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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H36O5
Molecular Weight 368.5075
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CARBOPROST

SMILES

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

InChI

InChIKey=DLJKPYFALUEJCK-IIELGFQLSA-N
InChI=1S/C21H36O5/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/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H36O5
Molecular Weight 368.5075
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Carboprost is an analogue of naturally occurring prostaglandin F2alpha. Administered intramuscularly carboprost stimulates in the gravid uterus myometrial contractions similar to labor contractions at the end of a full term pregnancy. It is indicated for aborting pregnancy between the 13th and 20th weeks of gestation as calculated from the first day of the last normal menstrual period and for the treatment of postpartum hemorrhage due to uterine atony, which has not responded to conventional methods of management. The most frequent adverse reactions observed are related to its contractile effect on smooth muscle: vomiting, diarrhea, nausea, fever and flushing. Carboprost may augment the activity of other oxytocic agents. Concomitant use with other oxytocic agents is not recommended.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HEMABATE
Preventing
HEMABATE

Cmax

ValueDoseCo-administeredAnalytePopulation
2060 pg/mL
250 μg 1 times / 2 hours multiple, intramuscular
CARBOPROST plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1332 pg × h/mL
250 μg 1 times / 2 hours multiple, intramuscular
CARBOPROST plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 min
250 μg 1 times / 2 hours multiple, intramuscular
CARBOPROST plasma
Homo sapiens

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
1. Abortion and Indications 1–4: An initial dose of 1 mL of HEMABATE Sterile Solution (containing the equivalent of 250 micrograms of carboprost) is to be administered deep in the muscle with a tuberculin syringe. Subsequent doses of 250 micrograms should be administered at 1½ to 3½ hour intervals depending on uterine response. An optional test dose of 100 micrograms (0.4 mL) may be administered initially. The dose may be increased to 500 micrograms (2 mL) if uterine contractility is judged to be inadequate after several doses of 250 micrograms (1 mL). The total dose administered of carboprost tromethamine should not exceed 12 milligrams and continuous administration of the drug for more than two days is not recommended. 2. For Refractory Postpartum Uterine Bleeding: An initial dose of 250 micrograms of HEMABATE Sterile Solution (1 mL of HEMABATE) is to be given deep, intramuscularly. In clinical trials it was found that the majority of successful cases (73%) responded to single injections. In some selected cases, however, multiple dosing at intervals of 15 to 90 minutes was carried out with successful outcome. The need for additional injections and the interval at which these should be given can be determined only by the attending physicians as dictated by the course of clinical events. The total dose of HEMABATE should not exceed 2 milligrams (8 doses).
Route of Administration: Intramuscular
In Vitro Use Guide
The pEC50 values obtained for carboprost (as a measure of potency) on 146 myometrial strips from 19 donors, in relation to the two contractile parameters (the maximum amplitude (MAMP) and the mean contractile force above baseline (MCF)) were 6.0 for MAMP and 5.8 for MCF.
Substance Class Chemical
Record UNII
7B5032XT6O
Record Status Validated (UNII)
Record Version