Phenacetin
Phenacetin is a phenylacetamide that was formerly used as analgesic but nephropathy and methemogobinemia led to its withdrawal from the market. Substrate of AADAC. p-phenetidine is the product of hydrolysis responsible for the nephrotoxicity of phenacetin
General
Type : Acetanilide
Chemical_Nomenclature : N-(4-ethoxyphenyl)acetamide
Canonical SMILES : CCOC1=CC=C(C=C1)NC(=O)C
InChI : 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)
InChIKey : CPJSUEIXXCENMM-UHFFFAOYSA-N
Other name(s) : Acetophenetidin || N-(4-Ethoxyphenyl)acetamide || Acetphenetidin || Acetophenetidine
MW : 179.21
Formula : C10H13NO2
CAS_number : 62-44-2
PubChem : 4754
UniChem : CPJSUEIXXCENMM-UHFFFAOYSA-N
Target
Structures : No structure
Families : Arylacetamide_deacetylase
References (15)
| Title : Role of human AADAC on hydrolysis of eslicarbazepine acetate and effects of AADAC genetic polymorphisms on hydrolase activity - Hirosawa_2021_Drug.Metab.Dispos__ |
| Author(s) : Hirosawa K , Fukami T , Tashiro K , Sakai Y , Kisui F , Nakano M , Nakajima M |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2021 |
| Abstract : |
| PubMedSearch : Hirosawa_2021_Drug.Metab.Dispos__ |
| PubMedID: 33446525 |
| Gene_locus related to this paper: human-AADAC |
| Title : Role of human AADAC on hydrolysis of eslicarbazepine acetate and effects of AADAC genetic polymorphisms on hydrolase activity - Hirosawa_2021_Drug.Metab.Dispos__ |
| Author(s) : Hirosawa K , Fukami T , Tashiro K , Sakai Y , Kisui F , Nakano M , Nakajima M |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2021 |
| Abstract : |
| PubMedSearch : Hirosawa_2021_Drug.Metab.Dispos__ |
| PubMedID: 33446525 |
| Gene_locus related to this paper: human-AADAC |
| Title : Role of human AADAC on hydrolysis of eslicarbazepine acetate and effects of AADAC genetic polymorphisms on hydrolase activity - Hirosawa_2021_Drug.Metab.Dispos__ |
| Author(s) : Hirosawa K , Fukami T , Tashiro K , Sakai Y , Kisui F , Nakano M , Nakajima M |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , : , 2021 |
| Abstract : |
| PubMedSearch : Hirosawa_2021_Drug.Metab.Dispos__ |
| PubMedID: 33446525 |
| Gene_locus related to this paper: human-AADAC |
| Title : Screening of specific inhibitors for human carboxylesterases or arylacetamide deacetylase - Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| Author(s) : Shimizu M , Fukami T , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 42 :1103 , 2014 |
| Abstract : |
| PubMedSearch : Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| PubMedID: 24751575 |
| Gene_locus related to this paper: human-AADAC , human-CES1 , human-CES2 |
| Title : Screening of specific inhibitors for human carboxylesterases or arylacetamide deacetylase - Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| Author(s) : Shimizu M , Fukami T , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 42 :1103 , 2014 |
| Abstract : |
| PubMedSearch : Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| PubMedID: 24751575 |
| Gene_locus related to this paper: human-AADAC , human-CES1 , human-CES2 |
| Title : Screening of specific inhibitors for human carboxylesterases or arylacetamide deacetylase - Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| Author(s) : Shimizu M , Fukami T , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 42 :1103 , 2014 |
| Abstract : |
| PubMedSearch : Shimizu_2014_Drug.Metab.Dispos_42_1103 |
| PubMedID: 24751575 |
| Gene_locus related to this paper: human-AADAC , human-CES1 , human-CES2 |
| Title : Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen - Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| Author(s) : Watanabe A , Fukami T , Takahashi S , Kobayashi Y , Nakagawa N , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :1532 , 2010 |
| Abstract : |
| PubMedSearch : Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| PubMedID: 20542992 |
| Title : Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen - Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| Author(s) : Watanabe A , Fukami T , Takahashi S , Kobayashi Y , Nakagawa N , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :1532 , 2010 |
| Abstract : |
| PubMedSearch : Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| PubMedID: 20542992 |
| Title : Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen - Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| Author(s) : Watanabe A , Fukami T , Takahashi S , Kobayashi Y , Nakagawa N , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 38 :1532 , 2010 |
| Abstract : |
| PubMedSearch : Watanabe_2010_Drug.Metab.Dispos_38_1532 |
| PubMedID: 20542992 |
| Title : Phenacetin deacetylase activity in human liver microsomes: distribution, kinetics, and chemical inhibition and stimulation - Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| Author(s) : Kudo S , Umehara K , Hosokawa M , Miyamoto G , Chiba K , Satoh T |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 294 :80 , 2000 |
| Abstract : |
| PubMedSearch : Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| PubMedID: 10871298 |
| Title : Phenacetin deacetylase activity in human liver microsomes: distribution, kinetics, and chemical inhibition and stimulation - Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| Author(s) : Kudo S , Umehara K , Hosokawa M , Miyamoto G , Chiba K , Satoh T |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 294 :80 , 2000 |
| Abstract : |
| PubMedSearch : Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| PubMedID: 10871298 |
| Title : Phenacetin deacetylase activity in human liver microsomes: distribution, kinetics, and chemical inhibition and stimulation - Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| Author(s) : Kudo S , Umehara K , Hosokawa M , Miyamoto G , Chiba K , Satoh T |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 294 :80 , 2000 |
| Abstract : |
| PubMedSearch : Kudo_2000_J.Pharmacol.Exp.Ther_294_80 |
| PubMedID: 10871298 |