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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 of 8-Chlorotheophylline

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

Molecular Formula C7H7ClN4O2
Molecular Weight 214.609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Dimenhydrinate

Approved Use

Dimenhydrinate Injection, USP is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness.

Launch Date

7.6118401E10
PubMed

PubMed

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

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intramuscular and intravenous administration is also used. Dimenhydrinate, an anti-nauseant/antiemetic, is the 8-chlorotheophylline salt of diphenhydramine. It contains not less than 53% and not more than 55.5% of diphenhydramine, and not less than 44% and not more than 47% of 8-chlorotheophylline, calculated on the dried basis.
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:46:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:46:22 UTC 2023
Record UNII
GE2UA340FM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
8-Chlorotheophylline
Systematic Name English
8-CHLORTHEOPHYLLINE
WHO-DD  
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
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-590-4
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
CAS
85-18-7
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
DRUG BANK
DB14132
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
PUBCHEM
10661
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
WIKIPEDIA
8-Chlorotheophylline
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
RS_ITEM_NUM
1492700
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
ALTERNATIVE
MESH
C030093
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
RS_ITEM_NUM
1121038
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
DAILYMED
GE2UA340FM
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID5043764
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
EVMPD
SUB23210
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
NSC
6113
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
RXCUI
236872
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
ALTERNATIVE
RXCUI
1546416
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
FDA UNII
GE2UA340FM
Created by admin on Fri Dec 15 15:46:22 UTC 2023 , Edited by admin on Fri Dec 15 15:46:22 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SUBSTANCE->BASIS OF STRENGTH
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY