Basic information
- CAS
83059-56-7- Standard SMILES
CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1C2CCC(CC2)[C@H]1C(=O)O- InChIKey
OMGPCTGQLHHVDU-SSXGPBTGSA-N- Molecular formula
- C23H32N2O5
- Average molar mass
- 416.5 g/mol
- Monoisotopic mass
- 416.23112213
Overview
Zabicipril is a non-thiol angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. As a prodrug, zabicipril is rapidly converted in vivo by de-esterification into its active form zabiciprilat. Zabiciprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Zabiciprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.
Names & identifiers
- Preferred name
- Zabicipril
- IUPAC
- (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-2-azabicyclo[2.2.2]octane-3-carboxylic acid
- English name
- Zabicipril
- Molecular formula
- C23H32N2O5
- Molecular weight
- 416.51
Names & synonyms
Zabicipril83059-56-7Zabiciprilum475035SS4CDTXSID70868694(3S)-2-((2S)-N-((1S)-1-Carboxy-3-phenylpropyl)alanyl)-2-azabicyclo(2.2.2)octane-3-carboxylic acid, 1-ethyl ester2-(N-(1-carboxy-3-phenylpropyl)alanyl)-2-azabicyclo(2.2.2)octane-3-carboxylic acid 1-ethyl esterRefChem:195819S-9650DTXCID101780775S9650Zabicipril [INN]
Show more names
(3S)-2-[(S)-2-[[(S)-1-Ethoxycarbonyl-3-phenylpropyl]amino]-1-oxopropyl]-2-azabicyclo[2.2.2]octane-3-carboxylic acid
(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-2-azabicyclo[2.2.2]octane-3-carboxylic acidZabiciprilum [Latin]UNII-475035SS4C(3s)-2-{n-[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-l-alanyl}-2-azabicyclo[2.2.2]octane-3-carboxylic acidZABICIPRIL [WHO-DD]SCHEMBL636681orb1819135CHEMBL3989608
Database identifiers
- CAS
83059-56-7- PubChem CID
- 71262
- DTXSID
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 95.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 10
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 611
Physicochemical properties
- Boiling point
- 616.166 · 616.166±55.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.201 · 1.201±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 3.127 · 3.127±0.20(predicted)
- FDA UNII
- 475035 SS4C · 475035SS4C
Chemistry & industry
Applications
UsesZabicipril is an orally active angiotensin-converting enzyme (ACE) inhibitor. Zabicipril can be used for the study of blood pressure and peripheral arterial insufficiency[1].
Upstream & downstream products
Upstream raw materials
Suppliers6 total
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
北京博奥森生物技术有限公司400-901-9800 18611424007 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…