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Structure of Irinotecan HCl Trihydrate
CAS No.: 136572-09-3
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CAS No. : | 136572-09-3 |
Formula : | C33H45ClN4O9 |
M.W : | 677.18 |
SMILES Code : | O=C(N1CCC(N2CCCCC2)CC1)OC3=CC=C4N=C5C(CN6C(C(COC([C@@]7(CC)O)=O)=C7C=C65)=O)=C(CC)C4=C3.[H]Cl.[H]O[H].[H]O[H].[H]O[H] |
Synonyms : |
CPT-11 hydrochloride trihydrate; Irinotecan(hydrochloride hydrate); CPT-11 HCl Trihydrate
|
MDL No. : | MFCD01765731 |
InChI Key : | KLEAIHJJLUAXIQ-JDRGBKBRSA-N |
Pubchem ID : | 60837 |
GHS Pictogram: | ![]() |
Signal Word: | Danger |
Hazard Statements: | H301 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Description |
Irinotecan hydrochloride trihydrate ((+)-Irinotecan hydrochloride trihydrate), a potent topoisomerase I inhibitor, exhibits antitumor properties[1].
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Target |
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In Vitro:
Cell Line
| Concentration | Treated Time | Description | References |
C2C12 cells | 50 μg/mL | 1 h | To evaluate the effect of SR12343 on FOLFIRI-induced markers of cellular senescence. SR12343 significantly reduced the expression levels of p53, p21, Tnfa, and Il1a. | PMC10906225 |
HT-29 | 20 µM | 1.5 h | To investigate the effects of irinotecan alone or in combination with 5-FU on the growth, metabolic activity, proliferation, and clonogenic survival of HT-29 cells. Results showed that irinotecan alone or in combination with 5-FU significantly inhibited the growth, metabolic activity, and clonogenic survival of HT-29 cells, and significantly increased the radiosensitivity of tumor cells. | PMC10299222 |
EC-109 | 0–125 μM | 48 h | To evaluate the inhibitory effect of Irinotecan on the proliferation of EC-109 cells, the results showed that Irinotecan significantly inhibited cell proliferation at micromolar concentrations. | PMC5981453 |
KYSE-450 | 0–125 μM | 48 h | To evaluate the inhibitory effect of Irinotecan on the proliferation of KYSE-450 cells, the results showed that Irinotecan significantly inhibited cell proliferation at micromolar concentrations. | PMC5981453 |
LAN-1 | 100, 10, 1 nM | 72 h | To study the cytotoxicity of SN-38, results showed that all SN-38-loaded NPs retained activity in the low nanomolar concentration range | PMC5564453 |
HeLa | 100, 10, 1 nM | 72 h | To study the cytotoxicity of SN-38, results showed that all SN-38-loaded NPs retained activity in the low nanomolar concentration range | PMC5564453 |
293T cells | 10 µM | 24 h | Increased the proportion of cells in S and G2/M phases, promoting CRISPR/Cas9-mediated homology-directed repair (HDR) efficiency | PMC10676593 |
BHK-21 cells | 1-10 µM | 48 h | Dose-dependent increase in dsDNA and ssODN-mediated knock-in (KI) efficiency | PMC10676593 |
pig fetal fibroblasts (PFFs) | 1-10 µM | 48 h | Dose-dependent increase in knock-in (KI) efficiency | PMC10676593 |
SW480 cells | 10 μM | 48 h | To evaluate the effect of Irinotecan on SW480 cells, results showed decreased cell viability after Irinotecan treatment. | PMC6947904 |
U87 cells | 10 μM | 72 h | Irinotecan showed anti-GBM activity in U87 cells with an IC50 value lower than other compounds. | PMC3898565 |
SK72 cells | 30 μM | Irinotecan showed anti-GBM activity in SK72 cells with an IC50 value of 30 μM. | PMC3898565 |
In Vivo:
Species
| Animal Model
| Administration | Dosage | Frequency | Description | References |
Mice | C57BL/6J mice | Intraperitoneal injection | 24 mg/kg | 3 times per week for 9 weeks | To evaluate the effect of FOLFIRI on, lean mass, and fat mass in mice. FOLFIRI significantly reduced, lean mass, and fat mass, and increased the expression of markers of cellular senescence. | PMC10906225 |
Mice | C57BL/6 mice | Intravenous injection | 40 mg/kg | Every 3 or 4 days for 4 to 6 administrations | In the orthotopic MC38 tumor model, the Ir-silicasome demonstrated improved pharmacokinetics and tumor drug content compared to free drug and Onivyde?, significantly enhancing therapeutic efficacy, prolonging survival, and reducing bone marrow and gastrointestinal toxicity. | PMC6554030 |
BALB/c nude mice | subcutaneous xenograft model | intraperitoneal injection | 5 mg/kg | twice per week, for approximately 50 days | To study the role of eIF3a in irinotecan sensitivity in vivo, it was found that eIF3a silencing significantly increased tumor resistance to irinotecan. | PMC9055905 |
NOD/SCID mice | ESCC cell line xenograft models | Intraperitoneal injection | 8 mg/kg | Twice a week for 3 weeks | To evaluate the antitumor effect of Irinotecan in ESCC xenograft models, the results showed that Irinotecan significantly inhibited tumor growth, but the effect was inferior to Gimatecan. | PMC5981453 |
pig | pig embryos | embryo injection | 5 µM | single injection, incubated for 6 days | Significantly increased knock-in (KI) frequency in pig embryos without impairing embryo development | PMC10676593 |
Nude mice | U87 cell subcutaneous xenograft model | Intraperitoneal injection | 0.5 mg/kg | Once daily for 5 days, followed by 2 days off | The combination of irinotecan with pitavastatin significantly inhibited tumor growth with lower toxicity. | PMC3898565 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT00483834 | Colorectal Cancer | Phase 2 | Completed | - | Canada, Ontario ... More >> Princess Margaret Hospital Toronto, Ontario, Canada, M5G 2M9 Less << |
NCT03245450 | Refractory or Recurrent Solid ... More >>Tumors Rhabdomyosarcoma Non-Rhabdomyosarcoma Soft Tissue Sarcoma Ewing Sarcoma Less << | Phase 1 Phase 2 | Recruiting | June 30, 2021 | Germany ... More >> Uniklinik RWTH Aachen Kinderklinik Recruiting Aachen, Germany Charite Virchow Kinderklinik - CC17 Recruiting Berlin, Germany Uniklinik Essen AoR Kinderklinik Recruiting Essen, Germany Klinik fur Kinder und Jugendmed - KKJM Recruiting Frankfurt, Germany Uniklinik Freiburg Kindermedizin Klinik IV Recruiting Freiburg, Germany Uniklinik Gottingen Kindermedizin Recruiting Gottingen, Germany Kinderklinik Muenchen Schwabing Not yet recruiting Muenchen, Germany Less << |
NCT02015754 | Colorectal Cancer | Phase 2 | Completed | - | United States, Maryland ... More >> The Johns Hopkins Hospital Baltimore, Maryland, United States, 21287 Less << |
NCT03175016 | Colon Cancer Liver Metastasis | Phase 2 Phase 3 | Recruiting | December 2019 | China, Tianjin ... More >> Tianjin Medical University Cancer Institute and Hospital Recruiting Tianjin, Tianjin, China, 300060 Contact: Zhi Guo, MD 13920076145 cjr.guozhi@vip.163.com Contact: Xueling Yang, MD 15620930669 yxueling123@163.com Sub-Investigator: Wenge Xing Less << |
NCT00540943 | Neoplasms, Colorectal | Phase 1 | Completed | - | France ... More >> GSK Investigational Site Saint Herblain, France, 44805 GSK Investigational Site Toulouse, France, 31052 Less << |
NCT00003225 | Colorectal Cancer | Phase 1 Phase 2 | Completed | - | United States, California ... More >> Jonsson Comprehensive Cancer Center, UCLA Los Angeles, California, United States, 90095-1781 Wilshire Oncology Medical Group, Inc. Rancho Cucamonga, California, United States, 91730 Less << |
NCT01494506 | Metastatic Pancreatic Cancer | Phase 3 | Completed | - | - |
NCT00393094 | High-Grade Gliomas | Phase 2 | Terminated(Terminated due to t... More >>he limitations of accrual.) Less << | - | United States, Maryland ... More >> National Institutes of Health Clinical Center, 9000 Rockville Pike Bethesda, Maryland, United States, 20892 Less << |
NCT01494506 | - | Completed | - | - | |
NCT02015754 | - | Completed | - | - | |
NCT00004919 | Unspecified Childhood Solid Tu... More >>mor, Protocol Specific Less << | Phase 1 | Completed | - | United States, California ... More >> COG Phase I Consortium Arcadia, California, United States, 91006-3776 Less << |
NCT00393094 | - | Terminated(Terminated due to t... More >>he limitations of accrual.) Less << | - | - | |
NCT00693719 | Breast Cancer | Phase 2 | Completed | - | United States, Arizona ... More >> Arizona Cancer Center at University of Arizona Health Sciences Center Tucson, Arizona, United States, 85724-5024 Less << |
NCT00160875 | Esophageal Cancer | Phase 2 Phase 3 | Completed | - | Canada, Ontario ... More >> University Health Network Toronto, Ontario, Canada, M5G 2M9 Less << |
NCT00693719 | - | Completed | - | - |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() | 1mg | 5mg | 10mg |
1 mM 5 mM 10 mM | 1.48mL 0.30mL 0.15mL | 7.38mL 1.48mL 0.74mL | 14.77mL 2.95mL 1.48mL |
Tags: Irinotecan hydrochloride | (+)-Irinotecan hydrochloride | CPT-11 hydrochloride | Topoisomerase | topoisomerase I inhibitor | SN-38 | DNA unwinding | apoptosis | 136572-09-3
Precautionary Statements-General | |
Code | Phrase |
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P102 | Keep out of reach of children. |
P103 | Read label before use |
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
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P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
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P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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