Name | Topotecan Hydrochloride |
Synonyms | Hycamtin HYDROCHLORIDE Topotecan HCl Topotecan Hydrochloride topetecan hydrochloride Nogitecan hydrochloride 5-PIPERAZIN-1-YL-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER 9-[(DIMETHYLAMINO)METHYL]-10-HYDROXY-(20S)-CAMPTOTHECIN, HCL (4S)-10-[(DIMETHYLAMINO)METHYL]-4-ETHYL-4,9-DIHYDROXY-1H-PYRANO[3',4',6-7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H,12H)-DIONE (4S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[346-7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, Hydrochloride, SKF-104864A, |
CAS | 119413-54-6 |
EINECS | 601-607-9 |
InChI | InChI=1/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 |
Molecular Formula | C23H24ClN3O5 |
Molar Mass | 457.91 |
Density | 1.49g/cm3 |
Melting Point | 213-218°C |
Boling Point | 782.9°C at 760 mmHg |
Flash Point | 427.3°C |
Solubility | H2O : 50 mg/mL (109.19 mM; Need ultrasonic);DMSO : 25 mg/mL (54.60 mM; Need ultrasonic |
Vapor Presure | 8.13E-26mmHg at 25°C |
Appearance | White to light yellow (Solid) |
Color | White to Off-White |
Storage Condition | Sealed in dry,Room Temperature |
Stability | Hygroscopic |
Refractive Index | 1.733 |
MDL | MFCD00866235 |
Use | Used as an antineoplastic agent |
Hazard Symbols | T - Toxic |
Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R46 - May cause heritable genetic damage |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
HS Code | 29420000 |
Reference Show more | 1. Yang, Hui, et al. "Intestinal absorption mechanisms of araloside A in situ single-pass intestinal perfusion and in vitro Caco-2 cell model." Biomedicine & Pharmacotherapy 106 (2018): 1563-1569.https://doi.org/10.1016/j.biopha.2018.07.117 2. Yi, Bo, and Huifang Shen. "Facile fabrication of crack-free photonic crystals with enhanced color contrast and low angle dependence." Journal of Materials Chemistry C 5.32 (2017): 8194-8200.https://doi.org/10.1039/C7TC01549F 3. He, Baoshan, et al. "Aptamer-based thin film gold electrode modified with gold nanoparticles and carboxylated multi-walled carbon nanotubes for detecting oxytetracycline in chicken samples." Food chemistry 300 (2019): 125179.https://doi.org/10.1016/j.foodc 4. [IF=5.34] Dong Shao et al."Identification of the active compounds and functional mechanisms of Jinshui Huanxian formula in pulmonary fibrosis by integrating serum pharmacochemistry with network pharmacology."PHYTOMEDICINE. 2022 Jul;102:154177 |
anti-tumor drug | topotecan hydrochloride is a water-soluble camptothecin derivative, which is a hydrochloride form of topotecan. It was successfully developed by SmithKline Beecham Company of the United States. In 1996, the FDA approved it to be listed in the United States under the trade name Hycamtin. It is a second-line therapeutic drug for the treatment of ovarian cancer (OVC). In 1999, the U.S. Food and Drug Administration (FDA) approved topotecan hydrochloride as a therapeutic drug for small cell lung cancer (SCLC), which has been listed in dozens of countries and regions such as the United Kingdom, Germany, and France. Phase III clinical trials for the treatment of non-small cell lung cancer, cervical cancer, and myelodysplastic syndrome are still in progress. Topotecan hydrochloride can enter the blood-brain barrier, and the effect of oral and intravenous injection is the same. The drug has low predictable bone marrow suppression toxicity, and other non-blood toxicity is mild. At present, domestic manufacturers have produced for the clinical treatment of small cell lung cancer, ovarian cancer and other tumors. Topotecan hydrochloride can inhibit the activity of topoisomerase I, which is required for DNA replication. After intravenous injection, this product is hydrolyzed in blood and excreted in urine. This product has a rapid serum clearance rate of 62L per hour, widely distributed in the body, and a half-life of about 2~3h. Preclinical tests show that this product has anti-tumor activity against all kinds of tumors. In phase I clinical trials, this product also has obvious anti-tumor effects on ovarian cancer patients who are resistant to cisplatin. |
clinical study | in a published randomized trial, 226 women with advanced ovarian cancer who failed or relapsed due to cisplatin or carboplatin were switched to this product and compared with paclitaxel. Of the 112 patients treated with topotecan hydrochloride, 22 were effective with an effective rate of 20%. Of the 114 patients treated with paclitaxel, 14 were effective with an effective rate of 12%. The average time to use this product to achieve significant improvement is 23 weeks, and the use of paclitaxel is 14 weeks. In an uncontrolled trial, of 111 women with refractory advanced ovarian cancer, 16 cases had better curative effect after medication, accounting for 14%. The curative effect lasted for an average of 16 weeks and survived for an average of 52 weeks. In a public trial, 67 patients with advanced ovarian cancer who had no effect on cisplatin and paclitaxel, 9 patients switched to this product, with an effective rate of 13%. |
adverse reactions | under a limited dose, this product can have toxic reactions such as bone marrow suppression, especially neutropenia. It also often causes thrombocytopenia and anemia, and sometimes requires transfusion of red blood cells and platelets. Nausea, vomiting, hair loss, diarrhea, abdominal pain, gastritis and weakness may also occur, but they are all mild. |
Use | Used as an anti-tumor drug A topoisomerase I inhibitor. Topocecan is a semisynthetic derivative of camptothecin with antineoplastic activity. During the S phase of the cell cycle, topotecan selectively stabilizes topoisomerase I-DNA covalent complexes, inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when complexes are encountered by the DNA replication machinery. Camptothecin is a cytotoxic quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. a topoisomerase I inhibitor with anti-cancer activity. |