Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H19N3S.ClH |
Molecular Weight | 297.847 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CCN(CC1=CC=CS1)C2=CC=CC=N2
InChI
InChIKey=BONORRGKLJBGRV-UHFFFAOYSA-N
InChI=1S/C14H19N3S.ClH/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14;/h3-8,11H,9-10,12H2,1-2H3;1H
Molecular Formula | C14H19N3S |
Molecular Weight | 261.386 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB04819
Sources: http://www.drugbank.ca/drugs/DB04819
Methapyrilene is an antihistamine and anticholinergic of the pyridine chemical class which was developed in the early 1950s. It was sold under the trade names Co-Pyronil and Histadyl EC. It has relatively strong sedative effects, to the extent that its primary use was as a medication for insomnia rather than for its antihistamine action. Together with scopolamine, it was the main ingredient in Sominex, Nytol, and Sleep-Eze. It also provided the sedative component of Excedrin PM. Manufacturers voluntarily withdrew methapyrilineb drug products from the market in May and June 1979, when methapyrilene was demonstrated to cause liver cancer in rats when given chronically.
Approval Year
Doses
Dose | Population | Adverse events |
---|---|---|
2.5 g single, oral Overdose |
healthy, 19 years |
Other AEs: Dizziness, Stomach cramps... |
25 mg single, intravenous Dose: 25 mg Route: intravenous Route: single Dose: 25 mg Sources: |
healthy, 20 - 35 years Health Status: healthy Age Group: 20 - 35 years Sex: M+F Sources: |
|
50 mg single, oral |
healthy, 20 - 35 years Health Status: healthy Age Group: 20 - 35 years Sex: M+F Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Delusions | 2.5 g single, oral Overdose |
healthy, 19 years |
|
Dizziness | 2.5 g single, oral Overdose |
healthy, 19 years |
|
Stomach cramps | 2.5 g single, oral Overdose |
healthy, 19 years |
PubMed
Title | Date | PubMed |
---|---|---|
Toxicology of vancomycin in laboratory animals. | 1981 Nov-Dec |
|
The carcinogenic effect of methapyrilene combined with nitrosodiethylamine given to rats in low doses. | 1992 Jul |
|
Effects of induction and inhibition of cytochromes P450 on the hepatotoxicity of methapyrilene. | 1998 Nov |
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The syrian hamster embryo (SHE) cell transformation assay: review of the methods and results. | 2001 |
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Microarray analysis of hepatotoxins in vitro reveals a correlation between gene expression profiles and mechanisms of toxicity. | 2001 Mar 31 |
|
Gliotoxin stimulates the apoptosis of human and rat hepatic stellate cells and enhances the resolution of liver fibrosis in rats. | 2001 Sep |
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Morphological transformation of Syrian hamster embryo cells at pH 6.7 by bemitradine, a nongenotoxic carcinogen. | 2001 Summer |
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Fluorescence polarization discriminates green fluorescent protein from interfering autofluorescence in a microplate assay for genotoxicity. | 2002 Apr 18 |
|
Advantages of glutamate dehydrogenase as a blood biomarker of acute hepatic injury in rats. | 2002 Jul |
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Methapyrilene toxicity: anchorage of pathologic observations to gene expression alterations. | 2002 Jul-Aug |
|
Diphenhydramine-induced wide complex dysrhythmia responds to treatment with sodium bicarbonate. | 2003 May |
|
Quantitative PCR deconstruction of discrepancies between results reported by different hybridization platforms. | 2004 Mar |
|
Cross-site comparison of gene expression data reveals high similarity. | 2004 Mar |
|
Interlaboratory evaluation of rat hepatic gene expression changes induced by methapyrilene. | 2004 Mar |
|
Overview of an interlaboratory collaboration on evaluating the effects of model hepatotoxicants on hepatic gene expression. | 2004 Mar |
|
Gene expression profiling reveals multiple toxicity endpoints induced by hepatotoxicants. | 2004 May 18 |
|
Comparison of the expression profiles induced by genotoxic and nongenotoxic carcinogens in rat liver. | 2005 Aug 4 |
|
Recent applications of DNA microarray technology to toxicology and ecotoxicology. | 2006 Jan |
|
Selection of new chemical entities with decreased potential for adverse drug reactions. | 2006 Nov 7 |
|
Toxicophores: investigations in drug safety. | 2006 Sep 1 |
|
Identification of the thiophene ring of methapyrilene as a novel bioactivation-dependent hepatic toxicophore. | 2008 Aug |
|
A toxicogenomics approach for early assessment of potential non-genotoxic hepatocarcinogenicity of chemicals in rats. | 2008 Aug 19 |
|
'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus. | 2008 Jun 3 |
|
Aqua-(2,2'-bipyridine-κN,N')bis-(thio-phene-2-carboxyl-ato-κO)copper(II). | 2009 Jul 11 |
|
Toxicogenomic biomarkers for liver toxicity. | 2009 Mar |
|
Functional and toxicological consequences of metabolic bioactivation of methapyrilene via thiophene S-oxidation: Induction of cell defence, apoptosis and hepatic necrosis. | 2009 Sep 15 |
|
GEM-TREND: a web tool for gene expression data mining toward relevant network discovery. | 2009 Sep 3 |
|
Toxicogenomics and cancer risk assessment: a framework for key event analysis and dose-response assessment for nongenotoxic carcinogens. | 2010 Dec |
|
Human embryonic stem cell derived hepatocyte-like cells as a tool for in vitro hazard assessment of chemical carcinogenicity. | 2011 Dec |
|
The genotoxic potential of methapyrilene using the alkaline Comet assay in vitro and in vivo. | 2011 Dec 18 |
|
Development and evaluation of a genomic signature for the prediction and mechanistic assessment of nongenotoxic hepatocarcinogens in the rat. | 2011 Nov |
|
Plasma microRNA profiles in rat models of hepatocellular injury, cholestasis, and steatosis. | 2012 |
|
Hepatic microRNA profiles offer predictive and mechanistic insights after exposure to genotoxic and epigenetic hepatocarcinogens. | 2012 Aug |
|
Comparison of hepatocarcinogen-induced gene expression profiles in conventional primary rat hepatocytes with in vivo rat liver. | 2012 Sep |
|
Pharmacokinetics explain in vivo/in vitro discrepancies of carcinogen-induced gene expression alterations in rat liver and cultivated hepatocytes. | 2013 Feb |
|
Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies. | 2013 Oct |
|
Detection of initiating potential of non-genotoxic carcinogens in a two-stage hepatocarcinogenesis study in rats. | 2014 |
|
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action. | 2014 |
|
Changes in the expression of miRNAs at the pericentral and periportal regions of the rat liver in response to hepatocellular injury: comparison with the changes in the expression of plasma miRNAs. | 2014 Aug 1 |
|
Comparative gene and protein expression analyses of a panel of cytokines in acute and chronic drug-induced liver injury in rats. | 2014 Oct 3 |
|
Urinary microRNA profiling for identification of biomarkers after cisplatin-induced kidney injury. | 2014 Oct 3 |
|
Disruption of spindle checkpoint function ahead of facilitation of cell proliferation by repeated administration of hepatocarcinogens in rats. | 2015 Dec |
|
Assessment of global and gene-specific DNA methylation in rat liver and kidney in response to non-genotoxic carcinogen exposure. | 2015 Dec 1 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2046705
Methapyrilene failed to induce formation of DNA adducts in L5178Y cell DNA at doses which induced mutations at the thymidine kinase locus. These data suggest that methapyrilene induces mutations in this system through an indirect genotoxic mechanism; e.g., via an oxidative mechanism or interaction with chromosomal proteins.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:17:22 UTC 2023
by
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Record UNII |
00S42N58OM
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29578
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EPA PESTICIDE CODE |
97006
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