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.
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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
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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. 
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- 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
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- 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