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MedKoo Cat#: 599002 | Name: Lisinopril R,S,S-diketopiperazine

Description:

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

Lisinopril R,S,S-diketopiperazine is a bioactive chemical.

Chemical Structure

Lisinopril R,S,S-diketopiperazine
CAS#219677-82-4

Theoretical Analysis

MedKoo Cat#: 599002

Name: Lisinopril R,S,S-diketopiperazine

CAS#: 219677-82-4

Chemical Formula: C21H29N3O4

Exact Mass: 387.2158

Molecular Weight: 387.48

Elemental Analysis: C, 65.10; H, 7.54; N, 10.84; O, 16.52

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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Synonym
Lisinopril R,S,S-diketopiperazine; Lisinopril specified impurity D [EP];
IUPAC/Chemical Name
(S)-2-((3S,8aR)-3-(4-aminobutyl)-1,4-dioxohexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-4-phenylbutanoic acid
InChi Key
FUEMHWCBWYXAOU-SQNIBIBYSA-N
InChi Code
InChI=1S/C21H29N3O4/c22-13-5-4-9-17-19(25)23-14-6-10-16(23)20(26)24(17)18(21(27)28)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18H,4-6,9-14,22H2,(H,27,28)/t16-,17+,18+/m1/s1
SMILES Code
O=C(O)[C@@H](N([C@H]1CCCCN)C([C@](CCC2)([H])N2C1=O)=O)CCC3=CC=CC=C3
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 387.48 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
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Transplant Proc. 2011 Sep;43(7):2524-30. doi: 10.1016/j.transproceed.2011.06.043. PubMed PMID: 21911117. 4: Kwakernaak AJ, Lambert G, Slagman MC, Waanders F, Laverman GD, Petrides F, Dikkeschei BD, Navis G, Dullaart RP. Proprotein convertase subtilisin-kexin type 9 is elevated in proteinuric subjects: relationship with lipoprotein response to antiproteinuric treatment. Atherosclerosis. 2013 Feb;226(2):459-65. doi: 10.1016/j.atherosclerosis.2012.11.009. Epub 2012 Nov 29. PubMed PMID: 23261172. 5: Su Z, Chen L, Liu Y, He X, Zhou Y, Xie Q, Yao S. 35 MHz quartz crystal microbalance and surface plasmon resonance studies on the binding of angiotensin converting enzyme with lisinopril. Biosens Bioelectron. 2011 Mar 15;26(7):3240-5. doi: 10.1016/j.bios.2010.12.033. Epub 2010 Dec 28. PubMed PMID: 21255995. 6: Ariff BB, Glor FP, Crowe L, Xu XY, Vennart W, Firmin DN, Thom SM, Hughes AD. Carotid artery hemodynamics: observing patient-specific changes with amlodipine and lisinopril by using MR imaging computation fluid dynamics. Radiology. 2010 Dec;257(3):662-9. doi: 10.1148/radiol.10100788. Epub 2010 Oct 8. PubMed PMID: 20935080. 7: Fried LF, Emanuele N, Zhang JH, Brophy M, Conner TA, Duckworth W, Leehey DJ, McCullough PA, O'Connor T, Palevsky PM, Reilly RF, Seliger SL, Warren SR, Watnick S, Peduzzi P, Guarino P; VA NEPHRON-D Investigators. Combined angiotensin inhibition for the treatment of diabetic nephropathy. N Engl J Med. 2013 Nov 14;369(20):1892-903. doi: 10.1056/NEJMoa1303154. Epub 2013 Nov 9. Erratum in: N Engl J Med. 2014;158:A7255. PubMed PMID: 24206457. 8: Qin W, Zhang Z, Tian Y, Xu F, Wang N, Chen Y. Rapid quantification of lisinopril in human plasma by liquid chromatography/tandem mass spectrometry. Biomed Chromatogr. 2007 Apr;21(4):415-21. PubMed PMID: 17221934. 9: Ali K, Rajkumar C, Fantin F, Schiff R, Bulpitt CJ. Irbesartan improves arterial compliance more than lisinopril. Vasc Health Risk Manag. 2009;5(4):587-92. Epub 2009 Jul 14. PubMed PMID: 19649309; PubMed Central PMCID: PMC2710973. 10: Ruggenenti P, Mise N, Pisoni R, Arnoldi F, Pezzotta A, Perna A, Cattaneo D, Remuzzi G. Diverse effects of increasing lisinopril doses on lipid abnormalities in chronic nephropathies. Circulation. 2003 Feb 4;107(4):586-92. PubMed PMID: 12566371. 11: Hollenberg NK, Anzalone DA, Falkner B, Fisher ND, Hopkins PN, Hsueh W, Hutchinson H, Krauss RM, Price DA, Raskin P, Reaven GM. Familial factors in the antihypertensive response to lisinopril. Am J Hypertens. 2001 Mar;14(3):218-23. PubMed PMID: 11281232. 12: Ostroumova OD, Kochetkov AI. [Effects of Amlodipine/Lisinopril Fixed-Dose Combination on Severity of Left Ventricular Hypertrophy and Parameters of Myocardial Stiffness in Patients With Hypertension]. Kardiologiia. 2016 Dec;56(11):27-37. Russian. PubMed PMID: 28290816. 13: Odovic J, Markovic B, Vladimirov S, Karljikovic-Rajic K. Evaluation of angiotensin-converting enzyme inhibitor's absorption with retention data of micellar thin-layer chromatography and suitable molecular descriptor. J Chromatogr Sci. 2015 Nov-Dec;53(10):1780-5. doi: 10.1093/chromsci/bmv091. Epub 2015 Jun 28. PubMed PMID: 26123666. 14: Torres VE, Abebe KZ, Chapman AB, Schrier RW, Braun WE, Steinman TI, Winklhofer FT, Brosnahan G, Czarnecki PG, Hogan MC, Miskulin DC, Rahbari-Oskoui FF, Grantham JJ, Harris PC, Flessner MF, Moore CG, Perrone RD; HALT-PKD Trial Investigators. Angiotensin blockade in late autosomal dominant polycystic kidney disease. N Engl J Med. 2014 Dec 11;371(24):2267-76. doi: 10.1056/NEJMoa1402686. Epub 2014 Nov 15. PubMed PMID: 25399731; PubMed Central PMCID: PMC4284824. 15: Jackson B, Cubela RB, Conway EL, Johnston CI. Lisinopril pharmacokinetics in chronic renal failure. Br J Clin Pharmacol. 1988 Jun;25(6):719-24. PubMed PMID: 2849471; PubMed Central PMCID: PMC1386449. 16: Egan BM, Fleissner MJ, Stepniakowski K, Neahring JM, Sagar KB, Ebert TJ. Improved baroreflex sensitivity in elderly hypertensives on lisinopril is not explained by blood pressure reduction alone. J Hypertens. 1993 Oct;11(10):1113-20. PubMed PMID: 8258676. 17: Fogari R, Mugellini A, Zoppi A, Lazzari P, Destro M, Rinaldi A, Preti P. Effect of successful hypertension control by manidipine or lisinopril on albuminuria and left ventricular mass in diabetic hypertensive patients with microalbuminuria. Eur J Clin Pharmacol. 2005 Aug;61(7):483-90. Epub 2005 Jul 15. PubMed PMID: 16021438. 18: Zacharis CK, Tzanavaras PD, Themelis DG, Theodoridis GA, Economou A, Rigas PG. Rapid spectrofluorimetric determination of lisinopril in pharmaceutical tablets using sequential injection analysis. Anal Bioanal Chem. 2004 Jul;379(5-6):759-63. Epub 2004 Feb 19. PubMed PMID: 14985906. 19: Poulsen PL, Ebbehøj E, Mogensen CE. Lisinopril reduces albuminuria during exercise in low grade microalbuminuric type 1 diabetic patients: a double blind randomized study. J Intern Med. 2001 May;249(5):433-40. PubMed PMID: 11350567. 20: De Tommasi E, Iacoviello M, Romito R, Ceconi C, Guida P, Massari F, Francolini G, Bertocchi F, Ferrari R, Rizzon P, Pitzalis MV. Comparison of the effect of valsartan and lisinopril on autonomic nervous system activity in chronic heart failure. Am Heart J. 2003 Nov;146(5):E17. PubMed PMID: 14597946.