CAS 59277-89-3|Acyclovir|2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one|acyclovir|zovir|Acycloguanosine|Aciclovir|Activir|Virovir|Virasorb|Geavir|Herpetad|Cycloviran|Zyclir|Avirax|Su...

基本信息

化学结构

分子式

C₈H₁₁N₅O₃

分子量

225.20464

精确质量

225.08618924

电荷

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)

InChIKey

MKUXAQIIEYXACX-UHFFFAOYSA-N

Canonic Smiles

OCCOCn1cnc2c1nc(N)[nH]c2=O

Isomeric Smiles

c12c(ncn2COCCO)c(=O)[nH]c(n1)N

计算属性

JChem

LogD (pH = 7.4)

-1.55

LogD (pH = 5.5)

-1.55

Log P

-1.55

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

10.16

极化表面积

114.76

极化性

21.59

摩尔折射率

55.07

LOG S

-1.39

数据来源

名称和标识

别名

AcyclovirAcycloguanosineAciclovirZyclirActivirGeavirAviraxCycloviranSupraviranVirasorbVirovirHerpetadZoviraxACYCLOGUANOSINE9-[(2-Hydroxyethoxy)-methyl]guanine;AcyclovirAciclovirMilavirAcyclovirMirolexSoothelipAcycloguanosine2-amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one9-[(2-Hydroxyethoxy)methyl]guanineacycloviracycloguanosine

IUPAC标准名

2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

IUPAC传统名

acyclovir zovir 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

国际非专利药品(INN)

aciclovirumaciclovir

商标名

Zovir

名称和标识

数据登录号

化合物性质

产品相关信息

药理学性质

相关基因信息

human ... HV1S(3365), NP(4860)

生物活性机理

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.

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,

Guanosine analog that acts as an antimetabolite.

Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.

化合物性质

分子相关蛋白质

分子图谱

暂无数据

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描述信息

Selleck Chemicals

S1807

Research Area: Infection
Biological Activity:
Acyclovir is a synthetic nucleoside analogue active against herpesviruses. It is a guanosine analogue antiviral drug. Aciclovir differs from previous nucleoside analogues in that it contains only a partial nucleoside structure: the sugar ring is replaced by an open-chain structure. It is selectively converted into acyclo-guanosine monophosphate (acyclo-GMP) by viral thymidine kinase, which is far more effective (3000 times) in phosphorylation than cellular thymidine kinase. [1]

MP Biomedicals

02154713

(9-[(2-Hydroxyethoxy)- methyl]guanine;Acyclovir) This product inhibits the replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase. It can be used to induce apoptosis in cells tra

Sigma Aldrich

A4669

Application
Acycloguanosine has been used to study herpes simplex virus latency and reactivation, as well as HIV retrovirus reproduction. Acycloguanosine inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.
Biochem/physiol Actions
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase.
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase. Acycloguanosine can be used to induce apoptosis in cells transfected with HSV-TK. Inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.

ChEBI

CHEBI:2453

An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Aciclovir

• Jennings, R. et al., Antimicrob. Agents Chemother., 1999, 43, 53-61, (acyclovir elaidate)

• Plass, M. et al., J.C.S. Perkin 2, 1999, 2641-2646, (uv, pmr, ir, Raman)

• Ger. Pat., 1976, 2 539 963; CA, 84, 180300p, (synth)

• Birnbaum, G.I. et al., Can. J. Chem., 1984, 62, 2646, (cryst struct)

• Alhede, B. et al., J.O.C., 1991, 56, 2139, (synth, cmr)

• Buck, I.M. et al., Tetrahedron, 1994, 50, 9195-9206, (synth)

• Stimac, A. et al., Synthesis, 1990, 461-464, (synth)

• Gao, H. et al., Synth. Commun., 2001, 31, 1399-1419, (synth)

• Arndt, K.A. et al., J. Am. Acad. Dermatol., 1988, 18, 188, (adverse effects)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 602; 628

• Ormrod, D. et al., Drugs, 2000, 59, 839-863; 1317-1359

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEC700; AEC725

• Elion, G.B. et al., Proc. Natl. Acad. Sci. U.S.A., 1977, 74, 5716, (pharmacol)

• Krasny, H.C. et al., Biochem. Pharmacol., 1986, 35, 4339, (metab)

• U.K. Pat., 1993, Norsk Hydro A/S, 2 260 319; CA, 119, 271633g, (acyclovir elaidate)

• Rees, P.J. et al., J. Antimicrob. Chemother., 1986, 18, 215-222, (pharmacokinet)

• Gao, H. et al., Synthesis, 2000, 329-351, (rev)

• Eur. Pat., 1984, Wellcome, 108 285; CA, 101, 192401e, (Desciclovir, synth, pharmacol)

• Krenitsky, T.A. et al., Proc. Natl. Acad. Sci. U.S.A., 1984, 81, 3209-3213, (synth, pharmacol)

• Chu, C.K. et al., J. Het. Chem., 1986, 23, 289, (rev)

• Petty, B.G. et al., Antimicrob. Agents Chemother., 1987, 31, 1317-1322, (pharmacokinet)

• Fiddian, A.P., Appl. Virol., 1984, 103, (rev, pharmacol)

• Reardon, J.E. et al., Adv. Pharmacol., 1991, 22, 1, (rev)

• Wagstaff, A.J. et al., Drugs, 1994, 47, 153, (rev)

• Kelley, J.L. et al., J. Het. Chem., 1986, 23, 271, (synth)

• Radl, S. et al., Cesk. Farm., 1987, 36, 58, (synth)

• Matsumoto, H. et al., Chem. Pharm. Bull., 1988, 36, 1153, (synth)

• De Miranda, P. et al., Antiviral Chem. Chemother., 1992, 3, 1, (metab, rev)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

IUPAC传统名

acyclovir zovir 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

国际非专利药品(INN)

aciclovirumaciclovir

商标名

Zovir

描述信息

S1807

A4669

An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Aciclovir

• Jennings, R. et al., Antimicrob. Agents Chemother., 1999, 43, 53-61, (acyclovir elaidate)

• Plass, M. et al., J.C.S. Perkin 2, 1999, 2641-2646, (uv, pmr, ir, Raman)

• Ger. Pat., 1976, 2 539 963; CA, 84, 180300p, (synth)

• Birnbaum, G.I. et al., Can. J. Chem., 1984, 62, 2646, (cryst struct)

• Alhede, B. et al., J.O.C., 1991, 56, 2139, (synth, cmr)

• Buck, I.M. et al., Tetrahedron, 1994, 50, 9195-9206, (synth)

• Stimac, A. et al., Synthesis, 1990, 461-464, (synth)

• Gao, H. et al., Synth. Commun., 2001, 31, 1399-1419, (synth)

• Arndt, K.A. et al., J. Am. Acad. Dermatol., 1988, 18, 188, (adverse effects)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 602; 628

• Ormrod, D. et al., Drugs, 2000, 59, 839-863; 1317-1359

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEC700; AEC725

• Elion, G.B. et al., Proc. Natl. Acad. Sci. U.S.A., 1977, 74, 5716, (pharmacol)

• Krasny, H.C. et al., Biochem. Pharmacol., 1986, 35, 4339, (metab)

• U.K. Pat., 1993, Norsk Hydro A/S, 2 260 319; CA, 119, 271633g, (acyclovir elaidate)

• Rees, P.J. et al., J. Antimicrob. Chemother., 1986, 18, 215-222, (pharmacokinet)

• Gao, H. et al., Synthesis, 2000, 329-351, (rev)

• Eur. Pat., 1984, Wellcome, 108 285; CA, 101, 192401e, (Desciclovir, synth, pharmacol)

• Krenitsky, T.A. et al., Proc. Natl. Acad. Sci. U.S.A., 1984, 81, 3209-3213, (synth, pharmacol)

• Chu, C.K. et al., J. Het. Chem., 1986, 23, 289, (rev)

• Petty, B.G. et al., Antimicrob. Agents Chemother., 1987, 31, 1317-1322, (pharmacokinet)

• Fiddian, A.P., Appl. Virol., 1984, 103, (rev, pharmacol)

• Reardon, J.E. et al., Adv. Pharmacol., 1991, 22, 1, (rev)

• Wagstaff, A.J. et al., Drugs, 1994, 47, 153, (rev)

• Kelley, J.L. et al., J. Het. Chem., 1986, 23, 271, (synth)

• Radl, S. et al., Cesk. Farm., 1987, 36, 58, (synth)

• Matsumoto, H. et al., Chem. Pharm. Bull., 1988, 36, 1153, (synth)

• De Miranda, P. et al., Antiviral Chem. Chemother., 1992, 3, 1, (metab, rev)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

药理学性质

化合物信息

ID:44444