Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D0O2IE
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| Former ID |
DNC001117
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| Drug Name |
Phenacetin
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| Synonyms |
phenacetin; 62-44-2; Acetophenetidin; N-(4-Ethoxyphenyl)acetamide; Acetphenetidin; Acetophenetidine; Acetophenetin; Phenacetine; p-Acetophenetidide; Contradouleur; Commotional; Achrocidin; Phenazetin; Contradol; Codempiral; 4'-Ethoxyacetanilide; 4-Ethoxyacetanilide; Acetamide, N-(4-ethoxyphenyl)-; p-Acetophenetidine; Fenacetina; Phenidin; Pyraphen; Phenacitin; Phenacetinum; Fenidina; Phenedina; Phenacet; Pertonal; Fenina; Phenin; Kalmin; p-Acetphenetidin; p-Acetophenetide; Phenazetina; Tetracydin; p-Ethoxyacetanilide; Stellacyl; Phenodyne; Imidazo[4,5-e][1,4]diazapine nucleotide (I)
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| Drug Type |
Small molecular drug
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| Indication | Analgesia [ICD-11: MB40.8; ICD-10: R20.0; ICD-9: 338] | Withdrawn from market | [1], [2] | |
| Structure |
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Download2D MOL |
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| Formula |
C10H13NO2
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| Canonical SMILES |
CCOC1=CC=C(C=C1)NC(=O)C
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| InChI |
1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
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| InChIKey |
CPJSUEIXXCENMM-UHFFFAOYSA-N
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| CAS Number |
CAS 62-44-2
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| PubChem Compound ID | ||||
| PubChem Substance ID |
9793, 73483, 841972, 3139201, 3724298, 7348354, 7847635, 8147859, 8149602, 8152917, 10321803, 10530552, 11112166, 11335755, 11360994, 11363676, 11366238, 11368800, 11372367, 11374228, 11376962, 11461966, 11466561, 11467681, 11485715, 11486202, 11489756, 11491219, 11492330, 11494596, 12016023, 14748329, 16962413, 17389770, 22388565, 24858936, 24887192, 24890660, 26611996, 26679408, 26747350, 26747351, 26752986, 26752987, 29223838, 36018734, 46507394, 47440229, 47959721, 48035093
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| ChEBI ID |
CHEBI:8050
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| SuperDrug ATC ID |
N02BE03
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| SuperDrug CAS ID |
cas=000062442
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| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
| Studied Microbe: Gut microbiota unspecific | [3], [4] | |||
| Metabolic Reaction | Deacetylation | |||
| Resulting Metabolite | P-phenetidin | |||
| Metabolic Effect | Decrease activity; Increase side effect (methemoglobinemia) | |||
| Description | Phenacetin can be metabolized to P-phenetidin by gut microbiota through deacetylation, which results in the decrease of drug's activity and the increase of the drug's side effect (methemoglobinemia). | |||
| Target and Pathway | Top | |||
|---|---|---|---|---|
| Target(s) | Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1) | Target Info | Inhibitor | [5] |
| Prostaglandin G/H synthase 1 (COX-1) | Target Info | Inhibitor | [6] | |
| BioCyc | C20 prostanoid biosynthesis | |||
| KEGG Pathway | Arachidonic acid metabolism | |||
| Metabolic pathways | ||||
| Platelet activation | ||||
| Serotonergic synapse | ||||
| NetPath Pathway | TGF_beta_Receptor Signaling Pathway | |||
| Panther Pathway | Inflammation mediated by chemokine and cytokine signaling pathway | |||
| Pathwhiz Pathway | Arachidonic Acid Metabolism | |||
| WikiPathways | Prostaglandin Synthesis and Regulation | |||
| Arachidonic acid metabolism | ||||
| Phase 1 - Functionalization of compounds | ||||
| Eicosanoid Synthesis | ||||
| Selenium Micronutrient Network | ||||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7402). | |||
| REF 2 | An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987)Dubach UC1, Rosner B, St rmer T.Author information1Department of Internal Medicine, Kantonsspital, Basel, Switzerland.AbstractBACKGROUND: Phenacetin abuse is known to produce kidney disease; salicylate use is supposed to prevent cardiovascular disease. We conducted a prospective, longitudinal epidemiologic study to examine the effects of these drugs on cause-specific mortality and on cardiovascular morbidity.METHODS: In 1968 we evaluated a study group of 623 healthy women 30 to 49 years old who had evidence of a regular intake of phenacetin, as measured by urinary excretion of its metabolites, and a matched control group of 621 women. Salicylate excretion was also measured. All subjects were examined over a period of 20 years.RESULTS: Life-table analyses of mortality during the 20 years, with adjustment for the year of birth, cigarette smoking, and length of follow-up, revealed significant differences between the groups in overall mortality (study group vs. control group, 74 vs. 27 deaths; relative risk, 2.2; 95 percent confidence interval, 1.5 to 3.3), deaths due to urologic or renal disease (relative risk, 16.1; 95 percent confidence interval, 3.9 to 66.1), deaths due to cancer (relative risk, 1.9; 95 percent confidence interval, 1.1 to 3.3), and deaths due to cardiovascular disease (relative risk, 2.9; 95 percent confidence interval, 1.5 to 5.5). The relative risk of cardiovascular disease (fatal or nonfatal myocardial infarction, heart failure, or stroke) was 1.8, and the 95 percent confidence interval 1.3 to 2.6. The odds ratio for the incidence of hypertension was 1.6, and the 95 percent confidence interval 1.2 to 2.1. The effects of phenacetin on morbidity and mortality, with adjustment for base-line salicylate excretion, were similar. In contrast, salicylate use had no effect on either mortality or morbidity.CONCLUSIONS: Regular use of analgesic drugs containing phenacetin is associated with an increased risk of hypertension and mortality and morbidity due to cardiovascular disease, as well as an increased riskof mortality due to cancer and urologic or renal disease. The use of salicylates carries no such risk.Comment inThe risks of phenacetin use. [N Engl J Med. 1991]PMID: 1984193 [PubMed - indexed for MEDLINE] Free full textSharePublication Types, MeSH Terms, SubstancesPublication TypesResearch Support, Non-U.S. Gov'tMeSH TermsAdultAgedAspirin/adverse effects*Cardiovascular Diseases/epidemiology*Cardiovascular Diseases/mortalityDose-Response Relationship, DrugFemaleHumansHypertension/epidemiologyKidney Diseases/mortalityLongitudinal StudiesMiddle AgedMortality*Neoplasms/mortalityPhenacetin/adverse effects*Prospective StudiesRiskSubstance-Related Disorders*Urologic Diseases/mortalitySubstancesPhenacetinAspirinLinkOut - more resourcesFull Text SourcesAtypon - PDFAtyponOvid Technologies, Inc.MedicalDrug Abuse - MedlinePlus Health InformationMiscellaneousACETYLSALICYLIC ACID - Hazardous Substances Data BankPHENACETIN - Hazardous Substances Data BankPubMed Commons home N Engl J Med. 1991 Jan 17;324(3):155-60. | |||
| REF 3 | Cometabolism of microbes and host: implications for drug metabolism and drug-induced toxicity. Clin Pharmacol Ther. 2013 Nov;94(5):574-81. | |||
| REF 4 | Human gut microbiota plays a role in the metabolism of drugs. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2016 Sep;160(3):317-26. | |||
| REF 5 | A potent "fat base" nucleotide inhibitor of IMP dehydrogenase. Biochemistry. 1998 Aug 25;37(34):11949-52. | |||
| REF 6 | Direct toxicity of nonsteroidal antiinflammatory drugs for renal medullary cells. Proc Natl Acad Sci U S A. 2001 Apr 24;98(9):5317-22. | |||
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