Gemopatrilat

Gemopatrilat
Clinical data
Other names	BMS-189921
ATC code	None;
Identifiers
	IUPAC name (6S)-Hexahydro-6-[(αS)-α-mercaptohydrocinnamido]-2,2-dimethyl-7-oxo-1H-azepine-1-acetic acid;
CAS Number	160135-92-2;
PubChem CID	9886079;
ChemSpider	8061752;
UNII	MU9089C77W;
KEGG	D04312;
ChEMBL	ChEMBL107747;
CompTox Dashboard (EPA)	DTXSID901029484 ;
Chemical and physical data
Formula	C19H26N2O4S
Molar mass	378.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(CCC[C@@H](C(=O)N1CC(=O)O)NC(=O)[C@H](CC2=CC=CC=C2)S)C;
	InChI InChI=1S/C19H26N2O4S/c1-19(2)10-6-9-14(18(25)21(19)12-16(22)23)20-17(24)15(26)11-13-7-4-3-5-8-13/h3-5,7-8,14-15,26H,6,9-12H2,1-2H3,(H,20,24)(H,22,23)/t14-,15-/m0/s1; Key:YRSVDSQRGBYVIY-GJZGRUSLSA-N;

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Gemopatrilat (INN)^[1] is an experimental drug that was never marketed.^[2] It acts as a vasopeptidase inhibitor.^[3]^[4] It inhibits both angiotensin-converting enzyme (ACE) and neutral endopeptidase (neprilysin).^[5]

References

^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 46" (PDF). World Health Organization. p. 200. Retrieved 2 March 2017.
^ "Gemopatrilat". AdisInsight. Highest Development Phases: Discontinued
^ Laverman GD, Van Goor H, Henning RH, De Jong PE, De Zeeuw D, Navis G (January 2003). "Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes". Kidney International. 63 (1): 64–71. doi:10.1046/j.1523-1755.2003.00708.x. PMID 12472769.
^ Wait JC, Vaccharajani N, Mitroka J, Jemal M, Khan S, Bonacorsi SJ, et al. (June 2006). "Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans". Drug Metabolism and Disposition. 34 (6): 961–70. doi:10.1124/dmd.105.007500. PMID 16540589. S2CID 25629874.
^ Hubner RA, Kubota E, Casley DJ, Johnston CI, Burrell LM (May 2001). "In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat". Journal of Hypertension. 19 (5): 941–6. doi:10.1097/00004872-200105000-00015. PMID 11393678. S2CID 9162678.

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[INN-1] "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 46" (PDF). World Health Organization. p. 200. Retrieved 2 March 2017.

[2] "Gemopatrilat". AdisInsight. Highest Development Phases: Discontinued

[3] Laverman GD, Van Goor H, Henning RH, De Jong PE, De Zeeuw D, Navis G (January 2003). "Renoprotective effects of VPI versus ACEI in normotensive nephrotic rats on different sodium intakes". Kidney International. 63 (1): 64–71. doi:10.1046/j.1523-1755.2003.00708.x. PMID 12472769.

[4] Wait JC, Vaccharajani N, Mitroka J, Jemal M, Khan S, Bonacorsi SJ, et al. (June 2006). "Metabolism of [14C]gemopatrilat after oral administration to rats, dogs, and humans". Drug Metabolism and Disposition. 34 (6): 961–70. doi:10.1124/dmd.105.007500. PMID 16540589. S2CID 25629874.

[5] Hubner RA, Kubota E, Casley DJ, Johnston CI, Burrell LM (May 2001). "In-vitro and in-vivo inhibition of rat neutral endopeptidase and angiotensin converting enzyme with the vasopeptidase inhibitor gemopatrilat". Journal of Hypertension. 19 (5): 941–6. doi:10.1097/00004872-200105000-00015. PMID 11393678. S2CID 9162678.

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