U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H23ClN6O
Molecular Weight 422.911
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOSARTAN

SMILES

CCCCC1=NC(Cl)=C(CO)N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NN=NN4

InChI

InChIKey=PSIFNNKUMBGKDQ-UHFFFAOYSA-N
InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)

HIDE SMILES / InChI

Molecular Formula C22H23ClN6O
Molecular Weight 422.911
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Losartan is a selective, competitive angiotensin II receptor type 1 (AT1) antagonist. Losartant is recommended as one of several preferred agents for the initial management of hypertension. Administration of losartan reduces the risk of stroke in patients with hypertension and left ventricular hypertrophy. Losartan is indicated for the treatment of diabetic nephropathy with an elevated serum creatinine and proteinuria in patients with type 2 diabetes and a history of hypertension.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.0 nM [Kd]
Conditions
PubMed

PubMed

TitleDatePubMed
Effects of losartan on ventricular remodeling in experimental infarction in rats.
2000 Dec
[Acute kidney failure and losartan: a recently observed event of antagonists of angiotensin II AT1 receptors].
2000 Sep
The role of ANG II and endothelin-1 in exercise-induced diastolic dysfunction in heart failure.
2001 Apr
Angiotensin II stimulates cardiac L-type Ca(2+) current by a Ca(2+)- and protein kinase C-dependent mechanism.
2001 Apr
Tonic suppression of spontaneous baroreceptor reflex by endogenous angiotensins via AT(2) subtype receptors at nucleus reticularis ventrolateralis in the rat.
2001 Apr
Atypical angiotensin receptors may mediate water intake induced by central injections of angiotensin II and of serotonin in pigeons.
2001 Apr 20
Left ventricular hypertrophy and angiotensin II antagonists.
2001 Feb
Angiotensin II increases vesicular trafficking in brain neurons.
2001 Feb
Expression of cell cycle proteins in blood vessels of angiotensin II-infused rats: role of AT(1) receptors.
2001 Feb
Angiotensin II induces migration and Pyk2/paxillin phosphorylation of human monocytes.
2001 Feb
Role of endothelin and isoprostanes in slow pressor responses to angiotensin II.
2001 Feb
Angiotensin II relaxes microvessels via the AT(2) receptor and Ca(2+)-activated K(+) (BK(Ca)) channels.
2001 Feb
Mortality after coronary artery occlusion in different models of cardiac hypertrophy in rats.
2001 Feb
Role of angiotensin II in altered baroreflex function of conscious rabbits during late pregnancy.
2001 Feb
Modulation of alveolar-capillary sodium handling as a mechanism of protection of gas transfer by enalapril, and not by losartan, in chronic heart failure.
2001 Feb
Combined therapy with an angiotensin II receptor blocker and an angiotensin-converting enzyme inhibitor in heart failure.
2001 Feb
DNA damage of lymphocytes in experimental chronic renal failure: beneficial effects of losartan.
2001 Feb
Different effects of angiotensin II and catecholamine on renal cell apoptosis and proliferation in rats.
2001 Feb
A two-state receptor model for the interaction between angiotensin II type 1 receptors and non-peptide antagonists.
2001 Feb 1
Angiotensin II type 1 receptor blockers.
2001 Feb 13
Comparative effect of ace inhibition and angiotensin II type 1 receptor antagonism on bioavailability of nitric oxide in patients with coronary artery disease: role of superoxide dismutase.
2001 Feb 13
Angiotensin II blockade reverses myocardial fibrosis in a transgenic mouse model of human hypertrophic cardiomyopathy.
2001 Feb 13
Acute administration of nicotine impairs the hypotensive responses to bradykinin in rats.
2001 Feb 16
Losartan and fetal toxic effects.
2001 Feb 3
[Well tolerated sartans. More normal blood pressure finally?].
2001 Feb 8
[Treating not only blood pressure. Advantages for microcirculation].
2001 Feb 8
Acute effects of E-3174, a human active metabolite of losartan, on the cardiovascular system in tachycardia-induced canine heart failure.
2001 Jan
Role of the central nervous system in the development of hypertension produced by chronic nitric oxide blockade in rats.
2001 Jan
Contribution of angiotensin II, endothelin 1 and the endothelium to the slow inotropic response to stretch in ferret papillary muscle.
2001 Jan
Functional expression of angiotensin II receptors in type-I cells of the rat carotid body.
2001 Jan
Losartan versus enalapril on cerebral edema and proteinuria in stroke-prone hypertensive rats.
2001 Jan
Relation of left ventricular geometry and function to systemic hemodynamics in hypertension: the LIFE Study. Losartan Intervention For Endpoint Reduction in Hypertension Study.
2001 Jan
New competition in the realm of renin-angiotensin axis inhibition; the angiotensin II receptor antagonists in congestive heart failure.
2001 Jan
Renal and vascular injury induced by exogenous angiotensin II is AT1 receptor-dependent.
2001 Jan
Angiotensin II inhibits rat arterial KATP channels by inhibiting steady-state protein kinase A activity and activating protein kinase Ce.
2001 Jan 15
Left ventricular hypertrophy with exercise and ACE gene insertion/deletion polymorphism: a randomized controlled trial with losartan.
2001 Jan 16
Central interactions between angiotensin II and PGD(2) in the regulation of vasopressin and oxytocin secretion in dehydrated rats.
2001 Jan 19
Mannitol-induced toxicity in a diabetic patient receiving losartan.
2001 Mar
Restoration of normal ventricular electrophysiology in renovascular hypertensive rabbits after treatment with losartan.
2001 Mar
Effect of angiotensin II on venodilator response to nitroglycerin.
2001 Mar
MK-954 (losartan potassium) exerts endothelial protective effects against reperfusion injury: evidence of an e-NOS mRNA overexpression after global ischemia.
2001 Mar
Identification, distribution, and expression of angiotensin II receptors in the normal human prostate and benign prostatic hyperplasia.
2001 Mar
AT(1) receptor blockers prevent sympathetic hyperactivity and hypertension by chronic ouabain and hypertonic saline.
2001 Mar
Effect of oral contraceptives on the renin angiotensin system and renal function.
2001 Mar
Cerebral Na concentration, Na appetite and thirst of sheep: influence of somatostatin and losartan.
2001 Mar
Glucocorticoid modulation of cardiovascular and autonomic function in preterm lambs: role of ANG II.
2001 Mar
Are angiotensin II receptor blockers more efficacious than placebo in heart failure? Implications of ELITE-2. Evaluation of Losartan In The Elderly.
2001 Mar 1
Effect of losartan on degree of mitral regurgitation quantified by echocardiography.
2001 Mar 1
The role of angiotensin receptor blockers in the management of chronic heart failure.
2001 Mar 12
Losartan reduces hematocrit in patients with chronic obstructive pulmonary disease and secondary erythrocytosis.
2001 Mar 6
Patents

Sample Use Guides

In Vivo Use Guide
For treatment of hypertension, Joint National Committee (JNC) 8 expert panel recommends initial dosage of 50 mg daily and target dosage of 100 mg daily (given in 1 dose or 2 divided doses) based on dosages used in randomized controlled studies.
Route of Administration: Oral
In Vitro Use Guide
From 30 to 40 min after confirmation of endothelium removal, the test compounds were incubated at a concentration of 0.1 uM. After an incubation period of 20 or 60 min, aortic preparations were treated with AII, using 3-fold increasing concentrations from 0.1 nM to 1 uM. Kb for binding with angiotensin receptor was 4 nM with 20 min incubation, and 9 nM with 60 min incubation.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:49:02 UTC 2019
Edited
by admin
on Mon Oct 21 20:49:02 UTC 2019
Record UNII
JMS50MPO89
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOSARTAN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ALLISARTAN
Brand Name English
LOSARTAN [MI]
Common Name English
LOZAP
Brand Name English
1H-IMIDAZOLE-5-METHANOL, 2-BUTYL-4-CHLORO-1-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-
Systematic Name English
ANGIZAAR
Brand Name English
LOSARTAN [INN]
Common Name English
2-BUTYL-4-CHLORO-1-(P-(O-1H-TETRAZOL-5-YLPHENYL)BENZYL)IMIDAZOLE-5-METHANOL
Common Name English
HGP1405
Code English
HGP-1405
Code English
DUP-89
Common Name English
LOSARTIC
Brand Name English
LOSARTAN [VANDF]
Common Name English
LOSARTAN [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000070
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
FDA ORPHAN DRUG 357211
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
LIVERTOX 573
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-ATC C09DA01
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-VATC QC09DA01
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
NDF-RT N0000175561
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-VATC QC09DB06
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-ATC C09CA01
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
EU-Orphan Drug EU/3/19/2142
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-VATC QC09CA01
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
WHO-ATC C09DB06
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
Code System Code Type Description
RXCUI
52175
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY RxNorm
HSDB
114798-26-4
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
CAS
114798-26-4
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
WIKIPEDIA
LOSARTAN
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
DRUG BANK
DB00678
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
IUPHAR
590
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
ChEMBL
CHEMBL191
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
EVMPD
SUB32953
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
ALTERNATIVE
EVMPD
SUB08593MIG
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
NCI_THESAURUS
C66869
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
EPA CompTox
114798-26-4
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
INN
6913
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
LactMed
114798-26-4
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
MERCK INDEX
M6911
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY Merck Index
MESH
D019808
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
PUBCHEM
3961
Created by admin on Mon Oct 21 20:49:02 UTC 2019 , Edited by admin on Mon Oct 21 20:49:02 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
Liver concentrations were estimated to be about 50 micromolar. this indicates that Losartan might inhibit the AA metabolism in the liver.
IC50
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
DERIVATIVE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
The present study characterizes the active losartan metabolite EXP3179 as a partial PPAR-gamma agonist.
Related Record Type Details
IMPURITY -> PARENT
NMBA is a priority toxic pollutant. FDA is temporarily not objecting to Losartan with NMBA below 9.82 ppm remaining on the market.
IMPURITY -> PARENT
Acceptable intake level of NDEA in ppm.
IMPURITY GENOTOXIC->PARENT
NDMA is an organic chemical that is part of a family of potent carcinogens.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC