Moexipril-d5 | CAS#1356929-49-1 | Moexipril quantification internal standard

MedKoo Cat#: 464419 | Name: Moexipril-d5

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Moexipril-d5 intended for use as an internal standard for the quantification of moexipril by GC- or LC-MS. Moexipril is a prodrug form of the angiotensin converting enzyme (ACE) inhibitor moexiprilat. It is converted to moexiprilat in vivo by side chain ester hydrolysis. Moexipril inhibits ACE in a cell-free assay (IC50 = 2.7 µM for the rabbit enzyme). It also inhibits phosphodiesterase 4 (IC50s = 38, 160, and 230 µM for PDE4B2, PDE4A5 and PDE4D5, respectively). Moexipril (0.1-30 mg/kg per day) reduces blood pressure in spontaneously hypertensive rats.1 It also reduces infarct volume in a rat model of focal cerebral ischemia when used at a concentration of 0.01 mg/kg.

Chemical Structure

Moexipril-d5

CAS#1356929-49-1

Theoretical Analysis

MedKoo Cat#: 464419

Name: Moexipril-d5

CAS#: 1356929-49-1

Chemical Formula: C27H29D5N2O7

Exact Mass: 503.2680

Molecular Weight: 503.61

Elemental Analysis: C, 64.39; H, 7.80; N, 5.56; O, 22.24

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 1,250.00	2 Weeks

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Synonym

Moexipril-d5; Moexipril d5;

IUPAC/Chemical Name

(S)-2-(((S)-1-ethoxy-1-oxo-4-(phenyl-d5)butan-2-yl)-L-alanyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

InChi Key

UWWDHYUMIORJTA-SBCWFVTISA-N

InChi Code

InChI=1S/C27H34N2O7/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)/t17-,21-,22-/m0/s1/i6D,7D,8D,9D,10D

SMILES Code

[2H]C1=C(C([2H])=C(C([2H])=C1CC[C@H](N[C@H](C(N2CC3=CC(OC)=C(C=C3C[C@H]2C(O)=O)OC)=O)C)C(OCC)=O)[2H])[2H]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Moexipril-d5 is the deuterium labeled Moexipril. Moexipril hydrochloride is a potent orally active non-sulfhydryl angiotensin converting enzyme(ACE) inhibitor.

In vitro activity:

With this objective, this study utilised a high-throughput computational approach that identified moexipril, a well tolerated and safe angiotensin-converting enzyme (ACE) inhibitor, as a PDE4 inhibitor. Experimentally this study showed that moexipril and two structurally related analogues acted in the micro molar range to inhibit PDE4 activity. Employing a FRET-based biosensor constructed from the nucleotide binding domain of the type 1 exchange protein activated by cAMP, EPAC1, this study demonstrated that moexipril markedly potentiated the ability of forskolin to increase intracellular cAMP levels. Finally, this study demonstrated that the PDE4 inhibitory effect of moexipril is functionally able to induce phosphorylation of the small heat shock protein, Hsp20, by cAMP dependent protein kinase A. Reference: Biochem Pharmacol. 2013 May 1;85(9):1297-305. https://pubmed.ncbi.nlm.nih.gov/23473803/

In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 503.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cameron RT, Coleman RG, Day JP, Yalla KC, Houslay MD, Adams DR, Shoichet BK, Baillie GS. Chemical informatics uncovers a new role for moexipril as a novel inhibitor of cAMP phosphodiesterase-4 (PDE4). Biochem Pharmacol. 2013 May 1;85(9):1297-305. doi: 10.1016/j.bcp.2013.02.026. Epub 2013 Mar 5. PMID: 23473803; PMCID: PMC3625111. 2. Ravati A, Junker V, Kouklei M, Ahlemeyer B, Culmsee C, Krieglstein J. 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. doi: 10.1016/s0014-2999(99)00211-3. PMID: 10408248. 3. Adeghate E, Hasan MY, Ponery AS, Nurulain SM, Petroianu GA. Subchronic exposure to high-dose ACE-inhibitor moexipril induces catalase activity in rat liver. Mol Cell Biochem. 2005 Dec;280(1-2):159-63. doi: 10.1007/s11010-005-8843-6. PMID: 16311918. 4. Ma YF, Stimpel M, Liang H, Pun S, Jee WS. Impact of antihypertensive therapy on the skeleton: effects of moexipril and hydrochlorothiazide on osteopenia in spontaneously hypertensive ovariectomized rats. J Endocrinol. 1997 Sep;154(3):467-74. doi: 10.1677/joe.0.1540467. PMID: 9379124.

In vitro protocol:

In vivo protocol:

1. Adeghate E, Hasan MY, Ponery AS, Nurulain SM, Petroianu GA. Subchronic exposure to high-dose ACE-inhibitor moexipril induces catalase activity in rat liver. Mol Cell Biochem. 2005 Dec;280(1-2):159-63. doi: 10.1007/s11010-005-8843-6. PMID: 16311918. 2. Ma YF, Stimpel M, Liang H, Pun S, Jee WS. Impact of antihypertensive therapy on the skeleton: effects of moexipril and hydrochlorothiazide on osteopenia in spontaneously hypertensive ovariectomized rats. J Endocrinol. 1997 Sep;154(3):467-74. doi: 10.1677/joe.0.1540467. PMID: 9379124.

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Epub 2015 Jun 16. PMID: 26076923; PMCID: PMC6329299. 10: Li AZ, Xu WJ. Crystal structure of [(2S)-1-[(3S)-3-carboxy-6,7-dimethoxy-1,2,3,4-tetra-hydroisoquinolin-2-yl]-1-oxo propan-2-yl][(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azanium chloride acetonitrile monosolvate. Acta Crystallogr Sect E Struct Rep Online. 2014 Sep 24;70(Pt 10):o1126-7. doi: 10.1107/S160053681402090X. PMID: 25484709; PMCID: PMC4257232. 11: Taşdemir HI, Kiliç E. Electrochemistry of moexipril: experimental and computational approach and voltammetric determination. Pharmazie. 2014 Sep;69(9):648-54. PMID: 25272934. 12: Tawakkol SM, Farouk M, Elaziz OA, Hemdan A, Shehata MA. Comparative study between univariate spectrophotometry and multivariate calibration as analytical tools for simultaneous quantitation of Moexipril and Hydrochlorothiazide. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:300-6. doi: 10.1016/j.saa.2014.05.061. Epub 2014 Jun 5. PMID: 24954754. 13: Odović J, Marković B, Vladimirov S, Karljiković-Rajić K. In vitro modeling of angiotensin-converting enzyme inhibitor's absorption with chromatographic retention data and selected molecular descriptors. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 15;953-954:102-7. doi: 10.1016/j.jchromb.2014.02.004. Epub 2014 Feb 10. PMID: 24583202. 14: Ebeid WM, Elkady EF, El-Zaher AA, El-Bagary RI, Patonay G. Synchronized separation of seven medications representing most commonly prescribed antihypertensive classes by using reversed-phase liquid chromatography: Application for analysis in their combined formulations. J Sep Sci. 2014 Apr;37(7):748-57. doi: 10.1002/jssc.201301298. Epub 2014 Mar 7. PMID: 24482404. 15: Martiniuc C, Braniste A, Braniste T. Angiotensin converting enzyme inhibitors and pulmonary hypertension. Rev Med Chir Soc Med Nat Iasi. 2012 Oct- Dec;116(4):1016-20. PMID: 23700881. 16: Cameron RT, Coleman RG, Day JP, Yalla KC, Houslay MD, Adams DR, Shoichet BK, Baillie GS. Chemical informatics uncovers a new role for moexipril as a novel inhibitor of cAMP phosphodiesterase-4 (PDE4). Biochem Pharmacol. 2013 May 1;85(9):1297-305. doi: 10.1016/j.bcp.2013.02.026. Epub 2013 Mar 5. PMID: 23473803; PMCID: PMC3625111. 17: Odovic JV, Markovic BD, Injac RD, Vladimirov SM, Karljikovic-Rajic KD. Correlation between ultra-high performance liquid chromatography-tandem mass spectrometry and reversed-phase thin-layer chromatography hydrophobicity data for evaluation of angiotensin-converting enzyme inhibitors absorption. J Chromatogr A. 2012 Oct 5;1258:94-100. doi: 10.1016/j.chroma.2012.08.038. Epub 2012 Aug 17. PMID: 22939460. 18: Stanisz B, Regulska K, Ratajczak T. First order derivative spectrophotometric and HPLC methods for determination of moexipril hydrochloride in the pure form, pharmeceutical formulations and evaluation of its stability. Acta Pol Pharm. 2012 May-Jun;69(3):389-95. PMID: 22594252. 19: Karra VK, Mullangi R, Pilli NR, Inamadugu JK, Ravi VB, Seshagiri Rao JV. A rapid and sensitive liquid chromatography-tandem mass spectrometric assay for moexipril, an angiotensin-converting enzyme inhibitor in human plasma. Biomed Chromatogr. 2012 Dec;26(12):1552-8. doi: 10.1002/bmc.2731. Epub 2012 Mar 14. PMID: 22419504. 20: Stanisz B, Regulska K, Kania J, Garbacki P. Effect of pharmaceutical excipients on the stability of angiotensin-converting enzyme inhibitors in their solid dosage formulations. Drug Dev Ind Pharm. 2013 Jan;39(1):51-61. doi: 10.3109/03639045.2012.657644. Epub 2012 Feb 20. PMID: 22348774.