| Identification | More | [Name]
Irinotecan hydrochloride trihydrate | [CAS]
136572-09-3 | [Synonyms]
[1,4'-BIPIPERIDINE]-1'-CARBOXYLIC ACID (S)-4,11-DIETHYL-3,4,12,14-TETRAHYDRO-4-HYDROXY-3,14-DIOXO-1H-PYRANO[3',4',6,7]INDOLIZINO[1,2-B]QUINOLIN-9-YL ESTER, HCL TRIHYDRATE
IRINOTECAN HCL TRIHYDRATE
IRINOTECAN HYDROCHLORIDE TRIHYDRATE
IRINOTECAN MONOHYDROCHLORIDE TRIHYDRATE
(s)-[1,4'-bipiperidine]-1'-carboxylic acid 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester hydrochloride trihydrate
(1,4’-bipiperidine)-1’-carboxylicacid,4,11-diethyl-3,4,12,14-tetrahydro-4-hyd
roxy-3,14-dioxo-1h-pyrano(3’,4’:6,7)indolizino(1,2-b)quinolin-9-ylester,mono
trihydrate,(s)-hydrochlorid
Irinotecan Hydrochlorid
Irinotecanhydrochloridetrihydrate(CPT-11)
IRINOTECON HCL TRIHYDRATE
(S)-[1,4'-Bipiperidine]-1'-carboxylic acid 4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester hydrochloride trihydrate | [EINECS(EC#)]
603-967-2 | [Molecular Formula]
C33H45ClN4O9 | [MDL Number]
MFCD01765731 | [Molecular Weight]
677.18 | [MOL File]
136572-09-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
250-256°C (dec.) | [Boiling point ]
257°C(lit.) | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO (up to 50 mg/ml), in Water (up to 4 mg/ml) or in Ethanol (up to 4 mg/ml). | [form ]
White solid. | [color ]
Yellow | [Water Solubility ]
Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming | [Merck ]
14,5091 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO, ethanol or distilled water may be stored at -20° for up to 3 months. | [InChIKey]
KLEAIHJJLUAXIQ-VRWBIZLENA-N | [SMILES]
N1(C2CCN(C(OC3C=CC4C(C=3)=C(CC)C3CN5C(C=3N=4)=CC3[C@](CC)(O)C(=O)OCC=3C5=O)=O)CC2)CCCCC1.[H]Cl.[H]O[H].[H]O[H].[H]O[H] |&1:24,r| | [CAS DataBase Reference]
136572-09-3(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Synthesis]
(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4';6,7]indolo[1,2-b]quinolin-9-yl[1,4'-bipiperidin]-1'-carboxylic acids were synthesized using (S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3. 4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidin]-1'-carboxylate trihydrate in the following general procedure: irinotecan hydrochloride (4.8 g), water (30 mL), ethanol (10 mL), and 5% hydrochloric acid solution (0.3 mL) were added to the reaction flask. The reaction mixture was heated to 75-80°C with continuous stirring until complete dissolution. Subsequently, the solution was cooled to 65°C and crystallization was induced by the addition of crystal seeds. The rate of cooling was controlled so that the solution was slowly cooled to 50 °C over 10 hours and then continued to 20 °C over the next 10 hours. Upon completion of crystallization, the solid product was collected by filtration and washed with pure water (16 mL). The resulting product was dried at room temperature and under atmospheric pressure to give 4.6 g of irinotecan hydrochloride trihydrate in 87% yield. The purity of the product was 99.9% by high performance liquid chromatography (HPLC). The structure of the product was confirmed by X-ray diffraction and infrared spectroscopy (IR) analysis to be consistent with form b as described in WO 03/074527. Microscopic observation showed that the average length of the crystals ranged from 50 μm to 200 μm. references: [1] Patent: WO2006/84941, 2006, A2. Location in patent: Page/Page column 6 [2] Patent: WO2006/84941, 2006, A2. Location in patent: Page/Page column 5-6 |
| Safety Data | Back Directory | [Risk Statements ]
22 | [Safety Statements ]
20/21-22 | [RTECS ]
DW1060750 | [HS Code ]
29349990 | [Toxicity]
dog,LD50,intravenous,40mg/kg (40mg/kg),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995. |
| Hazard Information | Back Directory | [Hazard]
Moderately toxic by ingestion. | [Description]
Irinotecan (136572-09-3) is a semi-synthetic derivative of camptothecin (Cat.# 10-1041) that is an FDA approved anticancer drug. It is a prodrug that is converted by tissue esterases to 7-ethyl-10-hydroxycamptothecin (SN-38, Cat.# 10-2425), a potent inhibitor of DNA topoisomerase I.1,2 Although irinotecan is also a topoisomerase inhibitor, SN-38 is approximately 1000 times as potent in purified enzyme studies. In vitro cytotoxicity assays show much greater variability in potency between the two (2-2000 fold).3 | [Chemical Properties]
White powder | [Uses]
A DNA topoisomerase inhibitor. | [Definition]
ChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine
based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. | [Brand name]
Camptosar (Pharmacia &Upjohn)
. | [References]
1) Kunimoto et al. (1987) Antitumor activity of 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy-camptothecin, a novel water-soluble derivative of camptothecin against murine tumors; Cancer Res., 47 5944
2) Mathijssen et al., (2002) Pharmacology of topoisomerase I inhibitors irinotecan (CPT-11) and topotecan; Curr. Cancer Drug Targets, 253 5892
3) Pfizer drug insert |
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