GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

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
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
Click here for help
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US 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Withdrawn drug?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, 2474
GtoPdb PubChem SID 178103189
PubChem CID 5311447
Search Google for chemical match using the InChIKey HRWCVUIFMSZDJS-SZMVWBNQSA-N
Search Google for chemicals with the same backbone HRWCVUIFMSZDJS
Search PubMed clinical trials spirapril
Search PubMed titles spirapril
Search PubMed titles/abstracts spirapril
UniChem Compound Search for chemical match using the InChIKey HRWCVUIFMSZDJS-SZMVWBNQSA-N
UniChem Connectivity Search for chemical match using the InChIKey HRWCVUIFMSZDJS-SZMVWBNQSA-N
Wikipedia Spirapril