40093-94-5

Basic information

• Product Name: 2'-DEOXY-L-CYTIDINE
• Synonyms: 2'-DEOXY-L-CYTIDINE;BETA-L-2'-DEOXYCYTIDINE;4-AMino-1-((2R,4R,5S)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidin-2(1H)-one;L-2'-deoxycytidine
• CAS NO: 40093-94-5
• Molecular Formula: C₉H₁₃N₃O₄
• Molecular Weight: 227.22
• Mol File: 40093-94-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 497.6 °C at 760 mmHg
• Flash Point: 254.8 °C
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 5.47E-12mmHg at 25°C
• Refractive Index: 1.719
• PKA: 14.03±0.60(Predicted)
• CAS DataBase Reference: 2'-DEOXY-L-CYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-DEOXY-L-CYTIDINE(40093-94-5)
• EPA Substance Registry System: 2'-DEOXY-L-CYTIDINE(40093-94-5)

Safety Data

• Hazardous Substances Data: 40093-94-5(Hazardous Substances Data)

Usage

Description

2'-Deoxy-L-cytidine, also known as L-dC or Torcitabine, is the β-L-enantiomer of the natural nucleoside D-cytidine. It is a promising antiviral agent that is currently under development for the treatment of chronic hepatitis B virus (HBV) infection. The drug has poor oral bioavailability, but its prodrug, valtorcitabine, has excellent oral bioavailability and has replaced torcitabine in clinical development.

Uses

Used in Antiviral Applications:
2'-Deoxy-L-cytidine is used as an antiviral agent for the treatment of chronic HBV infection. It has undergone preliminary phase I/II clinical trials in HBeAg-positive patients, initially as the 3u,5u-divalyl prodrug in escalating doses of 50, 100, 200, and 400 mg/day. Later, it was administered as the more stable monovaline ester form, valtorcitabine dihydrochloride, to four cohorts in doses of 300, 600, 900, and 1200 mg/day for 28 days.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2'-deoxy-L-cytidine is used as a key compound in the development of new antiviral drugs. Its prodrug, valtorcitabine, has shown excellent oral bioavailability, making it a more viable option for clinical development and potential treatment of chronic hepatitis B virus infection.

InChI:InChI=1/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m1/s1

Upstream product

• 951-77-9 2'-Deoxycytidine 
• 31615-99-3 3',5'-dibenzoyl-2'-deoxy-β-L-uridine 
• 219642-22-5 C₂₄H₂₀N₆O₆ 
• 219642-23-6 C₂₃H₂₁N₃O₆ 

Downstream Products

• 141771-76-8 5'-O-(dimethoxytrityl)-4-N-benzoyl-2'-deoxy-L-cytidine 
• 951-77-9 2'-Deoxycytidine 

Relevant articles and documents

The synthesis of 2'-deoxy-L-cytidine-3'-phosphate

Improvements in the synthesis of 2'-deoxy-L-cytidine-3'-phosphate from L-arabinose are described.