Product Name

Carboprost tromethamine

CAS Number

58551-69-2

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Product Name:
Carboprost tromethamine
CAS Number:
58551-69-2
Indication:
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.
Mode of Action:

Carboprost is a synthetic prostaglandin. It binds the prostaglandin E2 receptor, causing myometrial contractions, causuing the induction of labour or the expulsion of the placenta. Prostaglandins occur naturally in the body and act at several sites in the body including the womb (uterus). They act on the muscles of the womb, causing them to contract.

Pharmacodynamics:

Carboprost tromethamine administered intramuscularly stimulates in the gravid uterus myometrial contractions similar to labor contractions at the end of a full term pregnancy. Whether or not these contractions result from a direct effect of carboprost on the myome-trium has not been determined. Nonetheless, they evacuate the products of conception from the uterus in most cases. Postpartum, the resultant myometrial contractions provide hemostasis at the site of placentation. Carboprost tromethamine also stimulates the smooth muscle of the human gastrointestinal tract. This activity may produce the vomiting or diarrhea or both that is common when carbo-prost tromethamine is used to terminate pregnancy and for use postpartum. In laboratory animals and also in humans carboprost tromethamine can elevate body temperature. With the clinical doses of carboprost trometh-amine used for the termination of pregnancy, and for use postpartum, some patients do experience transient temperature increases. In laboratory animals and in humans large doses of carboprost tromethamine can raise blood pressure, probably by contracting the vascular smooth muscle. With the doses of carboprost tromethamine used for terminating pregnancy, this effect has not been clinically significant. In laboratory animals and also in humans carboprost tromethamine can elevate body temperature. With the clinical doses of carboprost tromethamine used for the termination of pregnancy, some patients do experience temperature increases. In some patients, carboprost tromethamine may cause transient bronchoconstriction.

Metabolism:

Metabolized in the lungs and liver. Metabolites are excreted in urine.

Toxicity:

Symptoms of overdose include irritation, nausea, vomiting, diarrhea, coughing, dyspnea, asthma, hypertension, flushing, and pyrexia.

IUPAC:
(Z)-7-[(1R, 2S, 3R, 5S)-3, 5-Dihydroxy-2-[(E, 3S)-3-hydroxy-3-methyl-oct-1-enyl]cyclopentyl]hept-5-enoic acid 2-amino-2-(hydroxymethyl)propane-1, 3-diol
ATC:
G02AD04
PubChem:
45266502
DrugBank:
DB00429 (APRD00847)
Formula:
C25-H47-NO8
Molecular Mass:
489.73
Synonyms:
(15S)-15-methyl-PGF2α tromethamine salt, (15S)-15-methylprostaglandin F2α tromethamine, 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9α,11β,13E,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-oate, 15(S)-15-methyl-PGF2α tromethamine salt, 15(S)-15-methylprostaglandin F2α tromethamine, Carboprost trometamol, Carboprost tromethamine
SMILES:
OCC([NH3+])(CO)CO.CCCCC[C@@](O)(C)C=C[C@H]1[C@@H](O)C[C@H](O)[C@@H]1CC=C/CCCC(=O)[O-]
AHFS Code:
76:00.00 — Oxytocics
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

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