| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H21ClN6O2 |
| Molecular Weight | 436.894 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1=NC(Cl)=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NN=NN4)C(O)=O
InChI
InChIKey=ZEUXAIYYDDCIRX-UHFFFAOYSA-N
InChI=1S/C22H21ClN6O2/c1-2-3-8-18-24-20(23)19(22(30)31)29(18)13-14-9-11-15(12-10-14)16-6-4-5-7-17(16)21-25-27-28-26-21/h4-7,9-12H,2-3,8,13H2,1H3,(H,30,31)(H,25,26,27,28)
| Molecular Formula | C22H21ClN6O2 |
| Molecular Weight | 436.894 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
E-3174 is an active carboxylic acid metabolite of losartan and is an antagonist of the angiotensin II receptor, type 1 (AT1). Losartan was the first orally active AT1 receptor antagonist available on the market, and it is the antagonist with which the greatest clinical experience has been accumulated. EXP3174 is 10 to 20 times more potent than losartan and has a longer duration of action than losartan. However, the oral bioavailability of EXP 3174 is very low. Thus, the drug on the market is losartan, but most of the losartan’s antihypertensive effect is due to EXP 3174.
Approval Year
Sample Use Guides
in dogs: EXP3174 (0.1 mg/kg + 0.01 mg/kg/min) or vehicle were infused in anesthetized dogs with recent (8.1 +/- 0.4 days) anterior myocardial infarction.
Route of Administration:
Intravenous
The response to angiotensin II, measured as the mean force development in response to increasing concentrations of angiotensin II, was recorded in the absence and presence of candesartan, 0.003-10 nmol/l, irbesartan, 1-100 nmol/l, losartan, 1-100 nmol/l, and EXP-3174, 0.01-10 nmol/l, for a period of 90 min. In contrast, irbesartan, losartan, and EXP-3174 all caused a parallel shift of the concentration-response curve. It appeared unlikely that losartan exerted any significant inhibitory effect at therapeutic plasma levels, and the main AT 1 - blocking effect observed after oral losartan is probably exerted by EXP-3174. It was concluded that AT 1 -receptor blockers differ in their ability to inhibit angiotensin II-mediated vascular contraction and that the antagonistic characteristics are similar in vessel preparations of different origins and with different degrees of AT 1 -receptor reserve.
