Irinotecan hydrochloride

Base Information

• Chemical Name: Irinotecan hydrochloride
• CAS No.: 100286-90-6
• Deprecated CAS: 111348-33-5
• Molecular Formula: C33H38N4O6^.HCl
• Molecular Weight: 623.149
• Hs Code.: 29399990
• European Community (EC) Number: 600-054-0
• NSC Number: 759878,616348
• UNII: 06X131E4OE
• DSSTox Substance ID: DTXSID6045953
• Wikidata: Q27106952
• NCI Thesaurus Code: C1381
• RXCUI: 153329
• Pharos Ligand ID: PZX523N3G85U
• ChEMBL ID: CHEMBL541887
• Mol file: 100286-90-6.mol

Synonyms:7 Ethyl 10 hydroxycamptothecin;7-ethyl-10-hydroxycamptothecin;Camptosar;Camptothecin 11;camptothecin-11;CPT 11;CPT-11;CPT11;irinotecan;irinotecan hydrochloride;Irrinotecan;NK012 compound;SN 38;SN 38 11;SN-38;SN-38-11;SN3811

Chemical Property of Irinotecan hydrochloride

Chemical Property:

• Appearance/Colour: Yellow crystalline powder
• Vapor Pressure: 1.31E-32mmHg at 25°C
• Melting Point: 250-256 ºC (dec.)
• Refractive Index: 67.7 ° (C=1, H2O)
• Boiling Point: 873.4 ºC at 760 mmHg
• Flash Point: 482 ºC
• PSA: 114.20000
• LogP: 4.76890
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO or DMF at approximately 20mg/ml. Sparingly solub
• Water Solubility.: Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 622.2558127
• Heavy Atom Count: 44
• Complexity: 1200

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Irinotecan Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.Cl
• Isomeric SMILES: CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7.Cl
• Recent ClinicalTrials: Risk-Based Therapy in Treating Younger Patients With Newly Diagnosed Liver Cancer
• Recent EU Clinical Trials: EXPLOITING CIRCULATING TUMOUR DNA TO INTENSIFY THE POST-OPERATIVE TREATMENT OF STAGE III AND HIGH-RISK STAGE II RESECTED COLON CANCER PATIENTS WITH ADJUVANT FOLFOXIRI AND/OR POST-ADJUVANT TRIFLURIDINE/TIPIRACIL.
• Recent NIPH Clinical Trials: Phase II Clinical Trial of Monotherapy with Irinotecan Hydrochloride (CPT-11) for Advanced or Recurrent Endometrial Cancer
• Description: lrinotecan hydrochloride, a semi-synthetic, water soluble derivative of the potent anticancer agent camptothecin, was launched in Japan for the treatment of lung, ovarian, and cervical cancers. lrinotecan exerts its antitumor activity via inhibition of topoisomerase I, a cellular enzyme that is involved in maintaining the topographic structure of DNA during the process of translation, transcription, and mitosis. lrinotecan undergoes de-esterification in vivo to yield an active metabolite, SN-38, which is 1000-fold more potent than the parent. Although being much less toxic than camptothecin, a significant number of patients in clinical trials exhibited side effects of leukopenia, diarrhea, nauseahromiting, and alopecia. Combination therapy of irinotecan with another widely used anticancer agent, cisplatin, has been reported to be superior to either agent alone. lrinotecan is in clinical trials for gastrointestinal, breast, skin, colorectal, pancreatic cancers, mesothelioma and non-Hodgkin's lymphoma.
• Uses: antineoplactic;'inhibitor of topoisomerase I Irinotecan hydrochloride has been used:in combination with 5-fluorouracil for screening growth inhibitory functionality in MDA-MB-231 breast cancer cells.in chemosensitivity screening of high-grade appendiceal (HGA) and low-grade appendiceal (LGA) organoids.as a chemotherapeutic agent in the cytotoxicity studies in combination with heat shock proteins inhibitors (HPSC1) in HT29 colon cancer cells. A DNA topoisomerase inhibitor
• Therapeutic Function: Antineoplastic
• Clinical Use: In combination with fluorouracil, this prodrug camptothecin analogue is considered to be first-line therapy in the treatment of metastatic colorectal cancer. It also has shown efficacy in small cell and nonsmall cell lung cancers when used in combination with cisplatin.
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: concentration reduced by St John’s wort - avoid. Antifungals: increased toxicity with itraconazole - avoid; concentration reduced by ketoconazole, but active metabolite of irinotecan increased - avoid. Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis). Antivirals: metabolism possibly inhibited by atazanavir (increased risk of toxicity). Cytotoxics: concentration of active metabolite of irinotecan increased by lapatinib, consider reducing dose of irinotecan; avoid with panitumumab; concentration possibly increased by sorafenib. Live vaccines: risk of generalised infections - avoid.

Technology Process of Irinotecan hydrochloride

There total 25 articles about Irinotecan hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

irinotecan (97682-44-5,130144-33-1) → irinotecan hydrochloirde (100286-90-6)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 0 ℃; for 2 - 3h; Product distribution / selectivity;

Reference yield: 90.0%

4-piperidinopiperidin (4897-50-1) + 7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) → irinotecan hydrochloirde (100286-90-6)

Guidance literature:

4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin; With triethylamine; In pyridine; dichloromethane; at 30 - 40 ℃; for 1.5h;

4-piperidinopiperidin; In pyridine; dichloromethane; for 0.5h;

Reference yield: 90.0%

4-piperidinopiperidine-1-carbonyl chloride hydrochloride (143254-82-4) + 7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) → irinotecan hydrochloirde (100286-90-6)

Guidance literature:

4-piperidinopiperidine-1-carbonyl chloride hydrochloride; 7-ethyl-10-hydroxycamptothecin; With pyridine; triethylamine; In dichloromethane; at 30 - 40 ℃; for 1.5h;

With 4-piperidinopiperidin; In dichloromethane; at 0 - 80 ℃; for 0.5h; pH=4.0;

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 20h; Product distribution / selectivity;

upstream raw materials:

irinotecan

4-piperidinopiperidin

7-ethyl-10-hydroxycamptothecin

4-piperidinopiperidine-1-carbonyl chloride hydrochloride

Downstream raw materials:

irinotecan

Refernces

• 1、 -. "Preparation method of irinotecan hydrochloride". Paragraph 0020; 0023; 0026; 0029; 0032. . Retrieved 2020/05/30.
• 2、 -. "Preparation method of irinotecan hydrochloride". Paragraph 0062; 0066. . Retrieved 2017/07/06.