U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C22H32O4
Molecular Weight 360.4879
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 6
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ILOPROST

SMILES

CC#CCC([H])(C)[C@@]([H])(/C(/[H])=C(\[H])/[C@]1([H])[C@@]2([H])C/C(=C(\[H])/CCCC(=O)O)/C[C@@]2([H])C[C@@]1([H])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

Molecular Formula C22H32O4
Molecular Weight 360.4879
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021779s006lbl.pdf

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

Curator's Comment:: # Bayer HealthCare Pharmaceuticals

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ventavis

Approved Use

Ventavis is indicated for the treatment of pulmonary arterial hypertension (WHO Group I) in patients with NYHA Class III or IV symptoms.

Launch Date

1.10419195E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
135 pg/mL
3 ng/kg/min other, intravenous
dose: 3 ng/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
ILOPROST serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
157 pg/mL
5 μg single, respiratory
dose: 5 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ILOPROST serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
251 pg/mL
1 μg/kg bw single, oral
dose: 1 μg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ILOPROST serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
119 pg × h/mL
3 ng/kg/min other, intravenous
dose: 3 ng/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
ILOPROST serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
47.8 pg × h/mL
5 μg single, respiratory
dose: 5 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ILOPROST serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
144 pg × h/mL
1 μg/kg bw single, oral
dose: 1 μg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ILOPROST serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.91 min
5 μg single, respiratory
dose: 5 μg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
ILOPROST serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
3 ng/kg/min other, intravenous
dose: 3 ng/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
ILOPROST serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4.4 ng/kg/min 1 times / day multiple, intravenous (mean)
MTD
Dose: 4.4 ng/kg/min, 1 times / day
Route: intravenous
Route: multiple
Dose: 4.4 ng/kg/min, 1 times / day
Sources: Page: p.1531
unhealthy, 14-55
n = 5
Health Status: unhealthy
Condition: Pulmonary hypertension
Age Group: 14-55
Sex: M+F
Population Size: 5
Sources: Page: p.1531
150 ug 2 times / day multiple, oral
MTD
Dose: 150 ug, 2 times / day
Route: oral
Route: multiple
Dose: 150 ug, 2 times / day
Sources: Page: p.197
unhealthy, 47-57
n = 32
Health Status: unhealthy
Condition: Raynaud's syndrome
Age Group: 47-57
Sex: M+F
Population Size: 32
Sources: Page: p.197
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache
Sources: Page: p.197
20 ug 24 times / day multiple, respiratory
Highest studied dose
Dose: 20 ug, 24 times / day
Route: respiratory
Route: multiple
Dose: 20 ug, 24 times / day
Sources: Page: p.816
unhealthy, 59.14+/-8.24
n = 7
Health Status: unhealthy
Condition: Pulmonary hypertension
Age Group: 59.14+/-8.24
Sex: M+F
Population Size: 7
Sources: Page: p.816
300 ug 2 times / day multiple, oral
Highest studied dose
Dose: 300 ug, 2 times / day
Route: oral
Route: multiple
Dose: 300 ug, 2 times / day
Sources:
unhealthy
n = 12
Health Status: unhealthy
Condition: Thromboangiitis obliterans
Population Size: 12
Sources:
5 ug 9 times / day multiple, respiratory
Recommended
Dose: 5 ug, 9 times / day
Route: respiratory
Route: multiple
Dose: 5 ug, 9 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pulmonary arterial hypertension
Sources: Page: p.1
Disc. AE: Syncope hypotensive, Pulmonary venous hypertension...
AEs leading to
discontinuation/dose reduction:
Syncope hypotensive
Pulmonary venous hypertension
Bronchospasm
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Headache Disc. AE
150 ug 2 times / day multiple, oral
MTD
Dose: 150 ug, 2 times / day
Route: oral
Route: multiple
Dose: 150 ug, 2 times / day
Sources: Page: p.197
unhealthy, 47-57
n = 32
Health Status: unhealthy
Condition: Raynaud's syndrome
Age Group: 47-57
Sex: M+F
Population Size: 32
Sources: Page: p.197
Bronchospasm Disc. AE
5 ug 9 times / day multiple, respiratory
Recommended
Dose: 5 ug, 9 times / day
Route: respiratory
Route: multiple
Dose: 5 ug, 9 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pulmonary arterial hypertension
Sources: Page: p.1
Pulmonary venous hypertension Disc. AE
5 ug 9 times / day multiple, respiratory
Recommended
Dose: 5 ug, 9 times / day
Route: respiratory
Route: multiple
Dose: 5 ug, 9 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pulmonary arterial hypertension
Sources: Page: p.1
Syncope hypotensive Disc. AE
5 ug 9 times / day multiple, respiratory
Recommended
Dose: 5 ug, 9 times / day
Route: respiratory
Route: multiple
Dose: 5 ug, 9 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Pulmonary arterial hypertension
Sources: Page: p.1
OverviewDrug as perpetrator​

Drug as perpetrator​

Drug as victim
PubMed

PubMed

TitleDatePubMed
A comparative study of PGI2 mimetics used clinically on the vasorelaxation of human pulmonary arteries and veins, role of the DP-receptor.
2013 Dec
Effective prevention of pseudothrombocytopenia in feline blood samples with the prostaglandin I2 analogue Iloprost.
2015 Aug 6
Iloprost supports early development of in vitro-produced porcine embryos through activation of the phosphatidylinositol 3-kinase/AKT signalling pathway.
2017 Jul
Patents

Sample Use Guides

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
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)
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:58:43 UTC 2021
Edited
by admin
on Sat Jun 26 11:58:43 UTC 2021
Record UNII
JED5K35YGL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ILOPROST
EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
PENTANOIC ACID, 5-((3AS,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-((1E,3S)-3-HYDROXY-4-METHYL-1-OCTEN-6-YNYL)-2(1H)-PENTALENYLIDENE)-, (5E)-
Common Name English
ILOPROST [MART.]
Common Name English
ILOPROST [INN]
Common Name English
ILOPROST [VANDF]
Common Name English
(5E)-(3AS,4R,5R,6AS)-5-HYDROXY-4-((1E)-(3S,4RS)-3-HYDROXY-4-METHYLOCT-1-EN-6-YNYL)-HEXAHYDROPENTALEN-2(1H)-YLIDENE)PENTANOIC ACID
Common Name English
ILOPROST [WHO-DD]
Common Name English
ZK-00036374
Code English
ILOPROST [MI]
Common Name English
VENTAVIS
Brand Name English
ILOPROST [EMA EPAR]
Common Name English
ENDOPROST
Brand Name English
ILOPROST [ORANGE BOOK]
Common Name English
ZK-36374
Code English
ILOPROST [USAN]
Common Name English
ILOMEDIN
Brand Name English
CILOPROST
Brand Name English
ZK 00036374
Code English
Classification Tree Code System Code
NDF-RT N0000011280
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 655118
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
WHO-ATC B01AC11
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
EMA ASSESSMENT REPORTS VENTSVIS (AUTHORIZED: HYPERTENSION, PULMONARY)
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
NDF-RT N0000011280
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
WHO-VATC QB01AC11
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 186904
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 364012
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
LIVERTOX 499
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
NCI_THESAURUS C1892
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
NDF-RT N0000011280
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
NCI_THESAURUS C78568
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 38789
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
EU-Orphan Drug EU/3/00/014
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 40089
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
NDF-RT N0000175603
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
FDA ORPHAN DRUG 324610
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
Code System Code Type Description
FDA UNII
JED5K35YGL
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
EVMPD
SUB08136MIG
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
DRUG CENTRAL
1422
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
INN
4972
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
WIKIPEDIA
ILOPROST
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
CAS
78919-13-8
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
NCI_THESAURUS
C48397
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
DRUG BANK
DB01088
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
PUBCHEM
5311181
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
IUPHAR
1895
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
EPA CompTox
78919-13-8
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
MERCK INDEX
M6212
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY Merck Index
RXCUI
40138
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY RxNorm
MESH
D016285
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL494
Created by admin on Sat Jun 26 11:58:44 UTC 2021 , Edited by admin on Sat Jun 26 11:58:44 UTC 2021
PRIMARY
Related Record Type Details
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