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
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00018 propan-1-ol Responsive image C(O)CC 0.0330
FDBF00047 propionic acid Responsive image CCC(=O)O 0.0395
FDBF00067 butane Responsive image CCCC 0.0680
FDBF00081 pentane Responsive image CCCCC 0.0316
FDBF00616 prop-2-en-1-ol Responsive image C=CCO 0.0072
FDBF01754 (3S)-pent-1-en-3-ol Responsive image CCC(C=C)O 0.0017
FDBF01762 (3S)-hex-1-en-3-ol Responsive image C(C)CC(C=C)O 0.0014
FDBF02801 (3aR,4R,5R,6aS)-2-methylene-4-vinyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image C(=C)C1C2C(OC(=C)C2)CC1O 0.0003
FDBF02813 (2Z,3aR,4R,5R,6aS)-2-ethylidene-4-[(E,3S)-3-hydroxypent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-ol Responsive image C(=CC(O)CC)C1C2C(OC(=CC)C2)CC1O 0.0003
27 , 3