Ifetroban

Ifetroban
Clinical data
ATC code	None;
Identifiers
	IUPAC name 3-[2-({(1S,2R,3S)-3-[4-(Pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]hept-2-yl}methyl)phenyl]propanoic acid;
CAS Number	143443-90-7;
PubChem CID	23724921;
DrugBank	DB12321;
ChemSpider	58452;
UNII	E833KT807K;
KEGG	D04500;
ChEMBL	ChEMBL2146062;
CompTox Dashboard (EPA)	DTXSID40869931 ;
Chemical and physical data
Formula	C25H32N2O5
Molar mass	440.540 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NCCCCC)c1nc(oc1)[C@@H]4C2O[C@@H](CC2)[C@@H]4Cc3ccccc3CCC(=O)O;

Ifetroban is a potent and selective thromboxane receptor antagonist.^[1] It has been studied in animal models for the treatment of myocardial ischemia, hypertension, stroke, thrombosis, cardiomyopathy, and for its effects on platelets.^[2]^[3]

Synthesis[]

Ifetroban synthesis: Drugs Future (c.f. Lednicer book 6).

References[]

^ Rosenfeld, Louis; Grover, Gary J.; Stier, Charles T. (2006). "Ifetroban Sodium: An Effective TxA2/PGH2 Receptor Antagonist". Cardiovascular Drug Reviews. 19 (2): 97–115. doi:10.1111/j.1527-3466.2001.tb00058.x. PMID 11484065.
^ Dockens RC, Santone KS, Mitroka JG, Morrison RA, Jemal M, Greene DS, Barbhaiya RH (August 2000). "Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans" (PDF). Drug Metabolism and Disposition. 28 (8): 973–80. PMID 10901709.
^ West, James D.; Galindo, Cristi L.; Kim, Kyungsoo; Shin, John Jonghyun; Atkinson, James B.; MacIas‐Perez, Ines; Pavliv, Leo; Knollmann, Bjorn C.; Soslow, Jonathan H.; Markham, Larry W.; Carrier, Erica J. (2019). "Antagonism of the Thromboxane‐Prostanoid Receptor as a Potential Therapy for Cardiomyopathy of Muscular Dystrophy". Journal of the American Heart Association. 8 (21): e011902. doi:10.1161/JAHA.118.011902. PMC 6898850. PMID 31662020.

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[1] Rosenfeld, Louis; Grover, Gary J.; Stier, Charles T. (2006). "Ifetroban Sodium: An Effective TxA2/PGH2 Receptor Antagonist". Cardiovascular Drug Reviews. 19 (2): 97–115. doi:10.1111/j.1527-3466.2001.tb00058.x. PMID 11484065.

[2] Dockens RC, Santone KS, Mitroka JG, Morrison RA, Jemal M, Greene DS, Barbhaiya RH (August 2000). "Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans" (PDF). Drug Metabolism and Disposition. 28 (8): 973–80. PMID 10901709.

[3] West, James D.; Galindo, Cristi L.; Kim, Kyungsoo; Shin, John Jonghyun; Atkinson, James B.; MacIas‐Perez, Ines; Pavliv, Leo; Knollmann, Bjorn C.; Soslow, Jonathan H.; Markham, Larry W.; Carrier, Erica J. (2019). "Antagonism of the Thromboxane‐Prostanoid Receptor as a Potential Therapy for Cardiomyopathy of Muscular Dystrophy". Journal of the American Heart Association. 8 (21): e011902. doi:10.1161/JAHA.118.011902. PMC 6898850. PMID 31662020.

[1]

[2]

[3]

Clinical data

ATC code	None
Identifiers
IUPAC name 3-[2-({(1S,2R,3S)-3-[4-(Pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]hept-2-yl}methyl)phenyl]propanoic acid
CAS Number	143443-90-7
PubChem CID	23724921
DrugBank	DB12321
ChemSpider	58452
UNII	E833KT807K
KEGG	D04500
ChEMBL	ChEMBL2146062
CompTox Dashboard (EPA)	DTXSID40869931
Chemical and physical data
Formula	C₂₅H₃₂N₂O₅
Molar mass	440.540 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NCCCCC)c1nc(oc1)[C@@H]4C2O[C@@H](CC2)[C@@H]4Cc3ccccc3CCC(=O)O