Moexiprilat | CAS#103775-14-0 | inhibitor

MedKoo Cat#: 584762 | Name: Moexiprilat

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Description:

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

Moexiprilat completely inhibits estrone-induced cardiac fibroblast growth.

Chemical Structure

Moexiprilat

CAS#103775-14-0

Theoretical Analysis

MedKoo Cat#: 584762

Name: Moexiprilat

CAS#: 103775-14-0

Chemical Formula: C25H30N2O7

Exact Mass: 470.2053

Molecular Weight: 470.52

Elemental Analysis: C, 63.82; H, 6.43; N, 5.95; O, 23.80

Price and Availability

Size	Price	Availability	Quantity
20mg	USD 1,300.00

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Synonym

Moexiprilat

IUPAC/Chemical Name

(3S)-2-((2S)-N-((1S)-1-Carboxy-3-phenylpropyl)alanyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid

InChi Key

CMPAGYDKASJORH-YSSFQJQWSA-N

InChi Code

InChI=1S/C25H30N2O7/c1-15(26-19(24(29)30)10-9-16-7-5-4-6-8-16)23(28)27-14-18-13-22(34-3)21(33-2)12-17(18)11-20(27)25(31)32/h4-8,12-13,15,19-20,26H,9-11,14H2,1-3H3,(H,29,30)(H,31,32)/t15-,19-,20-/m0/s1

SMILES Code

O=C([C@H]1N(C([C@H](C)N[C@H](C(O)=O)CCC2=CC=CC=C2)=O)CC3=C(C=C(OC)C(OC)=C3)C1)O

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

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Moexiprilat completely inhibits estrone-induced cardiac fibroblast growth.

In vitro activity:

In vitro, moexiprilat was a potent inhibitor of ACE in guinea pig serum as well as on purified ACE from rabbit lung with IC50 values of 2.6 and 4.9 nmol/l, respectively. Both, moexipril and moexiprilat inhibited the angiotensin I (ANG I)-induced contractions of rabbit aorta concentration-dependently, whereas contractions by other agents were not affected, indicating a high selectivity of both compounds for ACE. Reference: Arzneimittelforschung. 1997 Feb;47(2):132-44. https://pubmed.ncbi.nlm.nih.gov/9079232/

In vivo activity:

The effects of 2-2-(1-(ethoxycarbonyl)-3-phenylpropyl)-[amino-oxopropyl]-6,7-dimethoxy- 1,2,3,4-tetrahydroisoquinoline-3 carboxylic acid (moexiprilat), 17beta-oestradiol (E2), oestrone (ES) and angiotensin II (AII) on growth and activation of oestrogen receptors and the immediate-early gene egr-1 were investigated in neonatal rat cardiac fibroblasts of female and male origin. Moexiprilat (10(-7)M) completely inhibited oestrone-induced cardiac fibroblast growth. The induction of oestrogen receptor and egr-1 protein expression was time-dependent and inhibited by moexiprilat. Reference: Br J Pharmacol. 1997 Aug;121(7):1350-4. https://pubmed.ncbi.nlm.nih.gov/9257913/

Preparing Stock Solutions

The following data is based on the product molecular weight 470.52 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. Pines A, Fisman EZ. ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control. Am J Cardiovasc Drugs. 2003;3(5):351-60. doi: 10.2165/00129784-200303050-00006. PMID: 14728069. 2. Friehe H, Ney P. Pharmacological and toxicological studies of the new angiotensin converting enzyme inhibitor moexipril hydrochloride. Arzneimittelforschung. 1997 Feb;47(2):132-44. PMID: 9079232. 3. Grohé C, Kahlert S, Lóbbert K, van Eickels M, Stimpel M, Vetter H, Neyses L. Effects of moexiprilat on oestrogen-stimulated cardiac fibroblast growth. Br J Pharmacol. 1997 Aug;121(7):1350-4. doi: 10.1038/sj.bjp.0701263. PMID: 9257913; PMCID: PMC1564823. 4. Edling O, Bao G, Feelisch M, Unger T, Gohlke P. Moexipril, a new angiotensin-converting enzyme (ACE) inhibitor: pharmacological characterization and comparison with enalapril. J Pharmacol Exp Ther. 1995 Nov;275(2):854-63. PMID: 7473177.

In vitro protocol:

In vivo protocol:

1. Grohé C, Kahlert S, Lóbbert K, van Eickels M, Stimpel M, Vetter H, Neyses L. Effects of moexiprilat on oestrogen-stimulated cardiac fibroblast growth. Br J Pharmacol. 1997 Aug;121(7):1350-4. doi: 10.1038/sj.bjp.0701263. PMID: 9257913; PMCID: PMC1564823. 2. Edling O, Bao G, Feelisch M, Unger T, Gohlke P. Moexipril, a new angiotensin-converting enzyme (ACE) inhibitor: pharmacological characterization and comparison with enalapril. J Pharmacol Exp Ther. 1995 Nov;275(2):854-63. PMID: 7473177.

1: Grohé C, Kahlert S, Lóbbert K, van Eickels M, Stimpel M, Vetter H, Neyses L. Effects of moexiprilat on oestrogen-stimulated cardiac fibroblast growth. Br J Pharmacol. 1997 Aug;121(7):1350-4. PubMed PMID: 9257913; PubMed Central PMCID: PMC1564823. 2: Cawello W, Boekens H, Waitzinger J, Miller U. Moexipril shows a long duration of action related to an extended pharmacokinetic half-life and prolonged ACE inhibition. Int J Clin Pharmacol Ther. 2002 Jan;40(1):9-17. PubMed PMID: 11837383. 3: Hammes W, Hammes B, Büchsler U, Paar F, Bökens H. Simultaneous determination of moexipril and moexiprilat, its active metabolite, in human plasma by gas chromatography-negative-ion chemical ionization mass spectrometry. J Chromatogr B Biomed Appl. 1995 Aug 4;670(1):81-9. PubMed PMID: 7493088. 4: van Eickels M, Vetter H, Grohé C. Angiotensin-converting enzyme (ACE) inhibition attenuates insulin-like growth factor-I (IGF-I) induced cardiac fibroblast proliferation. Br J Pharmacol. 2000 Dec;131(8):1592-6. PubMed PMID: 11139436; PubMed Central PMCID: PMC1572499. 5: Gu L, Strickley RG. Preformulation stability studies of the new dipeptide angiotensin-converting enzyme inhibitor RS-10029. Pharm Res. 1988 Dec;5(12):765-71. PubMed PMID: 3247286. 6: Grohé C, Kahlert S, Löbbert K, Neyses L, van Eickels M, Stimpel M, Vetter H. Angiotensin converting enzyme inhibition modulates cardiac fibroblast growth. J Hypertens. 1998 Mar;16(3):377-84. PubMed PMID: 9557931. 7: Visor GC, Lin LH, Henry P, Singer L. Preclinical development and characterization of an intravenous dosage form for the ACE inhibitor RS-10029. J Parenter Sci Technol. 1989 Nov-Dec;43(6):271-6. PubMed PMID: 2600732. 8: Hutt V, Michaelis K, Verbesselt R, De Schepper PJ, Salomon P, Bonn R, Cawello W, Angehrn JC. Lack of a pharmacokinetic interaction between moexipril and hydrochlorothiazide. Eur J Clin Pharmacol. 1996;51(3-4):339-44. PubMed PMID: 9010710. 9: Brogden RN, Wiseman LR. Moexipril. A review of its use in the management of essential hypertension. Drugs. 1998 Jun;55(6):845-60. Review. PubMed PMID: 9617599. 10: Kóti J, Háda V, Petroianu G, Hasan MY, Tekes K, Szücs Z, Kalász H. Monitoring the metabolism of moexipril to moexiprilat using high-performance liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr Sci. 2006 Apr;44(4):214-8. PubMed PMID: 16620521. 11: Hecker M, Blaukat A, Bara AT, Müller-Esterl W, Busse R. ACE inhibitor potentiation of bradykinin-induced venoconstriction. Br J Pharmacol. 1997 Aug;121(7):1475-81. PubMed PMID: 9257930; PubMed Central PMCID: PMC1564840. 12: Hecker M, Bara AT, Busse R. Relaxation of isolated coronary arteries by angiotensin-converting enzyme inhibitors: role of endothelium-derived kinins. J Vasc Res. 1993 Sep-Oct;30(5):257-62. PubMed PMID: 8399986. 13: Kalász H, Petroianu G, Tekes K, Klebovich I, Ludányi K, Gulyás Z. Metabolism of moexipril to moexiprilat: determination of in vitro metabolism using HPLC-ES-MS. Med Chem. 2007 Jan;3(1):101-6. PubMed PMID: 17266629. 14: Hecker M, Pörsti I, Bara AT, Busse R. Potentiation by ACE inhibitors of the dilator response to bradykinin in the coronary microcirculation: interaction at the receptor level. Br J Pharmacol. 1994 Jan;111(1):238-44. PubMed PMID: 8012702; PubMed Central PMCID: PMC1910047. 15: van Eickels M, Grohé C, Löbbert K, Stimpel M, Vetter H. Angiotensin converting enzyme inhibitors block mitogenic signalling pathways in rat cardiac fibroblasts. Naunyn Schmiedebergs Arch Pharmacol. 1999 May;359(5):394-9. PubMed PMID: 10498289. 16: Hecker M, Bara AT, Busse R. Angiotensin-converting enzyme inhibitors unmask endogenous kinin production by bovine coronary artery endothelium. Eur Heart J. 1993 Nov;14 Suppl I:161-3. PubMed PMID: 8293768. 17: Pines A, Fisman EZ. ACE Inhibition with moexipril: a review of potential effects beyond blood pressure control. Am J Cardiovasc Drugs. 2003;3(5):351-60. Review. PubMed PMID: 14728069. 18: Chrysant SG, Chrysant GS. Pharmacological and clinical profile of moexipril: a concise review. J Clin Pharmacol. 2004 Aug;44(8):827-36. Review. PubMed PMID: 15286086. 19: Busse R, Fleming I, Hecker M. Endothelium-derived bradykinin: implications for angiotensin-converting enzyme-inhibitor therapy. J Cardiovasc Pharmacol. 1993;22 Suppl 5:S31-6. PubMed PMID: 7508049. 20: Hecker M, Dambacher T, Busse R. Role of endothelium-derived bradykinin in the control of vascular tone. J Cardiovasc Pharmacol. 1992;20 Suppl 9:S55-61. PubMed PMID: 1282631.