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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H38O5
Molecular Weight 382.5341
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CARBOPROST METHYL

SMILES

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

InChI

InChIKey=QQCOAAFKJZXJFP-XAYIDPIISA-N
InChI=1S/C22H38O5/c1-4-5-10-14-22(2,26)15-13-18-17(19(23)16-20(18)24)11-8-6-7-9-12-21(25)27-3/h6,8,13,15,17-20,23-24,26H,4-5,7,9-12,14,16H2,1-3H3/b8-6-,15-13+/t17-,18-,19+,20-,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H38O5
Molecular Weight 382.5341
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/monograph/carboprost-tromethamine.html

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HEMABATE

Approved Use

HEMABATE Sterile Solution 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 in the following conditions related to second trimester abortion: Failure of expulsion of the fetus during the course of treatment by another method; Premature rupture of membranes in intrauterine methods with loss of drug and insufficient or absent uterine activity; Requirement of a repeat intrauterine instillation of drug for expulsion of the fetus; Inadvertent or spontaneous rupture of membranes in the presence of a previable fetus and absence of adequate activity for expulsion. HEMABATE is indicated for the treatment of postpartum hemorrhage due to uterine atony which has not responded to conventional methods of management. Prior treatment should include the use of intravenously administered oxytocin, manipulative techniques such as uterine massage and, unless contraindicated, intramuscular ergot preparations. Studies have shown that in such cases, the use of HEMABATE has resulted in satisfactory control of hemorrhage, although it is unclear whether or not ongoing or delayed effects of previously administered ecbolic agents have contributed to the outcome. In a high proportion of cases, HEMABATE used in this manner has resulted in the cessation of life threatening bleeding and the avoidance of emergency surgical intervention.

Launch Date

1979
Preventing
HEMABATE

Approved Use

HEMABATE Sterile Solution 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 in the following conditions related to second trimester abortion: Failure of expulsion of the fetus during the course of treatment by another method; Premature rupture of membranes in intrauterine methods with loss of drug and insufficient or absent uterine activity; Requirement of a repeat intrauterine instillation of drug for expulsion of the fetus; Inadvertent or spontaneous rupture of membranes in the presence of a previable fetus and absence of adequate activity for expulsion. HEMABATE is indicated for the treatment of postpartum hemorrhage due to uterine atony which has not responded to conventional methods of management. Prior treatment should include the use of intravenously administered oxytocin, manipulative techniques such as uterine massage and, unless contraindicated, intramuscular ergot preparations. Studies have shown that in such cases, the use of HEMABATE has resulted in satisfactory control of hemorrhage, although it is unclear whether or not ongoing or delayed effects of previously administered ecbolic agents have contributed to the outcome. In a high proportion of cases, HEMABATE used in this manner has resulted in the cessation of life threatening bleeding and the avoidance of emergency surgical intervention.

Launch Date

1979
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2060 pg/mL
250 μg 1 times / 2 hours multiple, intramuscular
dose: 250 μg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CARBOPROST plasma
Homo sapiens
population: PREGNANT
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1332 pg × h/mL
250 μg 1 times / 2 hours multiple, intramuscular
dose: 250 μg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CARBOPROST plasma
Homo sapiens
population: PREGNANT
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20 min
250 μg 1 times / 2 hours multiple, intramuscular
dose: 250 μg
route of administration: Intramuscular
experiment type: MULTIPLE
co-administered:
CARBOPROST plasma
Homo sapiens
population: PREGNANT
age: ADULT
sex: FEMALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Uterotonic Medications: Oxytocin, Methylergonovine, Carboprost, Misoprostol.
2017 Jun
Patents

Sample Use Guides

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
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
Created
by admin
on Fri Dec 15 15:49:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:48 GMT 2023
Record UNII
UVV9BU3089
Record Status Validated (UNII)
Record Version
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Name Type Language
CARBOPROST METHYL
USAN  
USAN  
Official Name English
(15S)-15-METHYLPROSTAGLANDIN F2.ALPHA. METHYL ESTER
Common Name English
U-36,384
Code English
METHYL CARBOPROST
Common Name English
CARBOPROST METHYL [USAN]
Common Name English
CARBOPROST METHYL ESTER [MI]
Common Name English
CARBOPROST METHYL ESTER
MI  
Common Name English
CIS-METHYL CARBOPROST
Common Name English
(15S)-15-METHYL-PGF2.ALPHA. METHYL ESTER
Common Name English
U-36384
Code English
Carboprost methyl [WHO-DD]
Common Name English
PROSTA-5,13-DIEN-1-OIC ACID, 9,11,15-TRIHYDROXY-15-METHYL-, METHYL ESTER, (5Z,9.ALPHA.,11.ALPHA.,13E,15S)-
Common Name English
Code System Code Type Description
CAS
35700-21-1
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
MERCK INDEX
m3094
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY Merck Index
FDA UNII
UVV9BU3089
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
NCI_THESAURUS
C169825
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
PUBCHEM
5283105
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105943
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID701316447
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
SMS_ID
100000174740
Created by admin on Fri Dec 15 15:49:48 GMT 2023 , Edited by admin on Fri Dec 15 15:49:48 GMT 2023
PRIMARY
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