Iloprost

Iloprost
Clinical data
Trade names	Ventavis, Ilomedine
AHFS/Drugs.com	Monograph
MedlinePlus	a612032
License data	EU EMA: by INN; US DailyMed: Iloprost; US FDA: Iloprost;
Routes of; administration	Inhaled; Intravenous
ATC code	B01AC11 (WHO) ;
Legal status
Legal status	US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	The absolute bioavailability of inhaled iloprost has not been determined.
Metabolism	Iloprost is metabolized principally via β-oxidation of the carboxyl side chain. The main metabolite is tetranor-iloprost, which is found in the urine in free and conjugated form. In animal experiments, tetranor-iloprost was pharmacologically inactive.
Elimination half-life	20–30 minutes
Identifiers
	IUPAC name 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octan-3-ylidene}pentanoic acid;
CAS Number	78919-13-8 73873-87-7;
PubChem CID	5311181;
DrugBank	DB01088 ;
ChemSpider	4470703 ;
UNII	JED5K35YGL;
KEGG	D02721 ;
ChEMBL	ChEMBL236025 ;
CompTox Dashboard (EPA)	DTXSID2041046 ;
ECHA InfoCard	100.163.887
Chemical and physical data
Formula	C22H32O4
Molar mass	360.494 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)O;
	InChI InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1 ; Key:HIFJCPQKFCZDDL-ACWOEMLNSA-N ;
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Iloprost is a medication used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon and other diseases in which the blood vessels are constricted and blood cannot flow to the tissues. This damages the tissues and causes high blood pressure. There is ongoing research into using it as a frostbite treatment. Iloprost works by opening (dilating) the blood vessels to allow the blood to flow through again. It was developed by the pharmaceutical company Schering AG and is marketed by Bayer Schering Pharma AG in Europe and Actelion Pharmaceuticals in the USA. Iloprost is given via inhalation, and a therapeautic benefit of the drug is that a very low dose is required because of the deposition in the lung. Iloprost has few systemic side effects for that reason.

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