Drug Details

General Information of the Drug (ID: DR5601)
Name
Lovastatin
Synonyms
lovastatin; 75330-75-5; mevinolin; Mevacor; MK-803; Altoprev; Lovalord; Nergadan; Artein; 6alpha-Methylcompactin; Lovalip; Monacolin K; Lovastatine [French]; Lovastatinum [Latin]; Lovastatina [Spanish]; 6-alpha-Methylcompactin; Lovastatine; Mevinacor; Altocor; Hipovastin; Lovasterol; Cholestra; Closterol; Colevix; Hipolip; Lestatin; Lipivas; Lipofren; Lovastin; Lozutin; Paschol; Rodatin; Rovacor; Tecnolip; Teroltrat; Belvas; Lipdip; Mevlor; Sivlor; Taucor; UNII-9LHU78OQFD; MLS000069585; MSD 803; MFCD00072164; 9LHU78OQFD; MK 803; 2beta,6alpha-Dimethyl-8alpha-(2-methyl-1-oxobutoxy)-mevinic acid lactone; SMR000058779; (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate; (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate; CHEBI:40303; L-154803; Lovastatin, 98%; Lovastatin (Mevacor); (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate; HSDB 6534; NCGC00023509-03; Lovastatina; Lovastatinum; C24H36O5; DSSTox_CID_784; butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-; DSSTox_RID_75788; DSSTox_GSID_20784; Liposcler; 6 alpha-Methylcompactin; Rextat; Monakolin K; (1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (S)-2-methylbutanoate; (S)-(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate; Mevacor (TN); CHEMBL503; Lovastatin & Primycin; Lovastatin (USP/INN); SR-05000001880; (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-2-Methylbutanoic acid 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester; (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one; [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate; 1,2,6,7,8,8a-Hexahydro-beta,delta-dihydroxy-2,6-dimethyl-8-(2-methyl-1-oxobutyoxy)-1-naphthaleneheptanoic acid delta-lactone; BRN 3631989; Mevinolin from Aspergillus sp.; CCRIS 8092; 1cqp; Lovastatin,(S); ML-530B; Lovastatin [USAN:USP:INN:BAN]; (+)-mevinolin; (S)-((1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate; [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-tetrahydropyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate; Prestwick_819; CAS-75330-75-5; Lovastatin [USAN]; Mevinolin (lovastatin); Opera_ID_1578; Prestwick0_000516; Prestwick1_000516; Prestwick2_000516; Prestwick3_000516; Spectrum3_001873; Spectrum5_001294; Lovastatin (MK-803); EC 616-212-7; SCHEMBL3136; US9115116, lovastatin; BIDD:PXR0113; BSPBio_000471; BSPBio_001265; BSPBio_003346; Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-; cid_53232; MLS001055358; MLS006011867; US9353061, Lovastatina; ARONIS24208; BIDD:GT0749; DivK1c_001032; SPECTRUM1503977; SPBio_002392; BPBio1_000519; GTPL2739; MEGxm0_000398; DTXSID5020784; SCHEMBL14227102; ACon0_000534; ACon1_000390; BDBM34168; HMS503O05; KBio1_001032; KBio3_002848; AOB5269; C10AA02; Simvastatin impurity, lovastatin-; NINDS_001032; HMS1569H13; HMS1792O07; HMS1923O13; HMS1990O07; HMS2089M06; HMS2093O03; HMS2096H13; HMS2236F07; HMS3039N16; HMS3259F10; HMS3268C03; HMS3403O07; HMS3412H19; HMS3676H19; HMS3713H13; HMS3884B03; Pharmakon1600-01503977; (S)-((1S,3R,7S,8S,8AR)-8-(2-((2R,4R)-4-HYDROXY-6-OXO-TETRAHYDRO-2H-PYRAN-2-YL)ETHYL)-3,7-DIMETHYL-1,2,3,7,8,8A-HEXAHYDRONAPHTHALEN-1-YL) 2-METHYLBUTANOATE; 2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid; ACT02620; ALBB-027272; Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-; HY-N0504; MK-803; LOVALIP; MEVACOR; ZINC3812841; Tox21_110888; Tox21_201475; Tox21_300268; ANW-41686; BBL024473; CCG-39627; NSC633781; NSC758662; NSC779704; s2061; SBB080686; STK801953; AKOS005267139; Tox21_110888_1; CS-1990; DB00227; EBD2126857; KS-1082; MCULE-4740518260; MCULE-7087866108; Mevinolin from Aspergillus sp., powder; NC00713; NSC 758662; NSC-633781; NSC-758662; NSC-779704; IDI1_001032; NCGC00023509-04; NCGC00023509-05; NCGC00023509-06; NCGC00023509-07; NCGC00023509-08; NCGC00023509-09; NCGC00023509-10; NCGC00023509-11; NCGC00023509-13; NCGC00023509-14; NCGC00023509-16; NCGC00254157-01; NCGC00259026-01; 74133-25-8; AC-13961; Butanoic acid, 2-methyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-; G226; SMR000673570; SBI-0051881.P002; AB0108514; L0214; N1632; EN300-52515; C07074; D00359; J10136; S-7779; 28048-EP2269989A1; 28048-EP2270011A1; 28048-EP2272825A2; 28048-EP2272841A1; 28048-EP2277507A1; 28048-EP2277865A1; 28048-EP2280006A1; 28048-EP2281813A1; 28048-EP2284158A1; 28048-EP2286795A1; 28048-EP2287165A2; 28048-EP2287166A2; 28048-EP2289892A1; 28048-EP2292620A2; 28048-EP2295406A1; 28048-EP2295409A1; 28048-EP2298742A1; 28048-EP2298745A1; 28048-EP2298772A1; 28048-EP2298776A1; 28048-EP2298779A1; 28048-EP2301923A1; 28048-EP2301931A1; 28048-EP2301936A1; 28048-EP2305648A1; 28048-EP2308839A1; 28048-EP2311808A1; 28048-EP2311829A1; 28048-EP2314588A1; 96638-EP2287163A1; 96638-EP2305678A1; AB00052400-17; AB00052400_18; AB00052400_19; Mevinolin from Aspergillus sp., >=98% (HPLC); 117141-EP2272825A2; 117141-EP2298776A1; 330L755; A838030; Q417740; SR-01000000123; SR-01000000123-3; SR-05000001880-1; SR-05000001880-2; BRD-K09416995-001-06-8; BRD-K09416995-001-21-7; Z1258578375; (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-8-(2-((4R,6R)-4-hydroxy-2-oxo-2H-pyran-6-yl)ethyl)-3,7-dimethylnaphtyl(S)-2-methylbutyrat; (2S)-(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl-2-methyl butanoate; (2S)-2-Methylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester; (2S)-2-methylbutanoic acid [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-2-oxanyl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] ester; (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-8-[2-((3R,5R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl ester; [(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-[2-[(2R,4R)-4-oxidanyl-6-oxidanylidene-oxan-2-yl]ethyl]-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate; 1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate; 8-[2-((2R,4R)-4-hydroxy-6-oxo(2H-3,4,5-trihydropyran-2-yl))ethyl](1S,7S,8S,3R, 8aR)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthyl (2S)-2-methylbutanoate; 8-[2-(4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthale; Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-- oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R*),3alpha,7beta,8beta(2S*,4S*),8abeta))-
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Molecular Type
Small molecule
Disease Hypertriglyceridaemia [ICD-11: 5C80] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 3.013 mcg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 3.36 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Elimination
Following an oral dose of 14C-labeled lovastatin to man, 10% of the dose was excreted in urine and 83% in feces
Half-life
The concentration or amount of drug in body reduced by one-half in 13.37 hours
Metabolism
The drug is metabolized via serum paraoxonase
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.28759 micromolar/kg/day
Water Solubility
The ability of drug to dissolve in water is measured as 0.0004 mg/mL
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Formula
C24H36O5
PubChem CID
53232
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
CAS Number
CAS 75330-75-5
ChEBI ID
CHEBI:40303
TTD Drug ID
D06WTZ
DrugBank ID
DB00227
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Gamma tocotrienol      Bixa orellana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Neoplastic mouse +SA mammary epithelial cells Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Treatment with subeffective doses of Lovastatin or gamma-tocotrienol alone had no effect, whereas combined treatment of these compounds resulted in a relatively large decrease in intracellular levels of phosphorylated (activated) MAPK, JNK, p38, and Akt.
          Metformin      Galega officinalis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 Use of statin and metformin provides a synergistic improvement in gastrointestinal malignancies outcomes.
Target and Pathway
Target(s) HMG-CoA reductase (HMGCR)  Molecule Info  [4]
BioCyc Superpathway of geranylgeranyldiphosphate biosynthesis I (via mevalonate) Click to Show/Hide
2 Superpathway of cholesterol biosynthesis
3 Mevalonate pathway
KEGG Pathway Terpenoid backbone biosynthesis Click to Show/Hide
2 Metabolic pathways
3 Biosynthesis of antibiotics
4 AMPK signaling pathway
5 Bile secretion
NetPath Pathway IL5 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
3 TSH Signaling Pathway
Panther Pathway Cholesterol biosynthesis Click to Show/Hide
Pathwhiz Pathway Steroid Biosynthesis Click to Show/Hide
WikiPathways Statin Pathway Click to Show/Hide
2 Regulation of Lipid Metabolism by Peroxisome proliferator-activated receptor alpha (PPARalpha)
3 Activation of Gene Expression by SREBP (SREBF)
4 SREBF and miR33 in cholesterol and lipid homeostasis
5 Integrated Breast Cancer Pathway
6 SREBP signalling
7 Cholesterol Biosynthesis
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2739).
Reference 2 Synergistic antiproliferative effects of gamma-tocotrienol and statin treatment on mammary tumor cells. Lipids. 2007 Dec;42(12):1113-23.
Reference 3 Synergistic Benefit of Statin and Metformin in Gastrointestinal Malignancies. J Pharm Pract. 2017 Apr;30(2):185-194.
Reference 4 Microarray and biochemical analysis of lovastatin-induced apoptosis of squamous cell carcinomas. Neoplasia. 2002 Jul-Aug;4(4):337-46.
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