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Identification
NameCarboprost Tromethamine
Accession NumberDB00429  (APRD00847)
TypeSmall Molecule
GroupsApproved
Description

A nonsteroidal abortifacient agent that is effective in both the first and second trimesters of pregnancy. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(15S)-15-Methyl-pgf2alpha tromethamine saltNot AvailableNot Available
(15S)-15-Methylprostaglandin F2alpha tromethamineNot AvailableNot Available
1,3-Dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z,9alpha,11beta,13e,15S)-9,11,15-trihydroxy-15-methylprosta-5,13-dien-1-oateNot AvailableNot Available
15(S)-15-Methyl-pgf2alpha tromethamine saltNot AvailableNot Available
15(S)-15-Methylprostaglandin F2alpha tromethamineNot AvailableNot Available
CarboprostNot AvailableBAN, USAN, DCF
Carboprost trometamolNot AvailableNot Available
MethyldinoprostNot AvailableIS
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hemabateinjection, solution250 ug/mLintramuscularPharmacia and Upjohn Company1979-01-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thaminjection, solution3.6 g/100mLintravenousHospira, Inc.2009-11-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Hemabatesolution250 µgintramuscularPfizer Canada IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
CarboprostNot Available
DeviprostDr. Reddy's
Prostin 15MPfizer
ProstinfenemPfizer
ProstodinAstraZeneca
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number58551-69-2
WeightAverage: 489.6426
Monoisotopic: 489.330167485
Chemical FormulaC25H47NO8
InChI KeyUMMADZJLZAPZAW-OVXHCKHTSA-N
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
IUPAC Name
1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (5Z)-7-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-3-methyloct-1-en-1-yl]cyclopentyl]hept-5-enoate
SMILES
OCC([NH3+])(CO)CO.CCCCC[C@@](O)(C)\C=C\[C@H]1[C@@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)[O-]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Carbocyclic fatty acid
  • Branched fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclopentanol
  • Tertiary alcohol
  • Quaternary ammonium salt
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid salt
  • 1,2-aminoalcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aliphatic homomonocyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsCarboprost 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.
Mechanism of actionCarboprost is a synthetic prostaglandin. It binds the prostaglandin E2 receptor, causing myometrial contractions, casuing 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include irritation, nausea, vomiting, diarrhea, coughing, dyspnea, asthma, hypertension, flushing, and pyrexia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5755
Blood Brain Barrier-0.5581
Caco-2 permeable-0.6594
P-glycoprotein substrateSubstrate0.6894
P-glycoprotein inhibitor INon-inhibitor0.9445
P-glycoprotein inhibitor IINon-inhibitor0.9643
Renal organic cation transporterNon-inhibitor0.8922
CYP450 2C9 substrateNon-substrate0.8241
CYP450 2D6 substrateNon-substrate0.7916
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7693
CYP450 2C9 substrateNon-inhibitor0.8874
CYP450 2D6 substrateNon-inhibitor0.7649
CYP450 2C19 substrateNon-inhibitor0.8534
CYP450 3A4 substrateNon-inhibitor0.943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.933
Ames testNon AMES toxic0.9008
CarcinogenicityNon-carcinogens0.9422
BiodegradationReady biodegradable0.5
Rat acute toxicity2.4308 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9511
hERG inhibition (predictor II)Non-inhibitor0.9008
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintramuscular250 ug/mL
Injection, solutionintravenous3.6 g/100mL
Solutionintramuscular250 µg
Prices
Unit descriptionCostUnit
Hemabate 250 mcg/ml ampul92.89USD ml
Tham iv solution0.49USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point95-105 °CNot Available
water solubilityCarboprost tromethamine dissolves readily in water at room temperature at a concentration greater than 75 mg/mL.Not Available
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0622 mg/mLALOGPS
logP1.07ALOGPS
logP2.89ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.82 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity115.95 m3·mol-1ChemAxon
Polarizability42.51 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Ming Li, “CRYSTALS OF CARBOPROST TROMETHAMINE AND THE PREPARATION METHOD AS WELL AS THE USES THEREOF.” U.S. Patent US20130190404, issued July 25, 2013.

US20130190404
General ReferenceNot Available
External Links
ATC CodesG02AD04
AHFS Codes
  • 76:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.2 KB)
Interactions
Drug Interactions
Drug
CarbetocinMay enhance the adverse/toxic effect of Oxytocic Agents. Specifically, oxytocic effects may be enhanced.
OxytocinMay enhance the adverse/toxic effect of Oxytocic Agents. Specifically, oxytocic effects may be enhanced.
Food InteractionsNot Available

Targets

1. Prostaglandin E2 receptor EP1 subtype

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Prostaglandin E2 receptor EP1 subtype P34995 Details

References:

  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  2. Hay A, Wood S, Olson D, Slater D: Labour is associated with decreased expression of the PGF2{alpha} receptor (PTGFR) and a novel PTGFR splice variant in human myometrium but not decidua. Mol Hum Reprod. 2010 Jun 2. Pubmed
  3. Tsuboi K, Ichikawa A: [Reproduction physiology and prostanoids] Nippon Yakurigaku Zasshi. 2001 Apr;117(4):267-73. Pubmed
  4. Carrasco MP, Asboth G, Phaneuf S, Lopez Bernal A: Activation of the prostaglandin FP receptor in human granulosa cells. J Reprod Fertil. 1997 Nov;111(2):309-17. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 07, 2014 12:15