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

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

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

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

Downstream Products

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

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.

Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA 1

The effect of 20-ns pulses of 193-nm laser light on aqueous solutions of purine bases, (2′-deoxy)nucleosides, and (2′-deoxy)nucleotides was investigated, and monophotonic ionization was observed. Although (deoxy)ribose and (deoxy)ribose phosphates are also ionized by 193-nm light, the photoionization of the (deoxy)nucleosides and -tides takes place predominantly (90%) at the purine moiety, due to the much higher extinction coefficients at 193 nm of the bases as compared to the (deoxy)ribose phosphates. The quantum yields of photoionization (φPl) of the purines are in the range 0.01 to 0.08, based on φ(Cl-) at 193 nm of 0.46. As shown by comparison with data obtained from pulse radiolysis, the ionized purines, i.e., the radical cations, deprotonate in neutral solution, yielding neutral radicals. The radical cation of 1-methylguanosine, produced by photoionization in oxygen-saturated aqueous solution, deprotonates with the rate constant 3.5 × 105 s-1. In the absence of oxygen, the hydrated electrons resulting from the photoionization react with the untransformed purine derivatives to yield the corresponding radical anions. As these are rapidly protonated by water (as concluded from pulse radiolysis), the photoionization in deaerated neutral solution results in two different neutral radicals: a deprotonated radical cation and a protonated radical anion.