29984-33-6

Basic information

• Product Name: Vidarabine monophosphate
• Synonyms: ARA-AMP;9-BETA-D-ARABINOFURANOSYLADENINE-5'-MONOPHOSPHATE;9-BETA-D-ARABINOFURANOSYL-ADENINE-5'-MONOPHOSPHORIC ACID;9-BETA-D-ARABINOFURANOSYLADENINE MONOPHOSPHATE;9-(5-O-PHOSPHONO-BETA-D-ARABINOFURANOSYL)-9H-PURIN-6-AMINE;ADENINE-9-BETA-D-ARABINOFURANOSIDE-5'-MONOPHOSPHATE;ADENINE-BETA-D-ARABINOFURANOSIDE-5'-PHOSPHATE;VIDARABINE PHOSPHATE
• CAS NO: 29984-33-6
• Molecular Formula: C₁₀H₁₄N₅O₇P
• Molecular Weight: 347.22
• EINECS: 249-990-8
• Mol File: 29984-33-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 213 °C
• Boiling Point: 798.5 °C at 760 mmHg
• Flash Point: 436.7 °C
• Appearance: White to Off-white/Powder
• Density: 2.32 g/cm³
• Vapor Pressure: 6.7E-27mmHg at 25°C
• Storage Temp.: Store at 0°C
• PKA: 1.86±0.10(Predicted)
• Water Solubility: Soluble in water at 4mg/ml
• CAS DataBase Reference: Vidarabine monophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Vidarabine monophosphate(29984-33-6)
• EPA Substance Registry System: Vidarabine monophosphate(29984-33-6)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/22-40-23/24/25-36/37/38
• Safety Statements: 37/39-24/25-45-36/37/39-22-36-26
• RIDADR: 2811
• RTECS: AU6204000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 29984-33-6(Hazardous Substances Data)

Usage

Description

Vidarabine monophosphate, also known as 9-(5-O-Phosphono-beta-D-arabinofuranosyl)adenine, is an antiviral drug that is an adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of vidarabine and possesses antiviral and potentially antineoplastic properties. It is characterized by its crystalline chemical properties.

Uses

Used in Antiviral Applications:
Vidarabine monophosphate is used as an antiviral agent for disrupting viral DNA synthesis. It acts as a competitive viral DNA polymerase inhibitor, making it active against herpes simplex and varicella zoster viruses in vivo.
Used in Chronic Hepatitis B Treatment:
Vidarabine monophosphate is used as a therapeutic agent for treating chronic hepatitis B, demonstrating quick effects and clear curative effects in patients.
Used in Herpes Infections Treatment:
Vidarabine monophosphate is used as an antiviral agent for treating various herpes infections, including herpes zoster, herpes simplex, and genital herpes, due to its broad-spectrum anti-virus effect and ability to inhibit a variety of DNA viruses.
Used in Clinical Anti-Virus Treatment:
Vidarabine monophosphate is used as a common drug in clinical settings for anti-virus treatment, particularly for the aforementioned viral infections.

Safety Profile

Moderately toxic byintraperitoneal route. When heated to decomposition itemits very toxic fumes of POx and NOx.

InChI:InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/p-2/t4-,6-,7+,10-/m1/s1

Upstream product

• 78-40-0 triethyl phosphate 
• 5536-17-4 arabinosyl adenine 
• 61-19-8 5'-adenosine monophosphate 
• 52989-04-5 phosphoric acid mono-((6aS)-7c-acetoxy-4-acetylamino-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-e]purin-8t-ylmethyl) ester 
• 28220-13-5 8-bromo-O^2'-(toluene-4-sulfonyl)-[5']adenylic acid 
• 28220-12-4 O^2'-(toluene-4-sulfonyl)-[5']adenylic acid 
• 52940-98-4 6-acetylamino-9-[O³-acetyl-O⁵-phosphono-O²-(toluene-4-sulfonyl)-β-D-ribofuranosyl]-7,9-dihydro-purin-8-one 
• 58-61-7 L-adenosine 

Relevant articles and documents

Synthesis method and application of vidarabine monophosphate

The invention belongs to the field of medicine synthesis, and discloses a synthesis method and application of vidarabine monophosphate. According to the synthesis method, 5-iodo-2-((phosphonooxy) methyl)-4-(tosyloxy)tetrahydrofuran-3-yl acetate and tert-butyl (8-hydroxy-9H-purin-6-yl)carbamate are subjected to condensation, epoxidation, ring opening and desulfurization reaction, and the vidarabine monophosphate is synthesized. According to the synthesis method of vidarabine monophosphate, provided by the invention, the industrial production steps are further simplified, the total reaction yield is improved, and the industrial production cost is reduced. The method is suitable for synthesizing vidarabine monophosphate, and the synthesized vidarabine monophosphate is used for preparing vidarabine monophosphate for injection.

Preparation method of vidarabine monophasphate

The invention discloses a preparation method of vidarabine monophosphate. The preparation method comprises the following two steps: crude product synthesis and crude product refining. In a crude product synthesis stage, reaction conditions are controlled severely, side reaction and production of related substances are reduced effectively, and high percent conversion of a target product is ensured.Meanwhile, because most of side products of reaction are dissolved in the reaction system and the target product is not dissolved in the reaction system basically, aftertreatment is facilitated to improve the purity of the product. The method is simple in process, high in product yield, high in purity and high in reaction selectivity; any special equipment is not used during production; and the preparation method is suitable for industrial production.

Synthetic method of vidarabine monophosphate

The invention provides a synthetic method of vidarabine monophosphate. The synthetic method comprises the following steps: a) making an intermediate shown as a formula (II) react with a solid sulfurizing agent and strong-acid ion exchange resin to obtain an intermediate shown as a formula (III), wherein the solid sulfurizing agent is selected from sodium sulfide, a sodium sulfide hydrate, sodium hydrosulfide or a sodium hydrosulfide hydrate; b), desulfurizing the intermediate shown as the formula (III) to obtain the vidarabine monophosphate. In the method, the intermediate shown as the formula (II) is subjected to sulfhydrylation through the solid sulfurizing agent such as the sodium sulfide, the sodium bisulfide, the sodium sulfide hydrate or the sodium hydrosulfide hydrate and the strong-acid ion exchange resin, and is desulfurized to obtain the vidarabine monophosphate, so that the use of hydrogen sulfide is avoided, and the pressure on the environment is lowered. Meanwhile, by adopting the synthetic method provided by the invention, the yield is 30 percent or more, and the purity of an obtained product is 99.8 percent or more.