Responsive image

IUPAC name


1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoate

SMILES


OCC([NH3+])(CO)CO.CCCCC[C@@](O)(C)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)[O-]

Compound class


Oxytocics; Abortifacient Agents, Nonsteroidal; Prostaglandins; Genito Urinary System and Sex Hormones; Uterotonics; Tromethamine;

Therapeutic area


For aborting pregnancy between the 13th and 20th weeks of gestation as calculated from the first day of the last normal menstrual period and in the following conditions related to second trimester abortion: 1. Failure of expulsion of the fetus during the course of treatment by another method; 2. Premature rupture of membranes in intrauterine methods with loss of drug and insufficient or absent uterine activity; 3. Requirement of a repeat intrauterine instillation of drug for expulsion of the fetus; 4. Inadvertent or spontaneous rupture of membranes in the presence of a previable fetus and absence of adequate activity for expulsion. Also for the treatment of postpartum hemorrhage due to uterine atony which has not responded to conventional methods of management.

Common name


Carboprost Tromethamine

IUPAC name


1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoate

SMILES


OCC([NH3+])(CO)CO.CCCCC[C@@](O)(C)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)[O-]

INCHI


InChI=1S/C21H36O5.C4H11NO3/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25;5-4(1-6,2-7)3-8/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25);6-8H,1-3,5H2/b7-5-,14-12+;/t16-,17-,18+,19+,21+;/m1./s1

FORMULA


C25H47NO8

Responsive image

Common name


Carboprost Tromethamine

IUPAC name


1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoate

Molecular weight


367.500

clogP


3.807

clogS


-2.811

HBond Acceptor


5

HBond Donor


3

Total Polar
Surface Area


100.82

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
FDBF00933 (1R,3S,4R)-4-vinylcyclopentane-1,3-diol Responsive image C1C(C(CC1O)C=C)O 0.0003
FDBF00938 (1R,3S,4S)-4-[(Z)-but-2-enyl]cyclopentane-1,3-diol Responsive image CC=CCC1CC(CC1O)O 0.0003
FDBF00942 (1R,3S,4S)-4-[(Z)-pent-2-enyl]cyclopentane-1,3-diol Responsive image C(C=CCC1CC(CC1O)O)C 0.0003
FDBF00943 (1S,3S,4S,5S)-4-[(Z)-but-2-enyl]-5-vinyl-cyclopentane-1,3-diol Responsive image CC=CCC1C(C(CC1O)O)C=C 0.0003
FDBF00944 (3S)-3-methylhex-1-en-3-ol Responsive image C(C(C=C)(O)C)CC 0.0003
28 , 3