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
FDBF00042 propan-2-ol Responsive image CC(O)C 0.0278
FDBF00047 propionic acid Responsive image CCC(=O)O 0.0395
FDBF00075 (Z)-but-2-ene Responsive image CC=CC 0.0069
FDBF00932 (1R,3S,4S)-4-methylcyclopentane-1,3-diol Responsive image CC1CC(CC1O)O 0.0003
FDBF00935 (1R,3S,4S)-4-allylcyclopentane-1,3-diol Responsive image C(=C)CC1CC(CC1O)O 0.0003
FDBF00937 2-methylbut-3-en-2-ol Responsive image C(O)(C)(C)C=C 0.0003
FDBF00939 (2S)-pentan-2-ol Responsive image C(O)(C)CCC 0.0010
FDBF00941 (1S,3S,4S,5S)-4-allyl-5-vinyl-cyclopentane-1,3-diol Responsive image C(=C)CC1C(C(CC1O)O)C=C 0.0003
28 , 3