Exatecan Intermediate 1 (CAS 110351-94-5), also known as (S)-4-Ethyl-4-hydroxy-7,8-dihydro-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione or (4S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione, is a key synthetic intermediate in the production of Exatecan (DX-8951) . This compound is also identified as a key intermediate in the synthesis of Irinotecan and other Camptothecin analogs .
Role in Exatecan and ADC Synthesis:
Exatecan is a water-soluble camptothecin analog and a non-prodrug that exhibits potent antitumor activity as a DNA topoisomerase I inhibitor . It is widely used as a cytotoxin payload in antibody-drug conjugates (ADCs) for targeted cancer therapy . Exatecan interferes with the proliferation and division of tumor cells by interacting with DNA, thereby inhibiting tumor growth . This compound serves as a critical building block (compound 6) in the multi-step synthesis of the API, introducing the tricyclic core structure essential for the drug's biological activity . Exatecan is primarily used in research for various cancers including ovarian, lung, and breast cancers .
Key Features:
-
High Purity: ≥ 98% (HPLC), meeting rigorous quality standards
-
Key Intermediate: Essential for the synthesis of Exatecan API and Camptothecin analogs
-
ADC Payload Precursor: Used in the development of antibody-drug conjugates
-
Well-characterized with available analytical data
-
Regulatory Support: Can be provided with detailed characterization data
Chemical Characteristics:
-
Molecular formula: C₁₃H₁₃NO₅
-
Molecular weight: 263.25 g/mol
-
Melting point: 183-185°C (decomp.)
-
Boiling point: 666.6±55.0 °C (Predicted)
-
Density: 1.50±0.1 g/cm³ (Predicted)
-
LogP: -0.8 to -0.94
-
pKa: 11.20±0.20 (Predicted)
-
SMILES: CCC1(C2=C(COC1=O)C(=O)N3CCC(=O)C3=C2)O
-
InChIKey: IGKWOGMVAOYVSJ-ZDUSSCGKSA-N
Applications:
-
Pharmaceutical R&D: As a key intermediate in the synthesis of Exatecan API, Irinotecan, and other Camptothecin analogs
-
ADC Development: Used as a precursor for ADC cytotoxin payloads
-
Analytical R&D: Serves as a reference standard for quality control (QC) and analytical method development (AMV)
-
Cancer Research: Used in studies involving topoisomerase I inhibition and targeted cancer therapy
-
Regulatory Submissions: Used in ANDA and DMF filings for Exatecan-related drug products
Packaging: ___ (e.g.: 1g, 5g, 10g, 25kg per package, as per customer's request)
Storage: Powder: -20°C for up to 3 years; 4°C for up to 2 years. In solvent: -80°C for 6 months; -20°C for 1 month . Recommended storage temperature: 2-8°C (Refrigerator), sealed in dry conditions