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MedKoo Cat#: 530312 | Name: MDL-100240

Description:

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

MDL-100240 is a dual inhibitor of angiotensin-converting enzyme (ACE) and neprilysin. MDL 100240 is a pro-drug that, upon conversion to MDL 100173, acts as a potent dual inhibitor of ACE and NEP with a balanced activity on both enzymes. MDL 100240 showed an impressive effectiveness both in preventing and in regressing hypertension-induced vascular remodeling and cardiac hypertrophy. Accordingly, MDL 100240 is being developed for the treatment of cardiovascular diseases, including hypertension and congestive heart failure.

Chemical Structure

MDL-100240
MDL-100240
CAS#142695-08-7

Theoretical Analysis

MedKoo Cat#: 530312

Name: MDL-100240

CAS#: 142695-08-7

Chemical Formula: C26H28N2O5S

Exact Mass: 480.1719

Molecular Weight: 480.58

Elemental Analysis: C, 64.98; H, 5.87; N, 5.83; O, 16.65; S, 6.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
MDL-100240; MDL 100240; MDL100240.
IUPAC/Chemical Name
(4S,7S,12bR)-7-((S)-2-(acetylthio)-3-phenylpropanamido)-6-oxo-1,2,3,4,6,7,8,12b-octahydrobenzo[c]pyrido[1,2-a]azepine-4-carboxylic acid
InChi Key
AIEZUMPHACQOGT-BJESRGMDSA-N
InChi Code
InChI=1S/C26H28N2O5S/c1-16(29)34-23(14-17-8-3-2-4-9-17)24(30)27-20-15-18-10-5-6-11-19(18)21-12-7-13-22(26(32)33)28(21)25(20)31/h2-6,8-11,20-23H,7,12-15H2,1H3,(H,27,30)(H,32,33)/t20-,21+,22-,23-/m0/s1
SMILES Code
O=C([C@@H]1CCC[C@@](C2=CC=CC=C2C[C@@H]3NC([C@@H](SC(C)=O)CC4=CC=CC=C4)=O)([H])N1C3=O)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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 480.58 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.

Recalculate based on batch purity %
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
1: Seccia TM, Belloni AS, Guidolin D, Sticchi D, Nussdorfer GG, Pessina AC, Rossi GP. The renal antifibrotic effects of angiotensin-converting enzyme inhibition involve bradykinin B2 receptor activation in angiotensin II-dependent hypertension. J Hypertens. 2006 Jul;24(7):1419-27. PubMed PMID: 16794493. 2: Cirillo I, Martin NE, Brennan B, Barrett JS. The effect of food on the pharmacokinetics of a dual angiotensin-converting enzyme/neutral endopeptidase inhibitor, M100240. J Clin Pharmacol. 2004 Dec;44(12):1379-84. PubMed PMID: 15545308. 3: Emmons GT, Argenti R, Martin LL, Martin NE, Jensen BK. Pharmacokinetics of M100240 and MDL 100,173, a dual angiotensin-converting enzyme/neutral endopeptidase inhibitor, in healthy young and elderly volunteers. J Clin Pharmacol. 2004 Aug;44(8):901-5. PubMed PMID: 15286094. 4: Pfister M, Martin NE, Haskell LP, Barrett JS. Optimizing dose selection with modeling and simulation: application to the vasopeptidase inhibitor M100240. J Clin Pharmacol. 2004 Jun;44(6):621-31. PubMed PMID: 15145970. 5: Rizzoni D, Rossi GP, Porteri E, Sticchi D, Rodella L, Rezzani R, Sleiman I, De Ciuceis C, Paiardi S, Bianchi R, Nussdorfer GG, Agabiti-Rosei E. Bradykinin and matrix metalloproteinases are involved the structural alterations of rat small resistance arteries with inhibition of ACE and NEP. J Hypertens. 2004 Apr;22(4):759-66. PubMed PMID: 15126918. 6: Martin NE, Howell SR, Martin LL, Cirillo I, Barrett JS. No clinically relevant CYP3A induction with the dual angiotensin-converting enzyme/neutral endopeptidase inhibitor, M100240. J Clin Pharmacol. 2004 Apr;44(4):379-87. PubMed PMID: 15051745. 7: Hwang KK, Martin NE, Jiang L, Zhu C. Permeation prediction of M100240 using the parallel artificial membrane permeability assay. J Pharm Pharm Sci. 2003 Sep-Dec;6(3):315-20. PubMed PMID: 14738711. 8: Hwang KK, Jiang L, Ren Y, Martin LL, Martin NE. Site-specific absorption of M100240 and MDL 100,173 in rats evaluated using Sweetana-Grass diffusion chamber technology. J Pharmacol Toxicol Methods. 2002 Sep-Oct;48(2):97-101. PubMed PMID: 14565566. 9: Shah B, Emmons G, Rohatagi S, Martin NE, Jensen BK. Mass balance study of [14C]M100240, a dual angiotensin-converting enzyme/neutral endopeptidase inhibitor, in healthy male subjects. Am J Ther. 2003 Sep-Oct;10(5):356-62. PubMed PMID: 12975720. 10: Martin NE, Collison KR, Martin LL, Tardif S, Wilding I, Wray H, Barrett JS. Pharmacoscintigraphic assessment of the regional drug absorption of the dual angiotensin-converting enzyme/neutral endopeptidase inhibitor, M100240, in healthy volunteers. J Clin Pharmacol. 2003 May;43(5):529-38. PubMed PMID: 12751274. 11: Rossi GP. Dual ACE and NEP inhibitors: a review of the pharmacological properties of MDL 100240. Cardiovasc Drug Rev. 2003 Spring;21(1):51-66. Review. PubMed PMID: 12595917. 12: Rossi GP, Cavallin M, Rizzoni D, Bova S, Mazzocchi G, Agabiti-Rosei E, Nussdorfer GG, Pessina AC. Dual ACE and NEP inhibitor MDL-100,240 prevents and regresses severe angiotensin II-dependent hypertension partially through bradykinin type 2 receptor. J Hypertens. 2002 Jul;20(7):1451-9. PubMed PMID: 12131544. 13: Rossi GP, Bova S, Sacchetto A, Rizzoni D, Agabiti-Rosei E, Neri G, Nussdorfer GG, Pessina AC. Comparative effects of the dual ACE-NEP inhibitor MDL-100,240 and ramipril on hypertension and cardiovascular disease in endogenous angiotensin II-dependent hypertension. Am J Hypertens. 2002 Feb;15(2 Pt 1):181-8. PubMed PMID: 11863255. 14: Rousso P, Buclin T, Nussberger J, Brunner-Ferber F, Brunner HR, Biollaz J. Bioavailability of repeated oral administration of MDL 100,240, a dual inhibitor of angiotensin-converting enzyme and neutral endopeptidase in healthy volunteers. Eur J Clin Pharmacol. 2000 Jan;55(10):749-54. PubMed PMID: 10663454. 15: MDL 100240. Drugs R D. 1999 Apr;1(4):348-9. PubMed PMID: 10566061. 16: Rousso P, Buclin T, Nussberger J, Décosterd LA, La Roche SD, Brunner-Ferber F, Brunner HR, Biollaz J. Effects of a dual inhibitor of angiotensin converting enzyme and neutral endopeptidase, MDL 100,240, on endocrine and renal functions in healthy volunteers. J Hypertens. 1999 Mar;17(3):427-37. PubMed PMID: 10100082. 17: Rousso P, Buclin T, Nussberger J, Brunner-Ferber F, Brunner HR, Biollaz J. Effects of MDL 100,240, a dual inhibitor of angiotensin-converting enzyme and neutral endopeptidase on the vasopressor response to exogenous angiotensin I and angiotensin II challenges in healthy volunteers. J Cardiovasc Pharmacol. 1998 Mar;31(3):408-17. PubMed PMID: 9514186. 18: Gardiner SM, Kemp PA, Brunner-Ferber F, Bennett T. Comparative effects of the dual metallopeptidase inhibitor, MDL 100,240 and of enalaprilat on regional and on cardiac haemodynamics in conscious, hypertensive, transgenic ((mRen-2)27) rats. Br J Pharmacol. 1997 Dec;122(8):1694-701. PubMed PMID: 9422816; PubMed Central PMCID: PMC1565109. 19: Gardiner SM, Kemp PA, Brunner-Ferber F, Bennett T. Effects of the dual metallopeptidase inhibitor, MDL 100,240, on regional haemodynamic responses to vasoactive peptides in conscious rats. Br J Pharmacol. 1997 Dec;122(8):1687-93. PubMed PMID: 9422815; PubMed Central PMCID: PMC1565108. 20: Heath TG, Massad DD, Carroll JI, Mathews BS, Chang J, Scott DO, Kuo BS, Toren PC. Quantification of a dual angiotensin I-converting enzyme-neutral endopeptidase inhibitor and the active thiol metabolite in dog plasma by high-performance liquid chromatography with ultraviolet absorbance detection. J Chromatogr B Biomed Appl. 1995 Aug 4;670(1):91-101. PubMed PMID: 7493089.

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