An ACE inhibitor and active metabolite of cilazapril
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Pro-drug Form(s)
29777Cilazapril
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Cilazaprilat

Item No. 38118

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,9S)-9-[[(1S)-1-carboxy-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
CAS Number
90139-06-3
Synonyms
  • Ro 31-3113
Molecular Formula
C20H27N3O5
Formula Weight
389.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
aqueous base: Slightly solubleDMSO: Slightly soluble
SMILES
OC([C@H]1N(C2=O)N(CCC[C@@H]2N[C@H](C(O)=O)CCC3=CC=CC=C3)CCC1)=O
InChi Code
InChI=1S/C20H27N3O5/c24-18-15(8-4-12-22-13-5-9-17(20(27)28)23(18)22)21-16(19(25)26)11-10-14-6-2-1-3-7-14/h1-3,6-7,15-17,21H,4-5,8-13H2,(H,25,26)(H,27,28)/t15-,16-,17-/m0/s1
InChi Key
UVAUYSRYXACKSC-ULQDDVLXSA-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

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    5 mg

    $179

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    10 mg

    $253

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    Product Description

    Cilazaprilat is an inhibitor of angiotensin-converting enzyme (ACE; IC50 = 0.7 nM for the rat enzyme) and an active metabolite of cilazapril (Item No. 29777).1,2 It decreases creatine kinase release in primary neonatal rat cardiac myocytes in an in vitro model of ischemia-reperfusion injury induced by hypoxia and reoxygenation when used at a concentration of 10 µM.3 Intra-arterial administration of cilazaprilat (3 µg/kg per minute) increases coronary blood flow and fractional shortening in a dog model of coronary hypoperfusion-induced myocardial ischemia.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Perich, R.B., Jackson, B., and Johnston, C.I. Structural constraints of inhibitors for binding at two active sites on somatic angiotensin converting enzyme. Eur. J. Pharmacol. 266(3), 201-211 (1994).

    2. Takai, S., Matsuda, A., Usami, Y., et al. Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver. Bio. Pharm. Bull. 20(8), 869-873 (1997).

    3. Matoba, S., Tatsumi, T., Keira, N., et al. Cardioprotective effect of angiotensin-converting enzyme inhibition against hypoxia/reoxygenation injury in cultured rat cardiac myocytes. Circulation 99(6), 817-822 (1999).

    4. Kitakaze, M., Minamino, T., Node, K., et al. Beneficial effects of inhibition of angiotensin-converting enzyme on ischemic myocardium during coronary hypoperfusion in dogs. Circulation 92(4), 950-961 (1995).