Identification

Name
Dyphylline
Accession Number
DB00651  (APRD00769)
Type
Small Molecule
Groups
Approved
Description

A theophylline derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis. [PubChem]

Structure
Thumb
Synonyms
  • (+-)-7-(2,3-Dihydroxypropyl)theophylline
  • (+-)-Diprophylline
  • (+-)-Dyphylline
  • (±)-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-(beta,gamma-Dihydroxypropyl)theophylline
  • 7-(β,γ-dihydroxypropyl)theophylline
  • Dihydroxypropyl theopylin
  • Diprofilina
  • Diprophylline
  • Diprophyllinum
  • Dyphylline
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Protophylline Elixir 100mgElixir100 mgOralRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada
Protophylline Inj 500mg/2mlLiquid500 mgIntramuscular; IntravenousRougier Pharma Division Of Ratiopharm Inc1963-12-311999-09-27Canada
Protophylline Solution 100mgSolution100 mgOralRougier Pharma Division Of Ratiopharm Inc1965-12-311999-09-27Canada
Protophylline Sup 500mg AdultesSuppository500 mgRectalRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada
Protophylline Tab 200mgTablet200 mgOralRougier Pharma Division Of Ratiopharm Inc1962-12-311999-09-27Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LufyllinTablet200 mg/1OralMeda Pharmaceuticals Ltd1976-08-312016-02-29Us
International/Other Brands
Corphyllin (Nippon Shinyaku) / Dilor (Savage)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Jay-PhylDyphylline (100 mg/5mL) + Guaifenesin (50 mg/5mL)SyrupOralJay Mac Pharmaceuticals2006-05-022016-10-13Us
Categories
UNII
263T0E9RR9
CAS number
479-18-5
Weight
Average: 254.2426
Monoisotopic: 254.101504956
Chemical Formula
C10H14N4O4
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

Pharmacology

Indication

For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.

Structured Indications
Not Available
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
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A
inhibitor
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 4C
inhibitor
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 4D
inhibitor
Human
AAdenosine receptor A1
antagonist
Human
AAdenosine receptor A2a
antagonist
Human
AHigh affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
inhibitor
Human
AcAMP-specific 3',5'-cyclic phosphodiesterase 7B
inhibitor
Human
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
Toxicity

LD50=1954 mg/kg (orally in mice)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Dyphylline can be decreased when it is combined with 1,10-Phenanthroline.Experimental
3,4-DichloroisocoumarinThe serum concentration of Dyphylline can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Dyphylline can be decreased when it is combined with 4-(2-Aminoethyl)Benzenesulfonyl Fluoride.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Dyphylline.Approved
AdalimumabThe serum concentration of Dyphylline can be decreased when it is combined with Adalimumab.Approved
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Dyphylline.Approved, Investigational
Albinterferon Alfa-2BThe metabolism of Dyphylline can be decreased when combined with Albinterferon Alfa-2B.Investigational
AllopurinolThe serum concentration of Dyphylline can be increased when it is combined with Allopurinol.Approved
AlogliptinThe serum concentration of Dyphylline can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Dyphylline can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
AlprazolamThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Dyphylline.Approved, Illicit, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Dyphylline.Approved, Withdrawn
AmobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Amobarbital.Approved, Illicit
AmprenavirThe serum concentration of Dyphylline can be decreased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Dyphylline can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Dyphylline can be decreased when it is combined with Apixaban.Approved
AprotininThe serum concentration of Dyphylline can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArgatrobanThe serum concentration of Dyphylline can be decreased when it is combined with Argatroban.Approved, Investigational
AsunaprevirThe serum concentration of Dyphylline can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Dyphylline can be decreased when it is combined with Atazanavir.Approved, Investigational
AtenololAtenolol may decrease the bronchodilatory activities of Dyphylline.Approved
BarbexacloneThe serum concentration of Dyphylline can be decreased when it is combined with Barbexaclone.Experimental
BarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Barbital.Illicit
BatimastatThe serum concentration of Dyphylline can be decreased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Dyphylline can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Dyphylline can be decreased when it is combined with Benzamidine.Experimental
BetaxololBetaxolol may decrease the bronchodilatory activities of Dyphylline.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Dyphylline.Approved
BivalirudinThe serum concentration of Dyphylline can be decreased when it is combined with Bivalirudin.Approved, Investigational
BMS-906024The therapeutic efficacy of BMS-906024 can be decreased when used in combination with Dyphylline.Investigational
BoceprevirThe serum concentration of Dyphylline can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BopindololBopindolol may decrease the bronchodilatory activities of Dyphylline.Approved
BromazepamThe therapeutic efficacy of Bromazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
BupranololBupranolol may decrease the bronchodilatory activities of Dyphylline.Approved
CamazepamThe therapeutic efficacy of Camazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
CamostatThe serum concentration of Dyphylline can be decreased when it is combined with Camostat.Experimental
CandoxatrilThe serum concentration of Dyphylline can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Dyphylline can be decreased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Dyphylline can be decreased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Dyphylline can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarbimazoleThe serum concentration of Dyphylline can be increased when it is combined with Carbimazole.Approved, Investigational
CarteololCarteolol may decrease the bronchodilatory activities of Dyphylline.Approved
CE-326597The therapeutic efficacy of CE-326597 can be decreased when used in combination with Dyphylline.Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Dyphylline.Approved, Investigational
Cepeginterferon alfa-2BThe metabolism of Dyphylline can be decreased when combined with Cepeginterferon alfa-2B.Investigational
ChlordiazepoxideThe therapeutic efficacy of Chlordiazepoxide can be decreased when used in combination with Dyphylline.Approved, Illicit
ChlorotrianiseneThe serum concentration of Dyphylline can be increased when it is combined with Chlorotrianisene.Investigational, Withdrawn
CholesterolThe serum concentration of Dyphylline can be decreased when it is combined with Cholesterol.Experimental, Investigational
ChymostatinThe serum concentration of Dyphylline can be decreased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Dyphylline can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Dyphylline can be decreased when it is combined with Cilazapril.Approved
CimetidineThe metabolism of Dyphylline can be decreased when combined with Cimetidine.Approved
CinoxacinThe metabolism of Dyphylline can be decreased when combined with Cinoxacin.Approved, Investigational, Withdrawn
ClobazamThe therapeutic efficacy of Clobazam can be decreased when used in combination with Dyphylline.Approved, Illicit
ClonazepamThe therapeutic efficacy of Clonazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
CloranololCloranolol may decrease the bronchodilatory activities of Dyphylline.Experimental
ClorazepateThe therapeutic efficacy of Clorazepate can be decreased when used in combination with Dyphylline.Approved, Illicit
Conjugated estrogensThe serum concentration of Dyphylline can be increased when it is combined with Conjugated estrogens.Approved
Dabigatran etexilateThe serum concentration of Dyphylline can be decreased when it is combined with Dabigatran etexilate.Approved
DaidzeinThe serum concentration of Dyphylline can be increased when it is combined with Daidzein.Experimental
DarexabanThe serum concentration of Dyphylline can be decreased when it is combined with Darexaban.Investigational
DarunavirThe serum concentration of Dyphylline can be decreased when it is combined with Darunavir.Approved
DelanzomibThe serum concentration of Dyphylline can be decreased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Dyphylline can be decreased when it is combined with Delapril.Experimental
DelorazepamThe therapeutic efficacy of Delorazepam can be decreased when used in combination with Dyphylline.Approved, Illicit, Investigational
DiazepamThe therapeutic efficacy of Diazepam can be decreased when used in combination with Dyphylline.Approved, Illicit, Vet Approved
DienestrolThe serum concentration of Dyphylline can be increased when it is combined with Dienestrol.Approved, Investigational
DiethylstilbestrolThe serum concentration of Dyphylline can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
DisulfiramThe serum concentration of Dyphylline can be increased when it is combined with Disulfiram.Approved
DoxefazepamThe therapeutic efficacy of Doxefazepam can be decreased when used in combination with Dyphylline.Experimental
DoxofyllineThe risk or severity of adverse effects can be increased when Dyphylline is combined with Doxofylline.Approved, Investigational
EcabetThe serum concentration of Dyphylline can be decreased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Dyphylline can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Dyphylline can be decreased when it is combined with Elafin.Investigational
EnalaprilThe serum concentration of Dyphylline can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Dyphylline can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Dyphylline can be decreased when it is combined with Enalkiren.Experimental
EnoxacinThe metabolism of Dyphylline can be decreased when combined with Enoxacin.Approved, Investigational
Epigallocatechin GallateThe serum concentration of Dyphylline can be decreased when it is combined with Epigallocatechin Gallate.Investigational
EpimestrolThe serum concentration of Dyphylline can be increased when it is combined with Epimestrol.Experimental
EquolThe serum concentration of Dyphylline can be increased when it is combined with Equol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Dyphylline.Approved
EstazolamThe therapeutic efficacy of Estazolam can be decreased when used in combination with Dyphylline.Approved, Illicit
EstradiolThe serum concentration of Dyphylline can be increased when it is combined with Estradiol.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Dyphylline can be increased when it is combined with Estriol.Approved, Investigational, Vet Approved
Estrogens, esterifiedThe serum concentration of Dyphylline can be increased when it is combined with Estrogens, esterified.Approved
EstroneThe serum concentration of Dyphylline can be increased when it is combined with Estrone.Approved
Ethinyl EstradiolThe serum concentration of Dyphylline can be increased when it is combined with Ethinyl Estradiol.Approved
EtizolamThe therapeutic efficacy of Etizolam can be decreased when used in combination with Dyphylline.Approved
FaldaprevirThe serum concentration of Dyphylline can be decreased when it is combined with Faldaprevir.Investigational
FebuxostatThe serum concentration of the active metabolites of Dyphylline can be increased when Dyphylline is used in combination with Febuxostat.Approved
FleroxacinThe metabolism of Dyphylline can be decreased when combined with Fleroxacin.Approved
FludiazepamThe therapeutic efficacy of Fludiazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
FlumazenilThe therapeutic efficacy of Flumazenil can be decreased when used in combination with Dyphylline.Approved
FlumequineThe metabolism of Dyphylline can be decreased when combined with Flumequine.Withdrawn
FlunitrazepamThe therapeutic efficacy of Flunitrazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
FlurazepamThe therapeutic efficacy of Flurazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
FluvoxamineThe metabolism of Dyphylline can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Dyphylline is combined with Formoterol.Approved, Investigational
FosinoprilThe serum concentration of Dyphylline can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe serum concentration of Dyphylline can be decreased when it is combined with Fosphenytoin.Approved
GabexateThe serum concentration of Dyphylline can be decreased when it is combined with Gabexate.Investigational
GarenoxacinThe metabolism of Dyphylline can be decreased when combined with Garenoxacin.Investigational
GatifloxacinThe metabolism of Dyphylline can be decreased when combined with Gatifloxacin.Approved, Investigational
GeldanamycinThe serum concentration of Dyphylline can be decreased when it is combined with Geldanamycin.Experimental, Investigational
GemifloxacinThe metabolism of Dyphylline can be decreased when combined with Gemifloxacin.Approved, Investigational
GenisteinThe serum concentration of Dyphylline can be increased when it is combined with Genistein.Investigational
GM6001The serum concentration of Dyphylline can be decreased when it is combined with GM6001.Experimental
GrepafloxacinThe metabolism of Dyphylline can be decreased when combined with Grepafloxacin.Investigational, Withdrawn
HexestrolThe serum concentration of Dyphylline can be increased when it is combined with Hexestrol.Withdrawn
HexobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Hexobarbital.Approved
IdraparinuxThe serum concentration of Dyphylline can be decreased when it is combined with Idraparinux.Investigational
ImidaprilThe serum concentration of Dyphylline can be decreased when it is combined with Imidapril.Investigational
IndacaterolThe risk or severity of adverse effects can be increased when Dyphylline is combined with Indacaterol.Approved
IndinavirThe serum concentration of Dyphylline can be decreased when it is combined with Indinavir.Approved
Interferon Alfa-2a, RecombinantThe metabolism of Dyphylline can be decreased when combined with Interferon Alfa-2a, Recombinant.Approved, Investigational
Interferon Alfa-2b, RecombinantThe metabolism of Dyphylline can be decreased when combined with Interferon Alfa-2b, Recombinant.Approved
Interferon alfa-n1The metabolism of Dyphylline can be decreased when combined with Interferon alfa-n1.Approved, Investigational
Interferon alfa-n3The metabolism of Dyphylline can be decreased when combined with Interferon alfa-n3.Approved, Investigational
Interferon alfacon-1The metabolism of Dyphylline can be decreased when combined with Interferon alfacon-1.Approved, Investigational
Interferon beta-1aThe metabolism of Dyphylline can be decreased when combined with Interferon beta-1a.Approved, Investigational
Interferon beta-1bThe metabolism of Dyphylline can be decreased when combined with Interferon beta-1b.Approved
Interferon gamma-1bThe metabolism of Dyphylline can be decreased when combined with Interferon gamma-1b.Approved, Investigational
IsoflurophateThe serum concentration of Dyphylline can be decreased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IsoniazidThe serum concentration of Dyphylline can be increased when it is combined with Isoniazid.Approved
IsoprenalineThe serum concentration of Dyphylline can be decreased when it is combined with Isoprenaline.Approved
IxazomibThe serum concentration of Dyphylline can be decreased when it is combined with Ixazomib.Approved
LepirudinThe serum concentration of Dyphylline can be decreased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Dyphylline can be decreased when it is combined with Letaxaban.Investigational
LevofloxacinThe metabolism of Dyphylline can be decreased when combined with Levofloxacin.Approved, Investigational
LevothyroxineThe metabolism of Dyphylline can be increased when combined with Levothyroxine.Approved
LinagliptinThe serum concentration of Dyphylline can be decreased when it is combined with Linagliptin.Approved
LiothyronineThe metabolism of Dyphylline can be increased when combined with Liothyronine.Approved, Vet Approved
LiotrixThe metabolism of Dyphylline can be increased when combined with Liotrix.Approved
LisinoprilThe serum concentration of Dyphylline can be decreased when it is combined with Lisinopril.Approved, Investigational
LithiumThe serum concentration of Lithium can be decreased when it is combined with Dyphylline.Approved
LopinavirThe serum concentration of Dyphylline can be decreased when it is combined with Lopinavir.Approved
LorazepamThe therapeutic efficacy of Lorazepam can be decreased when used in combination with Dyphylline.Approved
LormetazepamThe therapeutic efficacy of Lormetazepam can be decreased when used in combination with Dyphylline.Approved
MedazepamThe therapeutic efficacy of Medazepam can be decreased when used in combination with Dyphylline.Experimental
MelagatranThe serum concentration of Dyphylline can be decreased when it is combined with Melagatran.Experimental
MepindololMepindolol may decrease the bronchodilatory activities of Dyphylline.Experimental
MestranolThe serum concentration of Dyphylline can be increased when it is combined with Mestranol.Approved
MethallenestrilThe serum concentration of Dyphylline can be increased when it is combined with Methallenestril.Experimental
MethimazoleThe serum concentration of Dyphylline can be increased when it is combined with Methimazole.Approved
MethohexitalThe serum concentration of Dyphylline can be decreased when it is combined with Methohexital.Approved
MethotrexateThe serum concentration of Dyphylline can be increased when it is combined with Methotrexate.Approved
MethylphenobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Methylphenobarbital.Approved
MethylthiouracilThe serum concentration of Dyphylline can be increased when it is combined with Methylthiouracil.Experimental
MetoprololMetoprolol may decrease the bronchodilatory activities of Dyphylline.Approved, Investigational
MexiletineThe metabolism of Dyphylline can be decreased when combined with Mexiletine.Approved
MidazolamThe therapeutic efficacy of Midazolam can be decreased when used in combination with Dyphylline.Approved, Illicit
MoexiprilThe serum concentration of Dyphylline can be decreased when it is combined with Moexipril.Approved
MoxestrolThe serum concentration of Dyphylline can be increased when it is combined with Moxestrol.Experimental
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Dyphylline can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Dyphylline can be decreased when it is combined with Nafamostat.Approved, Investigational
Nalidixic AcidThe metabolism of Dyphylline can be decreased when combined with Nalidixic Acid.Approved, Investigational
Natural alpha interferonThe metabolism of Dyphylline can be decreased when combined with Natural alpha interferon.Approved, Investigational
NebivololNebivolol may decrease the bronchodilatory activities of Dyphylline.Approved, Investigational
NelfinavirThe serum concentration of Dyphylline can be decreased when it is combined with Nelfinavir.Approved
NemonoxacinThe metabolism of Dyphylline can be decreased when combined with Nemonoxacin.Investigational
NetazepideThe therapeutic efficacy of Netazepide can be decreased when used in combination with Dyphylline.Investigational
NitrazepamThe therapeutic efficacy of Nitrazepam can be decreased when used in combination with Dyphylline.Approved
NitroaspirinThe serum concentration of Dyphylline can be decreased when it is combined with Nitroaspirin.Investigational
NorfloxacinThe metabolism of Dyphylline can be decreased when combined with Norfloxacin.Approved
OlodaterolThe risk or severity of adverse effects can be increased when Dyphylline is combined with Olodaterol.Approved
OmapatrilatThe serum concentration of Dyphylline can be decreased when it is combined with Omapatrilat.Investigational
OtamixabanThe serum concentration of Dyphylline can be decreased when it is combined with Otamixaban.Investigational
OxazepamThe therapeutic efficacy of Oxazepam can be decreased when used in combination with Dyphylline.Approved
Oxolinic acidThe metabolism of Dyphylline can be decreased when combined with Oxolinic acid.Experimental
OxprenololOxprenolol may decrease the bronchodilatory activities of Dyphylline.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Dyphylline is combined with Pancuronium.Approved
PazufloxacinThe metabolism of Dyphylline can be decreased when combined with Pazufloxacin.Investigational
PefloxacinThe metabolism of Dyphylline can be decreased when combined with Pefloxacin.Approved
Peginterferon alfa-2aThe metabolism of Dyphylline can be decreased when combined with Peginterferon alfa-2a.Approved, Investigational
Peginterferon alfa-2bThe metabolism of Dyphylline can be decreased when combined with Peginterferon alfa-2b.Approved
Peginterferon beta-1aThe metabolism of Dyphylline can be decreased when combined with Peginterferon beta-1a.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Dyphylline.Approved, Investigational
PentobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PentoxifyllineThe serum concentration of Dyphylline can be increased when it is combined with Pentoxifylline.Approved, Investigational
PerindoprilThe serum concentration of Dyphylline can be decreased when it is combined with Perindopril.Approved
PF-477736The therapeutic efficacy of PF-477736 can be decreased when used in combination with Dyphylline.Investigational
PhenobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Dyphylline can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Dyphylline can be decreased when it is combined with Phosphoramidon.Experimental
Pipemidic acidThe metabolism of Dyphylline can be decreased when combined with Pipemidic acid.Experimental
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Dyphylline.Approved
Piromidic acidThe metabolism of Dyphylline can be decreased when combined with Piromidic acid.Experimental
Polyestradiol phosphateThe serum concentration of Dyphylline can be increased when it is combined with Polyestradiol phosphate.Approved
Potassium IodideThe serum concentration of Dyphylline can be increased when it is combined with Potassium Iodide.Approved
PrazepamThe therapeutic efficacy of Prazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
PrimidoneThe serum concentration of Dyphylline can be decreased when it is combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Dyphylline can be decreased when it is combined with Prinomastat.Investigational
ProbenecidThe serum concentration of Dyphylline can be increased when it is combined with Probenecid.Approved
PromestrieneThe serum concentration of Dyphylline can be increased when it is combined with Promestriene.Investigational
PropafenoneThe serum concentration of Dyphylline can be increased when it is combined with Propafenone.Approved
PropylthiouracilThe serum concentration of Dyphylline can be increased when it is combined with Propylthiouracil.Approved
PrulifloxacinThe metabolism of Dyphylline can be decreased when combined with Prulifloxacin.Investigational
QuazepamThe therapeutic efficacy of Quazepam can be decreased when used in combination with Dyphylline.Approved, Illicit
QuinaprilThe serum concentration of Dyphylline can be decreased when it is combined with Quinapril.Approved, Investigational
QuinestrolThe serum concentration of Dyphylline can be increased when it is combined with Quinestrol.Approved
QuinineThe serum concentration of Dyphylline can be increased when it is combined with Quinine.Approved
RacecadotrilThe serum concentration of Dyphylline can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Dyphylline can be decreased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Dyphylline can be decreased when it is combined with Remikiren.Approved
RiociguatDyphylline may increase the hypotensive activities of Riociguat.Approved
RitonavirThe serum concentration of Dyphylline can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Dyphylline can be decreased when it is combined with Rivaroxaban.Approved
RosoxacinThe metabolism of Dyphylline can be decreased when combined with Rosoxacin.Approved, Investigational
RufloxacinThe metabolism of Dyphylline can be decreased when combined with Rufloxacin.Experimental
S-3304The serum concentration of Dyphylline can be decreased when it is combined with S-3304.Investigational
SaquinavirThe serum concentration of Dyphylline can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Dyphylline can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe serum concentration of Dyphylline can be decreased when it is combined with Secobarbital.Approved, Vet Approved
SecoisolariciresinolThe serum concentration of Dyphylline can be increased when it is combined with Secoisolariciresinol.Investigational
SimeprevirThe serum concentration of Dyphylline can be decreased when it is combined with Simeprevir.Approved
SitafloxacinThe metabolism of Dyphylline can be decreased when combined with Sitafloxacin.Experimental, Investigational
SitagliptinThe serum concentration of Dyphylline can be decreased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Dyphylline can be decreased when it is combined with Sivelestat.Investigational
SJG-136The therapeutic efficacy of SJG-136 can be decreased when used in combination with Dyphylline.Investigational
SparfloxacinThe metabolism of Dyphylline can be decreased when combined with Sparfloxacin.Approved, Investigational
SpiraprilThe serum concentration of Dyphylline can be decreased when it is combined with Spirapril.Approved
Synthetic Conjugated Estrogens, AThe serum concentration of Dyphylline can be increased when it is combined with Synthetic Conjugated Estrogens, A.Approved
Synthetic Conjugated Estrogens, BThe serum concentration of Dyphylline can be increased when it is combined with Synthetic Conjugated Estrogens, B.Approved
TelaprevirThe serum concentration of Dyphylline can be decreased when it is combined with Telaprevir.Approved, Withdrawn
TemafloxacinThe metabolism of Dyphylline can be decreased when combined with Temafloxacin.Withdrawn
TemazepamThe therapeutic efficacy of Temazepam can be decreased when used in combination with Dyphylline.Approved
TemocaprilThe serum concentration of Dyphylline can be decreased when it is combined with Temocapril.Experimental, Investigational
TertatololTertatolol may decrease the bronchodilatory activities of Dyphylline.Experimental
ThiabendazoleThe metabolism of Dyphylline can be decreased when combined with Thiabendazole.Approved, Vet Approved
ThiamylalThe serum concentration of Dyphylline can be decreased when it is combined with Thiamylal.Approved, Vet Approved
ThiopentalThe serum concentration of Dyphylline can be decreased when it is combined with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Dyphylline can be decreased when it is combined with Thiorphan.Experimental
Thyroid, porcineThe metabolism of Dyphylline can be increased when combined with Thyroid, porcine.Approved
TiboloneThe serum concentration of Dyphylline can be increased when it is combined with Tibolone.Approved, Investigational
TiclopidineThe metabolism of Dyphylline can be decreased when combined with Ticlopidine.Approved
TipranavirThe serum concentration of Dyphylline can be decreased when it is combined with Tipranavir.Approved, Investigational
TrandolaprilThe serum concentration of Dyphylline can be decreased when it is combined with Trandolapril.Approved
TriazolamThe therapeutic efficacy of Triazolam can be decreased when used in combination with Dyphylline.Approved
TrovafloxacinThe metabolism of Dyphylline can be decreased when combined with Trovafloxacin.Approved, Investigational, Withdrawn
UbenimexThe serum concentration of Dyphylline can be decreased when it is combined with Ubenimex.Experimental, Investigational
UlinastatinThe serum concentration of Dyphylline can be decreased when it is combined with Ulinastatin.Investigational
VildagliptinThe serum concentration of Dyphylline can be decreased when it is combined with Vildagliptin.Approved, Investigational
XimelagatranThe serum concentration of Dyphylline can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Dyphylline can be decreased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZafirlukastThe serum concentration of Zafirlukast can be decreased when it is combined with Dyphylline.Approved, Investigational
ZeranolThe serum concentration of Dyphylline can be increased when it is combined with Zeranol.Vet Approved
ZofenoprilThe serum concentration of Dyphylline can be decreased when it is combined with Zofenopril.Experimental
Food Interactions
Not Available

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
HMDB14789
KEGG Drug
D00691
KEGG Compound
C07819
PubChem Compound
3182
PubChem Substance
46504443
ChemSpider
3070
BindingDB
82016
ChEBI
4728
ChEMBL
CHEMBL1752
Therapeutic Targets Database
DAP000596
PharmGKB
PA164748027
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
ATC Codes
R03DA51 — Diprophylline, combinationsR03DA20 — Combinations of xanthinesR03DA01 — DiprophyllineR03DB01 — Diprophylline and adrenergics
MSDS
Download (65.7 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Teva pharmaceuticals usa inc
  • Savage laboratories inc div altana inc
  • Meda pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
SyrupOral
TabletOral200 mg/1
ElixirOral100 mg
LiquidIntramuscular; Intravenous500 mg
SolutionOral100 mg
SuppositoryRectal500 mg
TabletOral200 mg
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

Taxonomy

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
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, propane-1,2-diols (CHEBI:4728)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216]
  4. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216]
  5. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Iancu L, Shneur A, Cohen H: Trials with xanthine derivatives in systemic treatment of psoriasis. Dermatologica. 1979;159(1):55-61. [PubMed:225216]
  4. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603]
Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. Hariton C: Ocular hypotension induced by topical dopaminergic drugs and phosphodiesterase inhibitors. Eur J Pharmacol. 1994 Jun 2;258(1-2):85-94. [PubMed:7925603]
Kind
Protein
Organism
Human
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. [PubMed:2997628]
Kind
Protein
Organism
Human
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. [PubMed:2997628]
Kind
Protein
Organism
Human
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 have a role in muscle signal transduction.
Gene Name
PDE7A
Uniprot ID
Q13946
Uniprot Name
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
Molecular Weight
55504.475 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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 the control of cAMP-mediated neural activity and cAMP metabolism in the ...
Gene Name
PDE7B
Uniprot ID
Q9NP56
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 7B
Molecular Weight
51834.855 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:41