Details of the Drug

General Information of Drug (ID: DMWBHRY)

Drug Name
Olmesartan medoxomil
Synonyms
Benevas; Benicar; Olmetec; Olvance; Forest Brand of Olmesartan Medoxomil; Olmesartan medoximil; Sankyo Brand of Olmesartan Medoxomil; Cs 866; Benicar (TN); Berlin-Chemie Brand of Olmesartan Medoxomil; CS-866; CS-866DM; CS-866RN; DE-092; KS-1182; Olmetec (TN); Benicar, Olmetec,Olmesartan; Olmesartan medoxomil (JAN/USAN); (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate; (5-methyl-2-oxo-1,3-dioxolen-4-yl)methoxy-4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-(2-(tetrazol-5-yl)phenyl)phenyl)methylimidazol-5-carboxylate; 1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl) (1,1'-biphenyl)-4-yl)methyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl ester; 1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester; 1H-imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-,(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester
Indication
Disease Entry ICD 11 Status REF
High blood pressure BA00 Approved [1]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 558.6
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Elimination
0% of drug is excreted from urine in the unchanged form [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.023 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 2 mg/mL [2]
Chemical Identifiers
Formula
C29H30N6O6
IUPAC Name
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate
Canonical SMILES
CCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)C(=O)OCC5=C(OC(=O)O5)C)C(C)(C)O
InChI
InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)
InChIKey
UQGKUQLKSCSZGY-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
130881
ChEBI ID
CHEBI:31932
CAS Number
144689-63-4
TTD ID
D07UBG
VARIDT ID
DR00347
INTEDE ID
DR2455
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Angiotensin II receptor type-1 (AGTR1) TT8DBY3 AGTR1_HUMAN Antagonist [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [5]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [5]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [5]
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [7]
Organic anion transporting polypeptide 1B3 (SLCO1B3) DT9C1TS SO1B3_HUMAN Substrate [5]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [5]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [9]
Tight junction protein ZO-1 (TJP1) OTBDCUPK ZO1_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease High blood pressure
ICD Disease Classification BA00
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Angiotensin II receptor type-1 (AGTR1) DTT AGTR1 8.95E-01 1.34E-02 0.07
Organic anion transporter 3 (SLC22A8) DTP OAT3 5.19E-01 -8.88E-03 -2.08E-02
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
Organic anion transporter 1 (SLC22A6) DTP OAT1 7.18E-01 -4.56E-02 -1.42E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 9.45E-01 -5.34E-02 -9.01E-02
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 7.16E-01 -1.28E-02 -6.06E-02
Multidrug resistance-associated protein 4 (ABCC4) DTP MRP4 3.73E-06 2.82E-01 7.01E-01
Organic anion transporting polypeptide 1B3 (SLCO1B3) DTP OATP1B3 9.69E-01 1.16E-03 3.56E-03
Organic anion transporting polypeptide 1B1 (SLCO1B1) DTP OATP1B1 8.15E-01 6.20E-03 5.61E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Effect of angiotensin receptor blockade on endothelial function: focus on olmesartan medoxomil. Vasc Health Risk Manag. 2009;5(1):301-14.
2 BDDCS applied to over 900 drugs
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 Mechanism of diastolic stiffening of the failing myocardium and its prevention by angiotensin receptor and calcium channel blockers. J Cardiovasc Pharmacol. 2009 Jul;54(1):47-56.
5 Multiple human isoforms of drug transporters contribute to the hepatic and renal transport of olmesartan, a selective antagonist of the angiotensin II AT1-receptor. Drug Metab Dispos. 2007 Dec;35(12):2166-76.
6 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (dg:DG01913)
7 OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9.
8 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (dg:DG01665)
9 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.
10 Immunopathogenesis of olmesartan-associated enteropathy. Aliment Pharmacol Ther. 2015 Dec;42(11-12):1303-14. doi: 10.1111/apt.13413. Epub 2015 Oct 1.