Identification
- Generic Name
- Dinoprost tromethamine
- DrugBank Accession Number
- DB01160
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Dinoprost tromethamine (DB01160)
- Weight
- Average: 475.616
Monoisotopic: 475.314517421 - Chemical Formula
- C24H45NO8
- Synonyms
- Dinoprost trometamol
- Dinoprost tromethamine
- PGF2-alpha THAM
- PGF2A THAM
- PGF2alpha THAM
- Prostaglandin F2-alpha THAM
- Prostaglandin F2a tromethamine
- Prostaglandin F2alpha tham
- Prostin F2 Alpha
- External IDs
- U-14-583E
- U-14,583E
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AProstaglandin F2-alpha receptor agonistHumans UProstacyclin receptor antagonistHumans - 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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareCarboprost tromethamine Carboprost tromethamine may increase the uterotonic activities of Dinoprost tromethamine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Dinolytic (Pfizer) / Enzaprost F (Chinoin) / Prosmon (Fuji Yakuhin) / Prostin F2 Alpha (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Prostin F2 Alpha Solution 5 mg / mL Intra-amniotic Pfizer Canada Ulc 1974-12-31 2018-09-30 Canada 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Eicosanoids
- Direct Parent
- Prostaglandins and related compounds
- Alternative Parents
- Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Cyclopentanols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Cyclopentanol / Fatty acid / Hydrocarbon derivative / Hydroxy fatty acid
- Molecular Framework
- Not Available
- External Descriptors
- organic molecular entity (CHEBI:31502)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- CT6BBQ5A68
- CAS number
- 38562-01-5
- InChI Key
- 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
- 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
- NC(CO)(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
References
- Synthesis Reference
Morozowich, W.; U.S. Patent 3,657,327; April 18,1972; assigned to The Upjohn Company.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015291
- KEGG Drug
- D01352
- KEGG Compound
- C12786
- PubChem Compound
- 5282415
- PubChem Substance
- 46509164
- ChemSpider
- 4445570
- 23321
- ChEBI
- 31502
- ChEMBL
- CHEMBL1200896
- Therapeutic Targets Database
- DAP000826
- PharmGKB
- PA164781385
- Wikipedia
- Prostaglandin_F2alpha
- MSDS
- Download (51.3 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Pfizer Inc.
- Dosage Forms
Form Route Strength Solution Intra-amniotic 5 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 100-101 Morozowich, W.; U.S. Patent 3,657,327; April 18,1972; assigned to The Upjohn Company. water solubility 0.2 g/mL Not Available logP -0.12 Not Available - Predicted Properties
Property Value Source Water Solubility 0.117 mg/mL ALOGPS logP 3.11 ALOGPS logP 2.61 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 4.36 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 97.99 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 100.47 m3·mol-1 Chemaxon Polarizability 41.08 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9588 Blood Brain Barrier - 0.6473 Caco-2 permeable - 0.674 P-glycoprotein substrate Substrate 0.6903 P-glycoprotein inhibitor I Non-inhibitor 0.9204 P-glycoprotein inhibitor II Non-inhibitor 0.9821 Renal organic cation transporter Non-inhibitor 0.8743 CYP450 2C9 substrate Non-substrate 0.838 CYP450 2D6 substrate Non-substrate 0.7753 CYP450 3A4 substrate Non-substrate 0.5576 CYP450 1A2 substrate Non-inhibitor 0.6725 CYP450 2C9 inhibitor Non-inhibitor 0.9145 CYP450 2D6 inhibitor Non-inhibitor 0.764 CYP450 2C19 inhibitor Non-inhibitor 0.8258 CYP450 3A4 inhibitor Non-inhibitor 0.9349 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9466 Ames test Non AMES toxic 0.9033 Carcinogenicity Non-carcinogens 0.9383 Biodegradation Not ready biodegradable 0.7399 Rat acute toxicity 2.1479 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9677 hERG inhibition (predictor II) Non-inhibitor 0.8921
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 218.60014 predictedDeepCCS 1.0 (2019) [M+H]+ 220.9957 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.16177 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Prostaglandin f receptor activity
- Specific Function
- 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...
- Gene Name
- PTGFR
- Uniprot ID
- P43088
- Uniprot Name
- Prostaglandin F2-alpha receptor
- Molecular Weight
- 40054.1 Da
References
- Sakamoto K, Kamimura M, Kurozumi S, Ito S: Prostaglandin F2 alpha receptor. J Lipid Mediat Cell Signal. 1995 Oct;12(2-3):405-11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase.
- Gene Name
- PTGIR
- Uniprot ID
- P43119
- Uniprot Name
- Prostacyclin receptor
- Molecular Weight
- 40955.485 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
- Gene Name
- SLCO2A1
- Uniprot ID
- Q92959
- Uniprot Name
- Solute carrier organic anion transporter family member 2A1
- Molecular Weight
- 70043.33 Da
References
- Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 an...
- Gene Name
- SLCO3A1
- Uniprot ID
- Q9UIG8
- Uniprot Name
- Solute carrier organic anion transporter family member 3A1
- Molecular Weight
- 76552.135 Da
References
- Adachi H, Suzuki T, Abe M, Asano N, Mizutamari H, Tanemoto M, Nishio T, Onogawa T, Toyohara T, Kasai S, Satoh F, Suzuki M, Tokui T, Unno M, Shimosegawa T, Matsuno S, Ito S, Abe T: Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55