MedKoo Cat#: 526755 | Name: DMP-777

Description:

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

DMP-777 also known as L 694458, is a potent and orally active Leukocyte elastase (HLE) inhibitor. Oral dosing with DMP 777 caused a rapid increase in serum gastrin levels and severe hypochlorhydria. DMP 777 inhibited aminopyrine accumulation into rabbit parietal cells stimulated with either histamine or forskolin. DMP 777 reversed a stimulated proton gradient in isolated parietal cell tubulovesicles. DMP 777 acts as a protonophore with specificity for parietal cell acid-secretory membranes. DMP 777 in high doses leads to the specific loss of parietal cells.

Chemical Structure

DMP-777
DMP-777
CAS#157341-41-8

Theoretical Analysis

MedKoo Cat#: 526755

Name: DMP-777

CAS#: 157341-41-8

Chemical Formula: C31H40N4O6

Exact Mass: 564.2948

Molecular Weight: 564.68

Elemental Analysis: C, 65.94; H, 7.14; N, 9.92; O, 17.00

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 #
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Synonym
DMP-777; DMP 777; DMP777; L 694458; L-694,458.
IUPAC/Chemical Name
(S)-N-((R)-1-(benzo[d][1,3]dioxol-5-yl)butyl)-3,3-diethyl-2-(4-(4-methylpiperazine-1-carbonyl)phenoxy)-4-oxoazetidine-1-carboxamide
InChi Key
ZSDCIRYNTCVTMF-GIGWZHCTSA-N
InChi Code
InChI=1S/C31H40N4O6/c1-5-8-24(22-11-14-25-26(19-22)40-20-39-25)32-30(38)35-28(37)31(6-2,7-3)29(35)41-23-12-9-21(10-13-23)27(36)34-17-15-33(4)16-18-34/h9-14,19,24,29H,5-8,15-18,20H2,1-4H3,(H,32,38)/t24-,29+/m1/s1
SMILES Code
O=C(N1[C@@H](OC2=CC=C(C(N3CCN(C)CC3)=O)C=C2)C(CC)(CC)C1=O)N[C@@H](C4=CC=C(OCO5)C5=C4)CCC
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 564.68 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: Yamagata Y, Aikou S, Fukushima T, Kataoka H, Seto Y, Esumi H, Kaminishi M, Goldenring JR, Nomura S. Loss of HGF activator inhibits foveolar hyperplasia induced by oxyntic atrophy without altering gastrin levels. Am J Physiol Gastrointest Liver Physiol. 2012 Dec 1;303(11):G1254-61. doi: 10.1152/ajpgi.00107.2012. Epub 2012 Oct 11. PubMed PMID: 23064758; PubMed Central PMCID: PMC4888532. 2: Fernandes RA, Nallasivam JL. Enantioselective allylation of imines catalyzed by newly developed (-)-β-pinene-based π-allylpalladium catalyst: an efficient synthesis of (R)-α-propylpiperonylamine and (R)-pipecolic acid. Org Biomol Chem. 2012 Oct 14;10(38):7789-800. doi: 10.1039/c2ob26188j. PubMed PMID: 22910971. 3: Weis VG, Sousa JF, LaFleur BJ, Nam KT, Weis JA, Finke PE, Ameen NA, Fox JG, Goldenring JR. Heterogeneity in mouse spasmolytic polypeptide-expressing metaplasia lineages identifies markers of metaplastic progression. Gut. 2013 Sep;62(9):1270-9. doi: 10.1136/gutjnl-2012-302401. Epub 2012 Jul 7. PubMed PMID: 22773549; PubMed Central PMCID: PMC3762676. 4: Nam KT, O'Neal RL, Coffey RJ, Finke PE, Barker N, Goldenring JR. Spasmolytic polypeptide-expressing metaplasia (SPEM) in the gastric oxyntic mucosa does not arise from Lgr5-expressing cells. Gut. 2012 Dec;61(12):1678-85. doi: 10.1136/gutjnl-2011-301193. Epub 2011 Dec 23. PubMed PMID: 22198711; PubMed Central PMCID: PMC3767919. 5: Nam KT, Lee HJ, Sousa JF, Weis VG, O'Neal RL, Finke PE, Romero-Gallo J, Shi G, Mills JC, Peek RM Jr, Konieczny SF, Goldenring JR. Mature chief cells are cryptic progenitors for metaplasia in the stomach. Gastroenterology. 2010 Dec;139(6):2028-2037.e9. doi: 10.1053/j.gastro.2010.09.005. Epub 2010 Sep 18. PubMed PMID: 20854822; PubMed Central PMCID: PMC2997152. 6: Quante M, Marrache F, Goldenring JR, Wang TC. TFF2 mRNA transcript expression marks a gland progenitor cell of the gastric oxyntic mucosa. Gastroenterology. 2010 Dec;139(6):2018-2027.e2. doi: 10.1053/j.gastro.2010.08.003. Epub 2010 Aug 12. PubMed PMID: 20708616; PubMed Central PMCID: PMC2997174. 7: Aikou S, Fukushima Y, Ogawa M, Nozaki K, Saito T, Matsui T, Goldenring JR, Kaminishi M, Nomura S. Alterations in gastric mucosal lineages before or after acute oxyntic atrophy in gastrin receptor and H2 histamine receptor-deficient mice. Dig Dis Sci. 2009 Aug;54(8):1625-35. doi: 10.1007/s10620-009-0832-2. Epub 2009 Jun 9. PubMed PMID: 19507031. 8: Nozaki K, Weis V, Wang TC, Falus A, Goldenring JR. Altered gastric chief cell lineage differentiation in histamine-deficient mice. Am J Physiol Gastrointest Liver Physiol. 2009 Jun;296(6):G1211-20. doi: 10.1152/ajpgi.90643.2008. Epub 2009 Apr 9. PubMed PMID: 19359424; PubMed Central PMCID: PMC2697940. 9: Nozaki K, Ogawa M, Williams JA, Lafleur BJ, Ng V, Drapkin RI, Mills JC, Konieczny SF, Nomura S, Goldenring JR. A molecular signature of gastric metaplasia arising in response to acute parietal cell loss. Gastroenterology. 2008 Feb;134(2):511-22. doi: 10.1053/j.gastro.2007.11.058. Epub 2007 Dec 4. PubMed PMID: 18242217; PubMed Central PMCID: PMC2857727. 10: Nam KT, Varro A, Coffey RJ, Goldenring JR. Potentiation of oxyntic atrophy-induced gastric metaplasia in amphiregulin-deficient mice. Gastroenterology. 2007 May;132(5):1804-19. Epub 2007 Mar 24. PubMed PMID: 17484876. 11: Goldenring JR, Nomura S. Differentiation of the gastric mucosa III. Animal models of oxyntic atrophy and metaplasia. Am J Physiol Gastrointest Liver Physiol. 2006 Dec;291(6):G999-1004. Review. PubMed PMID: 17090722. 12: Ogawa M, Nomura S, Car BD, Goldenring JR. Omeprazole treatment ameliorates oxyntic atrophy induced by DMP-777. Dig Dis Sci. 2006 Mar;51(3):431-9. PubMed PMID: 16614949. 13: Ogawa M, Nomura S, Varro A, Wang TC, Goldenring JR. Altered metaplastic response of waved-2 EGF receptor mutant mice to acute oxyntic atrophy. Am J Physiol Gastrointest Liver Physiol. 2006 Apr;290(4):G793-804. Epub 2005 Nov 23. PubMed PMID: 16306133. 14: Nomura S, Yamaguchi H, Ogawa M, Wang TC, Lee JR, Goldenring JR. Alterations in gastric mucosal lineages induced by acute oxyntic atrophy in wild-type and gastrin-deficient mice. Am J Physiol Gastrointest Liver Physiol. 2005 Feb;288(2):G362-75. PubMed PMID: 15647607. 15: Buckley D, Haas MJ, Scholz TH, Sigvardson KW. Isolation and identification of a degradation product in a capsule formulation containing the elastase inhibitor, DMP 777. J Pharm Biomed Anal. 2001 Feb;24(4):651-7. PubMed PMID: 11272322. 16: Goldenring JR, Ray GS, Coffey RJ, Meunier PC, Haley PJ, Barnes TB, Car BD. Reversible drug-induced oxyntic atrophy in rats. Gastroenterology. 2000 Jun;118(6):1080-93. PubMed PMID: 10833483. 17: Dwyer TM, Farley JM. Human neutrophil elastase releases two pools of mucinlike glycoconjugate from tracheal submucosal gland cells. Am J Physiol Lung Cell Mol Physiol. 2000 Apr;278(4):L675-82. PubMed PMID: 10749744. 18: Zagrobelny J, Matuszewski BK, Kline WF, Vincent SH. Separation of the four stereoisomers of a potent inhibitor (L-694,458) of human leukocyte elastase and its determination in human plasma using achiral/chiral chromatography with column switching. J Pharm Biomed Anal. 1998 Sep 1;17(6-7):1057-64. PubMed PMID: 9884195. 19: Macdonald SJ, Belton DJ, Buckley DM, Spooner JE, Anson MS, Harrison LA, Mills K, Upton RJ, Dowle MD, Smith RA, Molloy CR, Risley C. Syntheses of trans-5-oxo-hexahydro-pyrrolo[3,2-b]pyrroles and trans-5-oxo-hexahydro-furo[3,2-b]pyrroles (pyrrolidine trans-lactams and trans-lactones): new pharmacophores for elastase inhibition. J Med Chem. 1998 Oct 8;41(21):3919-22. PubMed PMID: 9767628. 20: Luffer-Atlas D, Vincent SH, Painter SK, Arison BH, Stearns RA, Chiu SH. Orally active inhibitors of human leukocyte elastase. III. Identification and characterization of metabolites of L-694,458 by liquid chromatography-tandem mass spectrometry. Drug Metab Dispos. 1997 Aug;25(8):940-52. PubMed PMID: 9280402.