Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1270)
Drug Name
Phenacetin
Synonyms
Pertonal; Phenacet; Phenacetine; Phenacetinum; Phenacitin; Phenazetin; Phenazetina; Phenedina; Phenidin; Phenin; Phenodyne; Pyraphen; Acetophenetidin; Acetophenetidine; Acetophenetin; Acetphenetidin; Achrocidin; Codempiral; Commotional; Contradol; Contradouleur; Fenacetina; Fenidina; Fenina; Kalmin; N-(4-Ethoxyphenyl)acetamide; Stellacyl; Tetracydin; p-Acetophenetide; p-Acetophenetidide; p-Acetophenetidine; p-Acetphenetidin; p-Ethoxyacetanilide; phenacetin; 4'-Ethoxyacetanilide; 4-Ethoxyacetanilide; 62-44-2; Acetamide, N-(4-ethoxyphenyl)-
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 179.22 Topological Polar Surface Area 38.3
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4754
PubChem SID
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
ChEBI ID
ChEBI:8050
CAS Number
62-44-2
TTD Drug ID
D0O2IE
Formula
C10H13NO2
Canonical SMILES
CCOC1=CC=C(C=C1)NC(=O)C
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Alfentanil metabolite AM3 DM000034
1983
Oxidation - O-Deethylation 1 [8]
N-OH-phenacetin DM002762
29539
Oxidation - N-Oxidation 1 [8]
Acetaminophen glucuronide DM000606
83944
Conjugation - Glucuronidation 2 [8]
Acetaminophen sulfate DM000607
83939
Unclear 2 [8]
NAPQI DM002758
39763
Oxidation - Oxidation 2 [8]
Acetaminophen cysteine DM000605
83997
Conjugation - Conjugation 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002010 Phenacetin N-OH-phenacetin Oxidation - N-Oxidation CYP1A1 ... [8]
MR002011 Phenacetin Acetaminophen Oxidation - O-Deethylation CYP1A2 [8]
MR002012 Acetaminophen Acetaminophen glucuronide Conjugation - Glucuronidation UGT2B15 ... [8]
MR002013 Acetaminophen Acetaminophen sulfate Unclear HST ... [8]
MR002014 Acetaminophen NAPQI Oxidation - Oxidation CYP1A2 ... [8]
MR002009 NAPQI Acetaminophen cysteine Conjugation - Conjugation GSTM1 ... [8]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cholesterol 24-hydroxylase (CYP46A1) DME0028 Homo sapiens
CP46A_HUMAN
1.14.14.25
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2A13 (CYP2A13) DME0030 Homo sapiens
CP2AD_HUMAN
1.14.14.1
[4]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[6]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Sulfotransferase 1A4 (SULT1A4) DMEN007 Homo sapiens
ST1A4_HUMAN
1.14.13.39
[8]
⏷ Show the Full List of 11  DME(s)
References
1 Acetaminophen was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. Biochemistry. 2003 Dec 9;42(48):14284-92.
3 Identification of CYP3A4 as the enzyme involved in the mono-N-dealkylation of disopyramide enantiomers in humans. Drug Metab Dispos. 2000 Aug;28(8):937-44.
4 CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin, and theophylline. Drug Metab Dispos. 2007 Mar;35(3):335-9.
5 Activation of phenacetin O-deethylase activity by alpha-naphthoflavone in human liver microsomes. Xenobiotica. 1999 Sep;29(9):885-98.
6 Human cytochromes P450 mediating phenacetin O-deethylation in vitro: validation of the high affinity component as an index of CYP1A2 activity. J Pharm Sci. 1998 Dec;87(12):1502-7.
7 Involvement of CYP2E1 as A low-affinity enzyme in phenacetin O-deethylation in human liver microsomes. Drug Metab Dispos. 1999 Aug;27(8):860-5.
8 DrugBank(Pharmacology-Metabolism)Phenacetin

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