| Revision as of 22:08, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'UNII', 'ChEMBL', 'StdInChI', 'StdInChIKey', 'CASNo').← Previous edit |
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{{short description|Antihypertensive drug of the ACE inhibitor class}} |
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{{Unreferenced|date = February 2011}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| ImageFile = Cilazapril.svg |
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| Watchedfields = changed |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| verifiedrevid = 460036705 |
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| ImageSize = 121 |
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| ImageFile = Cilazapril structure.svg |
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| ImageName = Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-amin,-1-carbox) |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| IUPACName = Cilazapril |
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| ImageSize = 222 |
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| SystematicName = 9--10-oxo-octahydro-1''H''-pyridazinodiazepine-1-carboxylic acid{{Reference necessary|date=April 2011}} |
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| ImageName = Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-amin,-1-carbox) |
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| Section1 = {{Chembox Identifiers |
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| PIN = (1''S'',9''S'')-9-{amino}-10-oxooctahydro-6''H''-pyridazinodiazepine-1-carboxylic acid |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 19KW7PI29F |
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|Section1 = {{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 88768-40-5 --> |
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| IUPHAR_ligand = 6459 |
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| CASNo_Comment = <small>(1''S'',9''S'')-9-amin,-1-carbox</small> |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| PubChem = 2751 |
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| UNII = 8Q9454114Q |
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| PubChem_Ref = {{Pubchemcite|correct|pubchem}} |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| PubChem1 = 40467985 |
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| CASNo = 88768-40-5 |
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| PubChem1_Ref = {{Pubchemcite|correct|pubchem}} |
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| PubChem = 56330 |
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| PubChem1_Comment = <small>(1''R'',9''S'')-9-amin,-1-carbox</small> |
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| PubChem2 = 56330 |
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| PubChem1 = 40467985 |
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| PubChem1_Comment = (1''R'',9''S'')-(2''S'')-butylamino isomer |
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| PubChem2_Ref = {{Pubchemcite|correct|pubchem}} |
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| ChemSpiderID = 50831 |
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| PubChem2_Comment = <small>(1''S'',9''S'')-9-amin,-1-carbox</small> |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 50830 |
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| KEGG = D07699 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChemSpiderID1 = 50831 |
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| ChEBI = 3698 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL = 515606 |
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| ChemSpiderID2_Comment = <small>(1''S'',9''S'')-9-amin,-1-carbox</small> |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| KEGG = D07699 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01340 |
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| ChEMBL = <!-- blanked - oldvalue: 515606 --> |
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| ChEMBL_Ref = {{ebicite|corect|EBI}} |
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| ATCCode_prefix = C09 |
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| ATCCode_suffix = AA08 |
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| DrugBank = DB01340 |
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| SMILES = CCOC(=O)C(CCc1ccccc1)NC1CCCN2CCCC(N2C1=O)C(O)=O |
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| SMILES = CCOC(=O)C(CCc1ccccc1)NC1CCCN2CCCC(N2C1=O)C(O)=O |
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| StdInChI = 1S/C22H31N3O5.H2O/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26;/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28);1H2/t17-,18-,19-;/m0./s1 |
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| StdInChI = 1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28) |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JQRZBPFGBRIWSN-YOTVLOEGSA-N |
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| StdInChIKey = HHHKFGXWKKUNCY-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2 = {{Chembox Properties |
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| C = 22 |
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| H = 31 |
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| C=22 | H=31 | N=3 | O=5 |
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| N = 3 |
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| LogP = 2.212 |
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| O = 5 |
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| pKa = 2.285 |
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| pKb = 11.712 |
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| ExactMass = 417.226371117 g mol<sup>-1</sup> |
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| LogP = 2.212 |
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| pKa = 2.285 |
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| pKb = 11.712 |
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}} |
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}} |
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| Section3 = {{Chembox Pharmacology |
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|Section6={{Chembox Pharmacology |
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| AdminRoutes = Oral |
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| Legal_UK = POM |
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| ATCCode_prefix = C09 |
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| ATCCode_suffix = AA08 |
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| AdminRoutes = Oral |
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| Legal_UK = POM |
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}} |
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}} |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Cilazapril''' is an ] inhibitor (]) used for the treatment of ] and ].<ref>{{Cite journal |
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| last1 = Szucs | first1 = T. |
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| title = Cilazapril. A review |
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| journal = Drugs |
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| volume = 41 |
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| pages = 18–24 |
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| year = 1991 |
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| issue = Suppl 1 |
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| pmid = 1712267 |
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| doi=10.2165/00003495-199100411-00005 |
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| s2cid = 261123720 |
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}}</ref><ref>{{cite book|title=Austria-Codex|editor=Jasek, W|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=2007/2008|isbn=978-3-85200-181-4|language=German}}</ref> |
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<!-- Society and culture --> |
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'''Cilazapril''' is a ] ] inhibitor (]) used for the treatment of ] and ]. It is branded as Inhibace in Canada, Zapril in New Zealand, Vascace and Dynorm in Europe. According to (who have a partnership with the ) none of these are currently available in the ] as of May 2010. |
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It was patented in 1982 and approved for medical use in 1990.<ref name=Fis2006>{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=469 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA469 |language=en}}</ref> |
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==Chemistry== |
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Several stereo isomers exist of which, only one isomer is medically viable: cilazapril ((1S,9S)-9-amin,-1-carbox) |
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Of the eight possible ], only the all-(''S'')-form is medically viable.{{citation needed|date=February 2012}} |
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==Brand names== |
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It is branded as Dynorm, Inhibace, Vascace and many other names in various countries. None of these are available in the United States as of May 2010.<ref>"". '']''. Retrieved 28 May 2010.</ref> |
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==References== |
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==References== |
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{{reflist}} |
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Cilazapril monograph. Lexi-Comp Online, Lexi-Drugs Online, Lexi-Comp Inc. Hudson, OH. Available at: . Accessed October 5th, 2008. |
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{{ACE inhibitors}} |
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{{ACE inhibitors}} |
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{{Angiotensin receptor modulators}} |
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{{cardiovascular-drug-stub}} |
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{{cardiovascular-drug-stub}} |
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