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阿昔洛韦

阿昔洛韦用途

Acyclovir能抑制疱疹病毒的胸苷激酶,IC50为530-750nM。

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阿昔洛韦名称

[ CAS 号 ]:
59277-89-3

[ 中文名 ]:
阿昔洛韦

[ 英文名 ]:
Acyclovir

[中文别名 ]:

[英文别名 ]:

Zovir
9-((2-Hydroxyethoxy)methyl)guanine
EINECS 261-685-1
Poviral
aclovir
bw248u
Acyclo-V
Maynar
9-(2-Hydroxyethoxy)methylguanine
Vimrax

阿昔洛韦生物活性

[ 描述 ]:

Acyclovir能抑制疱疹病毒的胸苷激酶,IC50为530-750nM。

[ 相关类别 ]:

信号通路 >> 抗感染 >> HSV

研究领域 >> 感染

[参考文献]

[1]. Li Z, et al. Acyclovir treatment of skin lesions results in immune deviation in mice infected cutaneously with herpes simplex virus. Antivir Chem Chemother. 1999 Sep;10(5):251-7.

[2]. Shelley WB, Hashim M, Shelley ED. Acyclovir in the treatment of hand-foot-and-mouth disease. Cutis. 1996 Apr;57(4):232-4.

[3]. Collins P, Oliver NM. Sensitivity monitoring of herpes simplex virus isolates from patients receiving acyclovir. J Antimicrob Chemother. 1986 Oct;18 Suppl B:103-12.

[4]. Meyrick Thomas RH, Dodd HJ, Yeo JM, Oral acyclovir in the suppression of recurrent non-genital herpes simplex virus infection. Br J Dermatol. 1985 Dec;113(6):731-5.

[5]. Tang IY, Maddux MS, Veremis SA, Low-dose oral acyclovir for prevention of herpes simplex virus infection during OKT3 therapy. Transplant Proc. 1989 Feb;21(1 Pt 2):1758-60.

[相关活性小分子]

阿昔洛韦物理化学性质

[ 密度 ]:
1.8±0.1 g/cm3

[ 沸点 ]:
576.5±58.0 °C at 760 mmHg

[ 熔点 ]:
256-257°C

[ 分子式 ]:
C₈H₁₁N₅O₃

[ 分子量 ]:
225.205

[ 闪点 ]:
302.4±32.3 °C

[ 精确质量 ]:
225.086182

[ PSA ]:
119.05000

[ LogP ]:
-3.31

[ 外观性状 ]:
白色至淡黄色晶体粉末

[ 蒸汽压 ]:
0.0±1.7 mmHg at 25°C

[ 折射率 ]:
1.762

[ 储存条件 ]:
库房通风低温干燥,与食品原料分开存放

[ 稳定性 ]:
Stable. Incompatible with strong oxidizing agents.

[ 水溶解性 ]:
H2O: 0.7 mg/mL

阿昔洛韦MSDS

阿昔洛韦毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0791400

CHEMICAL NAME :: 6H-Purin-6-one, 1,9-dihydro-2-amino-9-((2-hydroxyethoxy)methyl)-

CAS REGISTRY NUMBER :: 59277-89-3

LAST UPDATED :: 199712

DATA ITEMS CITED :: 30

MOLECULAR FORMULA :: C8-H11-N5-O3

MOLECULAR WEIGHT :: 225.24

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ D1O2Q GZ IQ &T56 BN DN FVM INJ B1O2Q HZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 28 mg/kg/2D-I

TOXIC EFFECTS :: Brain and Coverings - changes in surface EEG Behavioral - hallucinations, distorted perceptions Lungs, Thorax, or Respiration - sputum

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 12 mg/kg/1D-I

TOXIC EFFECTS :: Brain and Coverings - meningeal changes Behavioral - somnolence (general depressed activity) Behavioral - antipsychotic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 100 mg/kg/5D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, allergic (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 80 mg/kg/4D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - hallucinations, distorted perceptions Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 486 mg/kg/17D-I

TOXIC EFFECTS :: Gastrointestinal - decreased motility or constipation Gastrointestinal - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 134 ug/kg/1D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 101 mg/kg/2D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - muscle contraction or spasticity

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 107 mg/kg/4D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Multiple routes

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 36 mg/kg/2D-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Behavioral - coma Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 860 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 620 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 724 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1118 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1118 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg/5D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes primarily in glomeruli Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 60 mg/kg

SEX/DURATION :: female 5-6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 200 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1200 mg/kg

SEX/DURATION :: female 1-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 300 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - rabbit Kidney

DOSE/DURATION :: 6800 ug/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 38,1771,1989

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阿昔洛韦安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xi

[ 风险声明 (欧洲) ]:
36/37/38

[ 安全声明 (欧洲) ]:
S22-S24/25

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
UP0791400

[ 海关编码 ]:
2933790090

阿昔洛韦合成路线

阿昔洛韦上下游产品

阿昔洛韦上游产品

阿昔洛韦下游产品

阿昔洛韦制备

方法一、以鸟嘌呤核苷为原料
N-7(或9)-二乙酰鸟嘌呤的制备 5L三颈瓶中分别加入鸟嘌呤核苷酸283g、10mol乙酐1.03L、2mol乙酸210ml，加热回流1h，加0.2mol PTS17.2g，再回流1h，减压蒸馏回收乙酐和乙酸，浓缩液加乙酸乙酯600ml，回流1.5h，冷却后过滤，得产品。
鸟嘌呤核苷酸[醋酐，醋酸，PTS]→[2h]N-7-(或9)-二乙酰鸟嘌呤
N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤的制备三颈瓶中加入N-7(或9)-二乙酰鸟嘌呤200g、2-氧杂-1，4-丁二醇二乙酸酯282g、PTSA9g、甲苯1.2L，回流24h后，迅速冷却至0℃，过滤，烘干，得产品。N-7(或9)-二乙酰鸟嘌呤[2-氧杂-1，4-丁二醇二乙酸酯，PTSA，甲苯]→[24h]N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤
无环鸟苷的制备将N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤0.5mol、25%甲胺水溶液2.7L置于三颈瓶中，搅拌下于35-37℃反应0.5h，减压浓缩至干，加350m1乙醇溶解，过滤，滤饼用乙醇洗涤，干燥得粗品。用40倍水重结晶得精品。
N-乙酰-9-[（2-乙酰氧基乙氧基）甲基]鸟嘌呤[甲胺]→[35-37℃,0.5h]无环鸟苷
方法二、以鸟嘌呤为原料
N，N-二乙酰鸟嘌呤的制备将鸟嘌呤5g置于圆底烧瓶中，加乙酐81ml，搅拌混合后加入少量乙酸和乙酸锌，加热回流16h，冷却，减压回收乙酸，冰浴冷却后过滤，乙醇及水洗后干燥，得产品。
鸟嘌呤[醋酐，醋酸，醋酸锌]→[16h]N,N-二乙酰鸟嘌呤
1，3-二氧五环的制备将乙二醇248g、多聚甲醛120g混合后，搅拌下缓慢滴加浓硫酸22.1g，加完后回流3h，反应液冷却至室温，移至分液漏斗中，加氯化钠饱和盐析，分取有机相，干燥后蒸馏，收集74-76℃馏分即产品。
乙二醇[多聚甲醛，浓硫酸]→[3h]1,3-二氧五环
N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤的制备将乙酐31g、乙酸5g对甲苯磺酸2g混合，搅拌下冷却至10℃以下，加二氧五环24g，并保持温度不超过40℃，冷至室温，加入甲苯78ml及N，N-二乙酰鸟嘌呤15g，搅拌回流1h，冷至室温，加入氯仿，过滤，干燥，得产品。
N,N-二乙酰鸟嘌吟[1，3-二氧五环，PST，醋酐，醋酸，甲苯]→N-乙酰-9-[（2-乙酰氧基乙氧基）甲基]鸟嘌呤
无环鸟苷的制备将上步所得的N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤与40%甲胺水溶液120ml混合，搅拌下加热1h，冷却后过滤，滤液减压浓缩，加乙醇洗涤，过滤，得粗品，用水重结晶，得无环鸟苷纯品。N-乙酰-9-[(2-乙酰氧基乙氧基)甲基]鸟嘌呤[甲基]→[3h]无环鸟苷。

将2-氯-9-(-2-羟乙氧基甲基)腺嘌呤与亚硝酸钠作用，得到的2-氯-9-(2-羟乙氧基甲基)次黄嘌呤(熔点>310℃)用液氨饱和，在125℃密闭加热5h即生成无环鸟苷。

方法1：以鸟嘌呤为原料。鸟嘌呤和乙酐混合，加入少量乙酸和乙酸锌，搅拌回流。减压蒸去过量的乙酐，冷至0℃过滤，滤饼用乙醇和水洗，干燥，得N，N，-二乙酰鸟嘌呤，收率92.6%。将乙酐、乙酸和对甲苯磺酸混合，冷至10℃以下。搅拌下加入二氧五环，控制内温在40℃以下。冷至室温，加入甲苯和N，N’-二乙酰鸟瞟呤，搅拌回流。冷至室温，加入氯仿，过滤。滤饼用氯仿洗，干燥后溶于40%甲胺水溶液，搅拌回流。冷却，过滤，滤液减压浓缩至浆状物，冷却后用乙醇洗，过滤。滤饼用水重结晶，得阿昔洛韦，收率75%，熔点255～258℃。
N，N’-二乙酰鸟嘌呤也可和2-氧杂-1，4-丁二醇二乙酸酯在二甲亚砜中，用对甲苯磺酸催化，于100℃下反应后，再进行层析得到阿昔洛韦的二乙酸酯，然后在饱和氨气的甲醇溶液中进行水解，得到阿昔洛韦，以鸟嘌呤计的总收率为43%。

方法2：鸟嘌呤三甲基硅烷化后，再和2-苄氧基乙氧基甲基氯反应后，再去掉苄基得阿昔洛韦，收率24%。

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阿昔洛韦海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

阿昔洛韦文献

Liquid chromatography tandem mass spectrometry quantitation of intracellular concentrations of ganciclovir and its phosphorylated forms.

Anal. Bioanal. Chem 407(12) , 3449-56, (2015)

Ganciclovir (GCV) is prescribed for cytomegalovirus infection which is a major issue in immunodepressed patients. It is however characterized by hematological toxicity. A better understanding of GCV c...

Comparison of in vitro release rates of acyclovir from cream formulations using vertical diffusion cells.

AAPS PharmSciTech 15(4) , 994-9, (2014)

Acyclovir, indicated in the treatment of herpes labialis ("cold sores"), is formulated as semisolid topical dosage forms and marketed in numerous countries. Since the formulations of the various acycl...

Transporter-mediated uptake of UDP-glucuronic acid by human liver microsomes: assay conditions, kinetics, and inhibition.

Drug Metab. Dispos. 43(1) , 147-53, (2014)

This study characterized the kinetics, variability, and factors that affect UDP-glucuronic acid (UDP-GlcUA) uptake by human liver microsomes (HLM). Biphasic kinetics were observed for UDP-GlcUA uptake...

更多文献

阿昔洛韦相关知识

[阿昔洛韦] - 说明书 - 作用 - 阿昔洛韦片(海王)副作用

2018-12-17 17:20:30

导读：阿昔洛韦（Aciclovir，ACV）又被写作Acyclovir或Acycloguanosine，又称无环鸟苷，是一种鸟嘌呤类似物类的抗病毒药物。主要用来治疗单纯疱疹病毒感染、水痘、带状疱疹。另外也应用在移植手术后，预防人类疱疹病毒第四型等巨细胞病毒感染的预防性投药。同时具有口服剂型与静脉注...

阿昔洛韦

阿昔洛韦用途

阿昔洛韦名称

阿昔洛韦生物活性

阿昔洛韦物理化学性质

阿昔洛韦MSDS

详细MSDS(安全技术说明书)

阿昔洛韦毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

阿昔洛韦安全信息

阿昔洛韦合成路线

详细合成路线

阿昔洛韦上下游产品

阿昔洛韦上游产品

阿昔洛韦下游产品

阿昔洛韦制备

阿昔洛韦海关

阿昔洛韦文献

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