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アシクロビル

アシクロビル 化学構造式
59277-89-3
CAS番号.
59277-89-3
化学名:
アシクロビル
别名:
アシクロビル;2-アミノ-9-(2-ヒドロキシエトキシメチル)-6,9-ジヒドロ-1H-プリン-6-オン;ゾビクロビル;アシクリル;ベルクスロン;2-アミノ-9-(2-ヒドロキシエトキシメチル)-9H-プリン-6-オール;アシロベック;2-アミノ-9-(2-ヒドロキシエトキシメチル)-1H-プリン-6(9H)-オン;アシビル;2-アミノ-6,9-ジヒドロ-9-[(2-ヒドロキシエトキシ)メチル]-1H-プリン-6-オン;アクチオス;ゾビラックス;シクロビラン;2-アミノ-9-[(2-ヒドロキシエトキシ)メチル]-9H-プリン-6(1H)-オン;ゾビアトロン;アストリック;アシクロメルク;アシクロビン;グロスパール;アクチダス
英語化学名:
Acyclovir
英語别名:
ACV;vipral;bw248u;Zyclir;Vimrax;Zoviax;w-248-u;virorax;aclovir;Poviral
CBNumber:
CB7126677
分子式:
C8H11N5O3
分子量:
225.2
MOL File:
59277-89-3.mol

アシクロビル 物理性質

融点 :
256-257°C
沸点 :
366.71°C (rough estimate)
比重(密度) :
1.3654 (rough estimate)
屈折率 :
1.8000 (estimate)
貯蔵温度 :
−20°C
溶解性:
H2O: 0.7 mg/mL
外見 :
powder
酸解離定数(Pka):
pKa 2.27 (Uncertain);9.25 (Uncertain)
色:
white
水溶解度 :
Soluble in 1M HCl at 50mg/ml. Soluble in water at 0.7mg/ml. Also soluble in DMSO
Merck :
14,146
安定性::
Stable. Incompatible with strong oxidizing agents.
CAS データベース:
59277-89-3(CAS DataBase Reference)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi,Xn
Rフレーズ  36/37/38-40-20/21/22
Sフレーズ  22-24/25-36-26-23
WGK Germany  2
RTECS 番号 UP0791400
国連危険物分類  IRRITANT
HSコード  29335990
有毒物質データの 59277-89-3(Hazardous Substances Data)
毒性 LD50 in mice (mg/kg): >10,000 orally; 1000 i.p. (Schaeffer)
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H320 眼刺激 眼に対する重篤な損傷性/眼刺激 性 2B 警告 P264, P305+P351+P338,P337+P313
注意書き
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。

アシクロビル 価格 もっと(30)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBOR-5147 アシクロビル
Acyclovir
59277-89-3 1g ¥3600 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01APOOR9240T アシクロビル
Acyclovir
59277-89-3 100mg ¥33000 2018-12-26 購入
東京化成工業 A1915 アシクロビル >98.0%(HPLC)
Acyclovir >98.0%(HPLC)
59277-89-3 1g ¥2300 2018-12-04 購入
東京化成工業 A1915 アシクロビル >98.0%(HPLC)
Acyclovir >98.0%(HPLC)
59277-89-3 5g ¥6600 2018-12-04 購入
Sigma-Aldrich Japan A0220000 European Pharmacopoeia (EP) Reference Standard
Aciclovir European Pharmacopoeia (EP) Reference Standard
59277-89-3 a0220000 ¥33600 2018-12-25 購入

アシクロビル 化学特性,用途語,生産方法

外観

白色~うすい黄色, 結晶~粉末

溶解性

本品0.1gに0.1mol/l水酸化ナトリウム溶液10mlでほとんど澄明

用途

ウイルス感染症の治療薬である。単純ヘルペスウイルスや水痘?帯状疱疹ウイルスに使われる。グラクソ?スミスクラインよりゾビラックス、一般薬としてヘルペシア、後発医薬品も多数。

用途

ウイルス DNA ポリメラーゼ / 逆転写酵素による基質の取り込みを競合的 に阻害し、DNA 鎖の伸長を停止することによ りウイルス増殖阻害作用を示します。

化学的特性

white to light yellow crystal powder

使用

Orally active acyclic nucleoside with inhibitory activity towards several herpes viruses. Antiviral

使用

hypnotic

定義

ChEBI: An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9.

brand name

Zovirax (GlaxoSmithKline).

抗菌性

Activity is restricted to viruses of the herpes group. Herpes simplex virus (HSV) types 1 and 2, simian herpes virus B and varicella zoster viruses (VZV) are susceptible to concentrations readily attainable in human plasma. The 50% inhibitory concentration (ID50) is 0.1 μmol for HSV-1 and HSV-2 and 3 μmol for VZV, concentrations much below those toxic to cells. Valaciclovir is metabolized to aciclovir, and has the same antiviral profile. Thymidine-kinase-negative HSV mutants and cytomegalovirus (CMV) do not code for thymidine kinase and are generally resistant. Although Epstein–Barr virus (EBV) may have reduced thymidine kinase activity, its DNA polymerase is susceptible to aciclovir triphosphate and shows intermediate susceptibility. Human herpes viruses 6 and 7 are less susceptible than EBV.

獲得抵抗性

Mutations in HSV that involve deficient thymidine kinase or an altered substrate are most common; alterations in the DNA polymerase gene also result in resistance. Resistant mutants may be found in wild virus populations; mutants lacking thymidine kinase activity may be readily induced by passage of HSV in the presence of the drug. Resistant strains have mostly been reported in immunocompromised patients, are generally thymidine-kinase negative, and have decreased virulence. Resistant mutants that retain thymidine kinase activity appear to retain virulence. Emergence of resistant HSV strains is less frequent in immunocompetent patients, occurring in about 2% of those receiving prolonged treatment.

応用例(製薬)

A synthetic acyclic purine nucleoside analog of the natural nucleoside 2′ deoxyguanosine, formulated for oral and topical use, and as the sodium salt for intravenous infusion. Valaciclovir (the l-valyl ester) is a prodrug formulation supplied as the hydrochloride for oral use.

生物活性

Antiviral agent, active against herpes simplex viruses HSV-1 and HSV-2 (EC 50 values are 0.85 and 0.86 μ M respectively). Interferes with viral DNA polymerization through competitive inhibition with guanosine triphosphate. Induces apoptosis in cells transfected with HSV-TK (suicidal gene therapy).

薬物動態学

Oral absorption, aciclovir: c. 20%
valaciclovir: c. 60%
Cmax 200 mg oral 4-hourly:1.4–4 μmol after 1.5–1.75 h
5 mg/kg 8-hourly intravenous infusion: 43.2 μmol steady state
10 mg/kg 8-hourly intravenous infusion: 88.9 μmol steady state
Plasma half-life: 3–3.3 h
Plasma protein binding: 15%
Absorption
Therapeutic drug levels are readily attained after oral or intravenous administration, although concentrations achieved by an oral dose are over 90% lower than those after intravenous therapy. Accumulation of the drug is unlikely in patients without renal dysfunction. Valaciclovir is readily absorbed and is converted rapidly and almost completely to aciclovir; absorption is unaffected by food. Peak plasma concentrations of 22 μmol are found in subjects after an oral dose of 1000 mg every 8 h; systemic exposure is comparable to that of intravenous aciclovir 5 mg/kg every 8 h. The peak plasma concentration and area under the concentration–time curve (AUC) do not increase proportionally with increasing doses, presumably due to reduced absorption. The time to peak aciclovir concentration is also dose dependent, ranging from 0.9 to 1.8 h after single oral doses of 100–1000 mg.
Distribution
Aciclovir is widely distributed in various tissues and body fluids. Delivery of the drug to the basal epidermis after topical administration is about 30–50% of that obtained by oral dosing. Aciclovir ointment penetrates the corneal epithelium. CSF concentrations are about 50% of simultaneous plasma concentrations. Vesicular fluid concentrations approximate those in plasma. The drug is actively secreted into breast milk at a concentration several times that of plasma. Placental cord blood contains levels of 69–99% of maternal plasma and the drug is 3–6 times more concentrated in amniotic fluid.
Metabolism
About 15% of an intravenous dose is metabolized in persons with normal renal function. The only significant urinary metabolite is 9-carboxymethoxymethylguanine, which has no antiviral activity. Less than 0.2% of the dose is recovered as the 8-hydroxylation product.
Excretion
Around 45–79% of a dose is recovered unchanged in urine, the percentage declining with decreasing creatinine clearance. In patients with renal failure, mean peak plasma concentrations nearly doubled and the elimination half-life increased to 19.5 h. Dosage reductions are advised for various stages of renal impairment. During hemodialysis the half-life is 5.7 h and after dialysis the plasma concentration is about 60% less than the predialysis concentration. Half-lives of 12–17 h have been reported for patients undergoing continuous peritoneal dialysis, with only 13% or less of administered drug being recovered in the 24-h dialysate. The half-life in patients undergoing arteriovenous hemofiltration/dialysis is about 20 h. Less than 1% of a dose of valaciclovir is recovered as unchanged drug in the urine. In multidose studies the amount of aciclovir recovered across dose levels ranged from about 40% to 50%. Between 7% and 12% of the dose is found as the 9-carboxymethoxymethylguanine metabolite. Overall, aciclovir accounts for 80–85% of total urinary recovery.

臨床応用

Aciclovir
Herpes simplex keratitis
Chickenpox and herpes zoster
Herpes simplex encephalitis and neonatal herpes
Prophylaxis of HSV infections in the severely immunocompromised
Valaciclovir
Herpes zoster and genital HSV infections

副作用

Few adverse reactions to topical, ocular, oral or intravenous formulations have been reported. Allergic contact dermatitis occasionally occurs with aciclovir cream. Superficial punctate keratopathy occurs in 10% of patients receiving the ophthalmic preparation; stinging or burning on application occurs in 4%. Less common complications include conjunctivitis, blepharitis and pain.
Transient increases in blood urea nitrogen and creatinine occur in 10% of patients given bolus injections. It can be largely avoided by reducing the rate of infusion, adequate hydration and dosage adjustment in renal failure. Nausea, vomiting, diarrhea and abdominal pain occasionally occur, particularly in association with a raised creatinine concentration. Acute reversible renal failure has been reported. Reconstituted aciclovir has a pH of about 11; severe inflammation and ulceration have been reported after extravasation at the infusion site. Encephalopathy, tremors, confusion, hallucinations, convulsions, psychiatric disorders, bone marrow depression and abnormal liver function have occasionally arisen. Skin rashes have been reported in a few patients but resolve on discontinuation of the drug.
Headache and nausea have been reported as side effects of valaciclovir, but occurred with similar frequency in subjects taking placebo.
Results of mutagenicity tests in vitro and in vivo indicate that aciclovir is unlikely to pose a genetic risk to humans, and the drug was not found to be carcinogenic in long-term studies in mice and rats. No detectable drug-related effects have been detected in pregnancy.

アシクロビル 上流と下流の製品情報

原材料

準備製品


アシクロビル 生産企業

Global( 383)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Zhengzhou Yuanli Biological Technology Co., Ltd
0086-371-67897895
info@zzyuanli.cn CHINA 120 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 10967 58
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19953 60
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3217 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22049 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2548 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 663 60
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 552 55

59277-89-3(アシクロビル)キーワード:


  • 59277-89-3
  • aclovir
  • Acycolguanosine
  • bw248u
  • vipral
  • virorax
  • w-248-u
  • wellcome-248u
  • Acyclovir (Patented-No Supply)
  • N(9)-Oxyethoxymethylguanine (Acyclovir)
  • Acyclovir USP24 EP2000
  • acyclovir USP &BP (Normal powder,Micro-powder)
  • Acyclovir USP
  • Acyclovir (base and/or unspecified salts)
  • ACYCLOVIR, PHARMA
  • 6H-Purin-6-one, 2-amino-1,9-dihydro-9-(2-hydroxyethoxy)methyl-
  • 9-(2-HYDROXYETHOXYMETHYL)GUANINE(ACYCLOVIR)
  • ACYCLOVIR [ACYCLOGUANOSINE]
  • ACETYLTHIAZOLE
  • Acicloftal
  • Cargosil
  • Gerpevir
  • Herpevir
  • Zyclir
  • δ-(L-α-Aminoadipyl)-Cys-D-Val
  • Poviral
  • Vimrax
  • 2-Amino-9-((2-hydroxyethoxy)methyl)-3H-purin-6(9H)-one
  • ACYCLOVIR USP (FOR STERILE PROCESS)(REJECTED GOODS RETURNING BACK TO THE SUPPLIER BE NO:8895640 DT 13.04.2015)
  • 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one
  • Acyclovir, 99%, inactivate the thymidine kinase of the herpesvirus
  • アシクロビル
  • 2-アミノ-9-(2-ヒドロキシエトキシメチル)-6,9-ジヒドロ-1H-プリン-6-オン
  • ゾビクロビル
  • アシクリル
  • ベルクスロン
  • 2-アミノ-9-(2-ヒドロキシエトキシメチル)-9H-プリン-6-オール
  • アシロベック
  • 2-アミノ-9-(2-ヒドロキシエトキシメチル)-1H-プリン-6(9H)-オン
  • アシビル
  • 2-アミノ-6,9-ジヒドロ-9-[(2-ヒドロキシエトキシ)メチル]-1H-プリン-6-オン
  • アクチオス
  • ゾビラックス
  • シクロビラン
  • 2-アミノ-9-[(2-ヒドロキシエトキシ)メチル]-9H-プリン-6(1H)-オン
  • ゾビアトロン
  • アストリック
  • アシクロメルク
  • アシクロビン
  • グロスパール
  • アクチダス
  • クロベート
  • ビクロックス
  • ビルレクス
  • ゾビスタット
  • 9-(2-ヒドロキシエトキシメチル)グアニン
  • 2-アミノ-9-(2-ヒドロキシエトキシメチル)-9H-プリン-6(1H)-オン
  • エアーナース
  • アシクログアノシン
  • アシクロフタル
  • アシロベック-DS
  • ナタジール
  • 2-アミノ-1,9-ジヒドロ-9-[(2-ヒドロキシエトキシ)メチル]-6H-プリン-6-オン
  • ビルヘキサル
  • アシロミン
  • アイラックス
  • ビゾクロス
  • ファルラックス
  • トミール
  • 9-[(2-ヒドロキシエトキシ)メチル]-1,9-ジヒドロ-2-アミノ-6H-プリン-6-オン
  • 2-アミノ-9-(2-ヒドロキシエトキシメチル)-1,6-ジヒドロ-9H-プリン-6-オン
  • 9-[(2-ヒドロキシエトキシ)メチル]グアニン
  • ヌクレオシド,ヌクレオチド&関連試薬
  • ヌクレオシドと類似体
  • 生化学
  • 試験研究用抗ウィルス剤
  • 試験研究用抗菌剤
  • 薬理研究用試薬
  • 抗ウイルス薬
  • 眼科用薬
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