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Details

Stereochemistry EPIMERIC
Molecular Formula C22H32O4
Molecular Weight 360.4871
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 6
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ILOPROST

SMILES

[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)C(C)CC#CC)[C@@]1([H])C\C(C2)=C\CCCC(O)=O

InChI

InChIKey=HIFJCPQKFCZDDL-ACWOEMLNSA-N
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

HIDE SMILES / InChI

Description

Iloprost is a second generation structural analog of prostacyclin (PGI) with about ten-fold greater potency than the first generation stable analogs, such as carbaprostacyclin. Iloprost binds with equal affinity to human prostacyclin (Prostanoid IP) and prostaglandin EP1 receptors. Iloprost constricts the ilium and fundus circular smooth muscle as strongly as prostaglandin E2 (PGE2) itself. Iloprost inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets. In whole animals, iloprost acts as a vasodilator, hypotensive, antidiuretic, and prolongs bleeding time. All of these properties help to antagonize the pathological changes that take place in the small pulmonary arteries of patients with pulmonary hypertension. Used for the treatment of pulmonary arterial hypertension.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.9 nM [Ki]
1.1 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ventavis

Cmax

ValueDoseCo-administeredAnalytePopulation
135 pg/mL
3 ng/kg/min other, intravenous
ILOPROST serum
Homo sapiens
157 pg/mL
5 μg single, respiratory
ILOPROST serum
Homo sapiens
251 pg/mL
1 μg/kg bw single, oral
ILOPROST serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
119 pg × h/mL
3 ng/kg/min other, intravenous
ILOPROST serum
Homo sapiens
47.8 pg × h/mL
5 μg single, respiratory
ILOPROST serum
Homo sapiens
144 pg × h/mL
1 μg/kg bw single, oral
ILOPROST serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.91 min
5 μg single, respiratory
ILOPROST serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
3 ng/kg/min other, intravenous
ILOPROST serum
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Ventavis is intended to be inhaled using either of two pulmonary drug delivery devices: the I-neb™ AAD® System or the Prodose® AAD® System. The first inhaled dose should be 2.5 mcg (as delivered at the mouthpiece). If this dose is well tolerated, dosing should be increased to 5.0 mcg and maintained at that dose; otherwise maintain the dose at 2.5 mcg. Ventavis should be taken 6 to 9 times per day (no more than once every 2 hours) during waking hours, according to individual need and tolerability. The maximum daily dose evaluated in clinical studies was 45 mcg (5 mcg 9 times per day).
Route of Administration: Respiratory
In Vitro Use Guide
Phosphatidylinositol 3-kinase (PI3K)/AKT signalling pathway was significantly activated by iloprost supplementation of early porcine embryos in a concentration-dependent manner (10-1000 nM)