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Spirapril

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Title: Spirapril  
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Spirapril

Spirapril
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
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  YesY
ATC code C09
PubChem
DrugBank
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  YesY
Chemical data
Formula C22H30N2O5S2 
Mol. mass 466.616 g/mol
 N   

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

  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.  
  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.  
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