denbufylline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 2984 |
| CHEMBL ID | 277465 |
| CHEBI ID | 92669 |
| SCHEMBL ID | 127152 |
| MeSH ID | M0128719 |
| Synonym |
|---|
| 57076-71-8 |
| 1,3-dibutyl-7-(2-oxo-propyl)-3,7-dihydro-purine-2,6-dione(denbufylline) |
| 1,3-dibutyl-7-(2-oxo-propyl)-3,7-dihydro-purine-2,6-dione |
| bdbm50047247 |
| 1,3-dibutyl-7-(2-oxo-propyl)-3,7-dihydro-purine-2,6-dione (denbufyllene) |
| BRD-K37792168-001-01-0 |
| brl-30892 |
| denbufylline |
| brl 30892 |
| 3,7-dihydro-1,3-dibutyl-7-(2-oxopropyl)-1h-purine-2,6-dione |
| denbufilina [spanish] |
| 1,3-di-n-butyl-7-(2-oxopropyl)xanthine |
| 7-acetonyl-1,3-dibutylxanthine |
| 1h-purine-2,6-dione, 3,7-dihydro-1,3-dibutyl-7-(2-oxopropyl)- |
| denbufyllinum [latin] |
| HSCI1_000304 |
| HMS2089J13 |
| CHEMBL277465 , |
| 1,3-dibutyl-7-(2-oxopropyl)purine-2,6-dione |
| denbufyllinum |
| denbufylline [inn:ban] |
| unii-04b949ko6f |
| 04b949ko6f , |
| denbufilina |
| FT-0603111 |
| denbufylline [inn] |
| denbufylline [mart.] |
| SCHEMBL127152 |
| AB01275458-01 |
| DTXSID30205687 |
| sr-05000001455 |
| SR-05000001455-1 |
| CHEBI:92669 |
| AKOS030239799 |
| 1,3-dibutyl-7-(2-oxopropyl)-1h-purine-2,6(3h,7h)-dione |
| Q27164375 |
| 1,3-di-n-butyl-7-(2'-oxopropyl)xanthine |
Denbufylline has been shown to selectively inhibit a low KM, Ca2+/calmodulin-independent phosphodiesterase isozyme. It increased the amplitude of the extracellularly recorded CA1 population spike evoked by electrical stimulation of the Schaffer collateral/commissural pathway.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Denbufylline, which has been shown to selectively inhibit a low KM, Ca2+/calmodulin-independent phosphodiesterase isozyme, concentration-dependently increased the amplitude of the extracellularly recorded CA1 population spike evoked by electrical stimulation of the Schaffer collateral/commissural pathway." | ( The low KM-phosphodiesterase inhibitor denbufylline enhances neuronal excitability in guinea pig hippocampus in vitro. Alzheimer, C; Ameri, A; Sutor, B; ten Bruggencate, G, 1990) | 1.27 |
| "1. Denbufylline has been examined for its ability to inhibit cyclic nucleotide phosphodiesterase isoenzymes from rat cardiac ventricle and cerebrum, as well as for its affinity for adenosine A1 and A2 receptors and the re-uptake site. " | ( The ability of denbufylline to inhibit cyclic nucleotide phosphodiesterase and its affinity for adenosine receptors and the adenosine re-uptake site. Jackman, SA; Nicholson, CD; Wilke, R, 1989) | 1.25 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Since denbufylline plasma concentrations were close to the assay limit of reliable determination, the disposition of the compound was assessed in terms of the pharmacokinetic parameters of three active metabolites." | ( Pharmacokinetics of denbufylline in healthy elderly subjects. Bosch, K; Brett, MA; Ellrich, E; Holz, B; Hötzel, L; Hust, R; Kurowski, H; Reim, HG, 1991) | 1.06 |
3,4-dipropyl-4,5,7,8-tetrahydro-3H-imidazo[1,2-i]-purin-5-one (1c) did not cause emesis in Suncus murinus at a dosage range of 10-100 mg/kg (po) An imidazole analogue of 1c (4c) and known PDE IV inhibitors such as rolipram and denbufylline caused emesis even at 10 or 30mg/kg.
| Excerpt | Relevance | Reference |
|---|---|---|
| " In order to obtain information on oxygen supply, energy metabolism and function of ischaemic calf muscle in rats and cats, muscle pO2, pH and contractility were measured before and after dosing of BRL 30892." | ( The effect of 7-(2'-oxopropyl)-1,3-di-n-butyl-xanthine (BRL 30892) on ischaemic skeletal muscle pO2, pH and contractility in cats and rats. Angersbach, D; Ochlich, P, 1984) | 0.27 |
| " When compounds were intraduodenally administered to the guinea pig, 1-(2'-ethoxyethyl)-, 1-(3'-methoxypropyl)-, 1-(3'-butenyl)-, and 1-[(dimethylamino)-ethyl]-3-propylxanthines, 1-methyl-7-(2'-oxopropyl)-3-propylxanthine, and denbufylline (1,3-di-n-butyl-7-(2'-oxopropyl)xanthine) effectively inhibited the acetylcholine-induced bronchospasm without heart stimulation or central nervous system-stimulation at the effective dosage range." | ( Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. Hasegawa, T; Iwasaki, N; Konno, K; Kurita, M; Miyamoto, K; Ohshima, T; Sakai, R; Sanae, F; Takagi, K; Yamamoto, Y, 1993) | 0.47 |
| " Among them, 3,4-dipropyl-4,5,7,8-tetrahydro-3H-imidazo[1,2-i]-purin-5-one (1c), which was the most selective and potent PDE IV inhibitor, did not cause emesis in Suncus murinus at a dosage range of 10-100 mg/kg (po), while an imidazole analogue of 1c (4c) and known PDE IV inhibitors such as rolipram and denbufylline caused emesis even at 10 or 30 mg/kg." | ( Selective inhibitors of cyclic AMP-specific phosphodiesterase: heterocycle-condensed purines. Kasugai, S; Miyamoto, K; Ohya, K; Sawanishi, H; Suzuki, H; Suzuki, N; Takagi, K; Waki, Y; Yamamoto, S, 1997) | 0.47 |
| " MMSE scores were found to be higher among patients who received denbufylline when these latter were combined as a single group, regardless of their diagnosis or dosage regimen." | ( Denbufylline in dementia: a double-blind controlled study. Korczyn, AD; Treves, TA, ) | 1.81 |
| "5 h after dosing with the GCP12 formulation and delivery was sustained for at least 5 h after dosing." | ( Sustained buccal delivery of the hydrophobic drug denbufylline using physically cross-linked palmitoyl glycol chitosan hydrogels. Koosha, F; Martin, L; Uchegbu, IF; Wilson, CG, 2003) | 0.57 |
| Class | Description |
|---|---|
| oxopurine | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cAMP-specific 3',5'-cyclic phosphodiesterase 4A | Homo sapiens (human) | IC50 (µMol) | 0.0851 | 0.0000 | 1.0680 | 10.0000 | AID155681; AID159781 |
| Adenosine receptor A2a | Homo sapiens (human) | Ki | 31.5000 | 0.0000 | 1.0609 | 9.7920 | AID30623 |
| Adenosine receptor A2b | Homo sapiens (human) | Ki | 31.5000 | 0.0002 | 1.6352 | 10.0000 | AID30623 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4B | Homo sapiens (human) | IC50 (µMol) | 0.0851 | 0.0000 | 1.1040 | 10.0000 | AID155681; AID159781 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4C | Homo sapiens (human) | IC50 (µMol) | 0.0851 | 0.0000 | 1.4651 | 10.0000 | AID155681; AID159781 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4D | Homo sapiens (human) | IC50 (µMol) | 0.0851 | 0.0000 | 1.1463 | 10.0000 | AID155681; AID159781 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID47039 | Increased transcription of human calcitonin luciferase reporter gene at 30 uM | 2002 | Journal of medicinal chemistry, May-23, Volume: 45, Issue:11 | Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers. |
| AID32158 | Binding affinity against Adenosine A1 receptor of cerebral cortex using [3H]-CPX | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID220053 | Inhibition of cAMP-phosphodiesterase (PDE) from trachealis muscle homogenate supernatant | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID233054 | Bronchoselectivity expressed as ratio of stimulatory activity in the right atrium (EC15) to relaxant activity in the tracheal muscle (EC50) | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID88906 | Calcitonin (CT) secretion/RIA assay to measure the ability of compound to increase cellular levels and secretion of human CT. | 2000 | Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6 | Novel and selective calcitonin-inducing agents. |
| AID159933 | Percent Rolipram activity of a standard U937 cell phosphodiesterase 4 (PDE4) enzyme assay at 30 uM of compound | 2002 | Journal of medicinal chemistry, May-23, Volume: 45, Issue:11 | Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers. |
| AID234621 | Bronchoselectivity, ratio of positive chronotropic action (ED15) to bronchodilator action (ED50) | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID155683 | Percent rolipram activity at 30 uM (PDE 30 assay) | 2000 | Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6 | Novel and selective calcitonin-inducing agents. |
| AID221858 | Bronchodilatory effect, 50% inhibition of spasmogen-induced response in male Hartley guinea pigs on intraduodenal administration | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID221856 | Positive chronotropic effect, 15% increase in heart rate of male Hartley guinea pigs on intraduodenal administration (mean of 3-5 animals) | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID75915 | In vitro guinea pig heart stimulation (right atrium) | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID88797 | Ability to increase Human calcitonin secretion | 2002 | Journal of medicinal chemistry, May-23, Volume: 45, Issue:11 | Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers. |
| AID73738 | Effective concentration required in vitro for tracheal muscle (from male Hartley guinea pigs) relaxation | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID209135 | Emetic effect in shrews at 30 mg/kg peroral dose, 3 of 3 animals affected | 1997 | Journal of medicinal chemistry, Sep-26, Volume: 40, Issue:20 | Selective inhibitors of cyclic AMP-specific phosphodiesterase: heterocycle-condensed purines. |
| AID90412 | CT-luci reporter gene assay to measure the ability to increase transcription of a luciferase receptor gene linked to the human CT gene. | 2000 | Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6 | Novel and selective calcitonin-inducing agents. |
| AID30623 | Binding affinity against Adenosine A2 receptor of striatal membrane using [3H]CGS-21680 | 1993 | Journal of medicinal chemistry, May-14, Volume: 36, Issue:10 | Bronchodilator activity of xanthine derivatives substituted with functional groups at the 1- or 7-position. |
| AID195319 | The compound was tested for its bone protection activity at 30 mg/kg/day by intra peritoneal administration. | 2000 | Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6 | Novel and selective calcitonin-inducing agents. |
| AID159781 | Inhibition of phosphodiesterase 4 (PDE4) | 2002 | Journal of medicinal chemistry, May-23, Volume: 45, Issue:11 | Pyrazolopyrimidine-2,4-dione sulfonamides: novel and selective calcitonin inducers. |
| AID155681 | Concentration at which 50% of the activity of the Phosphodiesterase 4 from Human U937 cells is inhibited | 2000 | Journal of medicinal chemistry, Mar-23, Volume: 43, Issue:6 | Novel and selective calcitonin-inducing agents. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 5 (13.51) | 18.7374 |
| 1990's | 24 (64.86) | 18.2507 |
| 2000's | 7 (18.92) | 29.6817 |
| 2010's | 1 (2.70) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 moderate demand-to-supply ratio for research on this compound.
| This Compound (16.24) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 2 (5.13%) | 5.53% |
| Reviews | 1 (2.56%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 36 (92.31%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||