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

General Information of Drug (ID: DR0110)
Drug Name
AI3-25184
Synonyms
Amyl nitrite; KSC492M8F; N-Phenyl nitrile; Nitramyl; Nitrous acid, pentyl ester; Nitrousacid, pentyl ester; Pentyl alcohol, nitrite; Pentyl nitrite; Pentyl nitrite, AldrichCPR; Pentylnitrite; UN 1113 (Related); amyl 1 nitrite; n-Amyl nitrite; n-Pentyl nitrite; n-pentylnitrite; nitrous acid pentyl ester; 463-04-7; AC1L1UC5; ACMC-1ACPW; AI3-25184; BRN 1701241; CCRIS 763; CHEBI:55344; CSDTZUBPSYWZDX-UHFFFAOYSA-N; DSSTox_CID_4522; DSSTox_GSID_24522; DSSTox_RID_77442; EINECS 207-332-7; H2HUX79FYK; SCHEMBL34065; UNII-H2HUX79FYK
Indication Achalasia [ICD11: DA21] Phase 1 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 117.15 Topological Polar Surface Area 38.7
Heavy Atom Count 8 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
10026
PubChem SID
8157247 ; 10523453 ; 15194387 ; 29228570 ; 46507839 ; 48422858 ; 49855423 ; 50234008 ; 51075377 ; 57325917 ; 61548046 ; 87351903 ; 87562079 ; 88826757 ; 104322178 ; 124759820 ; 125823538 ; 126584108 ; 126688727 ; 126728383 ; 127327779 ; 127327780 ; 127327781 ; 127670072 ; 131294400 ; 134224767 ; 134973651 ; 137009484 ; 142314899 ; 144210096 ; 151993050 ; 152171314 ; 160797929 ; 162096005 ; 162160866 ; 162264216 ; 162761000 ; 163809052 ; 164806469 ; 165252965 ; 174550429 ; 176327280 ; 184577973 ; 204380219 ; 223501932 ; 223670724 ; 223764611 ; 226420589 ; 241077705 ; 241153309
ChEBI ID
CHEBI:55344
CAS Number
463-04-7
TTD Drug ID
D01QLH
Formula
C5H11NO2
Canonical SMILES
CCCCCON=O
InChI
1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3
InChIKey
CSDTZUBPSYWZDX-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
N-nitrosomethylaniline DM003382 N. A. Unclear 1 [4]
Nitrosamine N-nitroso-N-methylaniline DM003381
101493
Oxidation - N-nitrosylation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003824 AI3-25184 Nitrosamine N-nitroso-N-methylaniline Oxidation - N-nitrosylation Unclear [5]
MR003825 AI3-25184 N-nitrosomethylaniline Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde dehydrogenase 2 (ALDH2) DME0077 Homo sapiens
ALDH2_HUMAN
1.2.1.3
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
References
1 ClinicalTrials.gov (NCT02428959) Diagnostic Utility of Amyl Nitrite in Patients With Suspected Achalasia Undergoing High Resolution Esophageal Manometry (HREM).
2 Mitochondrial aldehyde dehydrogenase mediates vasodilator responses of glyceryl trinitrate and sodium nitrite in the pulmonary vascular bed of the rat. Am J Physiol Heart Circ Physiol. 2010 Sep;299(3):H819-26.
3 Subunit specificity and organ distribution of glutathione transferase-catalysed S-nitrosoglutathione formation from alkyl nitrites in the rat. Biochem Pharmacol. 1997 Jan 10;53(1):117-20.
4 Lipidic nitrosating agents produced from atmospheric nitrogen dioxide and a nitrosamine produced in vivo from amyl nitrite
5 Demonstration of in vivo formation of the nitrosamine N-nitroso-N-methylaniline from amyl nitrite

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