Carboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties.
Carboprost main use is in the obstetrical emergency of postpartum hemorrhage which reduces postpartum bleeding during these circumstances.
Contents
1Indication
2Contraindication
3Precautions
4Adverse Effects
5Storage and Availability
6Synthesis
7See also
8References
9External links
Indication
Used in postpartum hemorrhage caused by uterine atony not controlled by other methods. One study has shown that carboprost tromethamine is more effective than oxytocin in preventing postpartum hemorrhage in high-risk patients undergoing cesarean delivery.[1] Carboprost is also used for the termination of pregnancy in the 2nd trimester.[2]
Unlabeled use:
Hemorrhagic Cystitis
PID
Contraindication
Contraindicated in severe cardiovascular, renal, and hepatic disease. It is also contraindicated in acute Pelvic Inflammatory Disease. Hypersensitivity to carboprost or any of its components is also a contraindication[2] Exert caution in asthmatic patients as carboprost may cause bronchospasm.
Precautions
asthma
anemia
jaundice
diabetes mellitus
seizure disorders
past uterine surgery
Adverse Effects
diarrhea (most common, may be sudden in onset)
flushing or hot flashes
fever
chills
nausea/vomiting
Storage and Availability
Carboprost is supplied with its salt derivative tromethamine in 1 milliliter ampules containing a 250 microgram/milliliter solution of the active drug. The drug must be refrigerated at a temperature between 2 – 8 degrees Celsius.[2]
Synthesis
A significant deactivating metabolic transformation of natural prostaglandins is enzymatic oxidation of the C-15 hydroxyl to the corresponding ketone. This is prevented, with retention of activity, by methylation to give the C-15 tertiary carbinol series.
Carboprost synthesis:[3][4] G. L. Bundy et al., DE 2121980; G. L. Bundy, U.S. Patent 3,728,382 (1971, 1973 both to Upjohn).
This molecular feature is readily introduced at the stage of the Corey lactone (1) by reaction with methyl Grignard reagent or trimethylaluminium. The resulting mixture of tertiary carbinols (2) is transformed to oxytocic carboprost (3) by standard transformations, including sepoaration of diastereomers, so that the final product is the C-15 analogue. This diastereomer is reputably freeer of porstaglandin side effects than the C-15 (S) isomer.
See also
Arbaprostil
References
^Bai, J; Sun, Q; Zhai, H (2014). "A comparison of oxytocin and carboprost tromethamine in the prevention of postpartum hemorrhage in high-risk patients undergoing cesarean delivery". Journal of Experimental and Therapeutic Medicine. 7 (1): 46–50. doi:10.3892/etm.2013.1379. PMC 3861477. PMID 24348762.
^ abcHemabate [Package Insert]. New York, NY: Pharmacia and Upjohn Company; 2014.
^Yankee, Ernest W.; Axen, Udo; Bundy, Gordon L. (1974). "Total synthesis of 15-methylprostaglandins". Journal of the American Chemical Society. 96 (18): 5865. doi:10.1021/ja00825a027. PMID 4416671.
^Bundy, G. (1971). "NOVEL PROSTAGLANDIN SYNTHESES". Ann. N.Y. Acad. Sci. 180: 76. doi:10.1111/j.1749-6632.1971.tb53186.x.
External links
Carboprost at the US National Library of Medicine Medical Subject Headings (MeSH)
Indman P (2004). "Use of carboprost to facilitate hysteroscopic resection of submucous myomas". J Am Assoc Gynecol Laparosc. 11 (1): 68–72. doi:10.1016/S1074-3804(05)60014-X. PMID 15104835.
Vukelić J (2001). "Second trimester pregnancy termination in primigravidas by double application of dinoprostone gel and intramuscular administration of carboprost tromethamine". Med Pregl. 54 (1–2): 11–6. PMID 11436877.
Ippoliti C, Przepiorka D, Mehra R, Neumann J, Wood J, Claxton D, Gajewski J, Khouri I, van Besien K, Andersson B (1995). "Intravesicular carboprost for the treatment of hemorrhagic cystitis after marrow transplantation". Urology. 46 (6): 811–5. doi:10.1016/S0090-4295(99)80349-5. PMID 7502421.
…Methylergonovine (0.2 mg intramuscularly, repeated every two to four hours up to three doses), or ; Carboprost tromethamine (Hemabate, 250 mcg intramuscularly; up to eight doses at intervals at least 15 minutes apart)…
…misoprostol and gemeprost induce labor more effectively and with fewer side effects than other PGs (eg, carboprost, sulprostone) and single-agent oxytocin or oxytocin in combination with other types of PGs . Both …
…(methylergonovine) or reactive airway disease (carboprost). In the absence of any medical contraindications, we suggest, in order of preference, oxytocin, carboprost (Hemabate), or misoprostol (Cytotec), and …
Mifepristone in combination with prostaglandins for termination of 10-16 weeks' gestation: a systematic review.
Chen QJ, Hou SP, Meads C, Huang YM, Hong QQ, Zhu HP, Cheng LN; for the EBM-CONNECT Collaboration.SourceNPFPC Key Laboratory of Contraceptives and Devices Shanghai Institute of Planned Parenthood Research, Shanghai, China.
European journal of obstetrics, gynecology, and reproductive biology.Eur J Obstet Gynecol Reprod Biol.2011 Dec;159(2):247-254. Epub 2011 Jul 8.
OBJECTIVES: Medical regimens using mifepristone in combination with prostaglandins have been widely available for women undergoing termination of pregnancy (TOP) at 10-16 weeks' gestation in China. We undertook a systematic review to compare different regimens of mifepristone with prostaglandins for
Methods of induction of labour: a systematic review.
Mozurkewich EL, Chilimigras JL, Berman DR, Perni UC, Romero VC, King VJ, Keeton KL.SourceDepartment of Obstetrics and Gynecology, Division of Maternal-Fetal Medicine, University of Michigan, 1500 E, Medical Center Drive, Ann Arbor, MI 48109-0264, USA. mozurk@umich.edu.
BMC pregnancy and childbirth.BMC Pregnancy Childbirth.2011 Oct 27;11:84.
ABSTRACT:BACKGROUND: Rates of labour induction are increasing. We conducted this systematic review to assess the evidence supporting use of each method of labour induction.METHODS: We listed methods of labour induction then reviewed the evidence supporting each. We searched MEDLINE and the Cochrane
Carboprost is a form of prostaglandin (a hormone-like substance that occurs naturally in the body). Prostaglandins help to control functions in the body such as blood pressure and muscle contractions. Carboprost is used to treat ...
Indications, dose, contra-indications, side-effects, interactions, cautions, warnings and other safety information for CARBOPROST. ... By deep intramuscular injection For Adult 250 micrograms, repeated if necessary, to be given at ...