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Identification
Name Dinoprost Tromethamine
Accession Number DB01160 (APRD00926)
Type small molecule
Groups approved
Description

The tromethamine (THAM) salt of the naturally occurring prostaglandin F2 alpha, dinoprost tromethamine occurs as a white to off-white, very hygroscopic, crystalline powder. Dinoprost tromethamine may also be known as dinoprost trometamol, PGF2 alpha THAM, or prostaglandin F2 alpha tromethamine.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Dinoprost, trometamol salt
  • PGF2-alpha THAM
  • PGF2alpha THAM
  • Prostaglandin F2-alpha THAM
  • Prostaglandin F2a tromethamine
  • Prostaglandin F2alpha tham
  • Prostin F2 Alpha
Synonyms
Dinoprost, trometamol salt
PGF2-alpha THAM
PGF2alpha THAM
Prostaglandin F2-alpha THAM
Prostaglandin F2a tromethamine
Prostaglandin F2alpha tham
Prostin F2 Alpha
Salts Not Available
Brand names
Name Company
Dinolytic
Ensaprost
Lutalyse
Panacelan F tromethamine salt
Pronalgon F
Prostalmon F
Zinoprost
Brand mixtures Not Available
Categories
  • Oxytocics
  • Abortifacient Agents, Nonsteroidal
  • Diagnostic aid (angiography)
  • Uterine stimulants
CAS number 38562-01-5
Weight Average: 475.616
Monoisotopic: 475.314517421
Chemical Formula C24H45NO8
InChI Key InChIKey=IYGXEHDCSOYNKY-RZHHZEQLSA-N
InChI
InChI=1S/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1
Plain Text
IUPAC Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; 2-amino-2-(hydroxymethyl)propane-1,3-diol
SMILES
OCC(N)(CO)CO.CCCCC[C@H](O)\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 Organic
Classes
  • Carboxylic Acids and Derivatives
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
Pharmacology
Indication Used for aborting second-trimester pregnancy (between the twelfth to eighteenth week of gestation) and in incomplete abortion or for therapeutic abortion in cases of intrauterine fetal death and congenital abnormalities incompatible with life. Also used at low-doses for medically indicated induction of labor at term. Also injected intra-arterially for use as a vasodilator to assist in angiography.
Pharmacodynamics Dinoprost tromethamine is the tromethamine (THAM) salt of the naturally occurring prostaglandin F2alpha. Prostaglandin F2alpha has several pharmacologic effects on the female reproductive system, including stimulation of myometrial activity, relaxation of the cervix, inhibition of steroidogenesis by corpora lutea, and can potentially lyse corpora lutea.
Mechanism of action Dinoprost tromethamine appears to act directly on the myometrium, but this has not been completely established. Dinoprost stimulates myometrial contractions (via its interaction with the prostaglandin receptors) in the gravid uterus that are similar to the contractions that occur in the term uterus during labor. These contractions are usually sufficient to cause abortion. Uterine response to prostaglandins increases gradually throughout pregnancy. Dinoprost also facilitates cervical dilatation and softening.
Absorption Slowly absorbed from the amniotic fluid into systemic circulation.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Enzymatic dehydrogenation primarily in the maternal lungs and also in the liver.
Route of elimination Not Available
Half life The half-life of dinoprost in amniotic fluid is 3 to 6 hours. The plasma half-life of dinoprost after intravenous administration is reported to be less than 1 minute.
Clearance Not Available
Toxicity Although overdose by intra-amniotic administration of dinoprost has not been reported, exaggeration of the nausea, vomiting, and diarrhea that occur with normal doses would be expected.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
Form Route Strength
Solution Intra-amniotic
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 100 oC
Experimental Properties
Property Value Source
water solubility 0.2 g/mL PhysProp
logP -0.12 PhysProp
Predicted Properties
Property Value Source
water solubility ALOGPS
logP 0 ALOGPS
logP 2.61 ChemAxon Molconvert
logS 0 ALOGPS
pKa 14.51 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 97.99 ChemAxon Molconvert
rotatable bond count 15 ChemAxon Molconvert
refractivity 100.47 ChemAxon Molconvert
polarizability 41.56 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D01352 Link_out
PubChem Compound 5282415 Link_out
PubChem Substance 46509164 Link_out
ChemSpider 4445570 Link_out
Therapeutic Targets Database DAP000826 Link_out
PharmGKB PA449344 Link_out
Drug Product Database 813605 Link_out
ATC Codes
  • G02AD01
AHFS Codes
  • 76:00.00
PDB Entries Not Available
FDA label Not Available
MSDS show (51.3 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Prostaglandin F2-alpha receptor

Pharmacological action: yes
Actions: agonist

Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum

Organism class: human
UniProt ID: P43088 Link_out
Gene: PTGFR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sakamoto K, Kamimura M, Kurozumi S, Ito S: Prostaglandin F2 alpha receptor. J Lipid Mediat Cell Signal. 1995 Oct;12(2-3):405-11. Pubmed

2. Prostacyclin receptor

Pharmacological action: unknown
Actions: antagonist

Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase

Organism class: human
UniProt ID: P43119 Link_out
Gene: PTGIR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:46