Spirapril

Last updated
Spirapril
Spirapril structure.svg
Clinical data
Trade names Renormax
AHFS/Drugs.com International Drug Names
Pregnancy
category
  • D
Routes of
administration 		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 50%
Metabolism converted to spiraprilat
Elimination half-life 30 to 35 hours
Excretion Hepatic and renal
Identifiers
  • (8S)-7-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H30N2O5S2
Molar mass 466.61 g·mol−1
3D model (JSmol)
  • O=C(OCC)[C@@H](N[C@H](C(=O)N2[C@H](C(=O)O)CC1(SCCS1)C2)C)CCc3ccccc3
  • InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1 Yes check.svgY
  • Key:HRWCVUIFMSZDJS-SZMVWBNQSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Spirapril, sold under the brand name Renormax among others, is an ACE inhibitor antihypertensive drug used to treat hypertension. It belongs to dicarboxy group of ACE inhibitors.[ citation needed ]

Contents

It was patented in 1980 and approved for medical use in 1995. [1]

Chemistry

Like many ACE inhibitors, this prodrug is converted to the active metabolite spiraprilat following oral administration. Unlike other members of the group, it is eliminated both by renal and hepatic routes, which may allow for greater use in patients with renal impairment. [2] However, data on its effect upon the renal function are conflicting. [3]

References

  1. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN   978-3-527-60749-5.
  2. ↑ Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G (February 1999). "Acute and chronic effects of spirapril, alone or in combination with isradipine on kidney function and blood pressure in patients with reduced kidney function and hypertension". Scandinavian Journal of Urology and Nephrology. 33 (1): 57–62. doi:10.1080/003655999750016294. PMID   10100366.
  3. ↑ Noble S, Sorkin EM (May 1995). "Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension". Drugs. 49 (5): 750–766. doi:10.2165/00003495-199549050-00008. PMID   7601014. S2CID   195691037.
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