Responsive image

Common name


Epoprostenol

IUPAC name


5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

SMILES


[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=O

Compound class


Platelet Aggregation Inhibitors; Antihypertensive Agents; Antithrombotic Agents; Blood and Blood Forming Organs; Platelet Aggregation Inhibitors Excl. Heparin; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C9 Inducers;

Therapeutic area


For the long-term intravenous treatment of primary pulmonary hypertension and pulmonary hypertension associated with the scleroderma spectrum of disease in NYHA Class III and Class IV patients who do not respond adequately to conventional therapy.

Common name


Epoprostenol

IUPAC name


5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

SMILES


[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(O2)=CCCCC(O)=O

INCHI


InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8?/t14-,16+,17+,18+,19-/m0/s1

FORMULA


C20H32O5

Responsive image

Common name


Epoprostenol

IUPAC name


5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

Molecular weight


352.465

clogP


3.414

clogS


-2.210

HBond Acceptor


5

HBond Donor


3

Total Polar
Surface Area


86.99

Number of Rings


2

Rotatable Bond


10

Drug ID Common name Structure CAS SMILE Frequency
FDBF00416 butan-1-ol Responsive image C(CC)CO 0.0134
FDBF02802 (2Z,3aS,5S,6aS)-2-ethylidene-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image O1C2C(CC(C2)O)CC1=CC 0.0003
FDBF02804 (2Z,3aS,5S,6aS)-2-propylidene-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image O1C2C(CC(C2)O)CC1=CCC 0.0003
FDBF02806 (2Z,3aR,4R,5R,6aS)-2-ethylidene-4-[(E)-3-hydroxyprop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image C(=CCO)C1C2C(OC(=CC)C2)CC1O 0.0003
FDBF02808 (3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxybut-1-enyl]-2-methylene-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image C(=CC(O)C)C1C2C(OC(=C)C2)CC1O 0.0003
FDBF02811 (3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxypent-1-enyl]-2-methylene-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image C(=CC(O)CC)C1C2C(OC(=C)C2)CC1O 0.0003
FDBF02814 (3aS,5S,6aS)-2-methylene-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image O1C2C(CC(C2)O)CC1=C 0.0003
27 , 3