Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H6N4O2 |
Molecular Weight | 166.1374 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2
InChI
InChIKey=PFWLFWPASULGAN-UHFFFAOYSA-N
InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
Molecular Formula | C6H6N4O2 |
Molecular Weight | 166.1374 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. 7-methylxanthine (7-MX) is a metabolite of caffeine and theobromine, and has been shown to have low toxicity and no carcinogenic effects. 7-MX is known as a non-selective adenosine antagonist and has been shown to work against myopia. 7-MX has little effect on the proliferation or apoptosis of human RPE cells; however, 7-MX disturbs the proportion of cells in the G1 stage and inhibits the expression of ADORA1, ADORA2A, and ADORA2B in short-term treatment. 7-MX has been confirmed to reduce the severity of myopia and eye elongation induced by forming deprivation in guinea pigs and to counteract the thinning of the posterior sclera and of collagen fibrils induced by form deprivation. A clinical trial showed that 7-MX reduced eye elongation and myopia progression in childhood myopia.
Approval Year
PubMed
Title | Date | PubMed |
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Caffeine metabolism before and after liver transplantation. | 2001 Feb |
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Determination of urinary methylated purine pattern by high-performance liquid chromatography. | 2001 Feb 10 |
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Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
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Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants. | 2003 May |
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Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004 Oct |
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Systemic 7-methylxanthine in retarding axial eye growth and myopia progression: a 36-month pilot study. | 2008 Dec |
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Altered expression of the caffeine synthase gene in a naturally caffeine-free mutant of Coffea arabica. | 2009 Oct |
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Adenosine receptor protein changes in guinea pigs with form deprivation myopia. | 2010 Nov |
Sample Use Guides
During a 12-months placebo-controlled trial, participants received one tablet every morning. The tablets had a diameter of 12 mm and a thickness of 3 mm. Active tablets contained 400 mg 7-MX. The peak serum concentration after an oral dose of 400 mg 7-MX in adults is around 20 umol/l with a half-life of 200 min.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29386874
To observe the growth of cells treated with 7-MX, primary human RPE cells were incubated with different concentrations (from 1 nmol/l to 1 mmol/l) of 7-MX. No statistically significantly growth alteration was noted at 24, 72, and 96 h. A slightly decreased cell proliferation rate was seen with 100 umol/l 7-MX at 48 h, but without statistically significant differences compared to the other concentrations. To observe the effects of 7-MX on the mRNA levels of ADORs, RPE cells were cultured with 10 umol/l 7-MX for 24, 48, and 72 h.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:48:39 GMT 2023
by
admin
on
Fri Dec 15 17:48:39 GMT 2023
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Record UNII |
E9M81NJM6G
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Record Status |
Validated (UNII)
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
PERCENT OF AMOUNT EXCRETED
MAJOR
PLASMA; URINE
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