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Fosfenopril

CAT: 0804-HY-107352-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-107352-01Size:5 mg
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Description
Fosfenopril (Fosinoprilat) is a potent angiotensin converting enzyme (ACE) inhibitor. Fosfenopril alleviates lipopolysaccharide (LPS) -induced inflammation by inhibiting TLR4/NF-κB signaling in monocytes[1][2].
CAS Number
95399-71-6
Product Name Alternative
Fosinoprilat; Fosinoprilic acid; SQ 27519
UNSPSC
12352005
Hazard Statement
H360
Target
Angiotensin-converting Enzyme (ACE) ; Interleukin Related; NF-κB; TNF Receptor; Toll-like Receptor (TLR)
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
COVID-19-anti-virus
Field of Research
Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/fosfenopril.html
Purity
99.85
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=P(CCCCC1=CC=CC=C1)(O)CC(N2C[C@H](C3CCCCC3)C[C@H]2C(O)=O)=O
Molecular Formula
C23H34NO5P
Molecular Weight
435.49
Precautions
H360
References & Citations
[1]Yang S, et al. Fosinoprilat alleviates lipopolysaccharide (LPS) -induced inflammation by inhibiting TLR4/NF-κB signaling in monocytes. Cell Immunol. 2013 Jul-Aug;284 (1-2) :182-6.|[2]DeForrest JM, et al. Fosinopril, a phosphinic acid inhibitor of angiotensin I converting enzyme: in vitro and preclinical in vivo pharmacology. J Cardiovasc Pharmacol. 1989 Nov;14 (5) :730-6.|[3]DeForrest JM, et al. Blood pressure lowering and renal hemodynamic effects of fosinopril in conscious animal models. J Cardiovasc Pharmacol. 1990 Jul;16 (1) :139-46.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
IL-1; IL-6; NF-κB; TLR4; TNFRSF5/CD40

Chemical Information

Fosinoprilat

Fosinoprilat is a phosphinic acid-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. An inhibitor of angiotensin converting enzyme (ACE), it is used as the phosphinate ester pro-drug fosinopril for treatment of hypertension and chronic heart failure. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor and an antihypertensive agent. It is a member of phosphinic acids and a L-proline derivative.

CAS Number95399-71-6
PubChem CID62956
IUPAC Name(2S,4S)-4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
Molecular FormulaC23H34NO5P
Molecular Weight435.5
XLogP3.8
Topological Polar Surface Area94.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count9
Heavy Atom Count30
Formal Charge0
Complexity627
SMILES
C1CCC(CC1)[C@@H]2C[C@H](N(C2)C(=O)CP(=O)(CCCCC3=CC=CC=C3)O)C(=O)O
InChI
InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
InChIKey
WOIWWYDXDVSWAZ-RTWAWAEBSA-N
Chemical Structure
2D Structure
2D structure of Fosinoprilat
CAS: 95399-71-6
CID: 62956
Formula: C23H34NO5P
MW: 435.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight435.5
XLogP33.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count9
Exact Mass435.21746018
Monoisotopic Mass435.21746018
Topological Polar Surface Area94.9 Ų
Heavy Atom Count30
Formal Charge0
Complexity627
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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