Tìm theo
Aciclovir
Các tên gọi khác (5 ) :
  • Aciclovir
  • Aciclovirum
  • Acycloguanosine
  • Acyclovir
  • Zovir
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 59277-89-3
ATC: D06BB03, J05AB01, S01AD03
ĐG : Actavis Group , http://www.actavis.com
CTHH: C8H11N5O3
PTK: 225.2046
A guanosine analog antiviral drug that acts as an antimetabolite. Aciclovir is used for the treatment of herpes simplex virus infections, varicella zoster (chickenpox) and herpes zoster (shingles).
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C8H11N5O3
Phân tử khối
225.2046
Monoisotopic mass
225.086189243
InChI
InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
InChI Key
InChIKey=MKUXAQIIEYXACX-UHFFFAOYSA-N
IUPAC Name
2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
Traditional IUPAC Name
aciclovir
SMILES
NC1=NC(=O)C2=C(N1)N(COCCO)C=N2
Độ tan chảy
255 °C
Độ hòa tan
2.5 mg/mL at 37°C
logP
-1.56
logS
-1.4
pKa (strongest acidic)
7.99
pKa (Strongest Basic)
2.63
PSA
114.76 Å2
Refractivity
54.63 m3·mol-1
Polarizability
21.51 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
7
H Bond Donor Count
3
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
caco2 Permeability
-6.15
pKa
2.27 and 9.25
Dược Lực Học : 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).
Cơ Chế Tác Dụng : A guanosine analog antiviral drug that acts as an antimetabolite. Aciclovir is used for the treatment of herpes simplex virus infections, varicella zoster (chickenpox) and herpes zoster (shingles). 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.
Dược Động Học :
▧ 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.
▧ 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.
▧ Route of Elimination :
Primarily excreted unchanged by the kidneys via active tubular secretion.
▧ Half Life :
2.5-3.3 hours
Độc Tính : 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.
Chỉ Định : For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox.
Tương Tác Thuốc :
  • 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.
Liều Lượng & Cách Dùng : Capsule - Oral - 200 mg
Cream - Topical - 5%
Ointment - Topical - 5%
Solution - Intravenous - 50 mg/mL
Solution - Intravenous - 500 mg, 1000 mg
Suspension - Oral - 200 mg/5 mL
Tablet - Buccal - 50 mg
Tablet - Oral - 400 mg, 800 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Sản phẩm biệt dược : Sitavig
  • Công ty :
    Sản phẩm biệt dược : Zovir
  • Công ty :
    Sản phẩm biệt dược : Zovirax
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00787
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2022
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506002
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06810
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00222
ChemSpider
http://www.chemspider.com/Chemical-Structure.1945.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0228-2605-11
PharmGKB
http://www.pharmgkb.org/drug/PA448045
Wikipedia
http://en.wikipedia.org/wiki/Aciclovir
RxList
http://www.rxlist.com/cgi/generic/acyclo.htm
Drugs.com
http://www.drugs.com/acyclovir.html
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