This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Zofenopril
Accession Number
DB13166
Type
Small Molecule
Groups
Experimental
Description

Zofenopril is a medication that protects the heart and helps reduce high blood pressure. It is an angiotensin-converting enzyme (ACE) inhibitor.

Structure
Thumb
Synonyms
  • Zofenil
  • Zofénopril
  • Zofenopril
  • Zofenoprilum
Product Ingredients
IngredientUNIICASInChI Key
Zofenopril calcium88ZQ329PU281938-43-4NSYUKKYYVFVMST-LETVYOFWSA-L
Categories
UNII
290ZY759PI
CAS number
81872-10-8
Weight
Average: 429.55
Monoisotopic: 429.106850573
Chemical Formula
C22H23NO4S2
InChI Key
IAIDUHCBNLFXEF-MNEFBYGVSA-N
InChI
InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1
IUPAC Name
(2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid
SMILES
[H][C@@](C)(CSC(=O)C1=CC=CC=C1)C(=O)N1C[C@]([H])(C[C@@]1([H])C(O)=O)SC1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AAngiotensin-converting enzyme
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Zofenopril.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Zofenopril.
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Zofenopril.
AcebutololAcebutolol may increase the hypotensive activities of Zofenopril.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Zofenopril.
AcemetacinThe therapeutic efficacy of Zofenopril can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acetylsalicylic acid is combined with Zofenopril.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Zofenopril.
AlfuzosinAlfuzosin may increase the hypotensive activities of Zofenopril.
AliskirenAliskiren may increase the hypotensive, nephrotoxic, and hyperkalemic activities of Zofenopril.
Food Interactions
Not Available

References

General References
  1. Nilsson P: Antihypertensive efficacy of zofenopril compared with atenolol in patients with mild to moderate hypertension. Blood Press Suppl. 2007 Oct;2:25-30. [PubMed:18046976]
  2. Mallion JM: An evaluation of the initial and long-term antihypertensive efficacy of zofenopril compared with enalapril in mild to moderate hypertension. Blood Press Suppl. 2007 Oct;2:13-8. [PubMed:18046974]
External Links
KEGG Drug
D08688
PubChem Compound
92400
PubChem Substance
347829273
ChemSpider
83422
BindingDB
50084629
ChEBI
78539
ChEMBL
CHEMBL331378
Wikipedia
Zofenopril
ATC Codes
C09BA15 — Zofenopril and diureticsC09AA15 — Zofenopril

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00311 mg/mLALOGPS
logP3.64ALOGPS
logP4.31ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.68 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.82 m3·mol-1ChemAxon
Polarizability44.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
N-acyl-L-alpha-amino acids / Thiobenzoic acids and derivatives / Benzoic acids and derivatives / Thiophenol ethers / Pyrrolidine carboxylic acids / Benzoyl derivatives / N-acylpyrrolidines / Alkylarylthioethers / Tertiary carboxylic acid amides / Thioesters
show 10 more
Substituents
N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / N-acyl-alpha-amino acid / Proline or derivatives / Thiobenzoic acid or derivatives / Benzoic acid or derivatives / Pyrrolidine carboxylic acid or derivatives / Thiophenol ether / Pyrrolidine carboxylic acid / N-acylpyrrolidine
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thioester, aryl sulfide, N-acyl-L-amino acid, L-proline derivative (CHEBI:78539)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent...
Gene Name
ACE
Uniprot ID
P12821
Uniprot Name
Angiotensin-converting enzyme
Molecular Weight
149713.675 Da
References
  1. Ambrosioni E: Defining the role of zofenopril in the management of hypertension and ischemic heart disorders. Am J Cardiovasc Drugs. 2007;7(1):17-24. [PubMed:17355163]

Drug created on February 11, 2017 08:59 / Updated on October 01, 2018 16:49