Responsive image

Common name


Dinoprostone

IUPAC name


(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

SMILES


CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

Compound class


Therapeutic area


For the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical ;

Common name


Dinoprostone

IUPAC name


(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

SMILES


CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

INCHI


InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

FORMULA


C20H32O5

Responsive image

Common name


Dinoprostone

IUPAC name


(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

Molecular weight


352.465

clogP


3.916

clogS


-2.502

HBond Acceptor


5

HBond Donor


3

Total Polar
Surface Area


94.83

Number of Rings


1

Rotatable Bond


12

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
FDBF00077 (Z)-pent-2-ene Responsive image C(C)C=CC 0.0065
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
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
FDBF02037 (2R,4S)-2-allyl-4-hydroxy-cyclopentanone Responsive image C(C1C(=O)CC(C1)O)C=C 0.0003
FDBF02039 (2R,4S)-2-[(Z)-but-2-enyl]-4-hydroxy-cyclopentanone Responsive image C(C=CC)C1C(=O)CC(C1)O 0.0003
FDBF02041 (2R,3R,4R)-2-[(Z)-but-2-enyl]-4-hydroxy-3-vinyl-cyclopentanone Responsive image C(C1C(=O)CC(C1C=C)O)C=CC 0.0003
32 , 4