Perindopril Related Compound 7
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Perindopril Related Compound 7

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An impurity of Perindopril which is a long-acting ACE inhibitor.

Category
Cyclic Amino Acids
Catalog number
BAT-008072
CAS number
80875-98-5
Molecular Formula
C9H15NO2
Molecular Weight
169.23
Perindopril Related Compound 7
IUPAC Name
(2S,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylic acid
Synonyms
L-(2S,3aS,7aS)-Octahydroindole-2-carboxylic Acid; [2S-(2α,3aβ,7aβ)]-Octahydro-1H-indole-2-carboxylic Acid; (2S,3aS,7aS)-2-Carboxyoctahydroindole; (2S,3aS,7aS)-Perhydroindole-2-carboxylic Acid; USP Perindopril Related Compound A
Appearance
White off-white solid
Purity
≥ 98% (HPLC)
Density
1.135 g/cm3
Melting Point
259-260 °C
Boiling Point
318.6ºC at 760 mmHg
Storage
Store at 2-8 °C
Solubility
Soluble in Methanol, Water
InChI
InChI=1S/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7-,8-/m0/s1
InChI Key
CQYBNXGHMBNGCG-FXQIFTODSA-N
Canonical SMILES
C1CCC2C(C1)CC(N2)C(=O)O
1.Antihypertensive properties of a new long-acting angiotensin converting enzyme inhibitor in renin-dependent and independent hypertensive models.
Nagata S1, Takeyama K, Fukuya F, Nagai R, Hosoki K, Nishimura K, Deguchi T, Karasawa T. Arzneimittelforschung. 1995 Aug;45(8):853-8.
The antihypertensive properties of a new long-acting, angiotensin-I-converting enzyme (ACE) inhibiting agent, (2S,3aS,7aS)-1-(N2-nicotinoyl-L-lysyl-gamma-D-glutamyl) octahydro-1H-indole-2-carboxylic acid (CAS 116662-73-8, DU-1777), were investigated orally in various experimental models of hypertension in comparison to a standard ACE inhibitor, lisinopril. The hypotensive potency of DU-1777 was not as marked as that of lisinopril in renin-dependent hypertensive models, i.e., two-kidney one-clip renal hypertensive rats (2K-1C RHR) (ED-20mmHg: 3.1 versus 1.0 mg/kg) or two-kidney two-clip renal hypertensive dogs (2K-2C RHD) (ED-20 mmHg: 2.5 versus 1.0 mg/kg), though the actions of the two drugs were both long-lasting and dose-related. When spontaneously hypertensive rats (SHR) were used, however, DU-1777 was as active as lisinopril (ED-20 mmHg: 17.9 versus 13.6 mg/kg). The most distinguishing results with DU-1777 were its hypotensive effects in renin-independent hypertensive models.
2.Possible involvement of ATP-dependent K-channel related mechanisms in the antihypertensive and cough suppressant effects of the novel ACE inhibitor (2S, 3aS, 7aS)-1-(N2-nicotinoyl-L-lysyl-gamma-D-glutamyl)octahydro-1H- indole-2-carboxylic acid.
Nagata S1, Takeyama K, Hosoki K, Karasawa T. Arzneimittelforschung. 1997 Jun;47(6):726-30.
The antihypertensive and cough suppressant mechanisms of DU-1777 ((2S,3aS,7aS)-1-(N2-nicotinoyl-L-lsyl-gamma-D-glutamyl )octahydro-1H-indole-2 -carboxylic acid, CAS 116662-73-8), a new long-acting angiotensin-1-converting enzyme (ACE) inhibitor, were investigated in vivo and in vitro. The antihypertensive effects of DU-1777 at 10 mg/kg p.o. and cromakalim at 0.3 mg/kg p.o. were partially (about 60%) or fully antagonized by glibenclamide at 10 mg/kg i.v. in 2-kidney, 1-clip renal hypertensive rats (2K-1C RHR). The antihypertensive effects of a Ca blocker (nifedipine) and other ACE inhibitors (captopril, alacepril, enalapril, lisinopril, imidapril and quanapril) were not antagonized by glibenclamide. In deoxycorticosterone acetate-salt hypertensive rats (DOCA-HR), the antihypertensive effects of DU-1777 at 3-30 mg/kg p.o. were fully antagonized by glibenclamide. However, in vitro, DU-1777 (10(-6)-10(-3) mol/l) did not affect aortic ring contractions induced by high K (30 mmol/l).
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