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, chemical name: 9-(5-O-Phosphono-beta-D-arabinofuranosyl)adenine is an anti deoxyribonucleic acid virus drug. IVidarabine triphosphate directly inhibits DNA polymerase and also acts as a chain terminator in DNA replication. An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 29984-33-6 differently. You can refer to the following data:
1. Antiviral.
2. Disrupts viral DNA synthesis. Competitive viral DNA polymerase inhibitor. Active against herpes simplex and varicella zoster viruses in vivo.

Application

Vidarabine monophosphate has broad-spectrum anti-virus effect and can inhibit a variety of DNA viruses. It is mainly used to treat chronic hepatitis B and other viral infections, such as herpes zoster, herpes simplex and genital herpes. It has quick effect and clear curative effect. It is a common drug for clinical anti-virus treatment.

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.

Preparation method of vidarabine monophosphate

The invention provides a preparation method of vidarabine monophosphate. According to the method, vidarabine and phosphoric acid are used as raw materials; highly acidic ion exchange resin is used as a catalyst; the vidarabine monophosphate is generated through a one-step esterification reaction. The process route is short; the yield is higher; the resin serving as the catalyst can be repeatedly used after being regenerated. The use of phosphorus oxychloride which is high in smoke formation and high in pungency is avoided in the reaction; the production operational safety is improved; the preparation method is more environment-friendly. The method is simple to operate; the industrialized production is easily realized; the production efficiency is improved.