DT-Web

DB00651 - Dyphylline


Identification
Name Dyphylline
Accession Number DB00651 (APRD00769)
Type small molecule
Description A theophylline derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 254.2426
Groups approved
Monoisotopic Weight 254.101504956
Pharmacology
Indication For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.
Mechanism of action The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.
Absorption Not Available
Protein binding 84%
Biotransformation Hepatic
Route of elimination Dyphylline exerts its bronchodilatory effects directly and, unlike the-ophylline, is excreted unchanged by the kidneys without being metabolized by the liver. Approximately 88% of a single oral dose can be recovered from the urine unchanged.
Toxicity LD50=1954 mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Acyclovir Acyclovir increases the effect and toxicity of dyphylline.
Adenosine This xanthine decreases the effect of adenosine
Bromazepam Dyphylline may decrease the therapeutic effect of bromazepam. Monitor for changes in the therapeutic effects of bromazepam if dyphylline is initiated, discontinued or dose changed.
Carbamazepine Carbamazepine may decrease the serum concentration of diphylline. Diphylline may decrease the serum concentration of carbamazepine. Monitor for changes in the therapeutic effect of both agents if concomitant therapy is initiated, discontinued or dose changed.
Cimetidine Increases the effect of theophylline
Ciprofloxacin Ciprofloxacin may increase the effect of dyphylline.
Clarithromycin Increases the effect and toxicity of theophylline
Disulfiram Increases the effect and toxicity of theophylline
Erythromycin The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, dyphylline.
Ethinyl Estradiol The contraceptive increases the effect and toxicity of theophylline
Fluvoxamine Increases the effect and toxicity of theophylline
Fosphenytoin Decreased effect of both products
Grepafloxacin Grepafloxacin may increase the effect of dyphylline.
Interferon Alfa-2a, Recombinant Interferon increases the effect and toxicity of theophylline
Interferon Alfa-2b, Recombinant Interferon increases the effect and toxicity of theophylline
Interferon alfa-n1 Interferon increases the effect and toxicity of theophylline
Isoniazid Increases the effect and toxicity of theophylline
Lithium Theophylline decreases serum levels of lithium
Mexiletine Mexiletine increases the effect and toxicity of theophylline
Nadolol Antagonism of action and increased effect of theophylline
Norfloxacin Norfloxacin may increase the effect of dyphylline.
Peginterferon alfa-2a Interferon increases the effect and toxicity of theophylline
Peginterferon alfa-2b Interferon increases the effect and toxicity of theophylline
Pentoxifylline Pentoxifylline increases the effect and toxicity of theophylline
Phenobarbital The barbiturate, phenobarbital, decreases the effect of dyphylline.
Phenytoin Decreased effect of both products
Pindolol Antagonism of action and increased effect of theophylline
Primidone The barbiturate, primidone, decreases the effect of dyphylline.
Propafenone Propafenone increases the effect of theophylline
Propranolol Antagonism of action and increased effect of theophylline
Rifampin Rifampin decreases the effect of theophylline
Temazepam Dyphylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Dyphylline is initiated, discontinued or dose changed.
Terbinafine Terbinafine increases the effect and toxicity of theophylline
Ticlopidine Ticlopidine increases the effect and toxicity of theophylline
Timolol Antagonism of action and increased effect of theophylline
Food Interactions Not Available

Targets


cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Name cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Gene Name PDE4B
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. - Pubmed
  • Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. - Pubmed
DTHybrid score Not Available
cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Name cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Gene Name PDE4A
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
  • Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. - Pubmed
  • Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. - Pubmed
DTHybrid score Not Available
cAMP-specific 3',5'-cyclic phosphodiesterase 4C
Name cAMP-specific 3',5'-cyclic phosphodiesterase 4C
Gene Name PDE4C
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. - Pubmed
  • Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. - Pubmed
DTHybrid score Not Available
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Name cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Gene Name PDE4D
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. - Pubmed
DTHybrid score Not Available
Adenosine A1 receptor
Name Adenosine A1 receptor
Gene Name ADORA1
Pharmacological action yes
Actions antagonist
References
  • Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. - Pubmed
DTHybrid score 0.6123
Adenosine A2a receptor
Name Adenosine A2a receptor
Gene Name ADORA2A
Pharmacological action yes
Actions antagonist
References
  • Schwabe U, Ukena D, Lohse MJ: Xanthine derivatives as antagonists at A1 and A2 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):212-21. - Pubmed
DTHybrid score 0.8644
High-affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
Name High-affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
Gene Name PDE7A
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
DTHybrid score Not Available
cAMP-specific 3',5'-cyclic phosphodiesterase 7B
Name cAMP-specific 3',5'-cyclic phosphodiesterase 7B
Gene Name PDE7B
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
DTHybrid score Not Available

Predictions


Id Partner name Gene Name Score
268 Adenosine A2b receptor ADORA2B 0.254
6216 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A PDE8A 0.2221
485 cGMP-inhibited 3',5'-cyclic phosphodiesterase A PDE3A 0.1914
6217 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B PDE8B 0.1777
204 cGMP-specific 3',5'-cyclic phosphodiesterase PDE5A 0.1256
4200 Cytochrome P450 1A2 CYP1A2 0.107
6040 6-phosphogluconate dehydrogenase, decarboxylating PGD 0.1014
4122 Histone deacetylase 2 HDAC2 0.0996
3806 cGMP-dependent 3',5'-cyclic phosphodiesterase PDE2A 0.0863
1830 5'-nucleotidase NT5E 0.0756
390 Adenosine A3 receptor ADORA3 0.0747
492 Histamine H1 receptor HRH1 0.0665
5360 High-affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A PDE9A 0.0661
6013 Cytochrome P450 2E1 CYP2E1 0.0653
695 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A PDE10A 0.0645
3957 Adenosine deaminase ADA 0.0592
2256 cGMP-inhibited 3',5'-cyclic phosphodiesterase B PDE3B 0.0551
6037 Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma PDE6G 0.0515
6143 Solute carrier family 22 member 7 SLC22A7 0.048
2684 Histidine triad nucleotide-binding protein 1 HINT1 0.0463
6021 Adenosine kinase ADK 0.0458
1792 Tissue-type plasminogen activator PLAT 0.0456
527 Prostacyclin receptor PTGIR 0.0423
73 Prostaglandin E2 receptor, EP1 subtype PTGER1 0.0388
4512 Cytochrome P450 3A4 CYP3A4 0.0374
6171 Solute carrier family 28 member 3 SLC28A3 0.037
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.037
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.0367
6152 Solute carrier organic anion transporter family member 2A1 SLCO2A1 0.0365
1898 Cytochrome P450 1B1 CYP1B1 0.0298
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0297
4119 Cytochrome P450 2D6 CYP2D6 0.0255
3970 Voltage-dependent N-type calcium channel subunit alpha-1B CACNA1B 0.0254
814 Ryanodine receptor 1 RYR1 0.0248
4160 Voltage-dependent calcium channel subunit alpha-2/delta-2 CACNA2D2 0.0244
6024 Cytochrome P450 1A1 CYP1A1 0.0241
574 Branched-chain-amino-acid aminotransferase, cytosolic BCAT1 0.024
1588 Multidrug resistance protein 1 ABCB1 0.0218
762 Voltage-dependent calcium channel subunit alpha-2/delta-1 CACNA2D1 0.0211
4924 Cytochrome P450 2C8 CYP2C8 0.021
777 Tumor necrosis factor TNF 0.0205
4757 Cytochrome P450 2C9 CYP2C9 0.0193
144 Hemoglobin subunit alpha HBA1 0.0146
2347 Proto-oncogene serine/threonine-protein kinase Pim-1 PIM1 0.0113
6107 Cytochrome P450 3A7 CYP3A7 0.0108
851 5'-AMP-activated protein kinase subunit beta-2 PRKAB2 0.0105
388 AMP deaminase 1 AMPD1 0.0105
6136 Multidrug resistance-associated protein 5 ABCC5 0.0104
4118 Cytochrome P450 3A5 CYP3A5 0.0102
3811 Cytochrome P450 19A1 CYP19A1 0.01
474 Acetylcholinesterase ACHE 0.0099
3923 Cholinesterase BCHE 0.0092
1291 cAMP response element-binding protein CREB1 0.0092
704 Long-chain-fatty-acid--CoA ligase 1 ACSL1 0.0091
386 Acetyl-coenzyme A synthetase, cytoplasmic ACSS2 0.0091
821 Acetyl-coenzyme A synthetase 2-like, mitochondrial ACSS1 0.0091
297 Adenylate cyclase type 1 ADCY1 0.0091
4198 Fructose-1,6-bisphosphatase 1 FBP1 0.0088
281 5'-AMP-activated protein kinase subunit beta-1 PRKAB1 0.0087
2164 Multidrug resistance-associated protein 4 ABCC4 0.0087
128 Adenine phosphoribosyltransferase APRT 0.0086
748 5'-AMP-activated protein kinase catalytic subunit alpha-1 PRKAA1 0.0084
10 Glycogen phosphorylase, liver form PYGL 0.0081
5691 DTDP-4-DEHYDRORHAMNOSE 3,5-EPIMERASE RMLC rmlC 0.0067
3361 Serpin B5 SERPINB5 0.0067
5694 Transcription antiterminator licT licT 0.0067
56 Delta-aminolevulinic acid dehydratase ALAD 0.0054
2356 Delta-aminolevulinic acid dehydratase hemB 0.0054
3613 Delta-aminolevulinic acid dehydratase hemB 0.0054
3674 Delta-aminolevulinic acid dehydratase hemB 0.0054
2286 Isocitrate dehydrogenase [NADP] icd 0.0051
2302 Isocitrate dehydrogenase [NADP] icd 0.0051
2771 Isocitrate dehydrogenase [NADP] icd 0.0051
4534 Cytohesin-2 CYTH2 0.0048
3668 Maltose-binding periplasmic protein precursor malE 0.0047
5692 Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B PDE1B 0.0042
2592 Beta-galactosidase lacZ 0.0042
315 Arginase-1 ARG1 0.004
24 Thymidylate synthase TMP1 0.0033
359 Thymidylate synthase TYMS 0.0033
2626 Thymidylate synthase thyA 0.0033
2729 Thymidylate synthase thyA 0.0033
5352 Thymidylate synthase THYA 0.0033
6263 cAMP-dependent protein kinase catalytic subunit alpha PRKACA 0.0032
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