Compounds > cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine
Page last updated: 2024-12-08

cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine: specific name and structure not given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID189926
CHEMBL ID112159
SCHEMBL ID10073562
MeSH IDM0196560

Synonyms (17)

Synonym
9-[[(5s)-2-hydroxy-2-oxo-1,4,2$l^{5}-dioxaphosphinan-5-yl]methyl]purin-6-amine
(5s)-5-[(6-aminopurin-9-yl)methyl]-2-hydroxy-1,4,2-dioxaphosphan-2-one
chpmpa
cyclic hpmpa
CHEMBL112159
cyclic(s)-hpmpa
113892-17-4
9h-purin-6-amine, 9-((2-hydroxy-2-oxido-1,4,2-dioxaphosphorinan-5-yl)methyl)-, (s)-
9h-purin-6-amine, 9-((2-hydroxy-1,4,2-dioxaphosphorinan-5-yl)methyl)-, p-oxide, (s)-
cyclic-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine
9h-purin-6-amine, 9-(((5s)-2-hydroxy-2-oxido-1,4,2-dioxaphosphorinan-5-yl)methyl)-
cyclic-hpmpa
SCHEMBL10073562
5-[(6-amino-9h-purin-9-yl)methyl]-2-hydroxy-1,4,2lambda~5~-dioxaphosphinan-2-one
DTXSID30921234
9-[[(5s)-2-hydroxy-2-oxo-1,4,2lambda5-dioxaphosphinan-5-yl]methyl]purin-6-amine
(5s)-5-((6-amino-9h-purin-9-yl)methyl)-2-hydroxy-1,4,2-dioxaphosphinane 2-oxide

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" (l)-Tyr-NH-i-Bu cHPMPA (11) was converted in rat or mouse plasma solely to two active metabolites and had significantly enhanced oral bioavailability vs parent drug 1 in a mouse model (39% vs <5%)."( Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
Borysko, KZ; Breitenbach, JM; Collins, M; Drach, JC; Hilfinger, JM; Kashemirov, BA; Krylov, IS; McKenna, CE; Peterson, LW; Serpi, M; Zakharova, VM, 2011)		0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID374197Selectivity index, ratio of CC50 for HEL299 cells to EC50 for Camelpox virus CML14 infected in HEL299 cells2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID217979Inhibitory concentration required against vaccinia virus in Vero cell culture2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A new approach to the synthesis of optically active alkylated adenine derivatives.
AID374207Antiviral activity against Camelpox virus CML1 infected in human PHK assessed as reduction in viral titer after 6 days postinfection by virus yield reduction assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID228284Cytotoxic concentration at which cell viability was reduced by 50%2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A new approach to the synthesis of optically active alkylated adenine derivatives.
AID374208Antiviral activity against Camelpox virus CML14 infected in human PHK assessed as reduction in viral titer after 6 days postinfection by virus yield reduction assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID324769Selectivity index, ratio of CC50 for african green monkey BSC1 cells ot EC50 for Simian virus 40 PML1 EK2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324759Cytotoxicity against mouse UC1B cells2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374202Selectivity index, ratio of CC50 for human PHK to EC50 for Camelpox virus CML14 infected in human PHK2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID636696Antiviral activity against Vaccinia virus Copenhagen infected in HFF cells incubated for 3 days by plaque reduction assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID636697Antiviral activity against HSV1 KOS infected in HFF cells incubated for 3 days by plaque reduction assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID324762Selectivity index, ratio of CC50 for mouse UC1B cells to EC50 of Murine polyomavirus 2PTA22007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID125073Inhibitory concentration required against Monkeypox virus in Vero cell culture2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A new approach to the synthesis of optically active alkylated adenine derivatives.
AID324756Antiviral activity against Murine polyomavirus PTA in mouse UC1B cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324767Cytotoxicity against african green monkey BSC1 cells2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324755Antiviral activity against Murine polyomavirus MN/RDE Toronto in mouse UC1B cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374206Antiviral activity against Camelpox virus CML14 infected in HEL299 cells assessed as reduction in viral titer after 6 days postinfection by virus yield reduction assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID374205Antiviral activity against Camelpox virus CML1 infected in HEL299 cells assessed as reduction in viral titer after 6 days postinfection by virus yield reduction assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID324764Antiviral activity against Simian virus 40 A2895 in african green monkey BSC1 cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324763Selectivity index, ratio of CC50 for mouse UC1B cells to EC50 of Murine polyomavirus LID12007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374196Selectivity index, ratio of CC50 for HEL299 cells to EC50 for Camelpox virus CML1 infected in HEL299 cells2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID324770Selectivity index, ratio of CC50 for african green monkey BSC1 cells ot EC50 for Simian virus 40 PML2 DAR2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374201Selectivity index, ratio of CC50 for human PHK to EC50 for Camelpox virus CML1 infected in human PHK2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID374194Antiviral activity against Camelpox virus CML14 infected in HEL299 cells assessed as inhibition of virus-induced cytopathic effect after 6 days by Giemsa staining2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID374203Cytotoxicity against HEL299 cells assessed as minimum cytotoxic concentration required for alteration in cell morphology after 4 days by microscopy2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID324768Selectivity index, ratio of CC50 for african green monkey BSC1 cells ot EC50 for Simian virus 40 A28952007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID636699Cytotoxicity against human KB cells after 48 hrs by crystal violet staining based spectrophotometric analysis2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID374200Cytotoxicity against human PHK after 4 days by Z1 Coulter counting analysis2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID636695Antiviral activity against Cowpox virus Brighton infected in HFF cells incubated for 3 days by plaque reduction assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID374193Antiviral activity against Camelpox virus CML1 infected in HEL299 cells assessed as inhibition of virus-induced cytopathic effect after 6 days by Giemsa staining2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID54326Inhibitory concentration required against Cowpox virus in Vero cell culture2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A new approach to the synthesis of optically active alkylated adenine derivatives.
AID636700Cytotoxicity against HFF cells after 48 hrs by visual cytotoxicity observation assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID324757Antiviral activity against Murine polyomavirus 2PTA2 in mouse UC1B cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324766Antiviral activity against Simian virus 40 PML2 DAR in african green monkey BSC1 cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374204Cytotoxicity against human PHK assessed as minimum cytotoxic concentration required for alteration in cell morphology after 4 days by microscopy2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID374198Antiviral activity against Camelpox virus CML1 infected in human PHK assessed as inhibition of virus-induced cytopathic effect after 6 days by Giemsa staining2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID374195Cytotoxicity against HEL299 cells after 4 days by Z1 Coulter counting analysis2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
AID324760Selectivity index, ratio of CC50 for mouse UC1B cells to EC50 of Murine polyomavirus MN/RDE Toronto2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324765Antiviral activity against Simian virus 40 PML1 EK in african green monkey BSC1 cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID636698Antiviral activity against HCMV Towne infected in HFF cells incubated for 10 days by plaque reduction assay2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: synthesis, stability, antiviral activity, and in vivo transport studies.
AID324761Selectivity index, ratio of CC50 for mouse UC1B cells to EC50 of Murine polyomavirus PTA2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID324758Antiviral activity against Murine polyomavirus LID1 ATCC VR-252 in mouse UC1B cells assessed as reduction of virus-induced cytopathogenicity2007Antimicrobial agents and chemotherapy, Jun, Volume: 51, Issue:6
Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.
AID374199Antiviral activity against Camelpox virus CML14 infected in human PHK assessed as inhibition of virus-induced cytopathic effect after 6 days by Giemsa staining2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (28.57)18.2507
2000's4 (57.14)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.41 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.92406-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cytosine
[no description available]		2.6930aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
adefovir
adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.		2.44206-aminopurines;
ether;
phosphonic acids		antiviral drug;
DNA synthesis inhibitor;
drug metabolite;
HIV-1 reverse transcriptase inhibitor;
nephrotoxic agent
cidofovir anhydrous
Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.		3.1150phosphonic acids;
pyrimidone		anti-HIV agent;
antineoplastic agent;
antiviral drug;
photosensitizing agent
9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine
[no description available]		2.0310
9-(s)-(3-hydroxy-2-(phosphonomethoxy)propyl)adenine
[no description available]		2.7330
9-(3-hydroxy-2-phosphonomethoxypropyl)-2,6-diaminopurine
9-(3-hydroxy-2-phosphonomethoxypropyl)-2,6-diaminopurine: RN refers to (S)-isomer		2.4420
9-(2,3-dihydroxypropyl)adenine, (s)-isomer
[no description available]		2.0210
cyclic-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine
cyclic-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine: prodrug for HPMPC; specific name and structure not given in first source		2.9340
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.6930divalent inorganic anion;
phosphite ion
6-phosphonylmethoxyethoxy-2,4-diaminopyrimidine
[no description available]		2.4420
2-acetylpyridine thiosemicarbazone
2-acetylpyridine thiosemicarbazone: RN given refers to parent cpd		2.0610
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		2.06102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
ganciclovir
[no description available]		2.69302-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
9-((2-phosphonylmethoxy)ethyl)guanine
9-((2-phosphonylmethoxy)ethyl)guanine: structure given in first source		2.0310phosphoethanolamine
ConditionIndicatedRelationship StrengthStudiesTrials
Cytomegalovirus
A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.		02.7130
Cytomegaloviral Retinitis
[description not available]		02.0310
Intraocular Pressure
The pressure of the fluids in the eye.		02.0310
Cytomegalovirus Retinitis
Infection of the retina by cytomegalovirus characterized by retinal necrosis, hemorrhage, vessel sheathing, and retinal edema. Cytomegalovirus retinitis is a major opportunistic infection in AIDS patients and can cause blindness.		02.0310