An ACE inhibitor
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Pro-drug Form(s)
15342Phortress 15558Ramipril
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Ramiprilat

Item No. 15557

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]-1-oxopropyl]octahydro-cyclopenta[b]pyrrole-2-carboxylic acid
CAS Number
87269-97-4
Synonyms
  • Ramipril Diacid
Molecular Formula
C21H28N2O5
Formula Weight
388.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O=C([C@H](C)N[C@H](C(O)=O)CCC1=CC=CC=C1)N2[C@]3([H])[C@](CCC3)([H])C[C@H]2C(O)=O
InChi Code
InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16-,17-,18-/m0/s1
InChi Key
KEDYTOTWMPBSLG-HILJTLORSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $69

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    5 mg

    $297

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    10 mg

    $525

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    Product Description

    Ramiprilat is the active metabolite of ramipril (Item No. 15558) and functions as an angiotensin-converting enzyme inhibitor (pKi = 9.08 in human heart) to suppress the conversion of angiotensin I to angiotensin II and the degradation of bradykinin, thereby preventing vasoconstriction.1,2 Furthermore, ramiprilat is reported to interfere with the targeting of B2 kinin receptors to endothelial cell membranes further preventing bradykinin signaling.2 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.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vago, T., Bevilacqua, M., Conci, F., et al. Angiotensin converting enzyme binding sites in human heart and lung: Comparison with rat tissues. Br. J. Pharmacol. 107(3), 821-825 (1992).

    2. Benzing, T., Fleming, I., Blaukat, A., 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).

    3. Yusuf, S., Sleight, P., Pogue, J., et al. Effects of an angiotensin-converting-enzyme inhibitor, ramipril, on cardiovascular events in high-risk patients. N. Engl. J. Med. 342(3), 145-153 (2000).

    4. Efsen, E., Særmark, T., Hansen, A., et al. Ramiprilate inhibits functional matrix metalloproteinase activity in Crohn’s disease fistulas. Basic Clin. Pharmacol. Toxicol. 109(3), 208-216 (2011).