A prodrug form of imidaprilat
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Active Metabolite(s)
38046Imidaprilat
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Imidapril (hydrochloride)

Item No. 18854

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4S-imidazolidinecarboxylic acid, monohydrochloride
CAS Number
89396-94-1
Synonyms
  • TA-6366
Molecular Formula
C20H27N3O6 • HCl
Formula Weight
441.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 25 mg/mlEthanol: 0.25 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
210 nm
SMILES
O=C(OCC)[C@@H](N[C@@H](C)C(N1C(N(C)C[C@H]1C(O)=O)=O)=O)CCC2=CC=CC=C2.Cl
InChi Code
InChI=1S/C20H27N3O6.ClH/c1-4-29-19(27)15(11-10-14-8-6-5-7-9-14)21-13(2)17(24)23-16(18(25)26)12-22(3)20(23)28;/h5-9,13,15-16,21H,4,10-12H2,1-3H3,(H,25,26);1H/t13-,15-,16-;/m0./s1
InChi Key
LSLQGMMMRMDXHN-GEUPQXMHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Imidapril is a prodrug form of the angiotensin-converting enzyme (ACE) inhibitor imidaprilat.1 Imidapril is converted to imidaprilat by carboxylesterase 1 (CES1).2 It inhibits swine renal cortex ACE activity in vitro (IC50 = 9.9 µM) and the angiotensin I-induced pressor response in normotensive rats.1 Imidapril (2 mg/kg) decreases blood pressure in spontaneously hypertensive and two kidney-one clip (2K-1C) renal hypertensive rats. It decreases stroke incidence and increases survival in stroke-prone spontaneously hypertensive rats fed a high-salt diet.3 Imidapril (5 mg/kg) reduces urinary albumin excretion, a marker of renal damage, in a mouse model of diabetes induced by streptozotocin (Item No. 13104).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kubo, M., Kato, J., Ochiai, T., et al. Pharmacological studies on (4S)-1-methyl-3-[(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino] propionyl]-2-oxo-imidazolidine-4-carboxylic acid hydrochloride (TA-6366), a new ACE inhibitor: I. ACE inhibitory and anti-hypertensive activities. Jpn. J. Pharmacol. 53(2), 201-210 (1990).

    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. Oriku, N., Sumikawa, H., Hashimoto, Y., et al. Prophylactic effect of imidapril on stroke in stroke-prone spontaneously hypertensive rats. Stroke 24(2), 245-252 (1993).

    4. Katoh, M., Ohmachi, Y., Kurosawa, Y., et al. Effects of imidapril and captopril on streptozotocin-induced diabetic nephropathy in mice. Eur. J. Pharmacol. 398(3), 381-387 (2000).