Details of the Drug

General Information of Drug (ID: DM07K2I)

• Drug Name: Eprosartan
• Synonyms: 133040-01-4; Teveten; F-108566; F 108566; UNII-2KH13Z0S0Y; (E)-4-((2-Butyl-5-(2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl)-1H-imidazol-1-yl)methyl)benzoic acid; (E)-2-Butyl-1-(p-carboxybenzyl)-alpha-2-thenylimidazole-5-acrylic acid; CHEMBL813; SK-108566; 2KH13Z0S0Y; CHEBI:4814; 4-({2-butyl-5-[(1E)-2-carboxy-3-(2-thienyl)prop-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; (E)-3-[2-n-butyl-1-{(4-carboxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid; SK&F 108566; SKF-108566; Teveten (TN); Eprosartan (USAN/INN); Eprosartan [USAN:BAN:INN]; SK&F-108566; (4-carboxybenzyl)imidazole-5-acrylic acid; (E)-alpha{[2-butyl-1-[(4-carboxyphenyl)methyl]-1H-imidazole-5-yl]methylene}-2-thiopheneproprionic acid; 4-({2-butyl-5-[(1E)-2-carboxy-3-(thiophen-2-yl)prop-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid; 4-[[2-butyl-5-[(E)-3-hydroxy-3-oxo-2-(thiophen-2-ylmethyl)prop-1-enyl]imidazol-1-yl]methyl]benzoic acid; [3H]eprosartan

Indication

Disease Entry	ICD 11	Status	REF
Hypertension	BA00-BA04	Approved	[1]

• Therapeutic Class: Antihypertensive Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 424.5
  Logarithm of the Partition Coefficient (xlogp); 4.5
  Rotatable Bond Count (rotbonds); 10
  Hydrogen Bond Donor Count (hbonddonor); 2
  Hydrogen Bond Acceptor Count (hbondacc); 6
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
  Bioavailability: The bioavailability of drug is 13% []
  Clearance: The drug present in the plasma can be removed from the body at the rate of 1.9 mL/min/kg [3]
  Elimination: 30% of drug is excreted from urine in the unchanged form [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 9 hours [3]
  Metabolism: The drug is not metabolised []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 26.921 micromolar/kg/day [4]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.017% [3]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.17 L/kg [3]
  Water Solubility: The ability of drug to dissolve in water is measured as 0.08 mg/mL [2]
• Chemical Identifiers:
  Formula: C23H24N2O4S
  IUPAC Name: 4-[[2-butyl-5-[(E)-2-carboxy-3-thiophen-2-ylprop-1-enyl]imidazol-1-yl]methyl]benzoic acid
  Canonical SMILES: CCCCC1=NC=C(N1CC2=CC=C(C=C2)C(=O)O)/C=C(\\CC3=CC=CS3)/C(=O)O
  InChI: InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+
  InChIKey: OROAFUQRIXKEMV-LDADJPATSA-N
• Cross-matching ID:
  PubChem CID: 5281037
  ChEBI ID: CHEBI:4814
  CAS Number: 133040-01-4
  DrugBank ID: DB00876
  TTD ID: D0T7US
  VARIDT ID: DR01208
  ACDINA ID: D00236

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	[5]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[6]

Molecular Expression Atlas of This Drug

• The Studied Disease: Hypertension
• ICD Disease Classification: BA00-BA04

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
Peptide transporter 1 (SLC15A1)	DTP	PEPT1	4.57E-01	2.15E-02	1.72E-01

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Eprosartan

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Aliskiren	DM1BV7W	Major	Increased risk of hyperkalemia by the combination of Eprosartan and Aliskiren.	Hypertension [BA00-BA04]	[7]
Captopril	DM458UM	Major	Increased risk of hyperkalemia by the combination of Eprosartan and Captopril.	Hypertension [BA00-BA04]	[8]
Quinapril	DMR8H31	Major	Increased risk of hyperkalemia by the combination of Eprosartan and Quinapril.	Hypertension [BA00-BA04]	[8]

Coadministration of a Drug Treating the Disease Different from Eprosartan (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Insulin-glulisine	DMQI0FU	Moderate	Increased risk of hypoglycemia by the combination of Eprosartan and Insulin-glulisine.	Acute diabete complication [5A2Y]	[9]
Insulin-aspart	DMX7V28	Moderate	Increased risk of hypoglycemia by the combination of Eprosartan and Insulin-aspart.	Acute diabete complication [5A2Y]	[10]
Cariprazine	DMJYDVK	Moderate	Additive hypotensive effects by the combination of Eprosartan and Cariprazine.	Bipolar disorder [6A60]	[11]
Ardeparin	DMYRX8B	Moderate	Increased risk of hyperkalemia by the combination of Eprosartan and Ardeparin.	Coronary thrombosis [BA43]	[8]
Selegiline	DM6034S	Moderate	Additive hypotensive effects by the combination of Eprosartan and Selegiline.	Depression [6A70-6A7Z]	[12]
Isocarboxazid	DMAF1NB	Moderate	Additive hypotensive effects by the combination of Eprosartan and Isocarboxazid.	Depression [6A70-6A7Z]	[12]
OPC-34712	DMHG57U	Moderate	Additive hypotensive effects by the combination of Eprosartan and OPC-34712.	Depression [6A70-6A7Z]	[11]
Procarbazine	DMIK367	Moderate	Additive hypotensive effects by the combination of Eprosartan and Procarbazine.	Hodgkin lymphoma [2B30]	[12]
Tolvaptan	DMIWFRL	Moderate	Increased risk of hyperkalemia by the combination of Eprosartan and Tolvaptan.	Hypo-osmolality/hyponatraemia [5C72]	[13]
ITI-007	DMUQ1DO	Moderate	Additive hypotensive effects by the combination of Eprosartan and ITI-007.	Insomnia [7A00-7A0Z]	[11]
Ozanimod	DMT6AM2	Moderate	Additive hypotensive effects by the combination of Eprosartan and Ozanimod.	Multiple sclerosis [8A40]	[12]
Promethazine	DM6I5GR	Moderate	Additive hypotensive effects by the combination of Eprosartan and Promethazine.	Nausea/vomiting [MD90]	[11]
Safinamide	DM0YWJC	Moderate	Additive hypotensive effects by the combination of Eprosartan and Safinamide.	Parkinsonism [8A00]	[12]
Rasagiline	DM3WKQ4	Moderate	Additive hypotensive effects by the combination of Eprosartan and Rasagiline.	Parkinsonism [8A00]	[12]
Levomepromazine	DMIKFEL	Moderate	Additive hypotensive effects by the combination of Eprosartan and Levomepromazine.	Psychotic disorder [6A20-6A25]	[11]
Quetiapine	DM1N62C	Moderate	Additive hypotensive effects by the combination of Eprosartan and Quetiapine.	Schizophrenia [6A20]	[11]
Mesoridazine	DM2ZGAN	Moderate	Additive hypotensive effects by the combination of Eprosartan and Mesoridazine.	Schizophrenia [6A20]	[11]
Aripiprazole	DM3NUMH	Moderate	Additive hypotensive effects by the combination of Eprosartan and Aripiprazole.	Schizophrenia [6A20]	[11]
Iloperidone	DM6AUFY	Moderate	Additive hypotensive effects by the combination of Eprosartan and Iloperidone.	Schizophrenia [6A20]	[11]
Paliperidone	DM7NPJS	Moderate	Additive hypotensive effects by the combination of Eprosartan and Paliperidone.	Schizophrenia [6A20]	[11]
Molindone	DMAH70G	Moderate	Additive hypotensive effects by the combination of Eprosartan and Molindone.	Schizophrenia [6A20]	[11]
Thiothixene	DMDINC4	Moderate	Additive hypotensive effects by the combination of Eprosartan and Thiothixene.	Schizophrenia [6A20]	[11]
Amisulpride	DMSJVAM	Moderate	Additive hypotensive effects by the combination of Eprosartan and Amisulpride.	Schizophrenia [6A20]	[11]
Asenapine	DMSQZE2	Moderate	Additive hypotensive effects by the combination of Eprosartan and Asenapine.	Schizophrenia [6A20]	[11]
Insulin-detemir	DMOA4VW	Moderate	Increased risk of hypoglycemia by the combination of Eprosartan and Insulin-detemir.	Type-1/2 diabete [5A10-5A11]	[9]
Insulin degludec	DMPL395	Moderate	Increased risk of hypoglycemia by the combination of Eprosartan and Insulin degludec.	Type-1/2 diabete [5A10-5A11]	[9]
Methdilazine	DMAUHQX	Moderate	Additive hypotensive effects by the combination of Eprosartan and Methdilazine.	Vasomotor/allergic rhinitis [CA08]	[11]
Trimeprazine	DMEMV9D	Moderate	Additive hypotensive effects by the combination of Eprosartan and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[14]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Ammonia	E00007	222	Alkalizing agent
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 4000	E00654	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
Haematite red	E00236	14833	Colorant
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent
Pregelatinized starch	E00674	Not Available	Binding agent; Diluent; Disintegrant

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Eprosartan 400 mg tablet	400 mg	Oral Tablet	Oral
Eprosartan Mesylate eq 600mg base tablet	eq 600mg base	Tablet	Oral
Eprosartan 600 mg tablet	600 mg	Oral Tablet	Oral
Eprosartan Mesylate eq 400mg base tablet	eq 400mg base	Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [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: 588).
• [2] BDDCS applied to over 900 drugs
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] 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
• [5] Clinical profile of eprosartan: a different angiotensin II receptor blocker. Cardiovasc Hematol Agents Med Chem. 2008 Oct;6(4):253-7.
• [6] High-affinity interaction of sartans with H+/peptide transporters. Drug Metab Dispos. 2009 Jan;37(1):143-9.
• [7] Health Canada "Potential risks of cardiovascular and renal adverse events in patients with type 2 diabetes treated with aliskiren (RASILEZ) or aliskiren/hydrochlorothiazide (RASILEZ HCT)." .
• [8] Product Information. Diovan (valsartan). Novartis Pharmaceuticals, East Hanover, NJ.
• [9] Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
• [10] Asplund K, Wiholm BE, Lithner F "Glibenclamide-associated hypoglycaemia: a report on 57 cases." Diabetologia 24 (1983): 412-7. [PMID: 6411511]
• [11] Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
• [12] Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
• [13] Product Information. Samsca (tolvaptan). Otsuka American Pharmaceuticals Inc, Rockville, MD.
• [14] Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.