8-Chlorotheophylline

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7ClN4O2
Molecular Weight	214.609
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=C(NC(Cl)=N2)C(=O)N(C)C1=O

InChI

InChIKey=RYIGNEOBDRVTHA-UHFFFAOYSA-N

InChI=1S/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8097701 | https://medlineplus.gov/druginfo/meds/a607046.html | https://www.drugs.com/international/8-chlorotheophylline.html | https://www.ncbi.nlm.nih.gov/pubmed/11835984 | https://www.drugbank.ca/drugs/DB14132 | https://www.ncbi.nlm.nih.gov/pubmed/21490354

Chlorotheophylline (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 (marketed as Draminate, Dramamine, Detensor and Gravol among others). Dimenhydrinate is primarily used to treat nausea, vomiting, and dizziness caused by motion sickness.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. Because adenosine causes a decrease in neuronal firing, blockade of the adenosine receptor causes the reverse effect resulting in excitation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11835984 \|https://www.ncbi.nlm.nih.gov/pubmed/3133696 \| https://www.drugbank.ca/drugs/DB14132	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nausea, vomiting, or vertigo of motion sickness 1 Sources: https://www.drugs.com/pro/dimenhydrinate.html	Preventing		Approved 8429	Dimenhydrinate Approved Use Dimenhydrinate Injection, USP is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness. Launch Date 1972

PubMed

Title	Date	PubMed
[Trials of symptomatic treatment of vertigo with ceric dioxalate-8-chlorotheophylline-diphenhydramine preparation].	1956 Sep-Oct	13407545
Complex formation influence on reaction rate. 3. Interaction of some isoalloxazines with 8-chlorotheophylline as determined by spectral, solubility, and kinetic methods.	1965 Sep	5881224
Effect of propylene glycol on the disposition of Dramamine in the rabbit.	1993 Mar-Apr	8097701
Isolation and characterization of impurities present in 8-chlorotheophylline.	2011 Jan	22131627

Patents

Sample Use Guides

In Vivo Use Guide

Dimenhydrinate in the injectable form is indicated when the oral form is impractical. Adults Nausea or vomiting may be expected to be controlled for approximately 4 hours with 50 mg, and prevented by a similar dose every 4 hours. Its administration may be attended by some degree of drowsiness in some patients, and 100 mg every 4 hours may be given in conditions in which drowsiness is not objectionable or is even desirable. For intramuscular administration, each milliliter (50 mg) of solution is injected as needed, but for intravenous administration, each milliliter (50 mg) of solution must be diluted in 10 mL of 0.9% Sodium Chloride Injection, USP and injected over a period of 2 minutes. Pediatric For intramuscular administration, 1.25 mg/kg of body weight or 37.5 mg/m2 of body surface area is administered four times daily. The maximum dose should not exceed 300 mg daily

Route of Administration: Oral

In Vitro Use Guide

The direct influence of sodium-8-chlorotheophyllinate (S8CT) on lymphocytes in vitro was examined by measuring their transformation rate (3H-thimidine uptake) and acid phosphatase activity. An enhanced transformation was only seen with B-lymphocytes showing a transformation index of 1.21 at concentrations of 10 and 100 ug S8CT per ml.

Name

Type

Language

8-Chlorotheophylline

Systematic Name

English

8-CHLORTHEOPHYLLINE

Common Name

English

CHLOROTHEOPHYLLINE

Systematic Name

English

8-CHLORO-1,3-DIMETHYL-7H-PURINE-2,6-DIONE

Systematic Name

English

8-CHLOROTHEOPHYLLINE [USP-RS]

Common Name

English

PAMABROM RELATED COMPOUND A [USP-RS]

Common Name

English

CHLORTHEOPHYLLINE

Common Name

English

NSC-6113

Code

English

8-chlortheophylline [WHO-DD]

Common Name

English

Code System Code Type Description

SMS_ID

100000088821