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
Thumb
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.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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.

TargetActionsOrganism
AcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A
inhibitor
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4C
inhibitor
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4D
inhibitor
Humans
AAdenosine receptor A1
antagonist
Humans
AAdenosine receptor A2a
antagonist
Humans
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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Dyphylline.
AbacavirDyphylline may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbirateroneThe serum concentration of Dyphylline can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Dyphylline.
AceclofenacAceclofenac may decrease the excretion rate of Dyphylline which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dyphylline which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Dyphylline which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Dyphylline which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Dyphylline which could result in a higher serum level.
AclidiniumDyphylline may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Corphyllin (Nippon Shinyaku) / Dilor (Savage)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Protophylline Elixir 100mgElixir100 mg / 15 mLOralRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada flag
Protophylline Inj 500mg/2mlLiquid500 mg / 2 mLIntramuscular; IntravenousRougier Pharma Division Of Ratiopharm Inc1963-12-311999-09-27Canada flag
Protophylline Solution 100mgSolution100 mg / 15 mLOralRougier Pharma Division Of Ratiopharm Inc1965-12-311999-09-27Canada flag
Protophylline Sup 500mg AdultesSuppository500 mg / supRectalRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada flag
Protophylline Tab 200mgTablet200 mg / tabOralRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LufyllinTablet400 mg/1OralMeda Pharmaceuticals Ltd1976-08-312015-01-31US flag
LufyllinTablet200 mg/1OralMeda Pharmaceuticals Ltd1976-08-312016-02-29US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ESPEKTAN A ŞURUP, 100 MLDyphylline (47 mg/5ml) + Chlorpheniramine maleate (4 mg/5ml) + Potassium Iodide (150 mg/5ml)SyrupNOBEL İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
ESPEKTAN ŞURUP, 100 MLDyphylline (47 mg/5ml) + Potassium Iodide (150 mg/5ml)SyrupNOBEL İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Dilex-G 400Dyphylline (200 mg/1) + Guaifenesin (400 mg/1)TabletOralPoly Pharmaceuticals2006-09-082011-09-30US flag
Dy GDyphylline (100 mg/5mL) + Guaifenesin (100 mg/5mL)LiquidOralCypress Pharmaceuticals, Inc.2001-10-312011-08-26US flag
Dyphylline and GuaifenesinDyphylline (200 mg/1) + Guaifenesin (200 mg/1)TabletOralBreckenridge Pharmaceutical, Inc.2001-08-012012-02-29US flag
Dyphylline GGDyphylline (200 mg/1) + Guaifenesin (200 mg/1)TabletOralPegasus Laboratories2006-12-182012-06-30US flag
Dyphylline GgDyphylline (100 mg/15mL) + Guaifenesin (100 mg/15mL)ElixirOralSilarx Pharmaceuticals, Inc.1996-12-052011-06-02US flag
Dyphylline GG ESDyphylline (200 mg/1) + Guaifenesin (300 mg/1)TabletOralBreckenridge Pharmaceutical, Inc.2008-02-012012-02-28US flag
Jay-PhylDyphylline (100 mg/5mL) + Guaifenesin (50 mg/5mL)SyrupOralJaymac Pharmaceuticals Llc2006-05-022012-10-31US flag
Lufyllin -GGDyphylline (100 mg/15mL) + Guaifenesin (100 mg/15mL)SolutionOralMeda Pharmaceuticals Ltd1968-06-012013-03-31US flag
Theospect ImprovedDyphylline (200 mg/1) + Guaifenesin (200 mg/1)TabletOralPRN Pharmacal2000-01-132010-05-03US flag

Categories

ATC Codes
R03DA20 — Combinations of xanthinesR03DB01 — Diprophylline and adrenergicsR03DA51 — Diprophylline, combinationsR03DA01 — Diprophylline
Drug Categories
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
Human Metabolome Database
HMDB0014789
KEGG Drug
D00691
KEGG Compound
C07819
PubChem Compound
3182
PubChem Substance
46504443
ChemSpider
3070
BindingDB
82016
RxNav
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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
FormRouteStrength
Syrup
Injection, solutionIntramuscular
TabletOral
SuppositoryRectal
TabletOral
LiquidOral
ElixirOral
Syrup
SyrupOral
Injection, solutionIntravenous200 MG/2ML
Injection, solutionIntravenous300 MG/10ML
TabletOral200 mg/1
TabletOral400 mg/1
SolutionOral
ElixirOral100 mg / 15 mL
LiquidIntramuscular; Intravenous500 mg / 2 mL
SolutionOral100 mg / 15 mL
SuppositoryRectal500 mg / sup
TabletOral200 mg / tab
Prices
Unit descriptionCostUnit
Afinitor 10 mg tablet247.58USD tablet
Afinitor 5 mg tablet234.75USD tablet
Lufyllin-400 tablet4.62USD tablet
Lufyllin 200 mg tablet3.15USD tablet
Dyphylline gg es tablet0.78USD tablet
Dyphylline gg tablet0.69USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155-157Jones, J.W. and Maney, P.V.; U.S. Patent 2,575,344; November 20,1951; assigned to the State of Iowa.
water solubility3.33E+005 mg/L (at 25 °C)MERCK INDEX (1996)
logP-1.9Not Available
logS-0.17ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
logP-0.98ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.9 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.09 m3·mol-1ChemAxon
Polarizability24.65 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.964
Blood Brain Barrier-0.6357
Caco-2 permeable-0.7332
P-glycoprotein substrateSubstrate0.5999
P-glycoprotein inhibitor INon-inhibitor0.9775
P-glycoprotein inhibitor IINon-inhibitor0.9792
Renal organic cation transporterNon-inhibitor0.9289
CYP450 2C9 substrateNon-substrate0.8343
CYP450 2D6 substrateNon-substrate0.8429
CYP450 3A4 substrateNon-substrate0.5446
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.946
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.978
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9758
Ames testNon AMES toxic0.799
CarcinogenicityNon-carcinogens0.8576
BiodegradationNot ready biodegradable0.6129
Rat acute toxicity1.8401 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9489
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-d159f2e06ae5688fe714
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9000000000-d159f2e06ae5688fe714
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0090000000-333eda23b5db828349a1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0390000000-b965183e8f0f1617c518
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0910000000-65b3ffefd28585f62d32
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0089-3900000000-e0a54464bc16e628c820
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05gj-9700000000-b192c58457f7957424f1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-001i-0920000000-973a36ebf151db89ccdc
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a59-2970000000-4ad8ef9bfa86cda3d221
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0089-2900000000-1b3e2d3408802f411886

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
  4. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  4. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
  5. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [Article]
  4. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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
  1. 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
  1. 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