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 |
|---|---|---|
| Assessment of global and gene-specific DNA methylation in rat liver and kidney in response to non-genotoxic carcinogen exposure. | 2015-12-01 |
|
| Disruption of spindle checkpoint function ahead of facilitation of cell proliferation by repeated administration of hepatocarcinogens in rats. | 2015-12 |
|
| Comparative gene and protein expression analyses of a panel of cytokines in acute and chronic drug-induced liver injury in rats. | 2014-10-03 |
|
| Urinary microRNA profiling for identification of biomarkers after cisplatin-induced kidney injury. | 2014-10-03 |
|
| 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. | 2014-08-01 |
|
| 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 |
|
| Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies. | 2013-10 |
|
| Pharmacokinetics explain in vivo/in vitro discrepancies of carcinogen-induced gene expression alterations in rat liver and cultivated hepatocytes. | 2013-02 |
|
| Comparison of hepatocarcinogen-induced gene expression profiles in conventional primary rat hepatocytes with in vivo rat liver. | 2012-09 |
|
| Hepatic microRNA profiles offer predictive and mechanistic insights after exposure to genotoxic and epigenetic hepatocarcinogens. | 2012-08 |
|
| Plasma microRNA profiles in rat models of hepatocellular injury, cholestasis, and steatosis. | 2012 |
|
| The genotoxic potential of methapyrilene using the alkaline Comet assay in vitro and in vivo. | 2011-12-18 |
|
| Human embryonic stem cell derived hepatocyte-like cells as a tool for in vitro hazard assessment of chemical carcinogenicity. | 2011-12 |
|
| Development and evaluation of a genomic signature for the prediction and mechanistic assessment of nongenotoxic hepatocarcinogens in the rat. | 2011-11 |
|
| Toxicogenomics and cancer risk assessment: a framework for key event analysis and dose-response assessment for nongenotoxic carcinogens. | 2010-12 |
|
| Collaborative study on fifteen compounds in the rat-liver Comet assay integrated into 2- and 4-week repeat-dose studies. | 2010-09-30 |
|
| Characterization of glutathione conjugates of duloxetine by mass spectrometry and evaluation of in silico approaches to rationalize the site of conjugation for thiophene containing drugs. | 2010-08-16 |
|
| Discrimination of carcinogens by hepatic transcript profiling in rats following 28-day administration. | 2009-11-13 |
|
| Functional and toxicological consequences of metabolic bioactivation of methapyrilene via thiophene S-oxidation: Induction of cell defence, apoptosis and hepatic necrosis. | 2009-09-15 |
|
| GEM-TREND: a web tool for gene expression data mining toward relevant network discovery. | 2009-09-03 |
|
| Aqua-(2,2'-bipyridine-κN,N')bis-(thio-phene-2-carboxyl-ato-κO)copper(II). | 2009-07-11 |
|
| Gene expression profiling in rat liver treated with compounds inducing elevation of bilirubin. | 2009-04 |
|
| Toxicogenomic biomarkers for liver toxicity. | 2009-03 |
|
| Primary rat hepatocytes as in vitro system for gene expression studies: comparison of sandwich, Matrigel and 2D cultures. | 2008-12 |
|
| A toxicogenomics approach for early assessment of potential non-genotoxic hepatocarcinogenicity of chemicals in rats. | 2008-08-19 |
|
| Identification of the thiophene ring of methapyrilene as a novel bioactivation-dependent hepatic toxicophore. | 2008-08 |
|
| 'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus. | 2008-06-03 |
|
| Gene expression profiling of methapyrilene-induced hepatotoxicity in rat. | 2008-02 |
|
| Literature-based compound profiling: application to toxicogenomics. | 2007-11 |
|
| Gene expression profiling of rat liver treated with serum triglyceride-decreasing compounds. | 2007-10 |
|
| Identification of genes implicated in methapyrilene-induced hepatotoxicity by comparing differential gene expression in target and nontarget tissue. | 2007-04 |
|
| Selection of new chemical entities with decreased potential for adverse drug reactions. | 2006-11-07 |
|
| Toxicophores: investigations in drug safety. | 2006-09-01 |
|
| Systems toxicology: integrated genomic, proteomic and metabonomic analysis of methapyrilene induced hepatotoxicity in the rat. | 2006-07 |
|
| Tissue distribution of quetiapine in 20 cases in Virginia. | 2006-05 |
|
| Gene expression analysis of the hepatotoxicant methapyrilene in primary rat hepatocytes: an interlaboratory study. | 2006-01 |
|
| Recent applications of DNA microarray technology to toxicology and ecotoxicology. | 2006-01 |
|
| Development of a large-scale chemogenomics database to improve drug candidate selection and to understand mechanisms of chemical toxicity and action. | 2005-09-29 |
|
| Comparison of the expression profiles induced by genotoxic and nongenotoxic carcinogens in rat liver. | 2005-08-04 |
|
| Discriminating different classes of toxicants by transcript profiling. | 2004-08 |
|
| Gene expression profiling reveals multiple toxicity endpoints induced by hepatotoxicants. | 2004-05-18 |
|
| Acute molecular markers of rodent hepatic carcinogenesis identified by transcription profiling. | 2004-04 |
|
| Quantitative PCR deconstruction of discrepancies between results reported by different hybridization platforms. | 2004-03 |
|
| Cross-site comparison of gene expression data reveals high similarity. | 2004-03 |
|
| Interlaboratory evaluation of rat hepatic gene expression changes induced by methapyrilene. | 2004-03 |
|
| Overview of an interlaboratory collaboration on evaluating the effects of model hepatotoxicants on hepatic gene expression. | 2004-03 |
|
| Effects of induction and inhibition of cytochromes P450 on the hepatotoxicity of methapyrilene. | 1998-11 |
|
| The carcinogenic effect of methapyrilene combined with nitrosodiethylamine given to rats in low doses. | 1992-07 |
|
| Toxicology of vancomycin in laboratory animals. | 1981-11-01 |
Patents
Sample Use Guides
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
Mon Mar 31 17:52:57 GMT 2025
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Mon Mar 31 17:52:57 GMT 2025
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| Record UNII |
00S42N58OM
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| Record Status |
Validated (UNII)
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C29578
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EPA PESTICIDE CODE |
97006
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PARENT -> SALT/SOLVATE |
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