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

General Information of Drug (ID: DR1725)
Drug Name
Zaleplon
Synonyms
Zerene; LJC 10846; LJC-10846; S62U433RMH; SKP-1041; Sonata; ZAL 846; ZAL-846; zaleplon; 151319-34-5; 3'-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)-N-ethylacetanilide; 3'-(3-Cyanopyrazolo(1,5-alpha)pyrimidin-7-yl)-N-ethylacetanilide; CHEBI:10102; CL 284,846; CL 284846; CL-284846; DEA No. 2781; L-846; L846; N-(3-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)phenyl)-N-ethylacetamide; N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide; UNII-S62U433RMH; HUNXMJYCHXQEGX-UHFFFAOYSA-N
Indication Insomnia [ICD11: 7A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 305.33 Topological Polar Surface Area 74.3
Heavy Atom Count 23 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5719
PubChem SID
9687 ; 5366116 ; 7847596 ; 8153504 ; 12014056 ; 14751928 ; 26719706 ; 29216208 ; 29224756 ; 46386657 ; 46508267 ; 48416707 ; 49831110 ; 49858710 ; 50064487 ; 57288874 ; 57322911 ; 58107163 ; 76325725 ; 81041179 ; 81093138 ; 87246409 ; 92308631 ; 92714203 ; 93166204 ; 103558703 ; 104179081 ; 104310058 ; 104829286 ; 124360324 ; 124659160 ; 125341659 ; 126629628 ; 126655581 ; 126669582 ; 128115429 ; 131299907 ; 134337580 ; 135017416 ; 135698186 ; 135710033 ; 136352570 ; 136897476 ; 137001621 ; 142240621 ; 144089038 ; 144205425 ; 160964301 ; 162011443 ; 162022385
ChEBI ID
CHEBI:10102
CAS Number
151319-34-5
TTD Drug ID
D09DWL
Formula
C17H15N5O
Canonical SMILES
CCN(C1=CC=CC(=C1)C2=CC=NC3=C(C=NN23)C#N)C(=O)C
InChI
1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3
InChIKey
HUNXMJYCHXQEGX-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
5-Oxo-zaleplon DM005335
135465917
Oxidation - Oxidationn 1 [6] , [3] , [7]
N-Desesethylzaleplon DM005337
9993635
Oxidation - N-dealkylation 1 [6] , [3] , [7]
DDZAL DM005338
72357328
Unclear 2 [6] , [3] , [7]
N-desethyl-5-oxo-ZAL (M1) DM005336
135453959
Oxidation - Oxidationn 2 [6] , [3] , [7]
N-desethyl-5-oxo-ZAL (M1) DM005336
135453959
Oxidation - N-dealkylation 2 [6] , [3] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013291 Zaleplon 5-Oxo-zaleplon Oxidation - Oxidationn AOX1 [6], [3], [7]
MR013293 Zaleplon N-Desesethylzaleplon Oxidation - N-dealkylation CYP3A4 [6], [3], [7]
MR013292 5-Oxo-zaleplon N-desethyl-5-oxo-ZAL (M1) Oxidation - N-dealkylation CYP3A4 [6], [3], [7]
MR013294 N-Desesethylzaleplon N-desethyl-5-oxo-ZAL (M1) Oxidation - Oxidationn Unclear [6], [3], [7]
MR013295 N-Desesethylzaleplon DDZAL Unclear Unclear [6], [3], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
⏷ Show the Full List of 11  DME(s)
References
1 Zaleplon was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of aldehyde oxidase enzyme activity in cryopreserved human hepatocytes. Drug Metab Dispos. 2012 Feb;40(2):267-75.
3 Metabolism of zaleplon by human liver: evidence for involvement of aldehyde oxidase. Xenobiotica. 2002 Oct;32(10):835-47.
4 Drug Interactions Flockhart Table
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Variability of Zaleplon 5-Oxidase Activity in Mice and Humans, and Inhibition by Raloxifene
7 Separation and identification of zaleplon metabolites in human urine using capillary electrophoresis with laser-induced fluorescence detection and liquid chromatography-mass spectrometry

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