Theophylline

Identification

Summary

Theophylline is a xanthine used to manage the symptoms of asthma, COPD, and other lung conditions caused by reversible airflow obstruction.

Brand Names
Elixophyllin, Elixophylline, Pulmophylline, Quibron-T, Theo-24, Theolair, Uniphyl
Generic Name
Theophylline
DrugBank Accession Number
DB00277
Background

A methylxanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Mechanistically, theophylline acts as a phosphodiesterase inhibitor, adenosine receptor blocker, and histone deacetylase activator. Theophylline is marketed under several brand names such as Uniphyl and Theochron, and it is indicated mainly for asthma, bronchospasm, and COPD.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 180.164
Monoisotopic: 180.06472552
Chemical Formula
C7H8N4O2
Synonyms
  • 1,3-dimethyl-7H-purine-2,6-dione
  • 1,3-dimethylxanthine
  • Teofilina
  • Theophyllin
  • Theophylline anhydrous
  • Theophylline, anhydrous

Pharmacology

Indication

For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAsthmaCombination Product in combination with: Guaifenesin (DB00874), Pseudoephedrine (DB00852)••••••••••••••••••
Used in combination for symptomatic treatment ofAsthmaCombination Product in combination with: D-glucose (DB01914)•••••••••••••••••••••• ••••••••
Used in combination to manageAsthmaCombination Product in combination with: Acetylcysteine (DB06151)••••••••••••
Used in combination to treatBronchitisCombination Product in combination with: Guaifenesin (DB00874), Pseudoephedrine (DB00852)••••••••••••••••••
Treatment ofBronchoconstriction••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Theophylline, an xanthine derivative chemically similar to caffeine and theobromine, is used to treat asthma and bronchospasm. Theophylline has two distinct actions in the airways of patients with reversible (asthmatic) obstruction; smooth muscle relaxation (i.e., bronchodilation) and suppression of the response of the airways to stimuli (i.e., non-bronchodilator prophylactic effects).

Mechanism of action

Theophylline relaxes the smooth muscle of the bronchial airways and pulmonary blood vessels and reduces airway responsiveness to histamine, methacholine, adenosine, and allergen. Theophylline competitively inhibits type III and type IV phosphodiesterase (PDE), the enzyme responsible for breaking down cyclic AMP in smooth muscle cells, possibly resulting in bronchodilation. Theophylline also binds to the adenosine A2B receptor and blocks adenosine mediated bronchoconstriction. In inflammatory states, theophylline activates histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones for transcription to begin.

TargetActionsOrganism
AAdenosine receptor A1
antagonist
Humans
AAdenosine receptor A2a
antagonist
Humans
AAdenosine receptor A2b
antagonist
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Humans
AcGMP-specific 3',5'-cyclic phosphodiesterase
inhibitor
Humans
AcAMP-specific 3',5'-cyclic phosphodiesterase 4A
inhibitor
Humans
AcGMP-inhibited 3',5'-cyclic phosphodiesterase A
inhibitor
Humans
AHistone deacetylase 2
activator
Humans
UCopine-1Not AvailableHumans
UMinor histocompatibility antigen H13Not AvailableHumans
UNodal modulator 1Not AvailableHumans
UPoly [ADP-ribose] polymerase 1Not AvailableHumans
UProtein RIC-3Not AvailableHumans
UTubulin monoglycylase TTLL3Not AvailableHumans
Absorption

Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form.

Volume of distribution
  • 0.3 to 0.7 L/kg
Protein binding

40%, primarily to albumin.

Metabolism

Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity.

Hover over products below to view reaction partners

Route of elimination

Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults.

Half-life

8 hours

Clearance
  • 0.29 mL/kg/min [Premature neonates, postnatal age 3-15 days]
  • 0.64 mL/kg/min [Premature neonates, postnatal age 25-57 days]
  • 1.7 mL/kg/min [Children 1-4 years]
  • 1.6 mL/kg/min [Children 4-12 years]
  • 0.9 mL/kg/min [Children 13-15 years]
  • 1.4 mL/kg/min [Children 16-17 years]
  • 0.65 mL/kg/min [Adults (16-60 years), otherwise healthy non-smoking asthmatics]
  • 0.41 mL/kg/min [Elderly (>60 years), non-smokers with normal cardiac, liver, and renal function]
  • 0.33 mL/kg/min [Acute pulmonary edema]
  • 0.54 mL/kg/min [COPD >60 years, stable, non-smoker >1 year]
  • 0.48 mL/kg/min [COPD with cor pulmonale]
  • 1.25 mL/kg/min [Cystic fibrosis (14-28 years)]
  • 0.31 mL/kg/min [Liver disease cirrhosis]
  • 0.35 mL/kg/min [acute hepatitis]
  • 0.65 mL/kg/min [cholestasis]
  • 0.47 mL/kg/min [Sepsis with multi-organ failure]
  • 0.38 mL/kg/min [hypothyroid]
  • 0.8 mL/kg/min [hyperthyroid]
Adverse Effects
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Toxicity

Symptoms of overdose include seizures, arrhythmias, and GI effects.

Pathways
PathwayCategory
Caffeine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1A2-2964(G/A)(A;A) / (G;A)A AlleleEffect Directly StudiedPatients with this genotype have reduced metabolism of theophylline.Details

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 Theophylline.
AbametapirThe serum concentration of Theophylline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Theophylline can be increased when combined with Abatacept.
AbirateroneThe metabolism of Theophylline can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Theophylline can be decreased when combined with Acalabrutinib.
Food Interactions
  • Avoid excessive or chronic alcohol consumption. Ingesting alcohol may reduce the clearance, and therefore increase the serum concentrations of theophylline.
  • Avoid St. John's Wort.
  • Take with or without food. Take consistently with regard to food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Theophylline sodium glycinate2S36N8T7538000-10-0AIJQWRAOMFRHTQ-UHFFFAOYSA-M
Product Images
International/Other Brands
Respbid / Slo-Bid / Theo 24 / Theo-Dur / Theodur G
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Elixir De TheophyllineElixir80 mg / 15 mLOralLaboratoire Atlas Inc1985-12-31Not applicableCanada flag
Pulmophylline ElxElixir80 mg / 15 mLOralLaboratoire Riva Inc1979-12-31Not applicableCanada flag
Quibron T SR Tab 300mgTablet, extended release300 mg / tabOralBristol Labs Division Of Bristol Myers Squibb1982-12-312004-08-05Canada flag
Quibron-TTablet300 mg/1OralMonarch Pharmaceuticals, Inc.2006-11-09Not applicableUS flag
Slo-bid 100Capsule, extended release100 mgOralAventis Pharma Ltd.1987-12-312003-07-22Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aa-theo LATablet, extended release200 mgOralAa Pharma Inc1993-12-31Not applicableCanada flag
Aa-theo LATablet, extended release300 mgOralAa Pharma Inc1993-12-31Not applicableCanada flag
Aa-theo LATablet, extended release100 mgOralAa Pharma Inc1993-12-31Not applicableCanada flag
Apo-theo ERTablet, extended release600 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-theo ERTablet, extended release400 mgOralApotex CorporationNot applicableNot applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BRONCHORETARD TAG200/NA350Theophylline (350 mg/1) + Theophylline (200 mg/1)Capsule, extended releaseOral2014-04-01Not applicableGermany flag
BRONCHORETARD TAG200/NA350Theophylline (350 mg/1) + Theophylline (200 mg/1)Capsule, extended releaseOral2014-04-01Not applicableGermany flag
CIDETOX® 125 MG CÁPSULASTheophylline (1 g) + Theophylline (125 mg)Capsule, extended releaseOralSERVICIO TECNICO GONHER FARMACEUTICA LTDA.2011-03-122017-10-04Colombia flag
CIDETOX® 125 MG CÁPSULASTheophylline (1 g) + Theophylline (125 mg)Capsule, extended releaseOralSERVICIO TECNICO GONHER FARMACEUTICA LTDA.2011-03-122017-10-04Colombia flag
I D M Expectorant TabTheophylline (70 mg / tab) + Guaifenesin (100 mg / tab) + Mepyramine maleate (12 mg / tab) + Potassium Iodide (160 mg / tab)TabletOralRougier Pharma Division Of Ratiopharm Inc1975-12-311999-09-27Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SenophyllineTheophylline (100 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
TALOTREN 200 MG KAPSUL, 30 ADETTheophylline (200 mg)CapsuleOralNOVARTİS ÜRÜNLERİ2019-11-262022-04-11Turkey flag
TALOTREN 350 MG KAPSUL, 30 ADETTheophylline (350 mg)CapsuleOralNOVARTİS ÜRÜNLERİ2018-07-312022-04-11Turkey flag

Categories

ATC Codes
R03DA54 — Theophylline, combinations excl. psycholepticsR03DA74 — Theophylline, combinations with psycholepticsR03DA20 — Combinations of xanthinesR03DA04 — TheophyllineR03DB04 — Theophylline and adrenergics
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 / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Lactam / Organic nitrogen compound
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dimethylxanthine (CHEBI:28177) / Purine alkaloids (C07130) / a small molecule (CPD-12479)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0I55128JYK
CAS number
58-55-9
InChI Key
ZFXYFBGIUFBOJW-UHFFFAOYSA-N
InChI
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
IUPAC Name
1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN1C2=C(NC=N2)C(=O)N(C)C1=O

References

Synthesis Reference

Nicolae S. Bodor, Kenneth B. Sloan, Yu-Neng Kuo, "Method for synthesizing certain selected pro-drug forms of theophylline." U.S. Patent US4000132, issued January, 1956.

US4000132
General References
Not Available
Human Metabolome Database
HMDB0001889
KEGG Drug
D00371
KEGG Compound
C07130
PubChem Compound
2153
PubChem Substance
46505949
ChemSpider
2068
BindingDB
82053
RxNav
10438
ChEBI
28177
ChEMBL
CHEMBL190
ZINC
ZINC000018043251
Therapeutic Targets Database
DAP000002
PharmGKB
PA451647
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
TEP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Theophylline
PDB Entries
1eht / 1o15 / 2a3a / 3rox / 4eoh / 5mzj / 6ico / 6tuz / 7vrk / 7vrm
show 4 more
FDA label
Download (85.2 KB)
MSDS
Download (75.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceHealthy Volunteers (HV)1
4CompletedHealth Services ResearchAsthma1
4CompletedPreventionAnesthetics Adverse Reaction / Kidney Diseases / Kidney Failure / Prophylaxis of Contrast-induced nephropathy1
4CompletedTreatmentAllergic Rhinitis (AR) / Asthma1
4CompletedTreatmentAsthma2

Pharmacoeconomics

Manufacturers
  • Fleming and co pharmaceuticals inc
  • Forest laboratories inc
  • Sanofi aventis us llc
  • Dm graham laboratories inc
  • Ucb inc
  • Whitby pharmaceuticals inc
  • Schwarz pharma inc
  • Schering corp
  • Central pharmaceuticals inc
  • Hospira inc
  • Inwood laboratories inc sub forest laboratories inc
  • Sandoz inc
  • Rp scherer north america div rp scherer corp
  • Ortho mcneil pharmaceutical inc
  • Schering corp sub schering plough corp
  • Fisons corp
  • Kv pharmaceutical co
  • Rp scherer north america
  • Hr cenci laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Lannett co inc
  • Panray corp sub ormont drug and chemical co inc
  • Alpharma us pharmaceuticals division
  • Cenci powder products inc
  • Halsey drug co inc
  • L perrigo co
  • Pharmaceutical assoc inc div beach products
  • Precision dose inc
  • Roxane laboratories inc
  • Taro pharmaceuticals usa inc
  • Wockhardt eu operations (swiss) ag
  • B braun medical inc
  • Baxter healthcare corp
  • 3m pharmaceuticals inc
  • Ferndale laboratories inc
  • Warner chilcott co llc
  • Monarch pharmaceuticals inc
  • Roerig div pfizer inc
  • Able laboratories inc
  • Glenmark generics ltd
  • Nostrum pharmaceuticals inc
  • Pliva inc
  • Pharmaceutical research assoc inc
  • Purdue pharmaceutical products lp
  • Graceway pharmaceuticals llc
  • Novartis consumer health inc
Packagers
  • Actavis Group
  • Amend
  • American Regent
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • Arcola Laboratories
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • B. Braun Melsungen AG
  • BASF Corp.
  • Baxter International Inc.
  • Bristol-Myers Squibb Co.
  • C.O. Truxton Inc.
  • Cardinal Health
  • Caremark LLC
  • Central Texas Community Health Centers
  • Comprehensive Consultant Services Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Equipharm Inc.
  • Forest Laboratories Inc.
  • Forest Pharmaceuticals
  • Glenmark Generics Ltd.
  • H and H Laboratories
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Inwood Labs
  • Inyx Usa Ltd.
  • Kaiser Foundation Hospital
  • Luitpold Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Marlop Pharmaceuticals Inc.
  • Mckesson Corp.
  • Mundipharma GmbH
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nostrum Laboratories Inc.
  • Nucare Pharmaceuticals Inc.
  • P F Laboratories Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Packaging Center
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Purdue Pharma LP
  • Qualitest
  • Remedy Repack
  • Rite Aid Corp.
  • Roxane Labs
  • Roxmar Laboratories
  • Sandhills Packaging Inc.
  • Sandoz
  • Sanofi-Aventis Inc.
  • Southwood Pharmaceuticals
  • Talbert Medical Management Corp.
  • Taro Pharmaceuticals USA
  • Tya Pharmaceuticals
  • UCB Pharma
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Warrick Pharmaceuticals Corp.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral300 mg
ElixirOral167 mg/25ml
SolutionOral0.67 %
SyrupOral533.33 g
TabletOral100 mg
Tablet, film coatedOral
Capsule, extended releaseOral350 mg/1
Capsule, extended releaseOral500 mg/1
Capsule, extended releaseOral
Tablet, delayed releaseOral
Tablet, delayed releaseOral300 mg
SyrupOral
ElixirOral533 mg
TabletOral350 MG
Tablet, delayed releaseOral100 mg
Capsule, extended releaseOral200 mg
Capsule, extended releaseOral400 mg
ElixirOral80 mg / 15 mL
Tablet, film coatedOral
Tablet, film coatedOral125 mg
GelOral0.5 g
InjectionIntravenous24 mg/ml
TabletOral
TabletOral150 MG
SyrupOral80 mg/15ml
TabletOral100.000 mg
SolutionIntravenous200 mg
SolutionIntravenous400 mg
ElixirOral0.533 g
TabletOral300 mg/1
SyrupOral
CapsuleOral
KitOral
Capsule, extended releaseOral100 mg
Capsule, extended releaseOral300 mg
Capsule, extended releaseOral50 mg
Tablet, extended releaseOral270 mg
CapsuleOral350 mg
Capsule, coated pellets
Capsule, coatedOral300 mg
SyrupOral0.533 g
Capsule, coatedOral200 mg
Capsule, coatedOral250 mg
CapsuleOral100 mg
CapsuleOral300 mg
Tablet
CapsuleOral100.000 mg
SuspensionOral
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral400 mg/1
Tablet, extended releaseOral450 MG
Tablet, extended releaseOral100 mg / srt
Tablet, extended releaseOral200 mg / srt
Tablet, extended releaseOral300 mg / srt
Tablet, extended releaseOral450 mg / srt
Tablet, extended releaseOral300 mg / tab
Tablet, extended releaseOral100 mg / tab
Capsule, extended releaseOral
SolutionOral80 mg / 15 mL
TabletOral125000 ug/1
TabletOral250000 ug/1
Tablet, extended releaseOral200 mg / tab
Tablet, extended releaseOral250 mg / tab
Tablet, extended releaseOral500 mg / tab
TabletOral250 mg
Tablet, film coatedOral250 mg
Tablet, effervescentOral
SuspensionOral2.5 g
Capsule, extended releaseOral350 MG
Capsule, extended releaseOral125 MG
Capsule, extended releaseOral250 MG
Capsule, extended releaseOral375 MG
Capsule, extended releaseOral500 MG
Capsule, extended releaseOral125 mg/1
Capsule, extended releaseOral200 mg/1
Capsule, extended releaseOral300 mg/1
LiquidOral80 mg/15mL
SolutionOral80 mg/15mL
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral450 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, extended releaseOral600 mg/1
SolutionIntravenous
LiquidOral80 mg / 15 mL
Tablet, extended releaseOral400 mg/1
Tablet, extended releaseOral300 mg/1
InjectionIntravenous
Injection, solutionIntravenous
Injection, solutionIntravenous160 mg/100mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous320 mg/100mL
Injection, solutionIntravenous40 mg/100mL
Injection, solutionIntravenous400 mg/100mL
Injection, solutionIntravenous80 mg/100mL
ElixirOral
Injection, solutionIntravenous200 mg
Tablet, film coatedOral150 mg
Tablet, film coatedOral300 mg
TabletOral300 mg
TabletOral400 mg
TabletOral
TabletOral400 mg/1
TabletOral600 mg/1
Tablet, extended releaseOral600 mg
Tablet, extended releaseOral
CapsuleOral200 mg
Capsule, coated pellets200 mg
Capsule
TabletOral125 mg
Tablet, extended releaseOral200 mg
CapsuleOral125 mg
TabletOral200 mg
Tablet, delayed releaseOral200 mg
Tablet, delayed releaseOral250 mg
Syrup
TabletRespiratory (inhalation)
SolutionOral
Tablet, coatedOral
Elixir
Tablet, extended releaseOral400 mg
TabletOral60 mg
Prices
Unit descriptionCostUnit
Elixophyllin GG 100-100 mg/15ml Solution 240ml Bottle60.98USD bottle
Uniphyl 600 mg 24 Hour tablet2.28USD tablet
Theo-24 400 mg 24 Hour Capsule2.04USD capsule
Theo-24 400 mg capsule sa1.97USD capsule
Uniphyl 400 mg 24 Hour tablet1.58USD tablet
Theo-24 300 mg 24 Hour Capsule1.45USD capsule
Theo-24 300 mg capsule sa1.4USD capsule
Theophylline 400 mg 24 Hour tablet1.27USD tablet
Theo-24 200 mg 24 Hour Capsule1.25USD capsule
Theo-24 200 mg capsule sa1.14USD capsule
Theochron 450 mg tablet sa0.94USD tablet
Theophylline CR 300 mg 12 Hour Capsule0.93USD capsule
Theo-24 100 mg 24 Hour Capsule0.83USD capsule
Theophylline CR 200 mg 12 Hour Capsule0.79USD capsule
Theophylline CR 450 mg 12 Hour tablet0.79USD tablet
Theo-24 100 mg capsule sa0.76USD capsule
Quibron 90-150 mg capsule0.73USD capsule
Theophylline CR 125 mg 12 Hour Capsule0.73USD capsule
Uniphyl 600 mg Sustained-Release Tablet0.68USD tablet
Uniphyl 400 mg Sustained-Release Tablet0.56USD tablet
Theochron 300 mg tablet sa0.54USD tablet
Theophylline CR 300 mg 12 Hour tablet0.51USD tablet
Theophylline CR 200 mg 12 Hour tablet0.4USD tablet
Theochron 200 mg tablet sa0.33USD tablet
Theophylline CR 100 mg 12 Hour tablet0.3USD tablet
Elixophyllin GG 100-100 mg/15ml Solution0.24USD ml
Theochron 100 mg tablet sa0.23USD tablet
Elixophyllin 80 mg/15ml Elixir0.2USD ml
Elixophyllin 80 mg/15 ml elix0.19USD ml
Apo-Theo La 300 mg Sustained-Release Tablet0.15USD tablet
Apo-Theo La 100 mg Sustained-Release Tablet0.14USD tablet
Apo-Theo La 200 mg Sustained-Release Tablet0.14USD tablet
Theophylline anhydrous powder0.08USD g
Theophylline 200 mg/100 ml d5w0.06USD ml
Theolair 5.3 mg/ml Liquid0.03USD ml
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)273 °CPhysProp
water solubility7360 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP-0.02HANSCH,C ET AL. (1995)
Caco2 permeability-4.35ADME Research, USCD
pKa8.81KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility22.9 mg/mLALOGPS
logP-0.26ALOGPS
logP-0.77Chemaxon
logS-0.9ALOGPS
pKa (Strongest Acidic)7.82Chemaxon
pKa (Strongest Basic)-0.78Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area69.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity44.93 m3·mol-1Chemaxon
Polarizability16.86 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9902
Caco-2 permeable+0.6172
P-glycoprotein substrateNon-substrate0.7281
P-glycoprotein inhibitor INon-inhibitor0.8939
P-glycoprotein inhibitor IINon-inhibitor0.911
Renal organic cation transporterNon-inhibitor0.8807
CYP450 2C9 substrateNon-substrate0.7738
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5974
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9933
CYP450 2D6 inhibitorNon-inhibitor0.9827
CYP450 2C19 inhibitorNon-inhibitor0.9895
CYP450 3A4 inhibitorNon-inhibitor0.9616
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9956
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9447
BiodegradationReady biodegradable0.5942
Rat acute toxicity2.7898 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8819
hERG inhibition (predictor II)Non-inhibitor0.8927
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0f79-6970000000-224461ad62a44dbdf860
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0fka-4900000000-878cab6882fd80efba3b
GC-MS Spectrum - EI-BGC-MSsplash10-001j-7900000000-a08735d528e738752429
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0900000000-d0882f7d959c726e7623
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9700000000-8d0e1898a6571fbca10a
GC-MS Spectrum - GC-MSGC-MSsplash10-0f79-6970000000-224461ad62a44dbdf860
Mass Spectrum (Electron Ionization)MSsplash10-00lr-9500000000-2c8464c2fe84464c207f
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-0092516012d6a2a93b31
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-4900000000-dcf52c18a6996f412b1a
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00kf-9000000000-09089337909892ef44cb
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-001j-7900000000-a08735d528e738752429
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-001i-0900000000-d0882f7d959c726e7623
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-c4943571126a44bb9e5a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-bc12ce29acd02fa749b8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-03k9-0900000000-d63f60043f186fbb9bc0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-070l-4900000000-d293ab2fa6199dbaf97a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-05ru-9400000000-dde4775588d52c83806f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-556e382f583d610ef1f0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-004i-0900000000-89e34f5158856ba33469
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-03k9-0900000000-65a6897d72954e875b00
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-070l-4900000000-df16604bd6c40cee8f24
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-05r3-9500000000-39a721dcecc86ed95507
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-1900000000-e67ff7ef9a955b90eb3f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-3900000000-1870952d98dbba22ace8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-7900000000-dc0e9606776c43a7823f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014j-9300000000-2c4c6490dda3ed3b563f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-26a6c0c23a465afdcde1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-01q9-1900000000-b11ca3441bb29fef1906
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0002-9400000000-63726fe0b49a9dc6ba7e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-9100000000-139f765bc9b5855960c6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00di-9000000000-88b5cb393b960973ac64
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00yi-9000000000-1ebbddce3c7133972546
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-0089-0900000000-e75bd6a75670c201ed82
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00kr-2900000000-7765c5608d9b8aa37976
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-2910000000-c9eb85b2c5aaf500073c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-f85319d9f010d9331358
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-aa13286b9e614fd8fe53
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-e15e11a3656aeeab5cd9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03mi-0900000000-2a03f291514704faa75f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03k9-2900000000-ab88f9462f7fd47e2cdb
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-02il-5900000000-10615507746dde65941c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-016r-9300000000-23b6aaf5dc6055695076
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9100000000-0cbbbe667a26bdb5e69c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-9000000000-ae6306e2b4613a843262
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-c4943571126a44bb9e5a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-bc12ce29acd02fa749b8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900000000-024b4b169aaa17d8a74e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-070l-4900000000-d293ab2fa6199dbaf97a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05ru-9400000000-dde4775588d52c83806f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-556e382f583d610ef1f0
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-89e34f5158856ba33469
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03k9-0900000000-65a6897d72954e875b00
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-070l-4900000000-983504ecebbfb75b5084
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05r3-9500000000-39a721dcecc86ed95507
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-03fr-0900000000-301f6a6c606c9a7b0a70
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0900000000-605dffad97fe00830afb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0900000000-a555f5610ea0cc93fb51
MS/MS Spectrum - , negativeLC-MS/MSsplash10-004i-0900000000-f549c20fef4bb5ca418e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0900000000-f1e7ed4d06480c676ae5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0089-0900000000-b98ed10778362fb92f0f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-da2d25abcc877a840ad2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-abde646c11db3466840e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0089-0900000000-dbb621bedc8cfcd20c79
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-2900000000-90c98019c1e8f7da070b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-7900000000-cb3893a87548cb64cf27
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ba-9400000000-0063418efb7894950690
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9100000000-f981abb3cf2d588f83ed
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9100000000-f0fbdf55d630257724bf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-9000000000-fe69541c14c87da8c124
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-1900000000-e67ff7ef9a955b90eb3f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-3900000000-1870952d98dbba22ace8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-7900000000-b5c4010c670127e11063
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014j-9300000000-2c4c6490dda3ed3b563f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-26a6c0c23a465afdcde1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-1900000000-c1f0683d1932a6c393f8
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-9400000000-63726fe0b49a9dc6ba7e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9100000000-139f765bc9b5855960c6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-88b5cb393b960973ac64
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00yi-9000000000-a92e0f58a066f6e1c88b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-08f49d05e8c651dd89ec
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-bad7ec3fbdf7e1eecae4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ba-9500000000-fadd3d94aac67bb5574b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9200000000-426452757fca6f6b9b76
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9100000000-52e441104cd15fca9363
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0900000000-d8a03644c7ee59de6416
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0900000000-6016ebc9f342f37971a7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0930000000-7539c4c857812dd013e7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-0930000000-17caee7404f50a2538bb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1900000000-d5c161725a650cbeb97c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-2910000000-c9eb85b2c5aaf500073c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-08b71a19d1a98ad63f16
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-cc9a16a03fd1ddcf16ce
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-a5a05251a356de41d694
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-cf6b68625e1da9625876
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-008a-3900000000-b451d483394707c14a45
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0103-8900000000-e4d7fe421701d95fcc8d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05mp-9200000000-50b208a506333287b29d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9100000000-42cf61435883947d7308
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-137.3869361
predicted
DarkChem Lite v0.1.0
[M-H]-137.7675361
predicted
DarkChem Lite v0.1.0
[M-H]-137.8720361
predicted
DarkChem Lite v0.1.0
[M-H]-137.4992361
predicted
DarkChem Lite v0.1.0
[M-H]-127.004715
predicted
DeepCCS 1.0 (2019)
[M+H]+138.1124361
predicted
DarkChem Lite v0.1.0
[M+H]+138.4654361
predicted
DarkChem Lite v0.1.0
[M+H]+138.5915361
predicted
DarkChem Lite v0.1.0
[M+H]+138.0519361
predicted
DarkChem Lite v0.1.0
[M+H]+129.84254
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.0264361
predicted
DarkChem Lite v0.1.0
[M+Na]+137.9284361
predicted
DarkChem Lite v0.1.0
[M+Na]+138.2415361
predicted
DarkChem Lite v0.1.0
[M+Na]+138.1423361
predicted
DarkChem Lite v0.1.0
[M+Na]+138.71461
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Adenosine receptor A1
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. Nantwi KD, Basura GJ, Goshgarian HG: Adenosine A1 receptor mRNA expression and the effects of systemic theophylline administration on respiratory function 4 months after C2 hemisection. J Spinal Cord Med. 2003 Winter;26(4):364-71. [Article]
  2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [Article]
Details
2. Adenosine receptor A2a
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. Pechlivanova DM, Georgiev VP: Effects of single and long-term theophylline treatment on the threshold of mechanical nociception: contribution of adenosine A1 and alpha2-adrenoceptors. Methods Find Exp Clin Pharmacol. 2005 Nov;27(9):659-64. [Article]
  2. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [Article]
Details
3. Adenosine receptor A2b
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2B
Uniprot ID
P29275
Uniprot Name
Adenosine receptor A2b
Molecular Weight
36332.655 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Philipp S, Yang XM, Cui L, Davis AM, Downey JM, Cohen MV: Postconditioning protects rabbit hearts through a protein kinase C-adenosine A2b receptor cascade. Cardiovasc Res. 2006 May 1;70(2):308-14. Epub 2006 Feb 23. [Article]
  3. Phelps PT, Anthes JC, Correll CC: Characterization of adenosine receptors in the human bladder carcinoma T24 cell line. Eur J Pharmacol. 2006 Apr 24;536(1-2):28-37. Epub 2006 Mar 3. [Article]
  4. Fozard JR, Baur F, Wolber C: Antagonist pharmacology of adenosine A2B receptors from rat, guinea pig and dog. Eur J Pharmacol. 2003 Aug 15;475(1-3):79-84. [Article]
  5. Holgate ST: The Quintiles Prize Lecture 2004. The identification of the adenosine A2B receptor as a novel therapeutic target in asthma. Br J Pharmacol. 2005 Aug;145(8):1009-15. [Article]
  6. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [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. 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. Lipworth BJ: Phosphodiesterase-4 inhibitors for asthma and chronic obstructive pulmonary disease. Lancet. 2005 Jan 8-14;365(9454):167-75. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. Wang K, Chen JQ, Chen Z, Chen JC: Inhibition of human phosphodiesterase 4A expressed in yeast cell GL62 by theophylline, rolipram, and acetamide-45. Acta Pharmacol Sin. 2002 Nov;23(11):1013-7. [Article]
  2. Haider S: Cyclic AMP level and phosphodiesterase activity during 17alpha,20beta-dihydroxy-4-pregnen-3-one induction and theophylline inhibition of oocyte maturation in the catfish, Clarias batrachus. Comp Biochem Physiol A Mol Integr Physiol. 2003 Feb;134(2):267-74. [Article]
  3. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [Article]
  4. Usta C, Sadan G, Tuncel B: The effect of the indomethacin on phosphodiesterase inhibitors mediated responses in isolated trachea preparations. Prostaglandins Leukot Essent Fatty Acids. 2004 Sep;71(3):137-41. [Article]
  5. Lee JM, Zemans RL, Hejazi M, Chin BB, Ladenson PW, Caturegli P: Modulation of thyroidal radioiodine uptake by theophylline. Exp Mol Pathol. 2004 Oct;77(2):116-20. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
Gene Name
PDE3A
Uniprot ID
Q14432
Uniprot Name
cGMP-inhibited 3',5'-cyclic phosphodiesterase A
Molecular Weight
124978.06 Da
References
  1. Rickards KJ, Andrews MJ, Waterworth TH, Alexander GB, Cunningham FM: Differential effects of phosphodiesterase inhibitors on platelet activating factor (PAF)- and adenosine diphosphate (ADP)-induced equine platelet aggregation. J Vet Pharmacol Ther. 2003 Aug;26(4):277-82. [Article]
  2. Wu BN, Lin RJ, Lo YC, Shen KP, Wang CC, Lin YT, Chen IJ: KMUP-1, a xanthine derivative, induces relaxation of guinea-pig isolated trachea: the role of the epithelium, cyclic nucleotides and K+ channels. Br J Pharmacol. 2004 Aug;142(7):1105-14. Epub 2004 Jul 5. [Article]
  3. Kajikawa S, Kigami D, Nakayama H, Doi K: Changes in submaxillary gland gene expression in F344 rats by multiple dosing of theophylline. Exp Anim. 2006 Apr;55(2):143-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC2
Uniprot ID
Q92769
Uniprot Name
Histone deacetylase 2
Molecular Weight
55363.855 Da
References
  1. Ito K, Lim S, Caramori G, Cosio B, Chung KF, Adcock IM, Barnes PJ: A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):8921-6. Epub 2002 Jun 17. [Article]
  2. Cosio BG, Tsaprouni L, Ito K, Jazrawi E, Adcock IM, Barnes PJ: Theophylline restores histone deacetylase activity and steroid responses in COPD macrophages. J Exp Med. 2004 Sep 6;200(5):689-95. Epub 2004 Aug 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Calcium-dependent phospholipid-binding protein that plays a role in calcium-mediated intracellular processes (PubMed:14674885). Involved in the TNF-alpha receptor signaling pathway in a calcium-dependent manner (PubMed:14674885). Exhibits calcium-dependent phospholipid binding properties (PubMed:9430674, PubMed:19539605). Plays a role in neuronal progenitor cell differentiation; induces neurite outgrowth via a AKT-dependent signaling cascade and calcium-independent manner (PubMed:23263657, PubMed:25450385). May recruit target proteins to the cell membrane in a calcium-dependent manner (PubMed:12522145). May function in membrane trafficking (PubMed:9430674). Involved in TNF-alpha-induced NF-kappa-B transcriptional repression by inducing endoprotease processing of the transcription factor NF-kappa-B p65/RELA subunit (PubMed:18212740). Also induces endoprotease processing of NF-kappa-B p50/NFKB1, p52/NFKB2, RELB and REL (PubMed:18212740).
Specific Function
Calcium ion binding
Gene Name
CPNE1
Uniprot ID
Q99829
Uniprot Name
Copine-1
Molecular Weight
59058.34 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Catalyzes intramembrane proteolysis of some signal peptides after they have been cleaved from a preprotein, resulting in the release of the fragment from the ER membrane into the cytoplasm. Required to generate lymphocyte cell surface (HLA-E) epitopes derived from MHC class I signal peptides (PubMed:11714810). May be necessary for the removal of the signal peptide that remains attached to the hepatitis C virus core protein after the initial proteolytic processing of the polyprotein (PubMed:12145199). Involved in the intramembrane cleavage of the integral membrane protein PSEN1 (PubMed:12077416, PubMed:11714810, PubMed:14741365). Cleaves the integral membrane protein XBP1 isoform 1 in a DERL1/RNF139-dependent manner (PubMed:25239945). May play a role in graft rejection (By similarity).
Specific Function
Aspartic endopeptidase activity, intramembrane cleaving
Gene Name
HM13
Uniprot ID
Q8TCT9
Uniprot Name
Minor histocompatibility antigen H13
Molecular Weight
41487.86 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
May antagonize Nodal signaling.
Specific Function
Carbohydrate binding
Gene Name
NOMO1
Uniprot ID
Q15155
Uniprot Name
Nodal modulator 1
Molecular Weight
134323.005 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This ...
Gene Name
PARP1
Uniprot ID
P09874
Uniprot Name
Poly [ADP-ribose] polymerase 1
Molecular Weight
113082.945 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Promotes functional expression of homomeric alpha-7 and alpha-8 nicotinic acetylcholine receptors at the cell surface. May also promote functional expression of homomeric serotoninergic 5-HT3 receptors, and of heteromeric acetylcholine receptors alpha-3/beta-2, alpha-3/beta-4, alpha-4/beta-2 and alpha-4/beta-4.
Specific Function
Acetylcholine receptor binding
Gene Name
RIC3
Uniprot ID
Q7Z5B4
Uniprot Name
Protein RIC-3
Molecular Weight
41091.77 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Monoglycylase which modifies alpha- and beta-tubulin, generating side chains of glycine on the gamma-carboxyl groups of specific glutamate residues within the C-terminal tail of alpha- and beta-tubulin. Involved in the side-chain initiation step of the glycylation reaction by adding a single glycine chain to generate monoglycine side chains. Not involved in elongation step of the polyglycylation reaction.
Specific Function
Atp binding
Gene Name
TTLL3
Uniprot ID
Q9Y4R7
Uniprot Name
Tubulin monoglycylase TTLL3
Molecular Weight
87413.395 Da
References
  1. Marwick JA, Wallis G, Meja K, Kuster B, Bouwmeester T, Chakravarty P, Fletcher D, Whittaker PA, Barnes PJ, Ito K, Adcock IM, Kirkham PA: Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802. doi: 10.1016/j.bbrc.2008.10.065. Epub 2008 Oct 23. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Ha HR, Chen J, Freiburghaus AU, Follath F: Metabolism of theophylline by cDNA-expressed human cytochromes P-450. Br J Clin Pharmacol. 1995 Mar;39(3):321-6. [Article]
  2. Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Gillam EM, Sutter TR, Strickland PT, Guengerich FP, Yamazaki H: Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ha HR, Chen J, Freiburghaus AU, Follath F: Metabolism of theophylline by cDNA-expressed human cytochromes P-450. Br J Clin Pharmacol. 1995 Mar;39(3):321-6. [Article]
  2. Zhang ZY, Kaminsky LS: Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation. Biochem Pharmacol. 1995 Jul 17;50(2):205-11. [Article]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [Article]
  2. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [Article]
  3. Wang L, Hu Z, Deng X, Wang Y, Zhang Z, Cheng ZN: Association between common CYP1A2 polymorphisms and theophylline metabolism in non-smoking healthy volunteers. Basic Clin Pharmacol Toxicol. 2013 Apr;112(4):257-63. doi: 10.1111/bcpt.12038. Epub 2012 Dec 20. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. Theophylline FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Saboury AA, Bagheri S, Ataie G, Amanlou M, Moosavi-Movahedi AA, Hakimelahi GH, Cristalli G, Namaki S: Binding properties of adenosine deaminase interacted with theophylline. Chem Pharm Bull (Tokyo). 2004 Oct;52(10):1179-82. [Article]
  2. Singh LS, Sharma R: Purification and characterization of intestinal adenosine deaminase from mice. Mol Cell Biochem. 2000 Jan;204(1-2):127-34. [Article]
  3. Bandyopadhyay BC, Poddar MK: Theophylline-induced changes in mammalian adenosine deaminase activity and corticosterone status: possible relation to immune response. Methods Find Exp Clin Pharmacol. 1997 Apr;19(3):181-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Sarkar MA, Hunt C, Guzelian PS, Karnes HT: Characterization of human liver cytochromes P-450 involved in theophylline metabolism. Drug Metab Dispos. 1992 Jan-Feb;20(1):31-7. [Article]
  2. Sutrisna E: The Impact of CYP1A2 and CYP2E1 Genes Polymorphism on Theophylline Response. J Clin Diagn Res. 2016 Nov;10(11):FE01-FE03. doi: 10.7860/JCDR/2016/21067.8914. Epub 2016 Nov 1. [Article]
  3. Kim YC, Lee AK, Lee JH, Lee I, Lee DC, Kim SH, Kim SG, Lee MG: Pharmacokinetics of theophylline in diabetes mellitus rats: induction of CYP1A2 and CYP2E1 on 1,3-dimethyluric acid formation. Eur J Pharm Sci. 2005 Sep;26(1):114-23. doi: 10.1016/j.ejps.2005.05.004. [Article]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhang ZY, Kaminsky LS: Characterization of human cytochromes P450 involved in theophylline 8-hydroxylation. Biochem Pharmacol. 1995 Jul 17;50(2):205-11. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48