Page last updated: 2024-10-15

9-(4-hydroxybutyl)guanine

Cross-References

ID SourceID
PubMed CID135433410
CHEMBL ID258513
SCHEMBL ID571645
SCHEMBL ID14595281
MeSH IDM0117247

Synonyms (18)

Synonym
2-amino-9-(4-hydroxybutyl)hydropurin-6-one
2-amino-9-(4-hydroxybutyl)-1h-purin-6-one
6h-purin-6-one, 2-amino-1,9-dihydro-9-(4-hydroxybutyl)-
2-amino-9-(4-hydroxybutyl)-1,9-dihydro-6h-purin-6-one
inchi=1/c9h13n5o2/c10-9-12-7-6(8(16)13-9)11-5-14(7)3-1-2-4-15/h5,15h,1-4h2,(h3,10,12,13,16
bdbm21868
9-(4-hydroxybutyl)guanine
2-amino-9-(4-hydroxybutyl)-6,9-dihydro-3h-purin-6-one
chembl258513 ,
23169-37-1
SCHEMBL571645
DVQJDXCYEPGOCF-UHFFFAOYSA-N
9-hydroxybutylguanine
SCHEMBL14595281
DTXSID90177750
2-amino-9-(4-hydroxybutyl)-6,9-dihydro-1h-purin-6-one
famciclovir impurity 2
2-amino-9-(4-hydroxybutyl)-1h-purin-6(9h)-one

Pharmacokinetics

ExcerptReference
" The extremely short half-life in plasma and the high clearance of 9-(4-hydroxybutyl)guanine as compared with those of (R)-9-(3,4-dihydroxybutyl)guanine probably made 9-(4-hydroxybutyl)guanine inefficacious when given intraperitoneally or orally to mice infected with herpesvirus."( Antiherpes effects and pharmacokinetic properties of 9-(4-hydroxybutyl) guanine and the (R) and (S) enantiomers of 9-(3,4-dihydroxybutyl)guanine.
Aoki, FY; Datema, R; Ericson, AC; Johansson, NG; Larsson, A; Oberg, B; Yisak, WA, 1985
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase Macacine alphaherpesvirus 1IC50 (µMol)177.00000.15002.57504.2000AID326127
Thymidine kinase, cytosolicHomo sapiens (human)Ki2.06000.09001.52137.0000AID210697
Thymidine kinaseHuman alphaherpesvirus 1 strain SC16IC50 (µMol)60.00000.10001.84917.9433AID241897
Thymidine kinase Human alphaherpesvirus 2IC50 (µMol)160.00000.10000.84621.6000AID241898
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID241897Inhibitory concentration against herpes simplex virus type 1 thymidine kinase2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Inhibition of herpes simplex virus thymidine kinases by 2-phenylamino-6-oxopurines and related compounds: structure-activity relationships and antiherpetic activity in vivo.
AID1572733Antiviral activity against Varicella-zoster virus Oka harboring thymidine kinase infected in HEL cells assessed as reduction in virus plaque formation2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID326131Activity of Herpes B virus recombinant thymidine kinase at 100 uM2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Sensitivity of monkey B virus (Cercopithecine herpesvirus 1) to antiviral drugs: role of thymidine kinase in antiviral activities of substrate analogs and acyclonucleosides.
AID86827Percentage of diphosphates (DP) in the second step of staggered assay mixture from step 1 was incubated with GMP kinase and crude extract of HSV-1 infected HeLa cells over night1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572740Cytostatic activity against human NCI-H460 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572729Antiviral activity against herpes simplex virus 1 KOS infected in HEL cells assessed as reduction in virus-induced cytopathogenicity by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID326127Inhibition of Herpes B virus recombinant thymidine kinase-mediated [3H]TdR phosphorylation2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Sensitivity of monkey B virus (Cercopithecine herpesvirus 1) to antiviral drugs: role of thymidine kinase in antiviral activities of substrate analogs and acyclonucleosides.
AID1572730Antiviral activity against herpes simplex virus 2 G infected in HEL cells assessed as reduction in virus-induced cytopathogenicity by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID241898Inhibitory concentration against herpes simplex virus type 2 thymidine kinase2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Inhibition of herpes simplex virus thymidine kinases by 2-phenylamino-6-oxopurines and related compounds: structure-activity relationships and antiherpetic activity in vivo.
AID164770Tested for its ability to inhibit calf spleen purine nucleoside phosphorylase (PNP)1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
Structure-based design of inhibitors of purine nucleoside phosphorylase. 5. 9-Deazahypoxanthines.
AID87443Percentage of triphosphates (TP) in the second step of staggered assay mixture from step 1 was incubated with GMP kinase and crude extract of HSV-1 infected HeLa cells over night1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572736Antiviral activity against Human cytomegalovirus Davis assessed as reduction in virus-induced cytopathogenicity by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID53487Inhibition of DNA polymerase1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572739Cytostatic activity against human HAP1 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID87640Antiviral activity against HSV-1 cell line (concentration required to prevent viral cytopathic effect in half of primary rabbit kidney cell cultures)1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID87302Percentage of monophosphates (MP) formed in the first step of staggered assay compound was incubated with HSV-1 thymidine kinase for 4 hr1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572735Antiviral activity against Human cytomegalovirus AD169 assessed as reduction in virus-induced cytopathogenicity by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID90940Antiviral activity against HCMV was determined; No inhibition1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.
AID53466Inhibition of DNA polymerase1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572738Cytostatic activity against human Capan1 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID230017Ratio of Ki values for guanine and related hypoxanthines in PNP inhibition assay1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
Structure-based design of inhibitors of purine nucleoside phosphorylase. 5. 9-Deazahypoxanthines.
AID87834Antiviral activity against HSV-2 cell line (concentration required to prevent viral cytopathic effect in half of primary rabbit kidney cell cultures)1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572737Cytostatic activity against human hTERT-RPE1 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572731Antiviral activity against thymidine kinase deficient and aciclovir resistant herpes simplex virus 1 KOS infected in HEL cells assessed as reduction in virus-induced cytopathogenicity by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572741Cytostatic activity against human DND41 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID210697Binding affinity towards HSV-1 thymidine kinase was determined1995Journal of medicinal chemistry, Jan-06, Volume: 38, Issue:1
Synthesis, properties, and pharmacokinetic studies of N2-phenylguanine derivatives as inhibitors of herpes simplex virus thymidine kinases.
AID82116Antiviral activity against HIV-1 was determined; No inhibition1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.
AID1572732Cytotoxicity against HEL cells assessed as effect on cell morphology at 0.32 to 200 uM by microscopic analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID87303Percentage of monophosphates (MP) in the second step of staggered assay mixture from step 1 was incubated with GMP kinase and crude extract of HSV-1 infected HeLa cells over night1988Journal of medicinal chemistry, Dec, Volume: 31, Issue:12
Synthesis and antiherpetic activity of (+/-)-9-[[(Z)-2-(hydroxymethyl)cyclopropyl]methyl]guanine and related compounds.
AID1572734Antiviral activity against thymidine kinase deficient Varicella-zoster virus 07-1 infected in HEL cells assessed as reduction in virus plaque formation2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572743Cytostatic activity against human K562 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572744Cytostatic activity against human Z138 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1572742Cytostatic activity against human HL60 cells2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.
AID1798138Thymidine Kinase Inhibition Assay from Article 10.1021/jm049059x: \\Inhibition of herpes simplex virus thymidine kinases by 2-phenylamino-6-oxopurines and related compounds: structure-activity relationships and antiherpetic activity in vivo.\\2005Journal of medicinal chemistry, Jun-02, Volume: 48, Issue:11
Inhibition of herpes simplex virus thymidine kinases by 2-phenylamino-6-oxopurines and related compounds: structure-activity relationships and antiherpetic activity in vivo.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (33.33)18.7374
1990's4 (33.33)18.2507
2000's2 (16.67)29.6817
2010's2 (16.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]