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...

General Information

Structure

Molecular Formula

C₈H₁₁N₅O₃

Molecular Mass

225.20464

Exact Mass

225.08618924

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

-1.55

LogD (pH = 5.5)

-1.55

Log P

-1.55

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.16

Polar Surface Area

114.76

Polarizability

21.59

Molar Refractivity

55.07

LOG S

-1.39

Data Source

Names and Identifiers

Synonyms

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

IUPAC name

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

IUPAC Traditional name

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

International Nonproprietary Name (INN)

aciclovirumaciclovir

Brand Name

Zovir

Names and Identifiers

Registration numbers

MDL Number

MFCD00057880

CAS Number

59277-89-3

EC Number

261-685-1

PubChem SID

2427807816204920753801304

PubChem CID

2022135398513

BKMS React Database

17305544061664741552717698154360153377

BRENDA Database

3.4.22.283.1.5.B16.3.4.22.7.1.1452.1.1.202.7.7.481.17.3.22.4.2.11.13.11.522.7.1.213.1.1.437.6.2.22.4.2.4

SABIO-RK Database

8017811011900

UniProt Database

A7KAU3Q16774P04407P0C0E6Q8VC69Q9QNF7P03176P09250Q4U2R8Q5RFD2Q4W8A3Q5RCH6P03177P17402O35956

Beilstein Number

1219402

Patent number

US2006058319EP1872775WO2005073233US2007197646US2007269420US2005282842EP1671624EP1844776WO2005077050US2007224255US2005203106EP1579874EP1762226GB2282759

CompTox Database

DTXSID1022556

NMRShiftDB Database

20025956

PubMed Citation Links

24346595116871272816621783085112602423311994034

DrugBank ID

DB00787

BRENDA Ligand Database

15337717698440616647415436015527173055

ACToR Database

59277-89-3

Reactom Database

R-HSA-6784959R-HSA-561041

Drug Central Database

MetaboLights Database

MTBLS379MTBLS673MTBLS2406MTBLS4967

KEGG ID

C06810

Protein Data Bank

3ix23mjr1pwy5i3c2ki54da7

KEGG DRUG Database

D00222

Reaxys Registry

1219402

PDBeChem Database

AC2

CHEBI ID

CHEBI:2453CHEBI:40459

BindingDB Database

LINCS Database

HMDB Database

Wikipedia Title

CHEMBL

SureChEMBL Database

Registration numbers

Properties

Product Information

Safety Information

Physical Property

Pharmacology Properties

Gene Information

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

Mechanism of Action

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.

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

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

International Nonproprietary Name (INN)

aciclovirumaciclovir

Brand Name

Zovir

Molecule Details

S1807

A4669

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

References

PubChem Literature

From Data Sources

• 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)

Bioactivity

PubChem BioAssay

Registration numbers

MDL Number

MFCD00057880

CAS Number

59277-89-3

EC Number

261-685-1

PubChem SID

2427807816204920753801304

PubChem CID

2022135398513

BKMS React Database

17305544061664741552717698154360153377

BRENDA Database

3.4.22.283.1.5.B16.3.4.22.7.1.1452.1.1.202.7.7.481.17.3.22.4.2.11.13.11.522.7.1.213.1.1.437.6.2.22.4.2.4

SABIO-RK Database

8017811011900

UniProt Database

A7KAU3Q16774P04407P0C0E6Q8VC69Q9QNF7P03176P09250Q4U2R8Q5RFD2Q4W8A3Q5RCH6P03177P17402O35956

Beilstein Number

1219402

Patent number

US2006058319EP1872775WO2005073233US2007197646US2007269420US2005282842EP1671624EP1844776WO2005077050US2007224255US2005203106EP1579874EP1762226GB2282759

CompTox Database

DTXSID1022556

NMRShiftDB Database

20025956

PubMed Citation Links

24346595116871272816621783085112602423311994034

DrugBank ID

DB00787

BRENDA Ligand Database

15337717698440616647415436015527173055

ACToR Database

59277-89-3

Reactom Database

R-HSA-6784959R-HSA-561041

Drug Central Database

MetaboLights Database

MTBLS379MTBLS673MTBLS2406MTBLS4967

KEGG ID

C06810

Protein Data Bank

3ix23mjr1pwy5i3c2ki54da7

KEGG DRUG Database

D00222

Reaxys Registry

1219402

PDBeChem Database

AC2

CHEBI ID

CHEBI:2453CHEBI:40459

BindingDB Database

LINCS Database

HMDB Database

Wikipedia Title

CHEMBL

SureChEMBL Database

Properties

Product Information

Safety Information

Physical Property

Pharmacology Properties

Gene Information

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

Mechanism of Action

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.

Molecule

ID:44444