Ramiprilat Chemical Properties

Melting point:

139-141°C

Boiling point:

632.2±55.0 °C(Predicted)

Density 

1.273±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.20±0.10(Predicted)

color 

White to Pale Yellow

Stability:

Hygroscopic

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-37/39

Ramiprilat Usage And Synthesis

Description

Ramiprilat is the active metabolite of ramipril and functions as an angiotensin-converting enzyme inhibitor (pK_i = 9.08 in human heart) to suppress the conversion of angiotensin I to angiotensin II and the degradation of bradykinin, thereby preventing vasoconstriction. Furthermore, ramiprilat is reported to interfere with the targeting of B₂ kinin receptors to endothelial cell membranes further preventing bradykinin signaling. In addition to its cardioprotective effects in both animal models and clinical studies, ramiprilat has been reported to inhibit matrix metalloproteinase-3 and -9 activity in isolated Crohn’s disease fistulas.

Chemical Properties

White to Off-White Solid

Uses

A metabolite of Ramipril (R111000).

Uses

Ramiprilat (Ramipril EP Impurity E) is a metabolite of Ramipril (R111000), and acts as an ACE inhibitor (1). Reduces the need for dialysis among patients previously on angiotensin-converting-enzyme inhibitors (2). Ramipril is used in stroke prevention. (3)

Definition

ChEBI: A dipeptide that is the active metabolite of ramipril. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.

in vitro

pretreatment with ramiprilat could significantly attenuate the recovery of b2 kinin receptors in while increasing that from membranes lacking caveolin, and such effect was not because of the inhibition of bradykinin degradation. ramiprilat could also decrease [3h]bradykinin binding to cr membranes. in addition, ramiprilat treatment led to reactivation of the b2 receptor in bradykinin-stimulated cells [1].

in vivo

in previous animal study, when compared with the control rats, diabetic rats showed decreased creatinine clearance rate, increased urinary protein excretion and blood pressure, as well as development of tubulointerstitial fibrosis, glomerulosclerosis, and inflammatory cell infiltration. furthermore, the blocking angiotensin ii with ramipril (the prodrug of ramiprilat) was able to significantly improve all of these parameters [2].

References

[1] t. benzing, i. fleming, a. blaukat, et al. angiotensin-converting enzyme inhibitor ramiprilat interferes with the sequestration of the b2 kinin receptor within the plasma membrane of native endothelial cells. circulation 99(15), 2034-2040 (1999).
[2] li c, yang cw, park cw, ahn hj, kim wy, yoon kh, suh sh, lim sw, cha jh, kim ys, kim j, chang ys, bang bk. long-term treatment with ramipril attenuates renal osteopontin expression in diabetic rats. kidney int. 2003 feb;63(2):454-63.
[3] warner gt, perry cm. ramipril: a review of its use in the prevention of cardiovascular outcomes. drugs. 2002;62(9):1381-405.

Ramiprilat(87269-97-4)Related Product Information

• Pyrrolidine
• Polyvinylpyrrolidone
• N-Methyl-2-pyrrolidone
• N-Vinyl-2-pyrrolidone
• Ramipril Diketopiperazine
• Ramipril Related Compound A (30 mg) ((2S,3aS,6aS)-1-[(S)2-[[(S)-1-(methoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid)
• RAMIPRIL RELATED COMPOUND B (20 MG) (RAMIPRIL ISOPROPYLESTER)
• Ramiprilat Diketopiperazine
• Carboxy styrene-butadiene latex
• Ramipril
• RAMIPRIL-D3
• RAMIPRILAT-D5 ACYL-B-D-GLUCURONIDE
• RAMIPRIL-D5 ACYL-B-D-GLUCURONIDE
• RAMIPRILAT ACYL-B-D-GLUCURONIDE
• RAMIPRILAT-D3
• (1R) RAMIPRILAT-D5
• Ramiprilat Diketopiperazine-d5
• RAMIPRILAT-D5