Spirapril

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Spirapril
File: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
Pregnancy
category
  • D
Routes of
administration
Oral
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 50%
Metabolism converted to spiraprilat
Biological half-life 30 to 35 hours
Excretion Hepatic and renal
Identifiers
CAS Number 83647-97-6
ATC code C09AA11 (WHO)
PubChem CID 5311447
Chemical data
Formula C22H30N2O5S2
Molar mass 466.616 g/mol[[Script error: No such module "String".]]
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Spirapril hydrochloride (Renormax) is an ACE inhibitor antihypertensive drug used to treat hypertension.

Like many ACE inhibitors, this is a prodrug which 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 is conflicting.[2]


It is produced synthetically by combining the following two pharmaceutical intermediates:

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

and

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

Footnotes

  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. PMID 7601014. 


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