Dyphylline
Identification
- Summary
Dyphylline is a theophylline derivative used to treat asthma, bronchospasm, and COPD.
- Generic Name
- Dyphylline
- DrugBank Accession Number
- DB00651
- Background
Dyphylline is a theophylline derivative with broncho- and vasodilator properties. It is typically used in the management of asthma, cardiac dyspnea, and bronchitis.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Dyphylline (DB00651)
- Weight
- Average: 254.2426
Monoisotopic: 254.101504956 - Chemical Formula
- C10H14N4O4
- Synonyms
- (±)-7-(2,3-dihydroxypropyl)theophylline
- (±)-diprophylline
- (±)-dyphylline
- (1,2-dihydroxy-3-propyl)thiophyllin
- 1,3-dimethyl-7-(2,3-dihydroxypropyl)xanthine
- 7-(2,3-dihydroxypropyl)-1,3-dimethylxanthine
- 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione
- 7-(2,3-dihydroxypropyl)theophylline
- 7-(β,γ-dihydroxypropyl)theophylline
- Dihydroxypropyl theopylin
- Diprofilina
- Diprophylline
- Diprophyllinum
- Dyphylline
Pharmacology
- Indication
For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Dyphylline, a xanthine derivative, is a bronchodilator used for relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Dyphylline is a xanthine derivative with pharmacologic actions similar to theophylline and other members of this class of drugs. Its primary action is that of bronchodilation, but it also exhibits peripheral vasodilatory and other smooth muscle relaxant activity to a lesser degree.
- 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.
Target Actions Organism AcAMP-specific 3',5'-cyclic phosphodiesterase 4B inhibitorHumans AcAMP-specific 3',5'-cyclic phosphodiesterase 4A inhibitorHumans AcAMP-specific 3',5'-cyclic phosphodiesterase 4C inhibitorHumans AcAMP-specific 3',5'-cyclic phosphodiesterase 4D inhibitorHumans AAdenosine receptor A1 antagonistHumans AAdenosine receptor A2a antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
84%
- Metabolism
Hepatic
- Route of elimination
Dyphylline exerts its bronchodilatory effects directly and, unlike theophylline, 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.
- Half-life
2 hours (range 1.8 - 2.1 hours)
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50=1954 mg/kg (orally in mice)
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Dyphylline. Abacavir Dyphylline may decrease the excretion rate of Abacavir which could result in a higher serum level. Abiraterone The serum concentration of Dyphylline can be increased when it is combined with Abiraterone. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Dyphylline. Aceclofenac Aceclofenac may decrease the excretion rate of Dyphylline which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Dyphylline which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Dyphylline which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Dyphylline which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Dyphylline which could result in a higher serum level. Aclidinium Dyphylline may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Corphyllin (Nippon Shinyaku) / Dilor (Savage)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Protophylline Elixir 100mg Elixir 100 mg / 15 mL Oral Rougier Pharma Division Of Ratiopharm Inc 1962-12-31 1999-09-27 Canada 
Protophylline Inj 500mg/2ml Liquid 500 mg / 2 mL Intramuscular; Intravenous Rougier Pharma Division Of Ratiopharm Inc 1963-12-31 1999-09-27 Canada Protophylline Solution 100mg Solution 100 mg / 15 mL Oral Rougier Pharma Division Of Ratiopharm Inc 1965-12-31 1999-09-27 Canada Protophylline Sup 500mg Adultes Suppository 500 mg / sup Rectal Rougier Pharma Division Of Ratiopharm Inc 1962-12-31 1999-09-27 Canada Protophylline Tab 200mg Tablet 200 mg / tab Oral Rougier Pharma Division Of Ratiopharm Inc 1962-12-31 1999-09-27 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lufyllin Tablet 400 mg/1 Oral Meda Pharmaceuticals Ltd 1976-08-31 2015-01-31 US 
Lufyllin Tablet 200 mg/1 Oral Meda Pharmaceuticals Ltd 1976-08-31 2016-02-29 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ESPEKTAN A ŞURUP, 100 ML Dyphylline (47 mg/5ml) + Chlorpheniramine maleate (4 mg/5ml) + Potassium Iodide (150 mg/5ml) Syrup NOBEL İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
ESPEKTAN ŞURUP, 100 ML Dyphylline (47 mg/5ml) + Potassium Iodide (150 mg/5ml) Syrup NOBEL İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dilex-G 400 Dyphylline (200 mg/1) + Guaifenesin (400 mg/1) Tablet Oral Poly Pharmaceuticals 2006-09-08 2011-09-30 US Dy G Dyphylline (100 mg/5mL) + Guaifenesin (100 mg/5mL) Liquid Oral Cypress Pharmaceuticals, Inc. 2001-10-31 2011-08-26 US Dyphylline and Guaifenesin Dyphylline (200 mg/1) + Guaifenesin (200 mg/1) Tablet Oral Breckenridge Pharmaceutical, Inc. 2001-08-01 2012-02-29 US Dyphylline GG Dyphylline (200 mg/1) + Guaifenesin (200 mg/1) Tablet Oral Pegasus Laboratories 2006-12-18 2012-06-30 US Dyphylline Gg Dyphylline (100 mg/15mL) + Guaifenesin (100 mg/15mL) Elixir Oral Silarx Pharmaceuticals, Inc. 1996-12-05 2011-06-02 US Dyphylline GG ES Dyphylline (200 mg/1) + Guaifenesin (300 mg/1) Tablet Oral Breckenridge Pharmaceutical, Inc. 2008-02-01 2012-02-28 US Jay-Phyl Dyphylline (100 mg/5mL) + Guaifenesin (50 mg/5mL) Syrup Oral Jaymac Pharmaceuticals Llc 2006-05-02 2012-10-31 US Lufyllin -GG Dyphylline (100 mg/15mL) + Guaifenesin (100 mg/15mL) Solution Oral Meda Pharmaceuticals Ltd 1968-06-01 2013-03-31 US Theospect Improved Dyphylline (200 mg/1) + Guaifenesin (200 mg/1) Tablet Oral PRN Pharmacal 2000-01-13 2010-05-03 US
Categories
- ATC Codes
- R03DA20 — Combinations of xanthines
- R03DA — Xanthines
- R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03DB — Xanthines and adrenergics
- R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03DA — Xanthines
- R03D — OTHER SYSTEMIC DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Alkaloids
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cardiovascular Agents
- Drugs for Obstructive Airway Diseases
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Peripheral Nervous System Agents
- Phosphodiesterase Inhibitors
- Purines
- Purinones
- Respiratory System Agents
- Vasodilating Agents
- Xanthine derivatives
- Xanthines and Adrenergics
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Xanthines
- Alternative Parents
- 6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Secondary alcohols / Lactams / 1,2-diols / Ureas show 6 more
- Substituents
- 1,2-diol / 6-oxopurine / Alcohol / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- oxopurine, propane-1,2-diols (CHEBI:4728)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 263T0E9RR9
- CAS number
- 479-18-5
- InChI Key
- KSCFJBIXMNOVSH-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
- IUPAC Name
- 7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
- SMILES
- CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O
References
- Synthesis Reference
Jones, J.W. and Maney, P.V.; U.S. Patent 2,575,344; November 20,1951; assigned to the State of Iowa.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014789
- KEGG Drug
- D00691
- KEGG Compound
- C07819
- PubChem Compound
- 3182
- PubChem Substance
- 46504443
- ChemSpider
- 3070
- BindingDB
- 82016
- 3714
- ChEBI
- 4728
- ChEMBL
- CHEMBL1752
- Therapeutic Targets Database
- DAP000596
- PharmGKB
- PA164748027
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Diprophylline
- MSDS
- Download (65.7 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Teva pharmaceuticals usa inc
- Savage laboratories inc div altana inc
- Meda pharmaceuticals inc
- Packagers
- Breckenridge Pharmaceuticals
- Great Southern Laboratories
- Lunsco Inc.
- Meda AB
- Novartis AG
- Savage Labs
- Dosage Forms
Form Route Strength Syrup Injection, solution Intramuscular Tablet Oral Suppository Rectal Tablet Oral Liquid Oral Elixir Oral Syrup Syrup Oral Injection, solution Intravenous 200 MG/2ML Injection, solution Intravenous 300 MG/10ML Tablet Oral 200 mg/1 Tablet Oral 400 mg/1 Solution Oral Elixir Oral 100 mg / 15 mL Liquid Intramuscular; Intravenous 500 mg / 2 mL Solution Oral 100 mg / 15 mL Suppository Rectal 500 mg / sup Tablet Oral 200 mg / tab - Prices
Unit description Cost Unit Afinitor 10 mg tablet 247.58USD tablet Afinitor 5 mg tablet 234.75USD tablet Lufyllin-400 tablet 4.62USD tablet Lufyllin 200 mg tablet 3.15USD tablet Dyphylline gg es tablet 0.78USD tablet Dyphylline gg tablet 0.69USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 155-157 Jones, J.W. and Maney, P.V.; U.S. Patent 2,575,344; November 20,1951; assigned to the State of Iowa. water solubility 3.33E+005 mg/L (at 25 °C) MERCK INDEX (1996) logP -1.9 Not Available logS -0.17 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 14.3 mg/mL ALOGPS logP -0.98 ALOGPS logP -1.9 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 13.91 ChemAxon pKa (Strongest Basic) -0.97 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 98.9 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 62.09 m3·mol-1 ChemAxon Polarizability 24.65 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.964 Blood Brain Barrier - 0.6357 Caco-2 permeable - 0.7332 P-glycoprotein substrate Substrate 0.5999 P-glycoprotein inhibitor I Non-inhibitor 0.9775 P-glycoprotein inhibitor II Non-inhibitor 0.9792 Renal organic cation transporter Non-inhibitor 0.9289 CYP450 2C9 substrate Non-substrate 0.8343 CYP450 2D6 substrate Non-substrate 0.8429 CYP450 3A4 substrate Non-substrate 0.5446 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.946 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.978 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9758 Ames test Non AMES toxic 0.799 Carcinogenicity Non-carcinogens 0.8576 Biodegradation Not ready biodegradable 0.6129 Rat acute toxicity 1.8401 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9489 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
- Gene Name
- PDE4B
- Uniprot ID
- Q07343
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4B
- Molecular Weight
- 83342.695 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
- Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4A
- Uniprot ID
- P27815
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4A
- Molecular Weight
- 98142.155 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
- Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4C
- Uniprot ID
- Q08493
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4C
- Molecular Weight
- 79900.795 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
- Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4D
- Uniprot ID
- Q08499
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4D
- Molecular Weight
- 91114.1 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Purine nucleoside binding
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- ADORA1
- Uniprot ID
- P30542
- Uniprot Name
- Adenosine receptor A1
- Molecular Weight
- 36511.325 Da
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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Identical protein binding
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- ADORA2A
- Uniprot ID
- P29274
- Uniprot Name
- Adenosine receptor A2a
- Molecular Weight
- 44706.925 Da
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. [Article]
Drug created on June 13, 2005 13:24 / Updated on June 12, 2021 10:51