NAV

8-chlorotheophylline

Targets (1)Enzymes (1)
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
8-chlorotheophylline
Accession Number
DB14132
Description

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
Thumb
3D
Similar Structures
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

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
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.

Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
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.

TargetActionsOrganism
AAdenosine receptor A2a
antagonist
Humans
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
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity
Not Available
Affected organisms
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of 8-chlorotheophylline can be increased when combined with Abatacept.
AbirateroneThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with 8-chlorotheophylline.
AcenocoumarolThe metabolism of 8-chlorotheophylline can be decreased when combined with Acenocoumarol.
AcetaminophenThe metabolism of 8-chlorotheophylline can be decreased when combined with Acetaminophen.
AcetazolamideAcetazolamide may increase the excretion rate of 8-chlorotheophylline which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirThe metabolism of 8-chlorotheophylline can be decreased when combined with Acyclovir.
AdalimumabThe serum concentration of 8-chlorotheophylline can be decreased when it is combined with Adalimumab.
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with 8-chlorotheophylline.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified

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
  1. Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [PubMed:3133696]
  2. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [PubMed:11835984]
ChemSpider
10211
BindingDB
50331852
RxNav
236872
ChEBI
59771
ChEMBL
CHEMBL88611
ZINC
ZINC000100018165
PDBe Ligand
H33
Wikipedia
8-Chlorotheophylline
PDB Entries
2uy3

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility9.41 mg/mLALOGPS
logP0.84ALOGPS
logP0.14ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)5.14ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity49.96 m3·mol-1ChemAxon
Polarizability19.37 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
Details1. 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. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [PubMed:11835984]
  2. Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [PubMed:3133696]

Enzymes

Details1. Cytochrome P450 1A2
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
  1. Coleman J., Cox A. and Cowley N. (2011). Side Effects of Drugs Annual. Elsevier.

Drug created on June 26, 2018 16:45 / Updated on June 12, 2020 16:53