Topotecan hydrochloride Produkt Beschreibung

Topotecan hydrochloride Struktur
119413-54-6
  • CAS-Nr.119413-54-6
  • Bezeichnung:Topotecan hydrochloride
  • Englisch Name:Topotecan hydrochloride
  • Synonyma:
    108563;Hycamtin;NSC 609669;SKF-104864A;Levulan-13C;SKFS 104864A;HYDROCHLORIDE;TOPOTECAN HCL;Nogitecan HCl;5-ALA HCl-13C
  • CBNumber:CB3361775
  • Summenformel:C23H24ClN3O5
  • Molgewicht:457.91
  • MOL-Datei:119413-54-6.mol
Topotecan hydrochloride physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :213-218°C
  • storage temp.  :Sealed in dry,Room Temperature
  • Aggregatzustand :Light yellow to greenish powder.
  • CAS Datenbank :119413-54-6(CAS DataBase Reference)
Sicherheit

Topotecan hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R25:Giftig beim Verschlucken.
    R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
    R46:Kann vererbbare Schäden verursachen.
  • S-Sätze Betriebsanweisung: S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
    S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
    S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  • Chemische Eigenschaften White Crystalline Solid
  • Originator Hycamtin,SmithKline Beecham Pharmaceuticals,UK
  • Verwenden Naturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer)
  • Verwenden antineoplastic; topoisomerase I inhibitor
  • Verwenden A DNA topoisomerase I inhibitor; semisynthetic analog of Camptothecin. Antineoplastic. Topotecan hydrochloride is a chemotherapy agent that is a topoisomerase 1 inhibitor.
  • Manufacturing Process Camptothecin (CPT) - a compound isolated from the bark, leaves and fruit of Camptotheca acuminate (Wall M. E. et al., J. Am. Chem. Soc. 88, 3888, 1966).
    10-Hydroxycamptothecin (10-HCPT) was prepared by subjecting CPT (3.2 g 0.0092 mol), 0.8 g of Pt0 (prepared by pre-reduction of 8 g of amorphous PtO2 in 80 ml of acetic acid for 1.5 h under 1 atm hydrogen pressure) and acetic acid to 1 atm of H2 for 8.5 h after which theoretical amount of H2 absorbed (slightly more than 0.4 L) and uptake of H2 gets slowed down. The reaction mixture was degassed under steam of helium and filtered through celite and washed with acetic acid (20 ml). The resulting solution was treated immediately with Pb(OAc)4 (6.4 g 0.014 mol) in portions and reaction mixture, stirred vigorously under helium for 30 min. Gumy residue was obtained on evaporation of solvent which was triturated with cold water (100 ml) to produce light brown solid. The solid was collected, washed with cold water and air dried overnight when a mixture of 10-HCPT (44%), acetyl 10- hydroxycamptothecin (10-AcHCPT, 26%) and unreacted CPT (32%) on HPLC basis was obtained. This crude mixture was combined with 150 ml of 50% acetic acid and heated under reflux conditions overnight. The reaction mixture was cooled, concentrated to 20 ml and treated with cold water (100 ml) to produce precipitate, which is filtered, washed with more cold water and dried to afford 2.1 g of solid containing 10-HCPT (70%), 10-AcCPT (1.2%) and CPT (21.3%) on the basis HPLC. Mixture was triturating with 0.5% aq HCl to dissolve the water-soluble. When insoluble CPT was removed by filtration. Water-soluble was extracted with chloroform and crystallized from boiling solution of 20% of MeOH in CHCl3 by adding EtOAC dropwise until turbidity appeared to obtain pure yellow 10-(HCPT), melting point 268°-270°C. 10-HCPT (0.364 g 0.01 mmol) and 40% aqueous dimethylamine (12 ml) was added in dichloromethane (50 ml) in which anhydrous potassium carbonate (2.17 g, 15 mmol) has been suspended. The reaction mixture was stirred at room temperature for 5 h, then filtered and solid extracted with ethylacetate (20 ml). The solvent is evaporated in vacuo giving a residue. The residue was triturated with 0.5% aq HCl (50 ml) to dissolve the water-soluble adduct. Water-soluble were partitioned with petroleum ether (3 times 50 ml) and followed by ethylacetate (3 times 50 ml). The aqueous layer was lyophilized as an off white hydrochloride salt of 9-[(dimethylamino)methyl]10- hydroxy(20S)-camptothecin (topotecan hydrochloride) yield 0.236 g (65%).
  • Trademarks Topotecan is INN and BAN.
  • Therapeutic Function Antineoplastic
  • Allgemeine Beschreibung Topotecan is supplied in 4-mg vials and administered IV forthe treatment of ovarian cancer, cervical cancer, and smallcell lung cancer in those patients who did not respond tofirst-line therapy. Following IV administration, the drug iswidely distributed with 10% to 35% of the agent bound toplasma proteins. There is evidence that the agent may crossthe blood-brain barrier to some extent. In plasma, an equilibriumis established between the lactone and the less activehydroxy acid with 20% of the drug present as the lactone 1hour after the infusion is complete. In contrast to irinotecan,both the lactone and the hydroxy acid bind equally well tohuman serum albumin. N-Demethylation of the tertiaryamine to give the secondary amine is mediated by CYP3A4and represents a minor route of metabolism. Glucuronidationof the parent and the phase I metabolites also occurs to a limited(10%) extent.Elimination occurs primarily in theurine, with 30% of the dose being recovered as unchangeddrug. The terminal elimination half-life is 2 to 3 hours. Themajor toxicity seen for topotecan is dose-limiting myelosuppression.Nausea and vomiting are seen in most (70%–80%)patients, along with diarrhea and abdominal pain. Other toxicitiesinclude headache myalgias, alopecia and elevation ofserum transaminases, alkaline phosphatases, and bilirubin.Microscopic hematuria (blood in the urine) may also be seen.
  • Pharmakokinetik Topotecan elimination is biphasic, with a terminal half-life of 2.0 to 3.5 hours. Lactone hydrolysis is rapid, and binding to serum proteins is limited to between 25 and 40%. CYP3A4-mediated N-dealkylation to mono?and didealkylated metabolites occurs to a limited extent, and the O-glucuronides that form at multiple points along the metabolic path are excreted via the kidney.
  • Clinical Use This active camptothecin analogue is used by the IV route in the treatment of ovarian and small cell lung cancer that has not responded to first-line therapy.
Topotecan hydrochloride Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Topotecan hydrochloride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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119413-54-6, Topotecan hydrochloride Verwandte Suche:
  • 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
  • HYDROCHLORIDE
  • topetecan hydrochloride
  • 5-PIPERAZIN-1-YL-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER
  • (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,
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, monohydrochloride, (4S)- (9CI)
  • 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-, monohydrochloride, (S)-
  • NSC 609669
  • SKFS 104864A
  • SKF-S 104864-A
  • TOPOTECAN MONOHYDROCHLORIDE
  • TOPOTECAN HCL
  • SKF-104864A
  • Topotecan Hydrochloride(TECANS)
  • (S)-10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione monohydrochloride
  • (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 Hydrochloride
  • 1,4-di[4-(3-phenoxypropoxy)-2-butynyl]piperazine
  • 1,4-di(4-benzhydryloxy-2-butynyl)piperazine
  • 1,4-di(4-benzyloxy-2-butynyl)piperazine
  • (S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-(H-Pyrano[3' , 4':6,7]indolizino[1,2-b]quinoline-3,14[4H,12H]-dione monohydrochloride
  • Topotecan Hydrochloride(TPT)
  • S-(6-thioxo-1,6-dihydro-pyrimidin-4-yl)-isothiourea
  • Topotecan hydrochloride(NSC-609699)
  • Topotecan, Hydrochloride Salt
  • Toputecan hydrochloride
  • 2-Methyl-4-piperidino-butan-2-ol
  • Topotecan HCl (HycaMtin)
  • 3-Methoxy-5-Methyl-4-MethylaMino-heptanoic acid tert-butyl ester
  • [2-(4-Methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester
  • Topotecan hydrocloride
  • Topotecan (Nogitecan) HCl
  • (3,5-Dimethoxy-phenyl)-(1H-pyrazol-3-ylmethyl)-amine
  • (2S)-2-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanamide
  • 1,1-Dimethyl-2-(2-oxo-2-phenyl-ethyl)-isothiourea
  • Benzyl-[1-(2-chloro-ethyl)-piperidin-3-yl]-amine
  • 1-Methyl-4-(toluene-4-sulfonyl)-piperazine
  • 1-Methyl-2-(3-methyl-pyrazol-1-yl)-ethylamine
  • 4,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
  • 5-bromo-7-methoxy-1,2,3,4-tetrahydroisoquinoline-4,6-diol
  • 8-methoxy-7-methyl-3,4-dihydroisoquinoline
  • TOPOTECAN HYDROCHLORIDE 99%
  • (2R)-2-amino-3-(3-methylimidazol-4-yl)propanoic acid
  • 108563
  • 10-[(Dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione hydrochloride
  • methyl 3-methyl-2-(methylamino)butanoate
  • N-methyl-5-azaspiro(2.3)hexane-2-carboxamide
  • {3-[4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-pyrazol-1-yl]-azetidin-3-yl}-acetonitrile
  • (2S)-2-(methylamino)-3-sulfanylpropanoic acid
  • (2R)-2-(methylamino)-3-sulfanylpropanoic acid
  • 4-(2-Oxo-butyl)-benzamidine
  • 2-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-ethylamine
  • 2-(3-Fluoro-benzylsulfanyl)-ethylamine
  • C-(5-m-Tolyl-[1,3,4]oxadiazol-2-yl)-methylamine
  • C-(5-p-Tolyl-[1,3,4]oxadiazol-2-yl)-methylamine
  • C-[5-(3-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-methylamine
  • C-[5-(3-Fluoro-phenyl)-[1,3,4]oxadiazol-2-yl]-methylamine
  • C-[5-(3-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-methylamine