Zofenopril-d5

Modify Date: 2024-01-04 08:41:28

Zofenopril-d5 Structure
Zofenopril-d5 structure
Common Name Zofenopril-d5
CAS Number 81872-10-8 Molecular Weight 429.552
Density 1.3±0.1 g/cm3 Boiling Point 646.3±55.0 °C at 760 mmHg
Molecular Formula C22H23NO4S2 Melting Point 129-131.5ºC(lit.)
MSDS N/A Flash Point 344.7±31.5 °C

 Use of Zofenopril-d5


Zofenopril is an angiotensin-converting enzyme (ACE) inhibitor with an IC50 of 81 μM.

 Names

Name zofenopril
Synonym More Synonyms

 Zofenopril-d5 Biological Activity

Description Zofenopril is an angiotensin-converting enzyme (ACE) inhibitor with an IC50 of 81 μM.
Related Catalog
Target

IC50: 81 μM (ACE)[1]

In Vitro Kinetic analyses demonstrate that enalapril inhibits the uptake of GlySar in a competitive manner (Ki approximately 6 mM). Fosinopril and Zofenopril have the greatest inhibitory potency (IC50 values of 55 and 81μM, respectively) while the other ACE inhibitors exhibit low-affinity interactions with the renal peptide transporter[1].
In Vivo Zofenopril, a sulphydrylic compound, at doses higher than 70 mg/kg i.p. produces significant protection (i.e. at 70 mg/kg, P=0.044, F=2.17, d.f.=18; at higher concentration P<0.05) against the tonic phase of the audiogenic seizure response. Pretreatment with Zofenopril (15 mg/kg, i.p.) is able to produce a consistent shift to the left of the dose-response curves and a significant reduction of ED50 values against clonus of some AEDs with the exceptions of diazepam, felbamate, phenobarbital and phenytoin compare with concurrent groups, suggesting an increase in anticonvulsant activity[2].
Cell Assay Studies are performed in rabbit renal brush border membrane vesicles in which the uptake of radiolabeled GlySar is examined in the absence and presence of captopril, enalapril, enalaprilat, fosinopril, lisinopril, quinapril, quinaprilat, ramipril and Zofenopril[1].
Animal Admin Male and female mice weighing 8 to12 g (22 to 26 days old) or 20 to 28 g (48 to 56 days old) are used. Mice are exposed to auditory stimulation, 45, 60 or 120 min following intraperitoneal (i.p.) administration of ACE inhibitors (including Zofenopril) (10 to 100 mg/kg) or vehicle and 45 min following i.p. injection of the AEDs studied. All ACE inhibitors are suspended in a 1% solution of Tween 80 before administration[2].
References

[1]. Lin CJ, et al. Competitive inhibition of glycylsarcosine transport by enalapril in rabbit renal brush border membrane vesicles: interaction of ACE inhibitors with high-affinity H+/peptide symporter. Pharm Res. 1999 May;16(5):609-15.

[2]. Sarro GD, et al. Fosinopril and zofenopril, two angiotensin-converting enzyme (ACE) inhibitors, potentiate the anticonvulsant activity of antiepileptic drugs against audiogenic seizures in DBA/2 mice. Pharmacol Res. 2012 Mar;65(3):285-96.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 646.3±55.0 °C at 760 mmHg
Melting Point 129-131.5ºC(lit.)
Molecular Formula C22H23NO4S2
Molecular Weight 429.552
Flash Point 344.7±31.5 °C
Exact Mass 429.106842
PSA 125.28000
LogP 3.78
Appearance of Characters crystalline | light yellow
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.659
Storage condition 2-8°C

 Safety Information

Hazard Codes Xn: Harmful;Xi: Irritant;
Risk Phrases R22
Safety Phrases 23-24/25
WGK Germany 3
RTECS QJ0875000

 Synthetic Route

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Zofenopril-d5 Structure

Zofenopril-d5

CAS#:81872-10-8

Literature: Tetrahedron Letters, , vol. 52, # 13 p. 1493 - 1494

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Zofenopril-d5 Structure

Zofenopril-d5

CAS#:81872-10-8

Literature: WO2010/84515 A2, ; Page/Page column 33 ;

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Zofenopril-d5 Structure

Zofenopril-d5

CAS#:81872-10-8

Literature: WO2010/84515 A2, ; Page/Page column 32 ;

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Zofenopril-d5 Structure

Zofenopril-d5

CAS#:81872-10-8

Literature: Krapcho; Turk; Cushman; Powell; DeForrest; Spitzmiller; Karanewsky; Duggan; Rovnvak; Schwartz; Natarajan; Godfrey; Ryono; Neubeck; Atwa; Petrillo Jr. Journal of Medicinal Chemistry, 1988 , vol. 31, # 6 p. 1148 - 1160

 Synonyms

L-Proline, 1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-, (4S)-
UNII-290ZY759PI
(4S)-N-((S)-3-Mercapto-2-methylpropionyl)-4-(phenylthio)-L-proline Benzoate (Ester)
Zoprace
(1(R*),2a,4a)-1-(3-(Benzoylthio)-2-methyl-1-oxopropyl)-4-(phenylthio)-L-proline
Zofenopril
(4S)-1-[(2S)-3-(Benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)-L-proline
Zofenoprilum
(2S,4S)-1-[(2S)-3-benzoylsulfanyl-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid
MFCD00004046
EINECS 201-705-8