Spirapril

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Spirapril
Spirapril.svg
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.
  • D
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 50%
Metabolism converted to spiraprilat
Half-life 30 to 35 hours
Excretion Hepatic and renal
Identifiers
CAS number 83647-97-6 YesY
ATC code C09AA11
PubChem CID 5311447
DrugBank DB01348
ChemSpider 4470933 YesY
UNII 96U2K78I3V YesY
KEGG D08529 YesY
ChEMBL CHEMBL431 YesY
Chemical data
Formula C22H30N2O5S2 
Mol. mass 466.616 g/mol
 N (what is this?)  (verify)

Spirapril hydrochloride (Renormax) is an ACE inhibitor antihypertensive drug used to treat hypertension. It belongs to dicarboxy group of ace inhibitor.

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.[1] However, data on its effect upon the renal function are conflicting.[2]

It is produced synthetically by combining these pharmaceutical intermediates:

(S)-1,4-Dithia-7-azaspiro(4,4)-nonane-8-carboxylic acid hydrobromide CAS 75776-79-3

and

N-[1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-Alanine (ECPPA) [1]

References[edit]

  1. ^ 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. 
  2. ^ 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.