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Revision as of 20:11, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit		Latest revision as of 16:59, 17 September 2024 edit undoNoleander (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers32,334 edits →Indication: abortion: add more cites; clarify that it is no longer commonly used for that purpose.
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			{{Short description|Chemical compound}}
	{{Drugbox
			{{Infobox drug
	| Verifiedfields = changed		| Verifiedfields = changed
	| verifiedrevid = 408786343		| verifiedrevid = 460018936
	| IUPAC_name = (5''Z'',9α,11α,13''E'',15''S'')-9,11,15-trihydroxy-15- methylprosta-5,13-dien-1-oic acid		| IUPAC_name = (5''Z'',9α,11α,13''E'',15''S'')-9,11,15-trihydroxy-15- methylprosta-5,13-dien-1-oic acid
	| image = Carboprost.svg		| image = Carboprost.svg
	<!--Clinical data-->		<!--Clinical data-->
	| tradename =		| pronounce =
			| tradename = Hemabate
	| Drugs.com = {{drugs.com|CONS|carboprost}}		| Drugs.com = {{drugs.com|CONS|carboprost}}
	| MedlinePlus = a600042		| MedlinePlus = a600042
			| licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) -->
	| pregnancy_category = c
			| licence_EU = <!-- EMA uses INN (or special INN_EMA) -->
			| DailyMedID = <!-- DailyMed may use generic or brand name (generic name preferred) -->
			| licence_US = <!-- FDA may use generic or brand name (generic name preferred) -->
			| pregnancy_AU = D
			| pregnancy_AU_comment =
			| pregnancy_category =
			| routes_of_administration = ]
			| class =
			| ATCvet =
			| ATC_prefix = G02
			| ATC_suffix = AD04
			| ATC_supplemental =
			<!-- Legal status -->
			| legal_AU = S4
			| legal_AU_comment = <ref>{{cite web | title=Carboprost-REACH (Reach Pharmaceuticals Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=28 July 2023 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/carboprost-reach-reach-pharmaceuticals-pty-ltd | access-date=10 September 2023}}</ref>
			| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
			| legal_BR_comment =
			| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
			| legal_CA_comment =
			| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
			| legal_DE_comment =
			| legal_NZ = <!-- Class A, B, C -->
			| legal_NZ_comment =
			| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
			| legal_UK_comment =
			| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
			| legal_US_comment =
			| legal_EU =
			| legal_EU_comment =
			| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
			| legal_UN_comment =
	| legal_status = Rx-only		| legal_status = Rx-only
	| routes_of_administration = Intravenous
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability =		| bioavailability =
	| protein_bound =		| protein_bound =
	| metabolism =		| metabolism =
	| elimination_half-life =		| elimination_half-life =
	<!--Identifiers-->		<!--Identifiers-->
			| index2_label = tromethamine
	| CASNo_Ref = {{cascite|correct|CAS}}
	| CAS_number_Ref = {{cascite|correct|??}}		| CAS_number_Ref = {{cascite|correct|CAS}}
	| CAS_number = 58551-69-2		| CAS_number = 35700-23-3
			| CAS_number2_Ref = {{cascite|correct|CAS}}
	| ATC_prefix = G02
			| CAS_number2 = 58551-69-2
	| ATC_suffix = AD04
			| UNII_Ref = {{fdacite|correct|FDA}}
	| ATC_supplemental =
			| UNII = 7B5032XT6O
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = U4526F86FJ
	| PubChem = 5281075		| PubChem = 5281075
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
	| DrugBank = <!-- blanked - oldvalue: APRD00847 -->		| DrugBank = DB00429
			| ChEBI = 3403
			| KEGG = D02343
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4444532		| ChemSpiderID = 4444532
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = U4526F86FJ
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 1201299 -->		| ChEMBL = 1237122
			<!--Chemical data-->
	| C=21 | H=36 | O=5
			| C=21 | H=36 | O=5
	| molecular_weight = 368.508 g/mol
	| smiles = O=C(O)CCC/C=C/C1(O)C(O)1/C=C/(O)(C)CCCCC		| smiles = O=C(O)CCC/C=C/C1(O)C(O)1/C=C/(O)(C)CCCCC
	| InChI = 1/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
	| InChIKey = DLJKPYFALUEJCK-MRVZPHNRBG
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = DLJKPYFALUEJCK-IIELGFQLSA-N		| StdInChIKey = DLJKPYFALUEJCK-IIELGFQLSA-N
			|drug_name=|alt=|caption=|type=|pregnancy_US=}}
	}}
	'''Carboprost''' (], trade names for the ] salts '''Hemabate''', '''Tham''') is a synthetic ] analogue of PGF<sub>2α</sub> (specifically, it is 15-methyl-PGF<sub>2α</sub>) with ] properties.		'''Carboprost''' (], trade names for the ] salts '''Hemabate''', '''Tham''') is a synthetic ] analogue of ] (specifically, it is 15-methyl-PGF<sub>2α</sub>) with ] properties.
	Carboprost induces ] and can trigger abortion in early pregnancy. It also reduces ].		Carboprost's main use is in the obstetrical emergency of ] which reduces ] during these circumstances.
	==Indication==		== 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.<ref>{{cite journal | vauthors = Bai J, Sun Q, Zhai H | title = A comparison of oxytocin and carboprost tromethamine in the prevention of postpartum hemorrhage in high-risk patients undergoing cesarean delivery | journal = Experimental and Therapeutic Medicine | volume = 7 | issue = 1 | pages = 46–50 | date = January 2014 | pmid = 24348762 | pmc = 3861477 | doi = 10.3892/etm.2013.1379 }}</ref>
	Used in postpartum hemorrhage caused by uterine atony not controlled by other methods.<br />Unlabeled use:
	* Hemorrhagic Cystitis
	* PID
			Carboprost was the first drug widely used for ]s. It is still sometimes used for second trimester abortions, but has generally been supplanted by the ]/] combination.<ref name = HemabatePI>Hemabate . New York, NY: Pharmacia and Upjohn Company; 2014.</ref><ref name="Mayo">"Carboprost" - Drug fact sheet, Mayo Clinic. Last updated: July 01, 2024
	==Contraindication==
			https://www.mayoclinic.org/drugs-supplements/carboprost-intramuscular-route/proper-use/drg-20067975</ref><ref name="Vuk">Vukelić J. Second trimester pregnancy termination in primigravidas by double application of dinoprostone gel and intramuscular administration of carboprost tromethamine. Med Pregl. 2001 Jan-Feb;54(1-2):11-6. English, Croatian. PMID: 11436877.</ref><ref name="Byg">Bygdeman, M., & Gemzell-Danielsson, K. (2008). An Historical Overview of Second Trimester Abortion Methods. Reproductive Health Matters, 16(sup31), 196–204. https://doi.org/10.1016/S0968-8080(08)31385-8</ref><ref name="Sch">Schwallie PC, Lamborn KR. Induction of abortion by intramuscular administration of (15S)-15-methyl PGF2 alpha. An overview of 815 cases. J Reprod Med. 1979 Dec;23(6):289-93. PMID: 392084.</ref><ref name="Bha">Bhaskar A, Dimov V, Baliga S, Kinra G, Hingorani V, Laumas KR. Plasma levels of 15 (S) 15-methyl-PGF 2 alpha-methyl ester following vaginal administration for induction of abortion in women. ''Contraception''. 1979 Nov;20(5):519-31. doi: 10.1016/0010-7824(79)90057-x. PMID: 527343.</ref>
	Contraindicated in severe cardiovascular, renal, and hepatic disease, also contraindicated in Pelvic Inflammatory Disease. Exert caution in asthmatic patients.
			== Contraindication ==
	==Precautions==
			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<ref name = HemabatePI />
			== Precautions ==
	* asthma		* asthma
	* anemia		* anemia
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	* past uterine surgery		* past uterine surgery
	==Adverse Effects==		== Adverse Effects ==
	* diarrhea (most common, may be sudden in onset)		* diarrhea (most common, may be sudden in onset)
			* flushing or hot flashes
	* fever		* fever
	* chills		* chills
	* nausea/vomiting		* nausea/vomiting
			== Storage and Availability ==
	==References==
			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.<ref name = HemabatePI />
			== 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.
			|assign=]|inventor1-last=Gordon|inventor1-first=Leonard|inventor2-last=Pike|inventor2-first=John Edward|inventor3-last=Schneider|inventor3-first=William Paul}}</ref> G. L. Bundy, {{US patent|3728382}} (1973 to ]).]]
			This molecular feature is readily introduced at the stage of the Corey lactone ('''1''') by reaction with methyl ] or ]. The resulting mixture of tertiary carbinols ('''2''') is transformed to oxytocic carboprost ('''3''') by standard transformations, including separation of diastereomers, so that the final product is the C-15 analogue. This diastereomer is reputably freeer of prostaglandin side effects than the C-15 (S) isomer.
			== References ==
	{{reflist}}		{{reflist}}
			== Further reading ==
	==External links==
			{{refbegin}}
			* {{cite journal | vauthors = Indman PD | title = Use of carboprost to facilitate hysteroscopic resection of submucous myomas | journal = The Journal of the American Association of Gynecologic Laparoscopists | volume = 11 | issue = 1 | pages = 68–72 | date = February 2004 | pmid = 15104835 | doi = 10.1016/S1074-3804(05)60014-X }}
			* {{cite journal | vauthors = Vukelić J | title = Second trimester pregnancy termination in primigravidas by double application of dinoprostone gel and intramuscular administration of carboprost tromethamine | journal = Medicinski Pregled | volume = 54 | issue = 1–2 | pages = 11–6 | year = 2001 | pmid = 11436877 }}
			* {{cite journal | vauthors = Ippoliti C, Przepiorka D, Mehra R, Neumann J, Wood J, Claxton D, Gajewski J, Khouri I, van Besien K, Andersson B | display-authors = 6 | title = Intravesicular carboprost for the treatment of hemorrhagic cystitis after marrow transplantation | journal = Urology | volume = 46 | issue = 6 | pages = 811–5 | date = December 1995 | pmid = 7502421 | doi = 10.1016/S0090-4295(99)80349-5 }}
			{{refend}}
			== External links ==
	* {{MeshName|Carboprost}}		* {{MeshName|Carboprost}}
	* {{cite journal | author = Indman P | title = Use of carboprost to facilitate hysteroscopic resection of submucous myomas. | journal = J Am Assoc Gynecol Laparosc | volume = 11 | issue = 1 | pages = 68–72 | year = 2004 | pmid = 15104835 | doi = 10.1016/S1074-3804(05)60014-X}}
	* {{cite journal | author = Vukelić J | title = Second trimester pregnancy termination in primigravidas by double application of dinoprostone gel and intramuscular administration of carboprost tromethamine. | journal = Med Pregl | volume = 54 | issue = 1–2 | pages = 11–6 | year = 2001| pmid = 11436877}}
	* {{cite journal | author = Ippoliti C, Przepiorka D, Mehra R, Neumann J, Wood J, Claxton D, Gajewski J, Khouri I, van Besien K, Andersson B | title = Intravesicular carboprost for the treatment of hemorrhagic cystitis after marrow transplantation | journal = Urology | volume = 46 | issue = 6 | pages = 811–5 | year = 1995 | pmid = 7502421 | doi = 10.1016/S0090-4295(99)80349-5}}
	{{Prostaglandins}}		{{Prostaglandins}}
	{{Oxytocics}}		{{Oxytocics}}
			{{Obstetric drugs}}
			{{Prostanoidergics}}
	]		]
			]
	]		]
			]
	{{genito-urinary-drug-stub}}