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

General Information of Drug (ID: DR0011)
Drug Name
BRN-3548355
Synonyms
NNK (carcinogen); 1-Butanone, 4-(methylnitrosoamino)-1-(3-pyridinyl)-; 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE; 4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; 4-(N-Nitroso-N-methylamino)-1-(3-pyridyl)-1-butanone; 4-Methylnitrosoamino-1-(3-pyridinyl)-1-butanone; 4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one; 64091-91-4; 7S395EDO61; CCRIS 1150; CHEBI:32692; MFCD00274580; N-Methyl-N-nitroso-4-oxo-4-(3-pyridyl)butyl amine; NNK; UNII-7S395EDO61
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 207.23 Topological Polar Surface Area 62.6
Heavy Atom Count 15 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
47289
ChEBI ID
CHEBI:32692
CAS Number
64091-50-5
Formula
C10H13N3O2
Canonical SMILES
CN(CCCC(=O)C1=CN=CC=C1)N=O
InChI
1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3
InChIKey
FLAQQSHRLBFIEZ-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
BRN-3548355 reactive intermediates DM006957 N. A. Unclear 1 [2]
NNAL DM002189
104856
Unclear 1 [4] , [2]
Unclear DM009999 N. A. Unclear 1 [3]
NNAL-glucuronide DM006956
183009
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007570 BRN-3548355 NNAL Unclear CBR1 ... [4], [2]
MR007572 BRN-3548355 BRN-3548355 reactive intermediates Unclear CYP [2]
MR007573 BRN-3548355 Unclear Unclear CYP2A13 [3]
MR014091 BRN-3548355 Unclear Unclear UGT2B7 [3]
MR007571 NNAL NNAL-glucuronide Unclear UGT [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Homo sapiens
AK1C1_HUMAN
1.1.1.149
[2]
Aldo-keto reductase 1C2 (AKR1C2) DME0233 Homo sapiens
AK1C2_HUMAN
1.1.1.357
[2]
Aldo-keto reductase 1C4 (AKR1C4) DME0198 Homo sapiens
AK1C4_HUMAN
1.1.1.357
[2]
Cytochrome P450 2A13 (CYP2A13) DME0030 Homo sapiens
CP2AD_HUMAN
1.14.14.1
[3]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[2]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[4] , [2]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[4] , [2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
⏷ Show the Full List of 8  DME(s)
References
1 Accumulation and persistence of DNA adducts in respiratory tissue of rats following multiple administrations of the tobacco specific carcinogen 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1986 Mar;46(3):1280-4.
2 Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta. Chem Biol Interact. 2001 Jan 30;130-132(1-3):737-48.
3 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism-related enzymes gene polymorphisms, NNK metabolites levels and urothelial carcinoma
4 Toxicokinetic and Genotoxicity Study of NNK in Male Sprague Dawley Rats Following Nose-Only Inhalation Exposure, Intraperitoneal Injection, and Oral Gavage

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