Iloprost

Iloprost
Clinical data


Trade names	Ventavis, Ilomedine
AHFS/Drugs.com	Monograph
License data	EU EMA: (inhalation) or Ilomedine (intravenous) Ventavis (inhalation) or Ilomedine (intravenous) US FDA: Iloprost
Pregnancy category	C
Routes of administration	Inhaled Intravenous
ATC code	B01AC11 (WHO)
Legal status
Legal status	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.
Biological half-life	20–30 minutes
Excretion	?
Identifiers
IUPAC name 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-inyl]-bicyclo[3.3.0]octan-3-ylidene}pentanoic acid
CAS Number	78919-13-8^Y
PubChem CID	5311181
DrugBank	DB01088^Y
ChemSpider	4470703^N
UNII	JED5K35YGL
KEGG	D02721^Y
ChEMBL	CHEMBL236025^Y
Chemical and physical data
Formula	C₂₂H₃₂O₄
Molar mass	360.48 g/mol
3D model (Jmol)	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^N Key:HIFJCPQKFCZDDL-ACWOEMLNSA-N^N
^NY (what is this?)

Iloprost is a drug used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon and other diseases in which the blood vessels are constricted and blood can't flow to the tissues. This damages the tissues and causes high blood pressure. 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 a synthetic analogue of prostacyclin PGI₂. Iloprost dilates systemic and pulmonary arterial vascular beds. It also affects platelet aggregation but the relevance of this effect to the treatment of pulmonary hypertension is unknown. The two diastereoisomers of iloprost differ in their potency in dilating blood vessels, with the 4S isomer substantially more potent than the 4R isomer. While Iloprost is an analog of PGI₂ that activates PGI₂'s receptor, the Prostacyclin receptor, to stimulate vasodilation, it has little selectivity in that it binds to and activates all four receptors for prostaglandin E2 viz., Prostaglandin EP1 receptor, Prostaglandin EP2 receptor, Prostaglandin EP3 receptor, and Prostaglandin EP4 receptor. Activation of the EP2 and EP4 receptors causs vasodilation but activation of the EP3 receptor causes vasoconstriction.

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Wikipedia