration in the subsequent experiments[1]. In Vivo NUB-7 metastatic model, the animals belonging to all the 4 groups are sacrificed after 14 days treatment. Compared with the control, Low dose metronomic (LDM) Topotecan (TP) and TP+Pazopanib (PZ) liver weights are significantly lower in TP+PZ-treated animals, compared with PZ. Microscopic tumors are visible in the livers of mice belonging to all the groups except TP+PZ confirming the ability of TP+PZ to control liver metastasis. In a previous dose-response study, the daily dose of oral metronomic Topotecan (0.5, 1.0, and 1.5 mg/kg) causes greater reduction in microvascular density compared with weekly maximum-tolerated dose regimen (7.5 and 15 mg/kg) in an ovarian cancer model, but the mice treated with 1.5 mg/kg daily, oral Topotecan show decreased food intake, and a lesser antitumor effect[2]. Cell Assay The U251, U87, GSCs-U251 and GSCs-U87 cells are seeded at a density of 2×104 cells per well in 96-well plates separately, and incubated for 24 h. Cells are administered with Shikonin and Topotecan (0.02, 0.2, 2, 20, 40 μM). After the treatment, 10 μL of cell counting kit-8 (CCK-8) is added into each well for additional 1-hour incubation at 37°C. The optical density (OD) is read with a microplate reader at 450 nm[1]. Animal Admin Mice[2] For subcutaneous xenograft studies, we used SK-N-BE, SH-SY5Y, KHOS, and RH30. 1×106 cells are implanted subcutaneously into the inguinal fat pad of each of nonobese diabetic/severe combined immune deficient (NOD/SCID) mice. When tumors reached 0.5 cm in diameter, the animals are randomized into 4 groups and treated daily by oral gavage. The animals are grouped as: Control group, LDM Topotecan group or LDM TP (1 mg/kg Topotecan), Pazopanib group or PZ (150 mg/kg Pazopanib) and combination group or TP+PZ (1 mg/kg Topotecan+150 mg/kg Pazopanib). To compare pulse Topotecan with LDM TP in KHOS osteosarcoma model, PZ is replaced by weekly oral dose of pulse Topotecan (SKF104864) or Pulse TP (15 mg/kg Topotecan (SKF104864)). The criteria for endpoint are tumor sizes exceeding 2.0 cm in diameter or animals showing signs of morbidity. The tumor sizes are measured on a daily basis until the endpoint or sacrifice. The long (D) and short diameters (d) are measured with calipers. Tumor volume (cm3) is calculated as V=0.5×D×d2. When the endpoint is reached or at the end of the treatment, the animals are sacrificed by cervical dislocation. References [1]. Zhang FL, et al. PLoS One. 2013 Nov 26;8(11):e81815.Topoisomerase I inhibitors, Shikonin and Topotecan, inhibit growth and induce apoptosis of glioma cells andglioma stem cells. [2]. Kumar S, et al. Metronomic oral topotecan with pazopanib is an active antiangiogenic regimen in mouse models of aggressive pediatric solid tumor. Clin Cancer Res. 2011 Sep 1;17(17):5656-67. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 782.9±60.0 °C at 760 mmHg Melting Point −114 °C(lit.) Molecular Formula C23H23N3O5 Molecular Weight 421.446 Flash Point 427.3±32.9 °C Exact Mass 421.163757 PSA 104.89000 LogP 1.08 Vapour density 1.3 (vs air) Vapour Pressure 0.0±2.8 mmHg at 25°C Index of Refraction 1.734 InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N SMILES CCC1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1 Storage condition 2-8°C Water Solubility H2O: soluble |
| Use of | Properties Name topotecan Synonym More Synonyms Topotecan hydrochloride hydrate Biological Activity Related Catalog Signaling Pathways >> Autophagy >> Autophagy Research Areas >> Cancer Topoisomerase I References [1]. Zhang FL, et al. PLoS One. 2013 Nov 26;8(11):e81815.Topoisomerase I inhibitors, Shikonin and Topotecan, inhibit growth and induce apoptosis of glioma cells andglioma stem cells. [2]. Kumar S, et al. Metronomic oral topotecan with pazopanib is an active antiangiogenic regimen in mouse models of aggressive pediatric solid tumor. Clin Cancer Res. 2011 Sep 1;17(17):5656-67. Chemical & Physical Properties Molecular Formula C23H23N3O5 Exact Mass 421.163757 PSA 104.89000 Vapour density 1.3 (vs air) Index of Refraction 1.734 InChIKey UCFGDBYHRUNTLO-QHCPKHFHSA-N Water Solubility H2O: soluble |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
| Related Products in API & Advanced Intermediates | ||
|---|---|---|
| Tiotropium bromide | 136310-93-5 | 2A-9012740 |
| Tiotropium bromide hydrate | 139404-48-1 | 2A-9012741 |
| Tipranavir | 17484-41-4 | 2A-9012744 |
| Tobramycin Base | 32986-56-4 | 2A-9012756 |
| Topiramate | 97240-79-4 | 2A-9012778 |
| Topotecan hydrochloride | 119413-54-6 | 2A-9012780 |
| Trandolapril | 87679-37-6 | 2A-9012794 |
| Trandolaprilat | 87679-71-8 | 2A-9012795 |
| Triamcinolone hexacetonide | 5611-51-8 | 2A-9012811 |
| Trimethoprim | 738-70-5 | 2A-9012849 |
| Browse all API & Advanced Intermediates products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS