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
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00018 propan-1-ol Responsive image C(O)CC 0.0330
FDBF00022 prop-1-ene Responsive image CC=C 0.0299
FDBF00067 butane Responsive image CCCC 0.0680
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
FDBF01756 (3R,4S)-3-hydroxy-4-[(E,3S)-3-hydroxybut-1-enyl]cyclopentanone Responsive image O=C1CC(C(C1)O)C=CC(O)C 0.0010
FDBF01765 (3S)-3-hydroxycyclopentanone Responsive image O=C1CCC(C1)O 0.0017
FDBF02038 (2R,3R,4R)-2-allyl-4-hydroxy-3-vinyl-cyclopentanone Responsive image C(C1C(=O)CC(C1C=C)O)C=C 0.0003
FDBF02040 (2R,4S)-4-hydroxy-2-[(Z)-pent-2-enyl]cyclopentanone Responsive image CCC=CCC1C(=O)CC(C1)O 0.0003
32 , 4