NAV

8-chlorotheophylline

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
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
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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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Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 8-chlorotheophylline.
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.
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
  1. Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [Article]
  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. [Article]
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-5a34e0e7d6dd7118e1f5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0290000000-2629ae67d495bebbb768
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-08gi-6690000000-50ec0be2b3fe348615b6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-0970000000-7ec9b8842d24ead9a65b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-a38b1472c89e4b2ee082
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3900000000-7b2761af2b6caba9d991
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.89885
predicted
DeepCCS 1.0 (2019)
[M+H]+139.2944
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.08824
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
  2. Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [Article]

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 at June 26, 2018 16:45 / Updated at June 12, 2020 16:53