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药品详细

Acyclovir(阿昔洛韦)

化学结构式图
中文名
阿昔洛韦
英文名
Acyclovir
分子式
C8H11N5O3
化学名
2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
分子量
Average: 225.2046
Monoisotopic: 225.086189243
CAS号
59277-89-3
ATC分类
D06B 未知;J05A Direct acting antivirals;S01A 抗感染药;J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A guanosine analog antiviral drug that acts as an antimetabolite. Acyclovir is used for the treatment of herpes simplex virus infections, varicella zoster (chickenpox) and herpes zoster (shingles).

生产厂家
  • Abbott laboratories
  • Actavis elizabeth llc
  • Actavis mid atlantic llc
  • Apotex inc etobicoke site
  • Apothecon inc div bristol myers squibb
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Belcher pharmaceuticals inc
  • Carlsbad technology inc
  • Dava pharmaceuticals inc
  • Genpharm inc
  • Glaxosmithkline
  • Hi tech pharmacal co inc
  • Hospira inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lek pharmaceutical and chemical co dd
  • Mylan laboratories inc
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Stason industrial corp
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. O’Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. Pubmed
  2. Gunness P, Aleksa K, Bend J, Koren G: Acyclovir-induced nephrotoxicity: the role of the acyclovir aldehyde metabolite. Transl Res. 2011 Nov;158(5):290-301. doi: 10.1016/j.trsl.2011.07.002. Epub 2011 Aug 3. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Purines and Purine Derivatives
  • Inosines
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Ethers
  • Alcohols and Polyols
  • Pyrimidines and Derivatives
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Cyanamides
  • Inosines
适应症
药理
Indication For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox.
Pharmacodynamics Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV. EC50 value of acyclovir against clinical herpes virus isolates was 1.3 μM (range: < 0.56 to 3.3 μM).
Mechanism of action Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase, and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase. Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA. Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator. One may consider aciclovir to be a prodrug as it is metabolized to more active compounds. Aciclovir is selective and low in cytotoxicity as the cellular thymidine kinase of normal, uninfected cells does not use aciclovir effectively as a substrate.
Absorption The oral bioavailability is 10% to 20%, and decreases with increasing dose. Food does not affect the absorption of acyclovir. The following are the pharmacokinetic parameters for 50 mg buccal tablet, Sitavig, in the saliva: AUC 0 - 24 hours = 2900±2400 mcg.h/mL; Cmax = 440±241 mcg/mL; Tmax = 7.95 ± 4.08 hours.
Volume of distribution Not Available
Protein binding 9%-33%
Metabolism
Hepatic, Acyclovir is metabolized to 9-[(carboxymethoxy)methyl]guanine (CMMG) and 8­ hydroxy-acyclovir (8-OH-ACV) by oxidation and hydroxylation. It is suggested in studies that acyclovir is first metabolized to acyclovir aldehyde by alcohol dehydrogenase and then converted to CMMG. The build up of acyclovir aldehyde may be the cause of acyclovir-induced nephrotoxicity in the absence of crystalluria.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Acyclovir
    		9-carboxymethoxymethylguanine Details
    Route of elimination Primarily excreted unchanged by the kidneys via active tubular secretion.
    Half life 2.5-3.3 hours
    Clearance Not Available
    Toxicity Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.
    Affected organisms
    • Human Herpes Virus
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 255 °C PhysProp
    water solubility 2.5 mg/mL at 37°C FDA label
    logP -1.56 KRISTL,A ET AL. (1993)
    Caco2 permeability -6.15 ADME Research, USCD
    pKa 2.27 and 9.25 FDA label
    Predicted Properties
    Property Value Source
    water solubility 9.08e+00 g/l ALOGPS
    logP -0.95 ALOGPS
    logP -1 ChemAxon
    logS -1.4 ALOGPS
    pKa (strongest acidic) 7.99 ChemAxon
    pKa (strongest basic) 2.63 ChemAxon
    physiological charge 0 ChemAxon
    hydrogen acceptor count 7 ChemAxon
    hydrogen donor count 3 ChemAxon
    polar surface area 114.76 ChemAxon
    rotatable bond count 4 ChemAxon
    refractivity 54.63 ChemAxon
    polarizability 21.51 ChemAxon
    药物相互作用
    Drug Interaction
    Aminophylline Acyclovir increases the effect and toxicity of theophylline
    Dyphylline Acyclovir increases the effect and toxicity of dyphylline.
    Oxtriphylline Aciclovir may increase the effect and toxicity of oxtriphylline.
    Theophylline Acyclovir may increase the effect and toxicity of theophylline.
    食物相互作用
    • Increase liquid intake.
    • Take without regard to meals.

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