9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine
vidarabine
CAS: 5536-17-4
Molecular Formula: C10H13N5O4
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Names and Identifiers
| Name | vidarabine |
| Synonyms | vidarabine 2'-ARAADENOSINE ARABINOSYL-ADENINE 9-BETA-D-ARABINOSYLADENINE ADENINE-BETA-D-ARABINOFURANOSIDE 9-BETA-D-ARABINOFURANOSYLADENINE ADENINE-9-BETA-D-ARABINOFURANOSIDE 9-.beta.-D-Arabinofuranosyladenine Adenine, 9-.beta.-D-arabinofuranosyl- 9-β-D-arabinopyranosyl-9H-purin-6-amine 6-AMINO-9-BETA-D-ARABINOFURANOSYLPURINE 6-Amino-9-.beta.-D-arabinofuranosylpurine 9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl- 9-.beta.-D-Arabinofuranosyl-9H-purin-6-amine ADENINE-9-BETA-D-ARABINOFURANOSIDE (VIDARABINE) 9H-purin-6-amine, 9-beta-D-glycero-pentofuranosyl- 9-(beta-D-glycero-Pentofuranosyl)-9H-purin-6-amine |
| CAS | 5536-17-4 |
| EINECS | 226-893-9 |
| InChI | InChI=1/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(16)1-19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1 |
| InChIKey | OIRDTQYFTABQOQ-UHTZMRCNSA-N |
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Physico-chemical Properties
| Molecular Formula | C10H13N5O4 |
| Molar Mass | 267.25 |
| Density | 1.3382 (rough estimate) |
| Melting Point | 260-265°C (dec.) |
| Boling Point | 410.43°C (rough estimate) |
| Specific Rotation(α) | D27 -5° (c = 0.25) |
| Flash Point | 340.6°C |
| Water Solubility | Soluble in DMF (10 mg/ml), 0.5 M HCl (50 mg/ml), DMSO (53 mg/ml at 25°C), ethanol (<1 mg/ml at 25°C), and water (3 mg/ml at 25°C). |
| Solubility | Slightly soluble in water (0.45 mg/ml), methanol, almost insoluble in ether. |
| Vapor Presure | 3.14E-17mmHg at 25°C |
| Appearance | White needle crystal or crystalline powder |
| Color | White to Off-white |
| Merck | 13,10039 |
| BRN | 624881 |
| pKa | pKa 3.55(H2Ot=20I=0.1 (KCl)) (Uncertain);11.4 (Uncertain) |
| Storage Condition | -20°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.7610 (estimate) |
| MDL | MFCD00065471 |
| Physical and Chemical Properties | This product is white needle-like crystal or crystalline powder. Odorless; Tasteless; Slightly soluble in water (0.45 mg/ml), methanol, almost insoluble in ether. mp259-261. The solubility of this product is 100 mg/ml. |
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Risk and Safety
| Risk Codes | R63 - Possible risk of harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | AU6200000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29349990 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 in mice (mg/kg): 4677 i.p.; >7950 orally (Kurtz) |
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Nature
Open Data Verified Data
- This product is white fine needle-like crystal or crystalline powder. Odorless; Tasteless; Slightly soluble in water, methanol, almost insoluble in ether. The melting point was 257-257.5 °c. Molecular weight 267. 24.
- This product can inhibit the synthesis of DNA Virus, for a broad spectrum of DNA Virus inhibitors, including Herpes Sinplex Virus Virus workers, type II and herpes zoster Virus the most obvious effect, varicella-zoster Virus, vaccinia virus Virus, hepatitis B Virus times. It also has inhibitory effect on gland Virus, pseudorabies Virus, EB Virus, Cytomegalovirus Virus, etc., but has no effect on ribonucleic acid (RNA) Virus. Anti-Virus mechanism: converted to vidarabine triphosphate (Ara-ATP) in vivo, competes with deoxyadenosine triphosphate, inhibits Virus of DNA polymerase (DNA-P), the activity of DNA polymerase in serum is reduced by about 90%; In addition, the product can be incorporated into the junction between nucleotides, inhibit nucleotide reductase, delay DNA chain extension, thereby inhibiting the synthesis of Virus.
Last Update：2024-01-02 23:10:35
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Use
Open Data Verified Data
- treatment of chronic hepatitis B, herpes simplex virus encephalitis, herpes zoster, genital herpes, neonatal herpes simplex infection, immune deficiency patients with varicella zoster infection, herpetic myelitis, keratitis and corneal uveitis, cytomegalovirus pneumonia.
- usage and dose of daily 10~15mg/kg body weight, 12h intravenous drip.
- preparation injection, 3% eye ointment.
Last Update：2022-01-01 11:12:36
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Safety
Open Data Verified Data
- The daily dose of 5 mg/kg, mild and rare side effects, when the dose of 10 mg/kg per day or more, may appear anorexia, Nausea, Vomit, Diarrhea, dizziness, Fatigue, etc. A small number of patients can appear myelosuppression, mainly for leukopenia and thrombocytopenia. Occasionally, it can cause Myalgia syndrome. Treatment of encephalitis patients may have tremor, ataxia pain abnormalities, brain wave abnormalities, especially prone to liver and renal insufficiency. This drug has teratogenic effect, pregnant women disabled. Nursing mothers, infants and liver, renal insufficiency with caution.
- dry, dark place preservation.
Last Update：2022-01-01 11:12:37
9-(beta-D-Arabinofuranosyl)-9H-purin-6-amine - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | vidarabine is an antiviral drug, and its phosphate ester-Vidarabine Monophosphate for Injection is commonly used in clinic. At present, vidarabine is one of the most widely used antiviral drugs in clinical practice, even reaching the level of abuse. The problem of drug use beyond the indication is prominent, resulting in more adverse reactions, the number of reports of serious adverse reactions increased, especially in children under 14 years of age using the adverse reactions occurred in about 80% of the total. |
| Introduction | Vidarabine (9-β-d-arabinofuranosyladenine) is a nucleoside anti-Virus drug, with a broad spectrum of anti Virus activity, the strongest effect on herpes zoster Virus and Virus, varicella zoster Virus, vaccinia Virus, hepatitis B Virus, Adenovirus Virus, pseudorabies Virus and some RNA tumors Virus were also effective. |
| function | vidarabine is the pharmaceutical industry in the manufacture of vidarabine monophosphate adenosine, adenosine triphosphate, coenzyme, fludarabine and a series of products such as the main raw materials of cyclic adenosine monophosphate drugs. Vidarabine monophosphate is a kind of anti-deoxyribonucleic acid (DNA) Virus drug, which can inhibit the replication of hepatitis B Virus; Fludarabine it has a significant effect on B- cell chronic lymphocytic leukemia (CLL), especially in patients who have failed conventional treatment, and can also be used for the pretreatment of aplastic anemia. |
| pharmacological action | This product is anti-deoxyribonucleic acid (DNA) Virus drug, its pharmacological action is combined with Virus deoxyribonucleic acid polymerase, the activity is reduced to inhibit DNA synthesis. After entering the cell, vidarabine monophosphate is phosphorylated to produce vidarabine diphosphate and vidarabine triphosphate (Ara-ATP). Anti-Virus activity is mainly caused by vidarabine triphosphate, and Ara-ATP competes with deoxyadenosine triphosphate to bind to Virus DNAP, thereby inhibiting the activity of the enzyme and the synthesis of Virus DNA, at the same time, it inhibits the activity of Virus nucleotide reductase, inhibits the synthesis of Virus DNA, and also inhibits the activity of Virus DNA terminal deoxynucleotidyl transferase, by allowing Ara-A to infiltrate into Virus of the DNA and ligate to the end of the 3 '-OH position of the DNA strand, continued DNA synthesis was inhibited by Virus. |
| preparation | 1) synthesis of 8-bromoadenosine (Ⅱ) in a 250mL reaction flask, water (180g), adenosine I (0.037mol,10g), acetic acid (10g) and sodium acetate (2.4g) were heated to 75 ℃, stirred until the solution was clear (about 0.5h) and then cooled to 30 ℃, bromine (0.044Mol, 7.1g) was added and the reaction was continued at 30 °c for 48h. After completion of the reaction, the reaction system was cooled to room temperature, filtered, washed with filter cake, dried, Yellow product II was obtained, the yield was 11.3g, the yield was 88.3%, and the HPLC purity was 98.8%. 2) synthesis of 8-bromo-3 '-O-P-Toluenesulfonyl adenosine (Ⅲ) in a 250ml reaction flask, add Ⅱ(0.029Mol, 10g), 1, 2-dichloroethane (110g) triethylamine (0.032mol,3.2g), dibutyltin oxide (0.004mol,1g), p-Toluenesulfonyl chloride (0.032mol,6.3g), react at 40 ℃ for 18h, and recover dibutyltin oxide by hot filtration, the filtrate was lowered to room temperature, product III was precipitated, and the crude product was obtained by filtration. After beating the crude product with methanol at room temperature and drying it at 50 ℃, 13.2g of light yellow powder was obtained, The yield was 90.0% and the HPLC purity was 99.2%. 3) 8-hydroxy-4-n-acetoxy-5 ′-acetoxymethyl-3 ′-O-P-Toluenesulfonyl adenosine (Ⅳ) was synthesized in a 100ml reaction flask, add III (0.02mol,10g), acetic acid (0.14mol,8.3g), acetic anhydride (0.21mol,21g), heated to 80 ℃ and refluxed for 8H, then, the acetic anhydride that did not participate in the reaction was removed by distillation under reduced pressure, the remaining material was cooled to room temperature, then water (5g) was added, stirred thoroughly, and then filtered to obtain crude IV, drying at 50 °c gave 9.4g of pure product with a yield of 88.0% and a HPLC purity of 98.4%. 4) synthesis of vidarabine (VI) in 100mL reaction flask, add IV (0.019mol,10g) and the mass fraction of 80% hydrazine hydrate (12g), heating to 80 ℃ for 48h after the reaction, 10g of hot water at 60 ° C. Was added to the reaction flask, and the distillation was continued under reduced pressure to bring out hydrazine hydrate remaining in the kettle, and the remaining solid, namely, crude 8-hydrazinoarabinosuoadenosine V, was obtained. In the same reaction flask, water (50.8g) and potassium permanganate (0.004Mol, 0.6g) were further added to the obtained crude 8-hydrazinovidarabine, and the reaction was stirred at 25 ° C. For 24 hours. The solid obtained by filtration of the reaction solution is vidarabine VI crude product. Water and activated carbon are added to the crude product. After decolorization by heating and boiling, the activated carbon is removed by hot filtration, after drying at 50 ℃, 3.4g of vidarabine was obtained, the yield was 67.0%, the HPLC purity was 99.3%, and the volatile fraction was 0.3% by oven method. |
| indication | vidarabine is an anti-deoxyribonucleic acid (DNA) Virus drug. Mainly by inhibiting Virus of DNA polymerase, blocking Virus of DNA synthesis, to inhibit Virus of the effect, only Virus of DNA such as simple cell rash Virus type 1 and type 2, herpes zoster Virus, varicella-Zoster Virus Virus, Cytomegalovirus Virus, hepatitis B Virus with anti Virus activity. However, vidarabine is metabolized to arabinosyl hypoxanthine in vivo, so that its antiviral activity is reduced. At present, the approved indications of vidarabine in China are stomatitis, dermatitis, encephalitis and cytomegalovirus infection caused by herpes simplex virus infection. |
| Use | has anti-Herpes Sinplex Virus HSV-1 and HSV-2 action for the treatment of Herpes Sinplex Virus meningitis, also used in immunosuppressed patients with herpes zoster and varicella infection. But not for Cytomegalovirus. The single phosphate ester of this product can inhibit the replication of hepatitis B Virus. When the dose of 10 mg/kg per day or more, may appear anorexia, Nausea, Vomit, Diarrhea, elevated transaminase, dizziness, Fatigue. A small number of bone marrow suppression, mainly for white blood cells and thrombocytopenia. This drug has teratogenic effect, pregnant women disabled. Nursing mothers, infants and liver, renal insufficiency with caution. Human medicine for herpes simplex encephalitis and herpes zoster |
| production method | Method 1: selective p-toluenesulfonylation of 5 '-adenine nucleotide (5'-AMP), hydrolysis dephosphorization, bromination, acetylation to give 8-hydroxy-n, 3 ', 5'-O-triethyl-2 '-O-P-Toluenesulfonyl adenosine, cyclization in methanol-ammonia, then in the methanol-hydrogen sulfide Ring 8-mercaptovidarabine, hydrogen stripping of sulfur can be obtained by the sugar adenosine. 5 '-adenine nucleotide [P-Toluenesulfonyl chloride] → 2'-O-P-Toluenesulfonyl adenosine 5 '-monophosphate [ammonia, formamide] → 2'-O-P-Toluenesulfonyl adenylate [Br2]→ 8-bromo-2 '-O-P-Toluenesulfonyl adenosine [acetic acid, acetic anhydride] → 8-hydroxy-n, 3', 5 '-O-triethyl-2'-O-P-Toluenesulfonyl adenosine [methanolic ammonia] → 8, 2 '-O-cyclic adenosine [methanol-hydrogen sulfide] → 8-mercaptoarabinoside adenosine [Raney nickel] → arabinoside adenosine method 2, using uridine as raw material, first react with phosphorus oxychloride and dimethylformamide, then, uridine arabinoside was obtained by hydrolysis under alkaline (pH = 9) conditions, and then hydrolyzed by pyrimidine nucleoside phosphorylase at 60 ℃, uracil was removed to obtain arabinoside -1-phosphate, by purine nucleoside phosphorylase catalysis, and adenine at 60 deg C condensation of vidarabine. Uridine [phosphorus oxychloride, dimethylformamide] →[pH9] uridine [pyrimidine nucleoside phosphorylase] →[60 ℃] arabino-1-phosphate [purine nucleoside phosphorylase] →[60 ℃] vidarabine. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | intraperitoneal-rat LD50: 1476 mg/kg; Oral-mouse LD50: 3057 mg/kg |
| stimulation data | Skin-rabbit 3% mild; Eye-rabbit 1% moderate |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:51
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