Responsive image

Common name


Alprostadil

IUPAC name


7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

SMILES


CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

Compound class


Platelet Aggregation Inhibitors; Vasodilator Agents; Prostaglandins; Genito Urinary System and Sex Hormones; Cardiovascular System; Drugs Used in Erectile Dysfunction; Cardiac Therapy; Urological Agents;

Therapeutic area


For palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Also for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.

Common name


Alprostadil

IUPAC name


7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

SMILES


CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

INCHI


InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1

FORMULA


C20H34O5

Responsive image

Common name


Alprostadil

IUPAC name


7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

Molecular weight


354.481

clogP


4.096

clogS


-3.220

HBond Acceptor


5

HBond Donor


3

Total Polar
Surface Area


94.83

Number of Rings


1

Rotatable Bond


13

Drug ID Common name Structure CAS SMILE Frequency
FDBF00004 acetic acid Responsive image CC(=O)O 0.0687
FDBF00041 ethanol Responsive image CCO 0.1474
FDBF00061 butyric acid Responsive image CCCC(=O)O 0.0131
FDBF00620 (2S)-but-3-en-2-ol Responsive image C=CC(O)C 0.0031
FDBF01749 (2R,3R,4R)-4-hydroxy-2-methyl-3-vinyl-cyclopentanone Responsive image O=C1C(C(C(C1)O)C=C)C 0.0017
FDBF01752 (2R,3R,4R)-2-ethyl-4-hydroxy-3-vinyl-cyclopentanone Responsive image O=C1C(C(C(C1)O)C=C)CC 0.0014
FDBF01753 (2R,4S)-4-hydroxy-2-propyl-cyclopentanone Responsive image O=C1C(CC(C1)O)CCC 0.0014
FDBF01757 (2R,3R,4R)-4-hydroxy-2-propyl-3-vinyl-cyclopentanone Responsive image O=C1C(C(C(C1)O)C=C)CCC 0.0014
FDBF01761 (2R,4S)-2-butyl-4-hydroxy-cyclopentanone Responsive image O=C1C(CC(C1)O)CCCC 0.0014
FDBF01764 (2R,3R,4R)-4-hydroxy-3-[(E,3S)-3-hydroxypent-1-enyl]-2-methyl-cyclopentanone Responsive image CCC(C=CC1C(C(=O)CC1O)C)O 0.0007
31 , 4