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	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 Y
ATC code	C09AA11
PubChem	CID 5311447
DrugBank	DB01348
ChemSpider	4470933 Y
UNII	96U2K78I3V Y
KEGG	D08529 Y
ChEMBL	CHEMBL431 Y
Chemical data
Formula	C22H30N2O5S2
Mol. mass	466.616 g/mol
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
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 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-carboxylic acid hydrobromide CAS 75776-79-3

and

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

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.