Dinoprostone

Identification

Summary

Dinoprostone is a prostaglandin used to induce labor or abortion as well as to treat nonmetastatic gestational trophoblastic disease.

Brand Names
Cervidil, Prepidil, Prostin E2
Generic Name
Dinoprostone
DrugBank Accession Number
DB00917
Background

Dinoprostone is a naturally occurring prostaglandin E2 (PGE2). It has important effects in labour. It also stimulates osteoblasts to release factors which stimualtes bone resorption by osteoclasts. As a prescription drug it is used as a vaginal suppository, to prepare the cervix for labour and to induce labour.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 352.4651
Monoisotopic: 352.224974134
Chemical Formula
C20H32O5
Synonyms
  • (15S)-prostaglandin E2
  • (5Z,11α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
  • (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
  • (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate
  • (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid
  • (Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid
  • Dinoproston
  • Dinoprostona
  • Dinoprostone
  • Dinoprostone Prostaglandin E2
  • Dinoprostonum
  • PGE2
  • Prostaglandin E2
External IDs
  • U-12,062
  • U-12062

Pharmacology

Indication

For the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGestational trophoblastic disease•••••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Dinoprostone is equivalent to prostaglandin E2 (PGE2). It stimulates labor and delivery by stimulating the uterine, and thus terminates pregnancy. Dinoprostone is also capable of stimulating the smooth muscle of the gastrointestinal tract of man. This activity may be responsible for the vomiting and/or diarrhea that is not uncommon when dinoprostone is used to terminate pregnancy.

Mechanism of action

Dinoprostone administered intravaginally stimulates the myometrium of the gravid uterus to contract in a manner that is similar to the contractions seen in the term uterus during labor, resulting in the evacuation of the products of conception from the uterus. It is believed that dinoprostone exerts its uterine effects via direct myometrial stimulation, but the exact mechanism of action is unkown. Other suggested mechanisms include the regulation of cellular membrane calcium transport and of intracellular concentrations of cyclic 3',5'-adenosine monophosphate. Dinoprostone also appears to produce local cervical effects including softening, effacement, and dilation. The exact mechanism of action for this effect is also unknown, but it has been suggested that this effect may be associated with collagen degradation caused by secretion of the enzyme collagenase as a partial response to locally administered dinoprostone.

TargetActionsOrganism
AProstaglandin E2 receptor EP2 subtype
agonist
Humans
AProstaglandin E2 receptor EP1 subtype
agonist
Humans
AProstaglandin E2 receptor EP3 subtype
agonist
Humans
AProstaglandin E2 receptor EP4 subtype
agonist
Humans
UProstaglandin D2 receptor 2
agonist
Humans
Absorption

Absorbed at a rate of 0.3 mg per hour over 12 hours while the vaginal system is in place.

Volume of distribution

Not Available

Protein binding

73%, to albumin

Metabolism

Rapid metabolism of dinoprostone occurs primarily in the local tissues; any systemic absorption of the medication is cleared mainly in the maternal lungs and, secondarily, at sites such as the liver and kidneys.

Route of elimination

The major route of elimination of the products of PGE2 metabolism is the kidneys.

Half-life

Less than 5 minutes.

Clearance

Not Available

Adverse Effects
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Toxicity

Oral, mouse: LD50 = 750 mg/kg; Oral, rat: LD50 = 500 mg/kg.

Pathways
PathwayCategory
Piroxicam Action PathwayDrug action
Rofecoxib Action PathwayDrug action
Diclofenac Action PathwayDrug action
Sulindac Action PathwayDrug action
Nabumetone Action PathwayDrug action
Valdecoxib Action PathwayDrug action
Antipyrine Action PathwayDrug action
Flurbiprofen Action PathwayDrug action
Nepafenac Action PathwayDrug action
Arachidonic Acid MetabolismMetabolic
Acetylsalicylic Acid Action PathwayDrug action
Ketorolac Action PathwayDrug action
Bromfenac Action PathwayDrug action
Meloxicam Action PathwayDrug action
Mefenamic Acid Action PathwayDrug action
Oxaprozin Action PathwayDrug action
Naproxen Action PathwayDrug action
Carprofen Action PathwayDrug action
Etoricoxib Action PathwayDrug action
Lumiracoxib Action PathwayDrug action
Phenylbutazone Action PathwayDrug action
Salsalate Action PathwayDrug action
Salicylate-Sodium Action PathwayDrug action
Acetaminophen Action PathwayDrug action
Etodolac Action PathwayDrug action
Ketoprofen Action PathwayDrug action
Ibuprofen Action PathwayDrug action
Celecoxib Action PathwayDrug action
Suprofen Action PathwayDrug action
Indomethacin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AcamprosateThe excretion of Acamprosate can be decreased when combined with Dinoprostone.
AcetazolamideThe excretion of Dinoprostone can be decreased when combined with Acetazolamide.
AcetylcholineThe risk or severity of adverse effects can be increased when Dinoprostone is combined with Acetylcholine.
AcetylcysteineThe excretion of Dinoprostone can be decreased when combined with Acetylcysteine.
Acetylsalicylic acidThe excretion of Dinoprostone can be decreased when combined with Acetylsalicylic acid.
Food Interactions
No interactions found.

Products

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International/Other Brands
Propess (Ferring Pharmaceuticals) / Prostarmon E (DCPC) / PROSTIN
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CervidilInsert10 mg / insertVaginalFerring Pharmaceuticals1997-06-17Not applicableCanada flag
CervidilInsert, extended release10 mg/1VaginalForest Laboratories1995-05-192015-12-31US flag
CervidilInsert10 mg/241mgVaginalFerring Pharmaceuticals Inc.1995-03-30Not applicableUS flag
DinoprostoneInsert10 mg/241mgVaginalFerring Pharmaceuticals Inc.2014-02-012014-03-31US flag
PrepidilGel0.5 mg/3gVaginalPharmacia and Upjohn Company LLC1992-12-09Not applicableUS flag

Categories

ATC Codes
G02AD02 — Dinoprostone
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 ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Cyclic ketone / Cyclopentanol / Fatty acid / Hydrocarbon derivative
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
prostaglandins E (CHEBI:15551) / Prostaglandins (C00584) / Prostaglandins (LMFA03010003)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
K7Q1JQR04M
CAS number
363-24-6
InChI Key
XEYBRNLFEZDVAW-ARSRFYASSA-N
InChI
InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
IUPAC Name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

References

Synthesis Reference

Yu-Wen Su, Meng-Hwan Lee, "Composition for inhibiting nitric oxide and/or prostaglandin E2 synthesis and method for inhibiting inflammation." U.S. Patent US20080268078, issued October 30, 2008.

US20080268078
General References
Not Available
Human Metabolome Database
HMDB0001220
KEGG Drug
D00079
KEGG Compound
C00584
PubChem Compound
5280360
PubChem Substance
46505549
ChemSpider
4444059
BindingDB
35847
RxNav
3478
ChEBI
15551
ChEMBL
CHEMBL548
ZINC
ZINC000003830713
Therapeutic Targets Database
DAP000360
PharmGKB
PA449345
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
P2E
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Prostaglandin_E2
PDB Entries
3wfh / 6ak3 / 7cx2 / 7d7m / 8bwr / 8gcp / 8gdb / 8gdc / 8sxb
MSDS
Download (69.1 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
  • Controlled therapeutics (scotland) ltd
Packagers
  • Controlled Therapeutics Ltd.
  • Forest Pharmaceuticals
  • Pfizer Inc.
  • Pharmacia Inc.
Dosage Forms
FormRouteStrength
InsertVaginal10 mg / insert
InsertVaginal10 mg/241mg
Insert, extended releaseVaginal10 mg/1
SuppositoryVaginal
InsertVaginal
GelEndocervical; Vaginal0.5 MG/3G
GelVaginal0.5 mg/3g
GelVaginal0.500 mg
GelVaginal1 MG/3G
GelVaginal2 MG/3G
GelEndocervical0.5 mg/2.5ml
GelVaginal0.5 mg
GelEndocervical0.5 mg / 2.5 mL
InsertVaginal10.000 mg
Insert, extended releaseVaginal10 mg
InsertVaginal10 mg
InsertVaginal1000000 mg
Injection, solution
SuppositoryVaginal20 mg/1
TabletVaginal3 mg
TabletVaginal
TabletOral0.5 mg
GelVaginal1 mg / 3 g
GelVaginal2 mg / 3 g
Prices
Unit descriptionCostUnit
Prostin e2 vaginal 20 mg sup1177.04USD each
Cervidil 10 mg vaginal insrt256.13USD each
Prepidil 0.5 mg/3 gm gel104.94USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5269321No1993-12-142012-07-14US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)67 °CPhysProp
water solubility58.1 mg/LNot Available
logP2.82HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.044 mg/mLALOGPS
logP3.31ALOGPS
logP3.23Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.3Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity99.44 m3·mol-1Chemaxon
Polarizability41 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9815
Blood Brain Barrier+0.8704
Caco-2 permeable+0.5245
P-glycoprotein substrateSubstrate0.5554
P-glycoprotein inhibitor INon-inhibitor0.9202
P-glycoprotein inhibitor IINon-inhibitor0.8983
Renal organic cation transporterNon-inhibitor0.9064
CYP450 2C9 substrateNon-substrate0.8211
CYP450 2D6 substrateNon-substrate0.8834
CYP450 3A4 substrateNon-substrate0.5292
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9502
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9725
Ames testNon AMES toxic0.9387
CarcinogenicityNon-carcinogens0.9201
BiodegradationReady biodegradable0.6056
Rat acute toxicity2.9631 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9087
hERG inhibition (predictor II)Non-inhibitor0.9138
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
GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)GC-MSsplash10-0059-4920000000-6108934d406ea4062761
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a73-5395000000-02aad995307bb6a67f94
GC-MS Spectrum - GC-MSGC-MSsplash10-0059-4920000000-6108934d406ea4062761
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00yi-0398000000-41c3a62b076046d87381
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, NegativeLC-MS/MSsplash10-00di-0495000000-df406a9e4cc995523a7e
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00dr-0592000000-928e66269ab2854faa42
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, NegativeLC-MS/MSsplash10-00dr-0590000000-b364a55fc0598d9265b5
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00dr-0890000000-b3a25d975f2a38d7e49f
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, NegativeLC-MS/MSsplash10-0079-0960000000-c67461d3bd965cbf289c
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-000i-0920000000-830ad149a4fe8f36e211
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, NegativeLC-MS/MSsplash10-07br-0910000000-35e5bd204c947e2c4bcc
LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, NegativeLC-MS/MSsplash10-05fs-0900000000-573b0c5a4593210b387a
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00yi-0398000000-612bce8f105beae0c5f2
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00di-0495000000-78584a9b664c5155b473
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0592000000-b37d658cf7b0d590aad4
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0590000000-985f93ab468aa6a8a1b8
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-00dr-0890000000-5757ca5e8720a47086dc
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-0079-0960000000-c67461d3bd965cbf289c
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-000i-0920000000-830ad149a4fe8f36e211
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-07br-0910000000-35e5bd204c947e2c4bcc
LC-MS/MS Spectrum - LC-ESI-QIT , negativeLC-MS/MSsplash10-05fs-0900000000-573b0c5a4593210b387a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-0294000000-9d89acbe9e631d718a4b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00or-0096000000-67e3460a07ad1397b529
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-0124e5605586cae5d90f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0039000000-7fc7f4b79aa4853811e7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-067r-0089000000-88811d557efaf3aa7d9b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-2489000000-5817660ffc264a808eac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01e9-7695000000-2ead48734800092d2e8c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aou-9800000000-6432bb5f85d57adbda95
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-217.8992855
predicted
DarkChem Lite v0.1.0
[M-H]-187.6606013
predicted
DarkChem Standard v0.1.0
[M-H]-215.3271855
predicted
DarkChem Lite v0.1.0
[M-H]-219.3183855
predicted
DarkChem Lite v0.1.0
[M-H]-199.32225
predicted
DeepCCS 1.0 (2019)
[M+H]+216.3196855
predicted
DarkChem Lite v0.1.0
[M+H]+215.5002855
predicted
DarkChem Lite v0.1.0
[M+H]+217.9471855
predicted
DarkChem Lite v0.1.0
[M+H]+220.7842855
predicted
DarkChem Lite v0.1.0
[M+H]+201.71782
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.0488855
predicted
DarkChem Lite v0.1.0
[M+Na]+197.1439596
predicted
DarkChem Standard v0.1.0
[M+Na]+214.7851855
predicted
DarkChem Lite v0.1.0
[M+Na]+218.7718855
predicted
DarkChem Lite v0.1.0
[M+Na]+207.63034
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the ...
Gene Name
PTGER2
Uniprot ID
P43116
Uniprot Name
Prostaglandin E2 receptor EP2 subtype
Molecular Weight
39759.945 Da
References
  1. Baryawno N, Sveinbjornsson B, Eksborg S, Orrego A, Segerstrom L, Oqvist CO, Holm S, Gustavsson B, Kagedal B, Kogner P, Johnsen JI: Tumor-growth-promoting cyclooxygenase-2 prostaglandin E2 pathway provides medulloblastoma therapeutic targets. Neuro Oncol. 2008 Oct;10(5):661-74. doi: 10.1215/15228517-2008-035. Epub 2008 Aug 20. [Article]
  2. Tamiji J, Crawford DA: Prostaglandin E(2) and misoprostol induce neurite retraction in Neuro-2a cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):450-6. doi: 10.1016/j.bbrc.2010.06.098. Epub 2010 Jun 27. [Article]
  3. Legler DF, Bruckner M, Uetz-von Allmen E, Krause P: Prostaglandin E2 at new glance: novel insights in functional diversity offer therapeutic chances. Int J Biochem Cell Biol. 2010 Feb;42(2):198-201. doi: 10.1016/j.biocel.2009.09.015. Epub 2009 Sep 27. [Article]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
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 importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
Molecular Weight
41800.655 Da
References
  1. Baryawno N, Sveinbjornsson B, Eksborg S, Orrego A, Segerstrom L, Oqvist CO, Holm S, Gustavsson B, Kagedal B, Kogner P, Johnsen JI: Tumor-growth-promoting cyclooxygenase-2 prostaglandin E2 pathway provides medulloblastoma therapeutic targets. Neuro Oncol. 2008 Oct;10(5):661-74. doi: 10.1215/15228517-2008-035. Epub 2008 Aug 20. [Article]
  2. Tamiji J, Crawford DA: Prostaglandin E(2) and misoprostol induce neurite retraction in Neuro-2a cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):450-6. doi: 10.1016/j.bbrc.2010.06.098. Epub 2010 Jun 27. [Article]
  3. Legler DF, Bruckner M, Uetz-von Allmen E, Krause P: Prostaglandin E2 at new glance: novel insights in functional diversity offer therapeutic chances. Int J Biochem Cell Biol. 2010 Feb;42(2):198-201. doi: 10.1016/j.biocel.2009.09.015. Epub 2009 Sep 27. [Article]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
Gene Name
PTGER3
Uniprot ID
P43115
Uniprot Name
Prostaglandin E2 receptor EP3 subtype
Molecular Weight
43309.335 Da
References
  1. Baryawno N, Sveinbjornsson B, Eksborg S, Orrego A, Segerstrom L, Oqvist CO, Holm S, Gustavsson B, Kagedal B, Kogner P, Johnsen JI: Tumor-growth-promoting cyclooxygenase-2 prostaglandin E2 pathway provides medulloblastoma therapeutic targets. Neuro Oncol. 2008 Oct;10(5):661-74. doi: 10.1215/15228517-2008-035. Epub 2008 Aug 20. [Article]
  2. Tamiji J, Crawford DA: Prostaglandin E(2) and misoprostol induce neurite retraction in Neuro-2a cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):450-6. doi: 10.1016/j.bbrc.2010.06.098. Epub 2010 Jun 27. [Article]
  3. Legler DF, Bruckner M, Uetz-von Allmen E, Krause P: Prostaglandin E2 at new glance: novel insights in functional diversity offer therapeutic chances. Int J Biochem Cell Biol. 2010 Feb;42(2):198-201. doi: 10.1016/j.biocel.2009.09.015. Epub 2009 Sep 27. [Article]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role...
Gene Name
PTGER4
Uniprot ID
P35408
Uniprot Name
Prostaglandin E2 receptor EP4 subtype
Molecular Weight
53118.845 Da
References
  1. Wise H: Lack of interaction between prostaglandin E2 receptor subtypes in regulating adenylyl cyclase activity in cultured rat dorsal root ganglion cells. Eur J Pharmacol. 2006 Mar 27;535(1-3):69-77. Epub 2006 Mar 20. [Article]
  2. Baryawno N, Sveinbjornsson B, Eksborg S, Orrego A, Segerstrom L, Oqvist CO, Holm S, Gustavsson B, Kagedal B, Kogner P, Johnsen JI: Tumor-growth-promoting cyclooxygenase-2 prostaglandin E2 pathway provides medulloblastoma therapeutic targets. Neuro Oncol. 2008 Oct;10(5):661-74. doi: 10.1215/15228517-2008-035. Epub 2008 Aug 20. [Article]
  3. Tamiji J, Crawford DA: Prostaglandin E(2) and misoprostol induce neurite retraction in Neuro-2a cells. Biochem Biophys Res Commun. 2010 Jul 30;398(3):450-6. doi: 10.1016/j.bbrc.2010.06.098. Epub 2010 Jun 27. [Article]
  4. Legler DF, Bruckner M, Uetz-von Allmen E, Krause P: Prostaglandin E2 at new glance: novel insights in functional diversity offer therapeutic chances. Int J Biochem Cell Biol. 2010 Feb;42(2):198-201. doi: 10.1016/j.biocel.2009.09.015. Epub 2009 Sep 27. [Article]
  5. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Prostaglandin j receptor activity
Specific Function
Receptor for prostaglandin D2 (PGD2). Coupled to the G(i)-protein. Receptor activation may result in pertussis toxin-sensitive decreases in cAMP levels and Ca(2+) mobilization. PI3K signaling is al...
Gene Name
PTGDR2
Uniprot ID
Q9Y5Y4
Uniprot Name
Prostaglandin D2 receptor 2
Molecular Weight
43267.15 Da
References
  1. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW: Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. Br J Pharmacol. 1998 Apr;123(7):1317-24. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [Article]
  2. Lu R, Chan BS, Schuster VL: Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2 Pt 2):F295-303. [Article]
  3. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [Article]
  2. Ohtsuki S, Kikkawa T, Mori S, Hori S, Takanaga H, Otagiri M, Terasaki T: Mouse reduced in osteosclerosis transporter functions as an organic anion transporter 3 and is localized at abluminal membrane of blood-brain barrier. J Pharmacol Exp Ther. 2004 Jun;309(3):1273-81. Epub 2004 Feb 4. [Article]
  3. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [Article]
  2. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [Article]
  3. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [Article]
  4. Morita N, Kusuhara H, Sekine T, Endou H, Sugiyama Y: Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1179-84. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [Article]
  2. Nishio T, Adachi H, Nakagomi R, Tokui T, Sato E, Tanemoto M, Fujiwara K, Okabe M, Onogawa T, Suzuki T, Nakai D, Shiiba K, Suzuki M, Ohtani H, Kondo Y, Unno M, Ito S, Iinuma K, Nunoki K, Matsuno S, Abe T: Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate. Biochem Biophys Res Commun. 2000 Sep 7;275(3):831-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
  2. Cattori V, van Montfoort JE, Stieger B, Landmann L, Meijer DK, Winterhalter KH, Meier PJ, Hagenbuch B: Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3. Pflugers Arch. 2001 Nov;443(2):188-95. [Article]
  3. Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Essential component of the Ost-alpha/Ost-beta complex, a heterodimer that acts as the intestinal basolateral transporter responsible for bile acid export from enterocytes into portal blood. Efficie...
Gene Name
SLC51A
Uniprot ID
Q86UW1
Uniprot Name
Organic solute transporter subunit alpha
Molecular Weight
37734.575 Da
References
  1. Seward DJ, Koh AS, Boyer JL, Ballatori N: Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82. Epub 2003 Apr 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Essential component of the Ost-alpha/Ost-beta complex, a heterodimer that acts as the intestinal basolateral transporter responsible for bile acid export from enterocytes into portal blood. Efficie...
Gene Name
SLC51B
Uniprot ID
Q86UW2
Uniprot Name
Organic solute transporter subunit beta
Molecular Weight
14346.195 Da
References
  1. Seward DJ, Koh AS, Boyer JL, Ballatori N: Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82. Epub 2003 Apr 28. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. [Article]
  2. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Thyroid hormone transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate.
Gene Name
SLCO4A1
Uniprot ID
Q96BD0
Uniprot Name
Solute carrier organic anion transporter family member 4A1
Molecular Weight
77192.505 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Thyroid hormone transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-gluc...
Gene Name
SLCO1C1
Uniprot ID
Q9NYB5
Uniprot Name
Solute carrier organic anion transporter family member 1C1
Molecular Weight
78695.625 Da
References
  1. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ: Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. Mol Endocrinol. 2002 Oct;16(10):2283-96. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [Article]
  2. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Tamai I, Nezu J, Uchino H, Sai Y, Oku A, Shimane M, Tsuji A: Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60. [Article]
  2. Abe T, Kakyo M, Tokui T, Nakagomi R, Nishio T, Nakai D, Nomura H, Unno M, Suzuki M, Naitoh T, Matsuno S, Yawo H: Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biol Chem. 1999 Jun 11;274(24):17159-63. [Article]
  3. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48