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MedKoo Cat#: 562511 | Name: Spiraprilat

Description:

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

Spiraprilat is an active metabolite of spirapril, an ACE inhibitor.

Chemical Structure

Spiraprilat
Spiraprilat
CAS#83602-05-5

Theoretical Analysis

MedKoo Cat#: 562511

Name: Spiraprilat

CAS#: 83602-05-5

Chemical Formula: C20H26N2O5S2

Exact Mass: 438.1283

Molecular Weight: 438.55

Elemental Analysis: C, 54.78; H, 5.98; N, 6.39; O, 18.24; S, 14.62

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
Spiraprilat; SCH-33861; SCH 33861; SCH33861; Spiraprilate;
IUPAC/Chemical Name
(8S)-7-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
InChi Key
FMMDBLMCSDRUPA-BPUTZDHNSA-N
InChi Code
InChI=1S/C20H26N2O5S2/c1-13(21-15(18(24)25)8-7-14-5-3-2-4-6-14)17(23)22-12-20(28-9-10-29-20)11-16(22)19(26)27/h2-6,13,15-16,21H,7-12H2,1H3,(H,24,25)(H,26,27)/t13-,15-,16-/m0/s1
SMILES Code
O=C([C@H](C1)N(C([C@@H](N[C@H](C(O)=O)CCC2=CC=CC=C2)C)=O)CC31SCCS3)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 438.55 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: Sramko M, Smiesko M, Remko M. Accurate aqueous proton dissociation constants calculations for selected angiotensin-converting enzyme inhibitors. J Biomol Struct Dyn. 2008 Jun;25(6):599-608. PubMed PMID: 18399693. 2: Schürer M, Erb K, Junge K, Schäfer HF, Schulz HU, Amschler S, Krupp S, Hermann R. Drug interaction of spirapril hydrochloride monohydrate and hydrochlorothiazide. A clinical study to compare the pharmacokinetics after administration of spirapril hydrochloride monohydrate tablets, hydrochlorothiazide tablets and fixed combination bi-layer tablets. Arzneimittelforschung. 2003;53(6):414-9. PubMed PMID: 12872612. 3: Schürer M, Amschler S, Schulz HU, Schäfer HF. Simultaneous determination of spirapril and spiraprilat in plasma by capillary gas chromatography-mass spectrometry. Arzneimittelforschung. 2003;53(5):307-13. PubMed PMID: 12854357. 4: Hayduk K, Kraul H. Efficacy and safety of spirapril in mild-to-moderate hypertension. J Cardiovasc Pharmacol. 1999 Aug;34 Suppl 1:S19-23. Review. PubMed PMID: 10499560. 5: Bellissant E, Chau NP, Thuillez C, Gerbeau C, Richard C, Giudicelli JF. Pharmacokinetic-pharmacodynamic model relating spiraprilat plasma concentrations to systemic and regional hemodynamic effects in congestive heart failure. J Cardiovasc Pharmacol. 1997 Aug;30(2):253-60. PubMed PMID: 9269955. 6: Shionoiri H, Naruse M, Minamisawa K, Ueda S, Himeno H, Hiroto S, Takasaki I. Fosinopril. Clinical pharmacokinetics and clinical potential. Clin Pharmacokinet. 1997 Jun;32(6):460-80. Review. PubMed PMID: 9195116. 7: Noble S, Sorkin EM. Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension. Drugs. 1995 May;49(5):750-66. Review. PubMed PMID: 7601014. 8: Haufe CC, Sierakowski B, Jansa U, Stein G. [Kidney function in hypertensive patients with chronic renal failure treated with the dual eliminated ACE-inhibitor spirapril]. Med Klin (Munich). 1994 Aug 15;89(8):416-20. German. PubMed PMID: 7968874. 9: Johnson BF, Johnson J, Surve A, Smith H. The Interaction of Hydrochlorothiazide with Spirapril: A Novel Ace Inhibitor. Am J Ther. 1994 Jun;1(1):4-7. PubMed PMID: 11835060. 10: Grass P, Gerbeau C, Kutz K. Spirapril: pharmacokinetic properties and drug interactions. Blood Press Suppl. 1994;2:7-13. PubMed PMID: 8061850. 11: Guitard C, Sassano P, Tzincoca C, Duchiez J, Safar ME. Placebo-controlled crossover comparison of spirapril at 3, 6, 12 and 24 mg once daily in mild to severe essential hypertension. Blood Press Suppl. 1994;2:61-8. PubMed PMID: 8061848. 12: Stein G, Sierakowski B, Grass P, Haufe CC, Jansa U, Weidinger G. Pharmacokinetics of spirapril and spiraprilat in patients with chronic renal failure. Blood Press Suppl. 1994;2:47-53. PubMed PMID: 8061846. 13: Meredith PA, Grass P, Guitard C, Elliott HL. Pharmacokinetics of spirapril in renal impairment. Blood Press Suppl. 1994;2:14-9. PubMed PMID: 8061840. 14: Nakazawa M, Ishihara T, Takahashi Y, Okuhira M, Imai S. Effects of spiraprilat, an angiotensin-converting enzyme inhibitor, on anesthetized dogs in a new model of acute left ventricular failure. J Cardiovasc Pharmacol. 1993 Oct;22(4):585-93. PubMed PMID: 7505361. 15: Krähenbühl S, Grass P, Surve A, Kutz K, Reichen J. Pharmacokinetics and haemodynamic effects of a single oral dose of the novel ACE inhibitor spirapril in patients with chronic liver disease. Eur J Clin Pharmacol. 1993;45(3):247-53. PubMed PMID: 8276049. 16: van den Meiracker AH, Man in 't Veld AJ, Admiraal PJ, Ritsema van Eck HJ, Boomsma F, Derkx FH, Schalekamp MA. Partial escape of angiotensin converting enzyme (ACE) inhibition during prolonged ACE inhibitor treatment: does it exist and does it affect the antihypertensive response? J Hypertens. 1992 Aug;10(8):803-12. PubMed PMID: 1325513. 17: Hossein-Nia M, Surve AH, Weglein R, Gerbeau C, Holt DW. Radioimmunoassays for spirapril and its active metabolite spiraprilate: performance and application. Ther Drug Monit. 1992 Jun;14(3):234-42. PubMed PMID: 1384174. 18: Gérard JL, Pussard E, Berdeaux A, Giudicelli JF. Hemodynamic and cardiac effects of spiraprilat in normal and sodium depleted conscious dogs. Fundam Clin Pharmacol. 1990;4(5):547-58. PubMed PMID: 2289746. 19: Smith EM, Swiss GF, Neustadt BR, McNamara P, Gold EH, Sybertz EJ, Baum T. Angiotensin converting enzyme inhibitors: spirapril and related compounds. J Med Chem. 1989 Jul;32(7):1600-6. PubMed PMID: 2544729.