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
FDBF00047 propionic acid Responsive image CCC(=O)O 0.0395
FDBF00081 pentane Responsive image CCCCC 0.0316
FDBF00416 butan-1-ol Responsive image C(CC)CO 0.0134
FDBF01747 (2R,4S)-4-hydroxy-2-methyl-cyclopentanone Responsive image O=C1C(CC(C1)O)C 0.0017
FDBF01748 (3R,4S)-3-hydroxy-4-vinyl-cyclopentanone Responsive image O=C1CC(C(C1)O)C=C 0.0017
FDBF01750 (3R,4S)-3-hydroxy-4-[(E)-3-hydroxyprop-1-enyl]cyclopentanone Responsive image O=C1CC(C(C1)O)C=CCO 0.0014
FDBF01758 (3R,4S)-3-hydroxy-4-[(E,3S)-3-hydroxypent-1-enyl]cyclopentanone Responsive image CCC(C=CC1CC(=O)CC1O)O 0.0007
FDBF01759 (2R,3R,4R)-4-hydroxy-3-[(E,3S)-3-hydroxybut-1-enyl]-2-methyl-cyclopentanone Responsive image O=C1C(C(C(C1)O)C=CC(O)C)C 0.0010
FDBF01762 (3S)-hex-1-en-3-ol Responsive image C(C)CC(C=C)O 0.0014
FDBF01765 (3S)-3-hydroxycyclopentanone Responsive image O=C1CCC(C1)O 0.0017
31 , 4