cilazaprilat   Click here for help

GtoPdb Ligand ID: 6461

Synonyms: Ro 31-3113
Approved drug
cilazaprilat is an approved drug
Compound class: Synthetic organic
Comment: Active compound derived by metabolism of prodrug cilazapril. Technically this compound is not an approved drug, as the approved drug is administered as a prodrug which is then metabolised to this active form. We mark both the prodrug and active form as 'approved' for clarity. Note that the prodrug, cilazapril, does not appear to have marketing approval for human use in the US or EU, although individual countries may have approved use of this drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 110.18
Molecular weight 389.2
XLogP 1.41
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)C(NC1CCCN2N(C1=O)C(CCC2)C(=O)O)CCc1ccccc1
Isomeric SMILES OC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
InChI InChI=1S/C20H27N3O5/c24-18-15(8-4-12-22-13-5-9-17(20(27)28)23(18)22)21-16(19(25)26)11-10-14-6-2-1-3-7-14/h1-3,6-7,15-17,21H,4-5,8-13H2,(H,25,26)(H,27,28)/t15-,16-,17-/m0/s1
No information available.
Summary of Clinical Use Click here for help
ACE inhibitor used for the treatment of hypertension and congestive heart failure
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cilazaprilat competes with angiotensisn I for binding to ACE thereby inhibiting its enzymatic conversion to angiotensin II. Reduced levels of angiotensin II leads to reduced blood pressure. However, we have been unable to find molecular data for this drug at the human target, to substantiate its MMOA.