Spirapril

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 ;
PubChem CID	5311447;
IUPHAR/BPS	6575;
DrugBank	DB01348 ;
ChemSpider	4470933 ;
UNII	96U2K78I3V;
KEGG	D08529 ;
ChEBI	CHEBI:135756;
ChEMBL	ChEMBL431 ;
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 ; Key:HRWCVUIFMSZDJS-SZMVWBNQSA-N ;
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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.^{[citation needed]}

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

^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN 978-3-527-60749-5.
^ Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G (February 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". Scandinavian Journal of Urology and Nephrology. 33 (1): 57–62. doi:10.1080/003655999750016294. PMID 10100366.
^ Noble S, Sorkin EM (May 1995). "Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension". Drugs. 49 (5): 750–766. doi:10.2165/00003495-199549050-00008. PMID 7601014. S2CID 195691037.

External links

Media related to Spirapril at Wikimedia Commons

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[Fis2006-1] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 468. ISBN 978-3-527-60749-5.

[2] Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G (February 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". Scandinavian Journal of Urology and Nephrology. 33 (1): 57–62. doi:10.1080/003655999750016294. PMID 10100366.

[3] Noble S, Sorkin EM (May 1995). "Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension". Drugs. 49 (5): 750–766. doi:10.2165/00003495-199549050-00008. PMID 7601014. S2CID 195691037.

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v t e Antihypertensive drugs acting on the renin–angiotensin system (C09)
ACE inhibitors ("-pril")	Sulfhydryl-containing: Captopril Rentiapril Zofenopril (+nebivolol) Dicarboxylate-containing: Enalapril^# (+lercanidipine, +nitrendipine) Benazepril (+amlodipine, +pimobendan) Cilazapril Delapril (+manidipine) Imidapril Lisinopril (+amlodipine, +HCT) Moexipril Perindopril (+amlodipine, +bisoprolol, +indapamide, +amlodipine and indapamide, +bisoprolol and amlodipine, +bisoprolol, amlodipine, and indapamide) Quinapril (+HCT) Ramipril (+amlodipine, +amlodipine and HCT, +bisoprolol, +felodipine) Spirapril Temocapril Trandolapril (+verapamil) Phosphonate-containing: Ceronapril Fosinopril (+HCT) Other/ungrouped: Alacepril
AIIRAs ("-sartan")	Azilsartan Candesartan (+amlodipine, +amlodipine and HCT) Eprosartan Fimasartan Irbesartan (+amlodipine, +amlodipine and HCT, +HCT) Losartan (+amlodipine, +HCT) Olmesartan (+amlodipine, +amlodipine and HCT, +HCT) Tasosartan^§ Telmisartan (+amlodipine, +amlodipine and HCT, +HCT) Valsartan (+aliskiren, +amlodipine, +amlodipine and HCT, +HCT, +lercanidipine, +nebivolol, +sacubitril)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine, +HCT, +amlodipine and HCT) Remikiren^§
Dual ACE/NEP inhibitors	Gemopatrilat Ilepatril Omapatrilat Sampatrilat
Neprilysin inhibitors	Sacubitril (+valsartan)
Other	Sparsentan
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III