ChemicalBook
Chinese Japanese Germany Korea

Irinotecan hydrochloride

Irinotecan hydrochloride
Irinotecan hydrochloride structure
CAS No.
100286-90-6
Chemical Name:
Irinotecan hydrochloride
Synonyms
CPT-II;CPT-11;campto;CTP-11;CS-1327;u10144oe;topotecin;U 101440E;IRINOTEC HCL;50MG/200MG/1KG
CBNumber:
CB8122429
Molecular Formula:
C33H39ClN4O6
Formula Weight:
623.15
MOL File:
100286-90-6.mol

Irinotecan hydrochloride Properties

Melting point:
250-256°C (dec.)
Boiling point:
257 °C
refractive index 
67.7 ° (C=1, H2O)
storage temp. 
2-8°C
solubility 
Soluble in DMSO or DMF at approximately 20mg/ml. Sparingly soluble in aqueous buffers. /n
Water Solubility 
Soluble in DMSO at 100mg/ml. Soluble in water at 25mg/ml with warming
Merck 
5091
CAS DataBase Reference
100286-90-6(CAS DataBase Reference)
FDA UNII
042LAQ1IIS
NCI Dictionary of Cancer Terms
irinotecan hydrochloride
NCI Drug Dictionary
irinotecan hydrochloride
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312a-P330-P501a
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  DW1060750
HS Code  29399990

Irinotecan hydrochloride price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I1406 Irinotecan hydrochloride topoisomerase inhibitor 100286-90-6 50mg $162 2021-03-22 Buy
Sigma-Aldrich I1406 Irinotecan hydrochloride topoisomerase inhibitor 100286-90-6 250mg $578 2021-03-22 Buy
Alfa Aesar J60743 Irinotecan hydrochloride 100286-90-6 250mg $693 2020-06-24 Buy
Alfa Aesar J60743 Irinotecan hydrochloride 100286-90-6 50mg $170 2020-06-24 Buy
Cayman Chemical 14180 Irinotecan (hydrochloride) ≥98% 100286-90-6 25mg $45 2018-11-13 Buy

Irinotecan hydrochloride Chemical Properties,Uses,Production

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.

Chemical Properties

Yellow Crystalline Powder

Originator

Yakult Honsha (Japan)

Uses

antineoplactic;'inhibitor of topoisomerase I

Uses

A DNA topoisomerase inhibitor

Definition

ChEBI: A hydrochloride obtained by combining irinotecan with one molar equivalent of hydrochloric acid. Used (in the form of its trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancr as 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.

Manufacturing Process

7-Ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin was synthesized by 2 methods.
Method 1.
7-Ethyl-10-hydroxycamptothecin (500 mg, 1.27 mmol) was suspended in dry dioxane (400 ml) and dissolved therein by adding triethylamine (2 ml) to the suspension under warming. This solution was stirred at room temperature while introducing thereinto phosgene prepared toties quoties by decomposing phosgene dimer (trichloromethoxychloroformate, 400 ml) in the presence of an active carbon catalyst. After 0.5 hours, consumption of the starting materials was confirmed and insoluble 10-chlorocarbonyloxy-7- ethylcamptothecin was removed by filtration.
10-Chlorocarbonyloxy-7-ethylcamptothecin (300 mg, 0.66 mmol) is suspended in dry dioxane (50 ml). To this suspension is added 4- piperidinopiperidine (330 mg, 1.96 mmol) as the amine, the reaction followed by the after-treatment was carried out whereby the 7-ethyl-10-[4-(1- piperidino)-1-piperidino]carbonyloxycamptothecin title compound (154 mg, 39.8%) was obtained.
Method 2.
7-Ethyl-10-hydroxycamptothecin (790 mg, 2.01 mmol) and 1-chlorocarbonyl- 4-piperidinopiperidine (910 mg, 3.95 mmol) were dissolved in anhydrous pyridine (50 ml), and the mixture was stirred for 1 hour at 20°C. The reaction mixture was evaporated to dryness in vacuo, the residue was dissolved in CHCl3 (200 ml). The solution was washed successively with a 7% aqueous solution of NaHCO3 (200 ml), a saturated aqueous solution NaCl, and the CHCl3 layer was filtered, and evaporated in vacuo. The residual material was decolorized by passing it through a short silica gel column. 7-Ethyl-10-[4-(1- piperidino)-1-piperidino]carbonyloxycamptothecin was obtained as a pale yellow mass, which was recrystallized from ethanol (ca. 60 ml) to give colorless needles (750 mg, 63.5% in yield).
To an ice-cooled suspension in distilled water (15 ml) of 7-ethyl-10-[1-(4- piperidino)piperidino]carbonyloxycamptothecin (1.00 g, 1.7 mmol) was added 0.1 N HCl (15.3 ml, 1.53 mmol), and the suspension was stirred vigorously for 5 minutes under cooling in an ice bath and filtered off. 7-Ethyl-10-[4-(1- piperidino)-1-piperidino]carbonyloxycamptothecin hydrochloride was obtained in yield 96%.

brand name

Camptosar (Pharmacia &Upjohn) ;Topotecin.

Therapeutic Function

Antineoplastic

General Description

Irinotecan is available in 100-mg or 5-mL vials for IV administrationand is used in combination with 5-FU and leucovorinas first-line treatment of metastatic colon cancer.The agent may also be used as a single agent in colorectalcancer as a second-line therapy when 5-FU therapy hasfailed. Additional uses include small cell lung cancer,NSCLC, cervical cancer, esophageal cancer, and gastric cancer Irinotecan is 30% to 60% plasma protein bound, whereasthe active metabolite SN-38 is 95% protein bound. Bindingof SN-38 as the lactone stabilizes the material to ring opening.The elimination of the agent occurs primarily in the bilewith a minor amount of renal elimination. The excretion ofactive metabolites or inactive metabolites such as the glucuronideSN-38G, which may be converted back to SN-38 inthe bile, has been associated with severe diarrhea. Irinotecanand SN-38 have half-lives of 8 and 14 hours, respectively.Irinotecan has two dose-limiting toxicities, myelosuppressionand diarrhea. The diarrhea occurs in two forms, earlyand late. The early form occurs within the first 24 hours afteradministration. It has been associated with inhibition ofacetylcholinesterase, which results in increased gut motility.This early phase is also associated with flushing, abdominalpain, and excessive sweating. Atropine can be used to relievethese symptoms but it is not recommended for prophylacticuse unless there has been a prior episode. The late-phasediarrhea occurs after 24 hours and has been associated withthe presence of active material, particularly SN-38 in the gut,and may last 3 to 10 days. The prolonged nature may lead todehydration and electrolyte imbalances. Loperamide therapyis recommended at the first appearance of a loose stool. If thediarrhea persists, additional agents may be used includingantibiotics that decrease β-glucosidase–producing bacteria inthe gut and prevent the overgrowth of pathogenic bacteria.111Other toxicities include emesis and alopecia.

Biological Activity

Inhibitor of DNA topoisomerase I that displays antitumor activity against a range of tumor types.

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.

Side effects

Delayed diarrhea induced by irinotecan is dose-limiting and potentially fatal, and vigorous loperamide therapy should be instituted at the first sign of symptoms. Acute diarrhea is attributed to the drug's ability to inhibit acetylcholinesterase and can be addressed through anticholinergic pretreatment. Pretreatment also helps patients to avoid “cholinergic syndrome,” a collection of annoying side effects that include flushing, sweating, blurred vision, lacrimation, and less commonly, bradycardia. Camptothecins also are myelosuppressive, and neutropenia can be severe, particularly in patients with elevated bilirubin levels. Extensive biotransformation also demands cautious use of irinotecan in patients with hepatic dysfunction.

Metabolism

The drug is slowly bioactivated in the liver through hydrolysis of the C10-carbamate ester. The catalyzing enzyme is a saturable carboxylesterase known as irinotecan-converting enzyme. Levels of active metabolite, known as SN-38, are 50- to 100-fold lower than the parent drug, but preferential protein binding of the lactone (95%) permits significant plasma levels of the optimally active SN-38 compared to the hydroxy acid metabolite. SN-38 has a terminal half-life of 11.5 hours (compared to 5.0–9.6 hours for the prodrug parent) and is glucuronidated at the C10 phenol before elimination. CYP3A4 also cleaves the terminal piperidine ring through oxidation at the α-carbons, followed by hydrolysis of the resultant amides, producing inactive metabolites. Excretion of the parent drug and metabolites is renal (14–37%) and, to a lesser extent, biliary.

Irinotecan hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products


Irinotecan hydrochloride Suppliers

Global( 368)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Shengda Pharma Limited
+86-755-85269922
WeChat:shengdapharm sales@shengdapharm.com CHINA 304 58
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20914 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales@fine-chemtech.com CHINA 890 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 297 58
Chengdu Biopurify Phytochemicals Ltd.
18482058008 18080483897
maggie@biopurify.com CHINA 2712 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58

Related articles


View Lastest Price from Irinotecan hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-30 Irinotecan hydrochloride
100286-90-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-11-09 Irinotecan hydrochloride
100286-90-6
US $0.00 / Kg/Bag 2Kg/Bag USP 20 tons Sinoway Industrial co., ltd.
2021-11-08 Irinotecan hydrochloride
100286-90-6
US $10.00 / KG 1KG 99.9% 100MT/Month Wuhan wingroup Pharmaceutical Co., Ltd

100286-90-6(Irinotecan hydrochloride)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved