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

General Information of Drug (ID: DR0986)
Drug Name
Lovastatin
Prodrug Info Lovastatin is the prodrug of 3''-Hydroxylovastatin
Synonyms
Lestatin; Lipdip; Lipivas; Lipofren; Lovalip; Lovalord; Lovastatina; Lovastatina [Spanish]; Lovastatine; Lovastatine [French]; Lovastatinum; Lovastatinum [Latin]; Lovasterol; Lovastin; Lozutin; MK 803; MK-803; MSD 803; Mevacor; Mevinacor; Altocor; Altoprev; Artein; Belvas; Cholestra; Closterol; Colevix; Hipolip; Hipovastin; Mevlor; Monacolin K; Nergadan; Paschol; Rodatin; Rovacor; Sivlor; Taucor; Tecnolip; Teroltrat; lovastatin; mevinolin; 6 alpha-Methylcompactin; 6-alpha-Methylcompactin; 6alpha-Methylcompactin; 75330-75-5; UNII-9LHU78OQFD
Indication Hypertriglyceridaemia [ICD11: 5C80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 404.5 Topological Polar Surface Area 72.8
Heavy Atom Count 29 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
53232
PubChem SID
9285 ; 496591 ; 623233 ; 855905 ; 7734777 ; 7847425 ; 7885508 ; 7979813 ; 8150103 ; 8182985 ; 10321765 ; 10852021 ; 11336207 ; 11361446 ; 11372945 ; 11462418 ; 11466544 ; 11467664 ; 11486128 ; 11491688 ; 11528634 ; 12012664 ; 12146073 ; 14806053 ; 14879393 ; 17389841 ; 22395934 ; 24896706 ; 25622285 ; 26612569 ; 26680612 ; 26697338 ; 26751557 ; 26759065 ; 34717349 ; 46391668 ; 46508223 ; 47515402 ; 47589078 ; 47662390 ; 47662391 ; 47662392 ; 47736583 ; 47959858 ; 47959859 ; 48035229 ; 48185079 ; 48334593 ; 48413948 ; 48416187
ChEBI ID
ChEBI:40303
CAS Number
75330-75-5
TTD Drug ID
D06WTZ
Formula
C24H36O5
Canonical SMILES
CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
InChI
1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey
PCZOHLXUXFIOCF-BXMDZJJMSA-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
beta-hydroxy acid of lovastatin DM006440
386477161
Hydrolysis - Hydrolysis 1 [4] , [5]
3''-Hydroxylovastatin DM006442
13116690
Unclear 2 [4]
6'-beta-Hydroxylovastatin DM006441
68178378
Oxidation - Hydrolyzationn 2 [2]
6'-Exomethylene lovastatin DM006443
68178377
Reduction - Reduction 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006921 Lovastatin beta-hydroxy acid of lovastatin Hydrolysis - Hydrolysis PON3 [4], [5]
MR006922 beta-hydroxy acid of lovastatin 6'-beta-Hydroxylovastatin Oxidation - Hydrolyzationn CYP3A4 ... [2]
MR006923 beta-hydroxy acid of lovastatin 3''-Hydroxylovastatin Unclear CES [4]
MR006924 beta-hydroxy acid of lovastatin 6'-Exomethylene lovastatin Reduction - Reduction Unclear [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[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
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Serum paraoxonase/lactonase 3 (PON3) DME0170 Homo sapiens
PON3_HUMAN
3.1.1.2
[4]
Serum paraoxonase/lactonase 3 (PON3) DME0170 Homo sapiens
PON3_HUMAN
3.1.1.2
[4] , [5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1260 Clostridium perfringens Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1386 Bifidobacterium adolescentis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1399 Enterocloster asparagiformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1424 Eubacterium limosum Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1428 Fusobacterium varium Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [6]
⏷ Show the Full List of 36  DME(s)
References
1 Simvastatin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacogenomics of statins: understanding susceptibility to adverse effects. Pharmgenomics Pers Med. 2016 Oct 3;9:97-106.
3 Metabolic interactions with statins. Tidsskr Nor Laegeforen. 2001 Jan 20;121(2):189-93.
4 Paraoxonases-1, -2 and -3: what are their functions? Chem Biol Interact. 2016 Nov 25;259(Pt B):51-62.
5 Human paraoxonases (PON1, PON2, and PON3) are lactonases with overlapping and distinct substrate specificities
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 In vitro susceptibility of cultured human methanogens to lovastatin. Int J Antimicrob Agents. 2017 Feb;49(2):176-182.
8 Comparison of cytochrome P-450-dependent metabolism and drug interactions of the 3-hydroxy-3-methylglutaryl-CoA reductase inhibitors lovastatin and pravastatin in the liver. Drug Metab Dispos. 1999 Feb;27(2):173-9.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.