Spirapril

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.

Spirapril
Clinical data
Trade namesRenormax
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • D
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability50%
Metabolismconverted to spiraprilat
Elimination half-life30 to 35 hours
ExcretionHepatic and renal
Identifiers
IUPAC name
  • (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
FormulaC22H30N2O5S2
Molar mass466.61 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC)[C@@H](N[C@H](C(=O)N2[C@H](C(=O)O)CC1(SCCS1)C2)C)CCc3ccccc3
InChI
  • 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 Y
  • Key:HRWCVUIFMSZDJS-SZMVWBNQSA-N Y
 NY (what is this?)  (verify)

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, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN 9783527607495.
  2. Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G (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". Scand J Urol Nephrol. 33 (1): 57–62. doi:10.1080/003655999750016294. PMID 10100366.
  3. Noble S, Sorkin E (1995). "Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension". Drugs. 49 (5): 750–66. doi:10.2165/00003495-199549050-00008. PMID 7601014.
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