This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- 8-chlorotheophylline
- DrugBank Accession Number
- DB14132
- Background
8-Chlorotheophylline is a stimulant drug of the xanthine chemical class, with physiological effects similar to caffeine. Its main use is in combination with Diphenhydramine as the antiemetic drug Dimenhydrinate. The stimulant properties of 8-chlorotheophylline are thought to ward off the drowsiness caused by diphenhydramine's anti-histamine activity in the central nervous system.
8-chlorotheophylline produces a number of effects including nervousness, restlessness, insomnia, headache, and nausea, which are primarily attributed to its ability to block the adenosine receptor 1,2. Because adenosine causes a decrease in neuronal firing, blockade of the adenosine receptor causes the reverse effect resulting in excitation.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 8-chlorotheophylline (DB14132)
- Weight
- Average: 214.609
Monoisotopic: 214.025753195 - Chemical Formula
- C7H7ClN4O2
- Synonyms
- 1,3-dimethyl-8-chloroxanthine
- 8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
- Chlorotheophylline
- Chlortheophylline
Pharmacology
- Indication
When used in combination with Diphenhydramine as the antiemetic Dimenhydrinate, 8-chlorotheophylline is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
8-chlorotheophylline produces a number of effects including nervousness, restlessness, insomnia, headache, and nausea, which are primarily attributed to its ability to block the adenosine receptor 1,2. Because adenosine causes a decrease in neuronal firing, blockade of the adenosine receptor causes the reverse effect resulting in excitation.
Target Actions Organism AAdenosine receptor A2a antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 8-chlorotheophylline. Abametapir The serum concentration of 8-chlorotheophylline can be increased when it is combined with Abametapir. Abatacept The metabolism of 8-chlorotheophylline can be increased when combined with Abatacept. Abiraterone The serum concentration of 8-chlorotheophylline can be increased when it is combined with Abiraterone. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with 8-chlorotheophylline. Acenocoumarol The metabolism of 8-chlorotheophylline can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of 8-chlorotheophylline can be decreased when combined with Acetaminophen. Acetazolamide Acetazolamide may increase the excretion rate of 8-chlorotheophylline which could result in a lower serum level and potentially a reduction in efficacy. Acyclovir The metabolism of 8-chlorotheophylline can be decreased when combined with Acyclovir. Adalimumab The serum concentration of 8-chlorotheophylline can be decreased when it is combined with Adalimumab. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- GE2UA340FM
- CAS number
- 85-18-7
- InChI Key
- RYIGNEOBDRVTHA-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)
- IUPAC Name
- 8-chloro-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
- SMILES
- CN1C2=C(NC(Cl)=N2)C(=O)N(C)C1=O
References
- General References
- Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [Article]
- Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [Article]
- External Links
- ChemSpider
- 10211
- BindingDB
- 50331852
- 236872
- ChEBI
- 59771
- ChEMBL
- CHEMBL88611
- ZINC
- ZINC000100018165
- PDBe Ligand
- H33
- Wikipedia
- 8-Chlorotheophylline
- PDB Entries
- 2uy3
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 9.41 mg/mL ALOGPS logP 0.84 ALOGPS logP 0.14 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 5.14 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 49.96 m3·mol-1 Chemaxon Polarizability 19.37 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [Article]
- Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Coleman J., Cox A. and Cowley N. (2011). Side Effects of Drugs Annual. Elsevier.
Drug created at June 26, 2018 16:45 / Updated at June 12, 2020 16:53