Irinotecan

Base Information Edit

Chemical Name:Irinotecan
CAS No.:97682-44-5
Molecular Formula:C₃₃H₃₈N₄O₆
Molecular Weight:586.688
Hs Code.:
European Community (EC) Number:691-567-9
NSC Number:728073
UNII:7673326042
DSSTox Substance ID:DTXSID1041051
Nikkaji Number:J261.801J
Wikipedia:Irinotecan
Wikidata:Q412197
NCI Thesaurus Code:C62040
RXCUI:51499
Pharos Ligand ID:PZX523N3G85U
Metabolomics Workbench ID:43059
ChEMBL ID:CHEMBL481
Mol file:97682-44-5.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

Suppliers and Price of Irinotecan

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
CPT 11
10mg
$ 480.00

TRC
(+)-Irinotecan
50mg
$ 60.00

Tocris
CPT11 ≥99%(HPLC)
10
$ 229.00

Tocris
CPT11 ≥99%(HPLC)
50
$ 960.00

DC Chemicals
Irinotecan >98%
1 g
$ 500.00

CSNpharm
Irinotecan
100mg
$ 92.00

CSNpharm
Irinotecan
50mg
$ 61.00

Crysdot
Irinotecan 98+%
100mg
$ 125.00

Chemtos
IrinotecanLabeledd10
25 mg
$ 1400.00

ChemScene
Irinotecan 99.84%
50mg
$ 72.00

Total 173 raw suppliers

Chemical Property of Irinotecan Edit

Chemical Property:

Melting Point:222-223°
Boiling Point:873.4 °C at 760 mmHg
PKA:11.20±0.20(Predicted)
Flash Point:482 °C
PSA：114.20000
Density:1.4 g/cm³
LogP:3.96690
Storage Temp.:2-8°C
Solubility.:Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:586.27913494
Heavy Atom Count:43
Complexity:1200

Purity/Quality:

99.0%, ^*data from raw suppliers

CPT 11 ^*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
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
Recent ClinicalTrials:A Phase I Dose Finding Study in Children With Solid Tumors Recurrent or Refractory to Standard Therapy
Recent EU Clinical Trials:A Phase 1/2 Open-Label, Umbrella Platform Design Study of Investigational Agents With Pembrolizumab (MK-3475) in Participants With Advanced Esophageal Cancer Previously Exposed to PD-1/PD-L1 Treatment (KEYMARKER-U06): Substudy 06B.
Recent NIPH Clinical Trials:C-PROWESS study
Description Irinotecan is a pentacyclic alkaloid with the chemical name 7-ethyl-10-[4-(1-piperidino)-1-piperidino]-carbonyloxycamptothecine. It has a bis-piperidine side chain contributing to its water solubility. Irinotecan belongs to the class of topoisomerase I inhibitors and is used in cancer chemotherapy.
Uses Irinotecan, marketed under the brand names Camptosar? and Campto?, used in the treatment of various cancers, including pulmonary, pancreatic, gastric, ovarian, cervical, colorectal, and others.
Mechanism of Action Irinotecan inhibits topoisomerase I, an enzyme involved in DNA replication and transcription, leading to DNA damage and cell death in cancer cells.
Pharmacokinetics Irinotecan is metabolized by carboxylesterase (CES) in the liver, where the active metabolite SN-38 is formed and rapidly deactivated by glucuronidation. In the intestine, poor SN-38 glucuronidation leads to its accumulation, causing gastrointestinal toxicity.
History and Development Irinotecan was approved for clinical use in Japan in 1994 and later in Europe (1995) and the USA (1996). Over the years, new formulations, such as liposomal irinotecan, have been developed to improve drug delivery and reduce side effects.
Production Methods Irinotecan is a semi-synthetic analog of the camptothecin alkaloid, isolated from the Chinese tree Camptotheca acuminata. It undergoes structural changes depending on the physiological pH of the cellular environment.
References [1] Irinotecan—Still an Important Player in Cancer Chemotherapy: A Comprehensive Overview
DOI 10.3390/ijms21144919
[2] Quantitative Investigation of Irinotecan Metabolism, Transport, and Gut Microbiome Activation
DOI 10.1124/dmd.121.000476
[3] All You Need to Know About UGT1A1 Genetic Testing for Patients Treated With Irinotecan: A Practitioner-Friendly Guide
DOI 10.1200/OP.21.00624

Technology Process of Irinotecan

There total 58 articles about Irinotecan 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: 95.0%

: 103816-19-9
4-piperidinopiperidine-1-carbonyl chloride

: 86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2
7-ethyl-10-hydroxycamptothecin

: 97682-44-5,130144-33-1
irinotecan

Guidance literature:: With pyridine; acetamide; triethylamine; In dichloromethane; at 30 - 40 ℃; for 2h; Product distribution / selectivity; Inert atmosphere;