Identification

Name
Dinoprost Tromethamine
Accession Number
DB01160  (APRD00926)
Type
Small Molecule
Groups
Approved, Vet 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
Synonyms
  • Dinoprost trometamol
  • PGF2-alpha THAM
  • PGF2alpha THAM
  • Prostaglandin F2-alpha THAM
  • Prostaglandin F2a tromethamine
  • Prostaglandin F2alpha tham
  • Prostin F2 Alpha
External IDs
U-14-583E / U-14,583E
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prostin F2 AlphaSolution5 mgIntra-amnioticPfizer1974-12-31Not applicableCanada
International/Other Brands
Dinolytic (Pfizer) / Enzaprost F (Chinoin) / Prosmon (Fuji Yakuhin) / Prostin F2 Alpha (Pfizer)
Categories
UNII
CT6BBQ5A68
CAS number
38562-01-5
Weight
Average: 475.616
Monoisotopic: 475.314517421
Chemical Formula
C24H45NO8
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
OCC(N)(CO)CO.CCCCC[[email protected]](O)\C=C\[[email protected]]1[[email protected]](O)C[[email protected]](O)[[email protected]@H]1C\C=C/CCCC(O)=O

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.

Structured Indications
Not Available
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.

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Human
UProstacyclin receptor
antagonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Aceclofenac.Approved, Investigational
AcemetacinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Acemetacin.Approved
Acetylsalicylic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Adapalene.Approved
AlclofenacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Alclofenac.Approved, Withdrawn
AlminoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Alminoprofen.Experimental
AndrographolideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Andrographolide.Investigational
AnisodamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Antipyrine.Approved
ApocyninThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Apocynin.Investigational
ApremilastThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Apremilast.Approved, Investigational
AzapropazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Balsalazide.Approved, Investigational
BendazacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bendazac.Experimental
BenorilateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Benorilate.Experimental
BenoxaprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Benoxaprofen.Withdrawn
BenzydamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Benzydamine.Approved
BevoniumThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bevonium.Experimental
BromfenacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bucillamine.Investigational
BufexamacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bufexamac.Experimental
BumadizoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Bumadizone.Experimental
Carbaspirin calciumThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Carbaspirin calcium.Experimental, Investigational
Carboprost TromethamineThe risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Dinoprost Tromethamine.Approved
CarprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Celecoxib.Approved, Investigational
ChloroquineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Chloroquine.Approved, Vet Approved
Choline magnesium trisalicylateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Choline magnesium trisalicylate.Approved
ClonixinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Clonixin.Approved
CurcuminThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Curcumin.Investigational
D-LimoneneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with D-Limonene.Investigational
DiclofenacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DifenpiramideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Difenpiramide.Experimental
DiflunisalThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Diflunisal.Approved
DroxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Duvelisib.Investigational
E-6201The therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with E-6201.Investigational
EpirizoleThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Epirizole.Approved
EtanerceptThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Etanercept.Approved, Investigational
EthenzamideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ethenzamide.Experimental
EtodolacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Etofenamate.Approved, Investigational
EtoricoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Evening primrose oil.Approved, Investigational
exisulindThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with exisulind.Investigational
FelbinacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Felbinac.Experimental
FenbufenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Fenbufen.Approved
FenoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Fenoprofen.Approved
FentiazacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Fentiazac.Experimental
FeprazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Feprazone.Experimental
Ferulic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ferulic acid.Experimental
FloctafenineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlunixinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Flunixin.Vet Approved
FlunoxaprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Flunoxaprofen.Experimental
FlurbiprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Flurbiprofen.Approved, Investigational
GuacetisalThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Guacetisal.Experimental
HigenamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Higenamine.Investigational
IbuprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Icatibant.Approved
Imidazole salicylateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Imidazole salicylate.Experimental
IndobufenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Indobufen.Investigational
IndomethacinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Indoprofen.Withdrawn
IsoxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Isoxicam.Withdrawn
KebuzoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Kebuzone.Experimental
KetoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Ketorolac.Approved
LeflunomideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Leflunomide.Approved, Investigational
LisofyllineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Lisofylline.Investigational
LonazolacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Lonazolac.Experimental
LornoxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Lornoxicam.Approved, Investigational
LoxoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Loxoprofen.Approved, Investigational
LumiracoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Magnesium salicylate.Approved
MasoprocolThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Masoprocol.Approved, Investigational
Meclofenamic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Metamizole.Investigational, Withdrawn
MizoribineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mizoribine.Investigational
MofebutazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mofebutazone.Experimental
Mycophenolate mofetilThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nabumetone.Approved
NafamostatThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nafamostat.Approved, Investigational
NaftifineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Naftifine.Approved
NaproxenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Naproxen.Approved, Vet Approved
NepafenacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nepafenac.Approved
NifenazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nifenazone.Experimental
Niflumic AcidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Niflumic Acid.Approved
NimesulideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NitroaspirinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Nitroaspirin.Investigational
OlopatadineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Olsalazine.Approved
OrgoteinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Orgotein.Vet Approved
OxaprozinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Oxaprozin.Approved
OxyphenbutazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Oxyphenbutazone.Approved, Withdrawn
ParecoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Parecoxib.Approved
ParthenolideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Parthenolide.Investigational
PhenylbutazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PirfenidoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Pirfenidone.Approved, Investigational
PiroxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Piroxicam.Approved, Investigational
PirprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Pirprofen.Experimental
PranoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Pranoprofen.Experimental, Investigational
ProglumetacinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Proglumetacin.Experimental
PropacetamolThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Propacetamol.Approved, Investigational
PropyphenazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Propyphenazone.Experimental
ProquazoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Proquazone.Experimental
PTC299The therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with PTC299.Investigational
ResveratrolThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Resveratrol.Approved, Experimental, Investigational
RofecoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
SalicylamideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Salsalate.Approved
SemapimodThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Semapimod.Investigational
SeratrodastThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Seratrodast.Approved
SerrapeptaseThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Serrapeptase.Investigational
SRT501The therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Suprofen.Approved, Withdrawn
SuxibuzoneThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Suxibuzone.Experimental
TarenflurbilThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tarenflurbil.Investigational
TenidapThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tenidap.Experimental
TenoxicamThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Teriflunomide.Approved
Tiaprofenic acidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tiaprofenic acid.Approved
TinoridineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tinoridine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tolmetin.Approved
TranilastThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tranilast.Approved, Investigational
TribenosideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Tribenoside.Experimental
TriptolideThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Triptolide.Investigational
ValdecoxibThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
ZaltoprofenThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Zaltoprofen.Approved, Investigational
ZileutonThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Zomepirac.Withdrawn
Food Interactions
Not Available

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
HMDB15291
KEGG Drug
D01352
KEGG Compound
C12786
PubChem Compound
5282415
PubChem Substance
46509164
ChemSpider
4445570
ChEBI
31502
ChEMBL
CHEMBL1200896
Therapeutic Targets Database
DAP000826
PharmGKB
PA164781385
Wikipedia
Prostaglandin_F2alpha
AHFS Codes
  • 76:00.00 — Oxytocics
MSDS
Download (51.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
SolutionIntra-amniotic5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)100-101Morozowich, W.; U.S. Patent 3,657,327; April 18,1972; assigned to The Upjohn Company.
water solubility0.2 g/mLNot Available
logP-0.12Not Available
Predicted Properties
PropertyValueSource
logP2.61ChemAxon
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.47 m3·mol-1ChemAxon
Polarizability41.56 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9588
Blood Brain Barrier-0.6473
Caco-2 permeable-0.674
P-glycoprotein substrateSubstrate0.6903
P-glycoprotein inhibitor INon-inhibitor0.9204
P-glycoprotein inhibitor IINon-inhibitor0.9821
Renal organic cation transporterNon-inhibitor0.8743
CYP450 2C9 substrateNon-substrate0.838
CYP450 2D6 substrateNon-substrate0.7753
CYP450 3A4 substrateNon-substrate0.5576
CYP450 1A2 substrateNon-inhibitor0.6725
CYP450 2C9 inhibitorNon-inhibitor0.9145
CYP450 2D6 inhibitorNon-inhibitor0.764
CYP450 2C19 inhibitorNon-inhibitor0.8258
CYP450 3A4 inhibitorNon-inhibitor0.9349
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9466
Ames testNon AMES toxic0.9033
CarcinogenicityNon-carcinogens0.9383
BiodegradationNot ready biodegradable0.7399
Rat acute toxicity2.1479 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9677
hERG inhibition (predictor II)Non-inhibitor0.8921
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Prostaglandin skeleton / Long-chain fatty acid / Hydroxy fatty acid / Cyclopentanol / Fatty acid / Unsaturated fatty acid / Cyclic alcohol / Secondary alcohol / Carboxylic acid derivative / Carboxylic acid
Molecular Framework
Not Available
External Descriptors
organic molecular entity (CHEBI:31502)

Targets

Kind
Protein
Organism
Human
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
  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:8777582]
Kind
Protein
Organism
Human
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
  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:17139284]
  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:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Transporters

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11907186]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11907186]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11907186]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11907186]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11907186]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:8787677]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:14631946]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34