spirapril   Click here for help

GtoPdb Ligand ID: 6575

Synonyms: Renormax® | SCH-33844
Approved drug
spirapril is an approved drug (FDA (1994))
Compound class: Synthetic organic
Comment: ACE inhibitor prodrug metabolised to spiraprilat
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 146.54
Molecular weight 466.16
XLogP 2.97
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOC(=O)C(NC(C(=O)N1CC2(CC1C(=O)O)SCCS2)C)CCc1ccccc1
Isomeric SMILES CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)C)CCc1ccccc1
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
InChI Key HRWCVUIFMSZDJS-SZMVWBNQSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1994))
Withdrawn drug? Yes
Is prodrug? Yes
Active form spiraprilat
IUPAC Name Click here for help
(7S)-8-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-8-azaspiro[4.4]nonane-7-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
6006 spirapril
Synonyms Click here for help
Renormax® | SCH-33844
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9619016
Reactome Reaction Reactome logo R-HSA-9619024
Other databases
CAS Registry No. 83647-97-6 (source: PubChem)
ChEMBL Ligand CHEMBL431
DrugBank Ligand DB01348
DrugCentral Ligand 2474
GtoPdb PubChem SID 178103189
PubChem CID 5311447
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Wikipedia Spirapril