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 names	Renormax
AHFS/Drugs.com	International Drug Names
Pregnancy category	D
Routes of administration	Oral
ATC code	C09AA11 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	50%
Metabolism	converted to spiraprilat
Elimination half-life	30 to 35 hours
Excretion	Hepatic 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	83647-97-6^Y
PubChem CID	5311447
IUPHAR/BPS	6575
DrugBank	DB01348^N
ChemSpider	4470933^Y
UNII	96U2K78I3V
KEGG	D08529^Y
ChEBI	CHEBI:135756
ChEMBL	ChEMBL431^Y
CompTox Dashboard (EPA)	DTXSID1044300
Chemical and physical data
Formula	C22H30N2O5S2
Molar mass	466.61 g·mol^−1
3D model (JSmol)	Interactive image
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.