A prodrug form of temocaprilat
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Active Metabolite(s)
22169Temocaprilat
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Temocapril (hydrochloride)

Item No. 18241

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[[(1S)-1-(ethoxycarbonyl)3-phenylpropyl]amino]tetrahydro-5-oxo-2-(2-thienyl)-1,4-thiazepine-4(5H)-acetic acid, monohydrochloride
CAS Number
110221-44-8
Synonyms
  • CS 622
Molecular Formula
C23H28N2O5S2 • HCl
Formula Weight
513.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mLDMF:PBS(pH 7.2)(1:1): 0.5 mg/mLDMSO: 20 mg/mLEthanol: 1 mg/mL
λmax
233 nm
SMILES
OC(CN1C([C@@H](N[C@@H](CCC2=CC=CC=C2)C(OCC)=O)CS[C@H](C3=CC=CS3)C1)=O)=O.Cl
InChi Code
InChI=1S/C23H28N2O5S2.ClH/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27;/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27);1H/t17-,18-,20-;/m0./s1
InChi Key
XDDQNOKKZKHBIX-ASBZXGSUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    50 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Temocapril is a prodrug form of the angiotensin-converting enzyme (ACE) inhibitor temocaprilat (Item No. 22169).1 Temocapril is converted to temocaprilat by carboxylesterase 1 (CES1).2 It prevents impairment of acetylcholine-induced relaxation in aortic rings isolated from diabetic rats in a model of streptozotocin-induced diabetes.3 Temocapril (0.1, 0.3, and 1 mg/kg) inhibits the angiotensin I-induced pressor response in normotensive rats.1 It prevents coronary vascular remodeling induced by L-NAME (Item No. 80210) in rats when administered at 0.1 mg/ml in the drinking water.4 Temocapril (1 mg/kg) reduces plasma glucose levels in a KKAy mouse model of type 2 diabetes.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Oizumi, K., Koike, H., Sada, T., et al. Pharmacological profiles of CS-622, a novel angiotensin converting enzyme inhibitor. Jpn. J. Pharmacol. 48(3), 349-356 (1988).

    2. Furihata, T., Hosokawa, M., Koyano, N., et al. Identification of di-(2-ethylhexyl) phthalate-induced carboxylesterase 1 in C57BL/6 mouse liver microsomes: Purification, cDNA cloning, and baculovirus-mediated expression. Drug Metab. Dispos. 32(10), 1170-1177 (2004).

    3. Pieper, G.M., and Siebeneich, W. Temocapril, an angiotensin converting enzyme inhibitor, protects against diabetes-induced endothelial dysfunction. Eur. J. Pharmacol. 403(1-2), 129-132 (2000).

    4. Takemoto, M., Egashira, K., Tomita, H., et al. Chronic angiotensin-converting enzyme inhibition and angiotensin II type 1 receptor blockade: effects on cardiovascular remodeling in rats induced by the long-term blockade of nitric oxide synthesis. Hypertension 30(6), 1621-1627 (1997).

    5. Shiuchi, T., Cui, T.-X., Wu, L., et al. ACE inhibitor improves insulin resistance in diabetic mouse via bradykinin and NO. Hypertension 40(3), 329-334 (2002).