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
Trade names	Renormax
AHFS/Drugs.com	International Drug Names
Pregnancy category	D
Routes of administration	Oral
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^Y
ATC code	C09AA11 (WHO)
PubChem	CID 5311447
IUPHAR/BPS	6575
DrugBank	DB01348^N
ChemSpider	4470933^Y
UNII	96U2K78I3V^Y
KEGG	D08529^Y
ChEMBL	CHEMBL431^Y
Chemical data
Formula	C₂₂H₃₀N₂O₅S₂
Molar 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
^NY (what is this?) (verify)

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

Spiraprilat — the active metabolite

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]

References

↑ 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.
↑ 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.

Antihypertensives: agents acting on the renin–angiotensin system (C09)

ACE inhibitors ("-pril")	Sulfhydryl-containing: Captopril Rentiapril Zofenopril Dicarboxylate-containing: Enalapril^# Benazepril Cilazapril Delapril Imidapril Lisinopril (+HCT) Moexipril Perindopril Quinapril (+HCT) Ramipril Spirapril Temocapril Trandolapril Phosphonate-containing: Fosinopril (+HCT) Other/ungrouped: Alacepril

AIIRAs/ ("-sartan")	Azilsartan Candesartan Eprosartan Fimasartan Irbesartan Losartan (+HCT) Olmesartan (+amlodipine) Tasosartan^§ Telmisartan (+HCT) Valsartan (+HCT, +amlodipine, +sacubitril)

Renin inhibitors/ ("-kiren")	Aliskiren (+amlodipine, +amlodipine and HCT) Remikiren^§

^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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