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Identification
Name Carboprost Tromethamine
Accession Number DB00429 (APRD00847)
Type small molecule
Groups approved
Description

A nonsteroidal abortifacient agent that is effective in both the first and second trimesters of pregnancy. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Carboprost
Hemabate
Tham
Brand mixtures Not Available
Categories
  • Oxytocics
  • Abortifacient Agents, Nonsteroidal
CAS number 58551-69-2
Weight Average: 489.6426
Monoisotopic: 489.330167485
Chemical Formula C25H47NO8
InChI Key InChIKey=UMMADZJLZAPZAW-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
Plain Text
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-]
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication 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: 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.
Pharmacodynamics Carboprost 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 action Carboprost 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Metabolized in the lungs and liver. Metabolites are excreted in urine.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include irritation, nausea, vomiting, diarrhea, coughing, dyspnea, asthma, hypertension, flushing, and pyrexia.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Hospira inc
Packagers
Dosage forms
Form Route Strength
Solution Intramuscular
Prices
Unit description Cost Unit
Hemabate 250 mcg/ml ampul 92.89 USD ml
Tham iv solution 0.49 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 95-105 °C Not Available
water solubility Carboprost tromethamine dissolves readily in water at room temperature at a concentration greater than 75 mg/mL. Not Available
logP 3.3 Not Available
Predicted Properties
Property Value Source
water solubility 6.22e-02 g/l ALOGPS
logP 1.07 ALOGPS
logP 2.89 ChemAxon
logS -3.9 ALOGPS
pKa (strongest acidic) 4.36 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 100.82 ChemAxon
rotatable bond count 15 ChemAxon
refractivity 115.95 ChemAxon
polarizability 42.51 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00682 Link_out
ChEBI 3404 Link_out
ChEMBL 3404 Link_out
Therapeutic Targets Database DAP001215 Link_out
PharmGKB PA164754883 Link_out
Drug Product Database 2230417 Link_out
RxList http://www.rxlist.com/cgi/generic/hemabate.htm Link_out
Drugs.com http://www.drugs.com/mtm/carboprost.html Link_out
ATC Codes
  • G02AD04
AHFS Codes
  • 76:00.00
PDB Entries Not Available
FDA label Not Available
MSDS show (49.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Prostaglandin E2 receptor, EP1 subtype

Pharmacological action: yes
Actions: agonist

Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues

Organism class: human
UniProt ID: P34995 Link_out
Gene: PTGER1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19