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Moexipril HCl (RS-10085) is a potent and orally bioactive nonsulfhydryl angiotensin converting enzyme (ACE) inhibitor, used for the treatment of hypertension and congestive heart failure. As a potent ACE inhibitor, Moexipril hydrochloride blocks the conversion of angiotensin I to angiotensin II. Moexipril in addition, has cardioprotective effects mediated through a combination of angiotensin II inhibition and bradykinin proliferation. The proliferation of bradykinin stimulates the production of prostaglandin E2 and nitric oxide.
Physicochemical Properties
| Molecular Formula | C₂₇H₃₅CLN₂O₇ |
| Molecular Weight | 535.03 |
| Exact Mass | 534.213 |
| CAS # | 82586-52-5 |
| Related CAS # | Moexipril;103775-10-6;Moexipril-d5;1356929-49-1;Moexipril-d5 hydrochloride |
| PubChem CID | 54889 |
| Appearance | White to off-white solid powder |
| Boiling Point | 709.3ºC at 760 mmHg |
| Melting Point | 141-161ºC |
| Flash Point | 382.8ºC |
| LogP | 3.715 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 37 |
| Complexity | 742 |
| Defined Atom Stereocenter Count | 3 |
| SMILES | CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC(=C(C=C3C[C@H]2C(=O)O)OC)OC.Cl |
| InChi Key | JXRAXHBVZQZSIC-QGCARJLFSA-N |
| InChi Code | InChI=1S/C27H34N2O7.ClH/c1-5-36-27(33)21(12-11-18-9-7-6-8-10-18)28-17(2)25(30)29-16-20-15-24(35-4)23(34-3)14-19(20)13-22(29)26(31)32;/h6-10,14-15,17,21-22,28H,5,11-13,16H2,1-4H3,(H,31,32);1H/t17-,21-,22?;/m0./s1 |
| Chemical Name | 2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride |
| Synonyms | SPM-925; SPM 925; SPM925; CI-925; CI 925; CI925;RS 10085; RS-10085; RS10085; Moexipril. |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Moexipril hydrochloride has little effect on platelet function and no anti-inflammatory qualities[2]. With IC50s of 2.6 and 4.9 nM, respectively, moexiprilat, which is the product of moexipril hydrochloride's hydrolysis, inhibits ACE in both rabbit lung and guinea pig serum[2]. With IC50s of 2.7 mM and 0.165 mM, respectively, moexipril hydrochloride (0.01 nM-0.1 mM) demonstrates strong efficacy against both plasma ACE and isolated ACE from rabbit lung[3]. In a dose-dependent way, moexipril hydrochloride (0-100 μM, 24 h) dramatically decreased the percentage of injured neurons[4]. The neurotoxicity caused by Fe2+/3+ is considerably reduced by moexipril hydrochloride (0-100 μM, 24 h)[4]. The fraction of apoptotic neurons is not significantly affected by moexipril hydrochloride dosage[4]. |
| ln Vivo | The blood-brain barrier cannot be crossed by moexipril hydrochloride[1]. The effects of moexipril hydrochloride (3 mg/kg, 30 mg/kg, and 10 mg/kg, respectively; po; once daily; 5 days) on renal hypertensive rats, spontaneously hypertensive rats, and perinephritic hypertensive dogs are dose-dependent and antihypertensive[3]. In NMRI mice, the infarct area on the mouse brain surface is dramatically reduced by moexipril hydrochloride (0.3 mg/kg, ip)[4]. In Long-Evans rats, moexipril hydrochloride (0.1 mg/kg, ip) dramatically reduces the cortical infarct volume[4]. |
| Animal Protocol |
Animal/Disease Models: Spontaneously hypertensive rats[3] Doses: 30 mg/kg Route of Administration: po (oral gavage); one time/day; 5 days Experimental Results: Caused a progressive lowering of mean blood pressure from pretreatment values of 180 +/- 7 mmHg to a trough on day 4 of 127 +/- 4 mmHg. Dose-dependently diminished arterial blood pressure, and inhibited plasma and tissue ACE activity. Animal/Disease Models: Renal hypertensive rats[3] Doses: 0.03-10 mg/kg Route of Administration: po (oral gavage); one time/day; 5 days Experimental Results: Caused a dose-dependent decrease in blood pressure with a threshold dose of 0.3 mg/kg. Lowered mean blood pressure by about 70 mmHg of 3 mg/kg. Animal/Disease Models: Perinephritic hypertensive dogs[3] Doses: 10 mg/kg Route of Administration: po (oral gavage); one time/day; 5 days Experimental Results: Caused a drop of mean blood pressure by 25 mmHg from pre-treatment control , which persisted for 24 h, by a rapid onset and a long duration of action. Animal/Disease Models: NMRI mice (male, Permanent focal ischemia)[4] Doses: 0, 0.03, 0.3, and 3 mg/kg Administration |
| References |
[1]. Chrysant, S.G. and G.S. Chrysant, Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol, 2004. 44(8): p. 827-36. [2]. Pharmacological and toxicological studies of the new angiotensin converting enzyme inhibitor moexipril hydrochloride. Arzneimittelforschung. 1997 Feb. 47(2):132-44. [3]. Moexipril, a new angiotensin-converting enzyme (ACE) inhibitor: pharmacological characterization and comparison with enalapril. J Pharmacol Exp Ther, 1995. 275(2): p. 854-63. [4]. Enalapril and moexipril protect from free radical-induced neuronal damage in vitro and reduce ischemic brain injury in mice and rats. Eur J Pharmacol. 1999 May 28;373(1):21-33. |
| Additional Infomation |
Moexipril hydrochloride is a dipeptide. Moexipril Hydrochloride is the hydrochloride salt form of moexipril, a prodrug and non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor with antihypertensive activity. Moexipril hydrochloride is hydrolized into its active form moexiprilat, which competitively inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the actions of the potent vasoconstrictor angiotensin II and leads to vasodilatation. It also prevents angiotensin II-induced aldosterone secretion by the adrenal cortex, thereby promoting diuresis and natriuresis. Moexipril hydrochloride also directly suppresses renin release. See also: Moexiprilat (has active moiety); Hydrochlorothiazide; moexipril hydrochloride (component of). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 50 mg/mL (93.45 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8691 mL | 9.3453 mL | 18.6905 mL | |
| 5 mM | 0.3738 mL | 1.8691 mL | 3.7381 mL | |
| 10 mM | 0.1869 mL | 0.9345 mL | 1.8691 mL |