CAS 7481-88-1

2′,3′-Didehydro-2′,3′-dideoxycytidine

Description:

2′,3′-Didehydro-2′,3′-dideoxycytidine, commonly known as ddC, is a synthetic nucleoside analog of cytidine. It is characterized by the absence of the 2′ and 3′ hydroxyl groups on the ribose sugar, which contributes to its role as an antiviral agent, particularly in the treatment of HIV. The compound exhibits a unique mechanism of action by inhibiting reverse transcriptase, an enzyme critical for viral replication. ddC is typically administered in its phosphate form, which enhances its bioavailability and efficacy. The substance is known for its potential side effects, including peripheral neuropathy and gastrointestinal disturbances. Its chemical structure includes a pyrimidine base, which is essential for its interaction with viral RNA. Due to its specific modifications, ddC is less susceptible to degradation by cellular enzymes, allowing for prolonged activity within the body. Overall, 2′,3′-Didehydro-2′,3′-dideoxycytidine represents an important class of antiviral drugs that have significantly contributed to the management of HIV/AIDS.

Formula: C₉H₁₁N₃O₃

InChI: InChI=1/C9H11N3O3.C8H12N4O5/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8;9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h1-4,6,8,13H,5H2,(H2,10,11,14);2-5,8,13-15H,1H2,(H2,9,16)/t6-,8+;3-,4-,5-,8-/m01/s1

InChI key: InChIKey=OOBICGOWICFMIX-POYBYMJQSA-N

SMILES: O=C1N([C@@H]2O[C@H](CO)C=C2)C=CC(N)=N1

Synonyms:

• 2′-Cytidinene, 2′,3′-dideoxy-
• Cytidine, 2′,3′-didehydro-2′,3′-dideoxy-
• 2′,3′-Didehydro-2′,3′-dideoxycytidine
• 2′,3′-Dideoxycytidin-2′-ene
• Cytosine, 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-
• 2',3'-Didehydro-2',3'-dideoxycytidine
• 1-(2,3-Dideoxy-β-D-glycero-2-pentenofuranosyl)-4-aminopyrimidin-2(1H)-one
• Zalcitabine Related Compound A (2'',3''-Didehydro-2'',3''-dideoxycytidine) (1724317)
• D4C
• Zalcitabine Related Compound A(Secondary Standards traceble to USP)
• 2',3'-dideoxycytidinene
• Cytidine, 2',3'-didehydro-2',3'-dideoxy-
• Dideoxycytidinene
• 2’,3’-Dideoxy-2’,3’-didehydro-cytidine, D4C
• 2,3’-didehydro-2’,3’-dideoxy-cytidin
• Zalcitabine Related CoMpound A
• 2’,3’-Dideoxy-2’,3’-didehydro-cytidine, D4C, HIV-1 inhibitor (related compound A of Zalcitabine)
• ZALCITABINE RELATED COMPOUND A (50 MG) (2',3'-DIDEHYDRO-2',3'-DIDEOXYCYTIDINE)
• 2’,3’-dideoxy-2’,3’-didehydrocytidine

Dideoxycytidinene

CAS: 7481-88-1

Nucleoside Derivatives - Didehydro-nucleoside; Drugs and Inhibitors; Related compound A of Zalcitabine

Formula: C₉H₁₁N₃O₃

Color and Shape: Solid

Molecular weight: 209.2

Ref: TM-TNU0996

Dideoxycytidinene

Controlled Product

CAS: 7481-88-1

Stability Hygroscopic
Applications Dideoxycytidinene, can be used for the synthesis of Zalcitabine (Z140000), which is pyrimidine nucleoside analogue with antiviral activity.
References van der Vliet, P.C. and Kwant, M.M.: Biochemistry, 20, 2628 (1981), Mitsuya, H., Broder, S.: Proc. Nat. Acad. Sci. USA, 83, 1911 (1986), Starnes, M.C., and Cheng, Y.: J. Biol. Chem., 262, 988 (1987),

Formula: C₉H₁₁N₃O₃

Color and Shape: Neat

Molecular weight: 209.20

Ref: TR-D439880

2',3'-Dideoxy-2',3'-didehydrocytidine

CAS: 7481-88-1

2',3'-Dideoxy-2',3'-didehydrocytidine (ddC) is a nucleoside analog that is used in the treatment of hepatitis B and C. This drug inhibits the reverse transcriptase enzyme and has cytostatic effects on viruses, for example, by preventing cell division. 2',3'-Dideoxy-2',3'-didehydrocytidine also inhibits viral replication by acting as an antigen and inducing antibody production. This drug binds to a variety of enzymes, including preparations of cellular enzymes, human immunodeficiency virus type 1 (HIV-1), and reverse transcriptase. The effective dose of ddC is 300 mg/day given orally.

Formula: C₉H₁₁N₃O₃

Purity: Min. 95%

Molecular weight: 209.2 g/mol

Ref: 3D-ND144874

Zalcitabine Related Compound A (2',3'-Didehydro-2',3'-dideoxycytidine) (DISCONTINUED)

CAS: 7481-88-1

Nucleic acids and their salts, whether or not chemically defined; other heterocyclic compounds, nesoi

Formula: C₉H₁₁N₃O₃

Color and Shape: Powder

Molecular weight: 209.08004

Ref: 45-1724317