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Omapatrilat: Difference between revisions

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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| IUPAC_name = (4''S'',7''S'',10a''S'')-5-oxo-4-{[(2''S'')-3-phenyl-2- sulfanylpropanoyl]amino}-2,3,4,7,8,9,10,10a-octahydropyrido[6,1-''b''] [1,3]thiazepine-7-carboxylic acid
| Watchedfields = changed
| image = Omapatrilat.svg
| verifiedrevid = 384076476
| CAS_number = 167305-00-2
| IUPAC_name = (4''S'',7''S'',10a''S'')-Octahydro-4-[(''S'')-α-mercaptohydrocinnamamido]-5-oxo-7''H''-pyrido[2,1-''b''][1,3]thiazepine-7-carboxylic acid
| CAS_supplemental =
| image = Omapatrilat.svg
| ATC_prefix = none
 
| ATC_suffix =
<!--Clinical data-->
| ATC_supplemental =
| tradename =
| PubChem = 656629
| DrugBankpregnancy_AU = <!-- A / B1 / B2 / B3 =/ C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| chemical_formula =
| pregnancy_category =
| C=19 | H=24 | N=2 | O=4 | S=2
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| molecular_weight = 408.534 g/mol
| smileslegal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII = -->
| synonymslegal_UK = <!-- GSL, P, POM, CD, or Class A, =B, C -->
| densitylegal_US = <!-- OTC / Rx-only / Schedule I, II, III, =IV, V -->
| legal_status = Development terminated
| melting_point =
| routes_of_administration =
| melting_high =
 
| melting_notes =
<!--Pharmacokinetic data-->
| boiling_point =
| bioavailability =
| boiling_notes =
| protein_bound =
| solubility =
| metabolism =
| specific_rotation =
| elimination_half-life =
| sec_combustion =
| excretion =
| bioavailability =
 
| protein_bound =
<!--Identifiers-->
| metabolism =
| CAS_number_Ref = {{cascite|correct|??}}
| elimination_half-life =
| CAS_number = 167305-00-2
| excretion =
| ATC_prefix = None
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| ATC_suffix =
| pregnancy_US = <!-- A / B / C / D / X -->
| ATC_supplemental =
| pregnancy_category=
| PubChem = 656629
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| DrugBank =
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| UNII_Ref = {{fdacite|changed|FDA}}
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| UNII = 36NLI90E7T
| legal_status =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| routes_of_administration =
| ChEMBL = 289556
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 570983
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D01970
 
<!--Chemical data-->
| chemical_formula =
| C=19 | H=24 | N=2 | O=4 | S=2
| smiles = c1ccc(cc1)C[C@@H](C(=O)N[C@H]2CCS[C@H]3CCC[C@H](N3C2=O)C(=O)O)S
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C19H24N2O4S2/c22-17(15(26)11-12-5-2-1-3-6-12)20-13-9-10-27-16-8-4-7-14(19(24)25)21(16)18(13)23/h1-3,5-6,13-16,26H,4,7-11H2,(H,20,22)(H,24,25)/t13-,14-,15-,16-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LVRLSYPNFFBYCZ-VGWMRTNUSA-N
| synonyms = BMS-186716
| density =
| melting_notes =
| boiling_point =
| solubility =
| specific_rotation =
| sec_combustion =
}}
'''Omapatrilat''' ([[International Nonproprietary Name|INN]]) is a novel [[antihypertensive agent]] that inhibits both [[neutral endopeptidase]] (NEP) and [[angiotensin converting enzyme]] (ACE). NEP inhibition results in elevated [[natriuretic]] peptide levels, promoting [[natriuresis]], [[diuresis]], [[vasodilation]], and reductions in preload and ventricular remodeling.
 
'''Omapatrilat''' ([[International Nonproprietary Name|INN]],<ref name = "INN">{{cite web | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 40 | url =https://www.who.int/medicines/publications/druginformation/innlists/RL43.pdf | publisher = World Health Organization | access-date = 2 March 2017 | page = 190}}</ref> proposed trade name '''Vanlev''') is an experimental [[antihypertensive agent]] that was never marketed.<ref>{{Cite web | url = http://adisinsight.springer.com/drugs/800020109 | title = Omapatrilat | work = Adis Insight | publisher = Springer Nature Switzerland AG }}</ref> It inhibits both [[neprilysin]] (neutral endopeptidase, NEP) and [[angiotensin-converting enzyme]] (ACE). NEP inhibition results in elevated [[Atrial natriuretic peptide|natriuretic]] peptide levels, promoting [[natriuresis]], [[:wikt:diuresis|diuresis]], [[vasodilation]], and reductions in preload and ventricular remodeling.
This drug from [[Bristol-Myers Squibb]] was not approved by the U.S. [[Food and Drug Administration]] due to [[angioedema]] safety concerns.<ref>Joshi Venugopal. (2003) Pharmacological modulation of the natriuretic peptide system. Expert Opinion on Therapeutic Patents 13:9, 1389</ref>
 
It was discovered and developed by [[Bristol-Myers Squibb]] but failed in clinical trials as a potential treatment for [[congestive heart failure]] due to safety concerns about its causing [[angioedema]].<ref>{{cite journal | vauthors = Venugopal J | title = Pharmacological Modulation of the Natriuretic Peptide System | journal = Expert Opinion on Therapeutic Patents | date = 2 March 2005 | volume = 13 | issue = 9 | pages = 1389–1409 | doi = 10.1517/13543776.13.9.1389 | s2cid = 85007768 }}</ref>
 
Omapatrilat [[angioedema]] was attributed to its dual mechanism of action, inhibiting both [[angiotensin-converting enzyme]] (ACE), and [[neprilysin]] (neutral endopeptidase), both of these enzymes are responsible for the metabolism of [[bradykinin]] which causes vasodilation, angioedema, and airway obstruction.
 
== See also ==
* [[Gemopatrilat]]
* [[Cilazapril]]
* [[Sacubitril]]
 
== References ==
{{Reflist}}
 
== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Liao WC, Vesterqvist O, Delaney C, Jemal M, Ferreira I, Ford N, Swanson B, Uderman H | display-authors = 6 | title = Pharmacokinetics and pharmacodynamics of the vasopeptidase inhibitor, omapatrilat in healthy subjects | journal = British Journal of Clinical Pharmacology | volume = 56 | issue = 4 | pages = 395–406 | date = October 2003 | pmid = 12968984 | pmc = 1884361 | doi = 10.1046/j.1365-2125.2003.01888.x }}
{{refend}}
 
{{Agents acting on the renin-angiotensin system}}
==References==
{{Angiotensin receptor modulators}}
{{reflist}}
 
[[Category:ACE inhibitors]]
[[Category:Heterocyclic compounds with 2 rings]]
[[Category:Carboxylic acids]]
[[Category:Lactams]]
[[Category:Propionamides]]
[[Category:Thiols]]
[[Category:Nitrogen heterocycles]]
[[Category:Sulfur heterocycles]]
[[Category:Abandoned drugs]]
 
{{antihypertensivecardiovascular-drug-stub}}
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