Irinotecan
Irinotecan
CAS: 97682-44-5
Molecular Formula: C33H38N4O6
Irinotecan - Names and Identifiers
| Name | Irinotecan |
| Synonyms | DQ-2805 SN-38-11 Irinotecan Irinotecan base Irinotecan(TECANS) Irinotecan Free Base Irinotecan (free Base) |
| CAS | 97682-44-5 |
| EINECS | 691-567-9 |
| InChI | InChI=1/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1 |
Irinotecan - Physico-chemical Properties
| Molecular Formula | C33H38N4O6 |
| Molar Mass | 586.68 |
| Density | 1.40±0.1 g/cm3(Predicted) |
| Melting Point | 222-223° |
| Boling Point | 873.4±65.0 °C(Predicted) |
| Solubility | Soluble in acidic solvents, insoluble in petroleum ether, chloroform, dichloromethane. |
| Appearance | Pale yellow crystal |
| Color | White to Brown |
| pKa | 11.20±0.20(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| MDL | MFCD01862255 |
| Physical and Chemical Properties | Irinotecan hydrochloride is light yellow powder with a melting point of 222~223 ℃. Very light yellow needle crystal or crystalline powder obtained from water with melting point of 256.5 ℃. [α]D20 +67.7 (C = 1, water). UV maximum absorption (ethanol):221,254,359,372nm(ε53800,36600,26200,25300). The Ph value of 2% aqueous solution is 4. Acute toxic LD50 mice (rng/kg):177.5 intraperitoneal injection, 765.3 oral. |
| Use | Antineoplastic drugs. It is a DNA synthesis inhibitor. Is a semi-synthetic derivative of camptothecin; Used for the preparation of irinotecan hydrochloride and irinotecan hydrochloride trihydrate; Anticancer drug. |
Irinotecan - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| RTECS | DW1061000 |
Irinotecan - Nature
Open Data Verified Data
light yellow powder, melting point 222-223 °c. Soluble in water, methanol, chloroform, dichloromethane and other solvents. UV absorption maximum (ethanol):221nm,254nm, 359nm, 372nm(e 36600,26200,25300). The pH value of 2% aqueous solution was 4.
Last Update：2025-06-10 22:55:16
Irinotecan - Preparation Method
Open Data Verified Data
preparation from camptothecin.
Last Update：2025-06-10 22:55:16
Irinotecan - Application
Open Data Verified Data
developed by yamult Honsha, Japan, was first launched in Japan in 1994. Antineoplastic drugs. It is a DNA synthesis inhibitor. Is a semi-synthetic derivative of camptothecin.
Last Update：2025-08-19 16:24:40
Irinotecan - Safety
Open Data Verified Data
LD50 mice (mg/kg):177.5 intraperitoneal injection, 765.3 by mouth.
Last Update：2025-06-10 22:55:16
Irinotecan - Reference Information
| Overview | Large-scale clinical reports show that irinotecan hydrochloride is effective for a variety of tumors such as colon cancer, small cell lung cancer, rectal cancer, leukemia and so on have obvious inhibitory effect, and the case of fluorouracil resistance is still effective. Therefore, irinotecan hydrochloride has attracted worldwide attention. |
| Use | antineoplastic agent. It is a DNA synthesis inhibitor. Is a semi-synthetic derivative of camptothecin. anticancer drugs. Anti-tumor drugs. It is a DNA synthesis inhibitor. Is a semi-synthetic derivative of camptothecin; Used for the preparation of irinotecan hydrochloride and irinotecan hydrochloride trihydrate; Anticancer drug. A camptothecin analog, a topoisomerase I inhibitor. Irinotecan is a camptothecin analog and topoisomerase I inhibitor. It may inhibit AChE. It is uesed to treat colon cancer, but it also moderates inhibition of dendritic cell differentiation and decreases the number of tumor vessels in glioma models. |
| production method | Camptothecin (I) is used as a raw material. (I)(1.00g,2.9 mmol) was suspended in 1.1 ml of water containing FeSO4 · 7H2O (Mg, mmol) and 2ml of propionaldehyde, and 11ml of concentrated sulfuric acid was added dropwise under cooling in an ice bath. 30% hydrogen peroxide (6.4 mg, mmol) was added with stirring. After stirring for a further 3H at room temperature, the mixture was diluted with water and extracted with chloroform (3 x 100ml). The extract was concentrated and the residue was passed through a silica gel column eluting with 2% methanol-chloroform. 7-ethylcamptothecin (II) was obtained as pale yellow needle-like crystals, yield 77%, melting point 258~261 ℃. Compound (II)(3.00g,8.0 mmol) and 50ml of 30% hydrogen peroxide were heated in 3.5 ml of acetic acid at 70-80 °c for 1 h. The reaction was concentrated to 1/3 volume at 45-55 °c and the residue was poured into 3L of ice water. The precipitated precipitate was collected by filtration and purified by recrystallization to give 78% G of 7-ethylcamptothecin -1-oxygen (III) in orange-yellow needle-like crystals with a yield of 255 and a melting point of °c. Compound (III)(1.00g,2.6 mmol) and 1 mol/L sulfuric acid were dissolved in 1L dioxane and bubbled with nitrogen for 20min. With stirring, a high-pressure mercury lamp (450W,Usio UM-452) with a Pyrex filter was irradiated for 30 minutes. The reaction solution was concentrated to dryness, and the residue was dissolved in 50ml of 10% methanol-chloroform. The solution was washed with 500ml of water, and both the organic layer and the inorganic layer were passed through a column filled with a Celite. The insolubles in both phases were adsorbed thereon and then eluted with 10% methanol-chloroform (3 x 200 ml). After the eluate was concentrated, the residue was washed with methanol and recrystallized to give 49% G of 7-ethyl-10-hydroxycamptothecin (IV) as pale yellow needle-like crystals with a yield of 216 and a melting point of °c. Compound (IV)(5.00g,12.8 mmol) was dissolved in 10L of dioxane and 50ml of triethylamine, and phosgene (produced by 3.75ml of diphosgene acting on activated carbon) was introduced under stirring at room temperature, and stirring was continued for 1 hour. After filtration, the filtrate was concentrated under reduced pressure. The residue was immersed in acetone and filtered to obtain 90.0% G of compound (V) as a colorless powder. Compound (V)(3.0g) The mixture was dissolved in a mixture of dichloromethane-methanol (500ml-150 ml) and pyridine (15ml), and a two-fold solution of compound (VI) in dichloromethane was added dropwise with stirring. After addition, stirring was continued for 15h at room temperature. It was concentrated to dryness under reduced pressure, and the residue was dissolved in dichloromethane, washed with 7% sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. Filtration and evaporation under reduced pressure. The residue was chromatographed on a silica gel column, eluting with 4% methanol-dichloromethane. The product was obtained as a light yellow powder with a yield of 79.8% and a melting point of 222-223 °c. It is also possible to convert the compound (V1) to the acyl chloride (VII) and then to condense with (IV). The procedure was as follows. Compound (VI)(60g) was dissolved in benzene and Diphosgene (50 ml) was added dropwise below 10 °c under stirring and nitrogen atmosphere. Benzene solution. After addition, stirring was continued for 1H at room temperature. The precipitated precipitate was collected by filtration and dissolved in methylene chloride. The solution was washed with a 7% sodium bicarbonate solution and dried over anhydrous magnesium sulfate. Filtration, concentration to dryness under reduced pressure and the residue was passed through a silica gel column, eluting with dichloromethane-acetone (500:1). Compound (VII) was obtained. Compound (IV) and 1.1-fold compound (VII) were dissolved in pyridine and stirred for 15h at room temperature. It was concentrated to dryness under reduced pressure, the residue was dissolved in dichloromethane, and 7% sodium bicarbonate solution was added and shaken. The organic layer was separated and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The product was obtained after chromatography of the residue on a silica gel column (eluent methanol-chloroform, 1:20). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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