IDPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy
Targets (5)Enzymes (3)Transporters (17)
Targets (5)Enzymes (3)Transporters (17)Biointeractions (28)

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Identification
NameDinoprostone
Accession NumberDB00917  (APRD00927)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
(15S)-Prostaglandin e2
(5Z,11alpha,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
Prepidil
Propess
Prostaglandin E2
Prostin e2
External IDs U-12,062 / U-12062
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CervidilInsert10 mgVaginalFerring Pharmaceuticals1997-06-17Not applicableCanada
CervidilInsert, extended release10 mg/1VaginalForest Laboratories1995-05-192015-12-31Us
CervidilInsert10 mg/241mgVaginalFerring Pharmaceuticals1995-03-30Not applicableUs
DinoprostoneInsert10 mg/241mgVaginalFerring Pharmaceuticals2014-02-01Not applicableUs
PrepidilGel.5 mg/3gVaginalPharmacia & Upjohn Inc1992-12-09Not applicableUs
Prepidil GelGel0.5 mgEndocervicalPfizer1990-12-31Not applicableCanada
Prostin E2Suppository20 mg/1VaginalPharmacia & Upjohn Inc1978-01-18Not applicableUs
Prostin E2 TabletsTablet0.5 mgOralPfizer1977-12-31Not applicableCanada
Prostin E2 Vaginal GelGel1 mgVaginalPfizer1991-12-31Not applicableCanada
Prostin E2 Vaginal GelGel2 mgVaginalPfizer1991-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PropessFerring Pharmaceuticals
Prostarmon EDCPC
PROSTINNot Available
Brand mixturesNot Available
Categories
UNIIK7Q1JQR04M
CAS number363-24-6
WeightAverage: 352.4651
Monoisotopic: 352.224974134
Chemical FormulaC20H32O5
InChI KeyXEYBRNLFEZDVAW-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[[email protected]](O)\C=C\[[email protected]]1[[email protected]](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
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.

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Prostaglandin E2 receptor EP2 subtypeProteinyes
agonist
HumanP43116 details
Prostaglandin E2 receptor EP1 subtypeProteinyes
agonist
HumanP34995 details
Prostaglandin E2 receptor EP3 subtypeProteinyes
agonist
HumanP43115 details
Prostaglandin E2 receptor EP4 subtypeProteinyes
agonist
HumanP35408 details
Prostaglandin D2 receptor 2Proteinunknown
agonist
HumanQ9Y5Y4 details
Related Articles
Absorption

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

Volume of distributionNot 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.

ClearanceNot Available
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Lornoxicam Action PathwayDrug actionSMP00700
Phenylbutazone Action PathwayDrug actionSMP00701
Salsalate Action PathwayDrug actionSMP00707
Acetaminophen Action PathwayDrug actionSMP00710
Arachidonic Acid MetabolismMetabolicSMP00075
Meloxicam Action PathwayDrug actionSMP00106
Mefenamic Acid Action PathwayDrug actionSMP00109
Magnesium salicylate Action PathwayDrug actionSMP00698
Nepafenac Action PathwayDrug actionSMP00702
Salicylate-sodium Action PathwayDrug actionSMP00708
Ketorolac Action PathwayDrug actionSMP00098
Suprofen Action PathwayDrug actionSMP00101
Valdecoxib Action PathwayDrug actionSMP00116
Diflunisal Action PathwayDrug actionSMP00289
Leukotriene C4 Synthesis DeficiencyDiseaseSMP00353
Trisalicylate-choline Action PathwayDrug actionSMP00703
Etodolac Action PathwayDrug actionSMP00084
Ibuprofen Action PathwayDrug actionSMP00086
Diclofenac Action PathwayDrug actionSMP00093
Bromfenac Action PathwayDrug actionSMP00102
Antipyrine Action PathwayDrug actionSMP00692
Antrafenine Action PathwayDrug actionSMP00693
Fenoprofen Action PathwayDrug actionSMP00696
Flurbiprofen Action PathwayDrug actionSMP00697
Lumiracoxib Action PathwayDrug actionSMP00699
Tenoxicam Action PathwayDrug actionSMP00706
Salicylic Acid Action PathwayDrug actionSMP00709
Piroxicam Action PathwayDrug actionSMP00077
Acetylsalicylic Acid Action PathwayDrug actionSMP00083
Ketoprofen Action PathwayDrug actionSMP00085
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Dinoprostone can be increased when it is combined with Abiraterone.Approved
AceclofenacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Aceclofenac.Approved
Acetylsalicylic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Adapalene.Approved
AndrographolideThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with HMPL-004.Investigational
AnisodamineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Anisodamine.Investigational
AntipyrineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Antipyrine.Approved
ApocyninThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Acetovanillone.Investigational
ApremilastThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Apremilast.Approved, Investigational
AzapropazoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Azelastine.Approved
AzithromycinThe metabolism of Dinoprostone can be decreased when combined with Azithromycin.Approved
BalsalazideThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Balsalazide.Approved, Investigational
BenoxaprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Benoxaprofen.Withdrawn
Betulinic AcidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Betulinic Acid.Investigational
BortezomibThe metabolism of Dinoprostone can be decreased when combined with Bortezomib.Approved, Investigational
BromfenacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bucillamine.Investigational
CaffeineThe metabolism of Dinoprostone can be decreased when combined with Caffeine.Approved
CarbamazepineThe metabolism of Dinoprostone can be increased when combined with Carbamazepine.Approved, Investigational
CarbetocinThe risk or severity of adverse effects can be increased when Dinoprostone is combined with Carbetocin.Approved
Carboprost TromethamineThe risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Dinoprostone.Approved
CarprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Celecoxib.Approved, Investigational
ChloroquineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Chloroquine.Approved, Vet Approved
Choline magnesium trisalicylateThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Trisalicylate-choline.Approved
CitalopramThe metabolism of Dinoprostone can be decreased when combined with Citalopram.Approved
ClonixinThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Clonixin.Approved
ClotrimazoleThe metabolism of Dinoprostone can be decreased when combined with Clotrimazole.Approved, Vet Approved
CurcuminThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Curcumin.Investigational
Cyproterone acetateThe serum concentration of Dinoprostone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DeferasiroxThe serum concentration of Dinoprostone can be increased when it is combined with Deferasirox.Approved, Investigational
DiclofenacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DiflunisalThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Diflunisal.Approved
DroxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Duvelisib.Investigational
E-6201The therapeutic efficacy of Dinoprostone can be decreased when used in combination with E6201.Investigational
EbselenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ebselen.Investigational
EltrombopagThe serum concentration of Dinoprostone can be increased when it is combined with Eltrombopag.Approved
EpirizoleThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Epirizole.Approved
EtanerceptThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etanercept.Approved, Investigational
EtodolacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etofenamate.Approved
EtoricoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etoricoxib.Approved, Investigational
FenbufenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Fenbufen.Approved
FenoprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Fenoprofen.Approved
FloctafenineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FlurbiprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Flurbiprofen.Approved, Investigational
FluvoxamineThe metabolism of Dinoprostone can be decreased when combined with Fluvoxamine.Approved, Investigational
HigenamineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Higenamine.Investigational
IbuprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Icatibant.Approved
IndomethacinThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Indoprofen.Withdrawn
IsoxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Isoxicam.Withdrawn
KebuzoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Kebuzone.Experimental
KetoprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ketorolac.Approved
LeflunomideThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Dinoprostone can be decreased when combined with Lidocaine.Approved, Vet Approved
LisofyllineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lisofylline.Investigational
LornoxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lornoxicam.Approved
LoxoprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Loxoprofen.Approved
LumiracoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Magnesium salicylate.Approved
MasoprocolThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Masoprocol.Approved
Meclofenamic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mefenamic acid.Approved
MeloxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Metamizole.Withdrawn
MexiletineThe metabolism of Dinoprostone can be decreased when combined with Mexiletine.Approved
MizoribineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mizoribine.Investigational
Mycophenolate mofetilThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nabumetone.Approved
NafamostatThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nafamostat.Approved, Investigational
NaftifineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Naftifine.Approved
NaproxenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Naproxen.Approved, Vet Approved
NCX 4016The therapeutic efficacy of Dinoprostone can be decreased when used in combination with NCX 4016.Investigational
NepafenacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nepafenac.Approved
NevirapineThe metabolism of Dinoprostone can be decreased when combined with Nevirapine.Approved
Niflumic AcidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Niflumic Acid.Approved
NimesulideThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nimesulide.Approved, Withdrawn
NitroaspirinThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nitroaspirin.Investigational
OlopatadineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Olsalazine.Approved
OsimertinibThe serum concentration of Dinoprostone can be decreased when it is combined with Osimertinib.Approved
OxaprozinThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Oxaprozin.Approved
OxyphenbutazoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Oxyphenbutazone.Withdrawn
OxytocinThe risk or severity of adverse effects can be increased when Dinoprostone is combined with Oxytocin.Approved, Vet Approved
ParecoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Parecoxib.Approved
Peginterferon alfa-2bThe serum concentration of Dinoprostone can be increased when it is combined with Peginterferon alfa-2b.Approved
PhenobarbitalThe metabolism of Dinoprostone can be increased when combined with Phenobarbital.Approved
PhenylbutazoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PimecrolimusThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PirfenidoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pirfenidone.Investigational
PiroxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Piroxicam.Approved, Investigational
PrimidoneThe metabolism of Dinoprostone can be increased when combined with Primidone.Approved, Vet Approved
PropacetamolThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Propacetamol.Approved
PTC299The therapeutic efficacy of Dinoprostone can be decreased when used in combination with PTC299.Investigational
ResveratrolThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Resveratrol.Experimental, Investigational
RifampicinThe metabolism of Dinoprostone can be increased when combined with Rifampicin.Approved
RofecoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
RopiniroleThe metabolism of Dinoprostone can be decreased when combined with Ropinirole.Approved, Investigational
SalicylamideThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salsalate.Approved
SimeprevirThe metabolism of Dinoprostone can be decreased when combined with Simeprevir.Approved
SRT501The therapeutic efficacy of Dinoprostone can be decreased when used in combination with SRT501.Investigational
SulfasalazineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Sulindac.Approved
SuprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Suprofen.Approved, Withdrawn
Tenofovir disoproxilThe metabolism of Dinoprostone can be decreased when combined with Tenofovir.Approved, Investigational
TenoxicamThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tenoxicam.Approved
TeriflunomideThe serum concentration of Dinoprostone can be increased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Dinoprostone can be decreased when combined with Theophylline.Approved
Tiaprofenic acidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tiaprofenic acid.Approved
TiclopidineThe metabolism of Dinoprostone can be decreased when combined with Ticlopidine.Approved
TinoridineThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tinoridine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tolmetin.Approved
TranilastThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tranilast.Approved, Investigational
ValdecoxibThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
VemurafenibThe serum concentration of Dinoprostone can be increased when it is combined with Vemurafenib.Approved
ZaltoprofenThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zaltoprofen.Approved
ZileutonThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zomepirac.Withdrawn
Food InteractionsNot Available
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 ReferencesNot Available
External Links
ATC CodesG02AD02 — Dinoprostone
AHFS Codes
  • 76:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (69.1 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Unknown StatusTreatmentFetal Demise / Fetal Membranes, Premature Rupture / PreEclampsia1
2CompletedTreatmentDelivery Uterine1
2CompletedTreatmentEarly Amniotomy, Unfavorable Cervix1
2CompletedTreatmentUnfavorable Cervix, Cervical Ripening1
2RecruitingNot AvailableInduction of Labour1
2RecruitingTreatmentInduction of Labour1
2RecruitingTreatmentInduction of Uterine contractions1
3CompletedNot AvailableInduction / Labour / PROM (Pregnancy)1
3CompletedTreatmentCervical Ripening / Induction of Labour2
3CompletedTreatmentCervical Ripening / Induction of Labour / Reducing Time to Vaginal Delivery1
3CompletedTreatmentLabour Pain1
3CompletedTreatmentPregnancy1
3Not Yet RecruitingTreatmentInduction of Labor Affected Fetus / Newborn1
3RecruitingTreatmentCervical Ripening2
3RecruitingTreatmentCervical Ripening / Pregnancy1
3Unknown StatusTreatmentMedical Induction of Labor Affecting Fetus1
4CompletedNot AvailableIntrapartum Fetal Monitoring / Pregnancy1
4CompletedTreatmentCervical Ripening / Induction of Labour1
4CompletedTreatmentPremature Rupture of Membranes at Term2
4Not Yet RecruitingTreatmentPremature Rupture of Fetal Membranes1
4RecruitingTreatmentInduction of Labour1
4RecruitingTreatmentPregnancy1
4TerminatedTreatmentCesarean Section / Vaginal Delivery1
4Unknown StatusTreatmentCervical Ripening1
4Unknown StatusTreatmentCervical Ripening / Induction of Labour1
Not AvailableCompletedNot Available"Migraine-like" Headache / Migraine-like Headache1
Not AvailableCompletedNot AvailableHeadaches / Migraines1
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Induction of Labour / Pregnancy1
Not AvailableCompletedTreatmentCervical Ripening / Induction of Uterine contractions1
Not AvailableCompletedTreatmentFailed Labour1
Not AvailableCompletedTreatmentInduction of Uterine contractions1
Not AvailableEnrolling by InvitationNot AvailableCervical Ripening / Labour; Induced / Pilot Study1
Not AvailableNot Yet RecruitingTreatmentFailed Medical or Unspecified Induction of Labor1
Not AvailableRecruitingTreatmentFailed Induction of Labor3
Not AvailableRecruitingTreatmentInduction of Labour1
Not AvailableRecruitingTreatmentMedical Induction of Labor Affecting Newborn1
Not AvailableRecruitingTreatmentNulliparous Women Who Scheduled for Labor Induction1
Not AvailableTerminatedTreatmentDelivery1
Not AvailableUnknown StatusNot AvailableInduction of Uterine contractions1
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Controlled therapeutics (scotland) ltd
Packagers
Dosage forms
FormRouteStrength
InsertVaginal10 mg
Insert, extended releaseVaginal10 mg/1
InsertVaginal10 mg/241mg
GelVaginal.5 mg/3g
GelEndocervical0.5 mg
SuppositoryVaginal20 mg/1
TabletOral0.5 mg
GelVaginal1 mg
GelVaginal2 mg
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)
US5269321 No1995-07-142012-07-14Us
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-0059-4920000000-6108934d406ea4062761View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negativesplash10-00yi-0398000000-41c3a62b076046d87381View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negativesplash10-00di-0495000000-df406a9e4cc995523a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negativesplash10-00dr-0592000000-928e66269ab2854faa42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negativesplash10-00dr-0590000000-b364a55fc0598d9265b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negativesplash10-00dr-0890000000-b3a25d975f2a38d7e49fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negativesplash10-0079-0960000000-c67461d3bd965cbf289cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negativesplash10-000i-0920000000-830ad149a4fe8f36e211View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negativesplash10-07br-0910000000-35e5bd204c947e2c4bccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negativesplash10-05fs-0900000000-573b0c5a4593210b387aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00yi-0398000000-612bce8f105beae0c5f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0495000000-78584a9b664c5155b473View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0592000000-b37d658cf7b0d590aad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0590000000-985f93ab468aa6a8a1b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00dr-0890000000-5757ca5e8720a47086dcView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative ParentsLong-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
SubstituentsProstaglandin skeleton / Long-chain fatty acid / Hydroxy fatty acid / Cyclopentanol / Fatty acid / Unsaturated fatty acid / Cyclic alcohol / Ketone / Cyclic ketone / Secondary alcohol
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptorsprostaglandins E (CHEBI:15551 ) / Prostaglandins (C00584 ) / Prostaglandins (LMFA03010003 )

Targets

Details
1. Prostaglandin E2 receptor EP2 subtype
Kind
Protein
Organism
Human
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 relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
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. [PubMed:18715952 ]
  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. [PubMed:20599704 ]
  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. [PubMed:19788928 ]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Details
2. Prostaglandin E2 receptor EP1 subtype
Kind
Protein
Organism
Human
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 important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues.
Gene Name:
PTGER1
Uniprot ID:
P34995
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. [PubMed:18715952 ]
  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. [PubMed:20599704 ]
  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. [PubMed:19788928 ]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241 ]
Details
3. Prostaglandin E2 receptor EP3 subtype
Kind
Protein
Organism
Human
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 of sodium and water reabsorption in kidney tubulus and contraction in uterine smooth muscle. The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G-I protei...
Gene Name:
PTGER3
Uniprot ID:
P43115
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. [PubMed:18715952 ]
  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. [PubMed:20599704 ]
  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. [PubMed:19788928 ]
  4. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241 ]
Details
4. Prostaglandin E2 receptor EP4 subtype
Kind
Protein
Organism
Human
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 in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function.
Gene Name:
PTGER4
Uniprot ID:
P35408
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. [PubMed:16545798 ]
  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. [PubMed:18715952 ]
  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. [PubMed:20599704 ]
  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. [PubMed:19788928 ]
  5. Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241 ]
Details
5. Prostaglandin D2 receptor 2
Kind
Protein
Organism
Human
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 also implicated in mediating PTGDR2 effects. PGD2 induced receptor internalization. CRTH2 internalization can be regulated by diverse kinases such as, PKC, PKA, ADRBK1/GRK2, GPRK5/GRK5 and GRK6. Recepto...
Gene Name:
PTGDR2
Uniprot ID:
Q9Y5Y4
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. [PubMed:9579725 ]

Enzymes

Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Details
2. Aromatase
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Details
3. Cytochrome P450 1A2
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Details
1. Solute carrier family 22 member 2
Kind
Protein
Organism
Human
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, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
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 ]
Details
2. Solute carrier family 22 member 1
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 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 ]
Details
3. Multidrug resistance-associated protein 5
Kind
Protein
Organism
Human
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
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. [PubMed:12835412 ]
Details
4. Solute carrier family 22 member 6
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
  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. [PubMed:9950961 ]
  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. [PubMed:9228014 ]
Details
5. Solute carrier family 22 member 8
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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 ]
  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. [PubMed:14762099 ]
  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. [PubMed:15100168 ]
Details
6. Solute carrier family 22 member 11
Kind
Protein
Organism
Human
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
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 ]
Details
7. Solute carrier family 22 member 7
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
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 ]
  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. [PubMed:12065749 ]
  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. [PubMed:9650585 ]
  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. [PubMed:11504818 ]
Details
8. Multidrug resistance-associated protein 4
Kind
Protein
Organism
Human
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
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. [PubMed:12835412 ]
Details
9. Solute carrier organic anion transporter family member 2B1
Kind
Protein
Organism
Human
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
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. [PubMed:10873595 ]
  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. [PubMed:10973807 ]
Details
10. Solute carrier organic anion transporter family member 1A2
Kind
Protein
Organism
Human
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 inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
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. [PubMed:11159893 ]
  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. [PubMed:11713643 ]
  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. [PubMed:8779893 ]
Details
11. Organic solute transporter subunit alpha
Kind
Protein
Organism
Human
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. Efficiently transports the major species of bile acids.
Gene Name:
SLC51A
Uniprot ID:
Q86UW1
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. [PubMed:12719432 ]
Details
12. Organic solute transporter subunit beta
Kind
Protein
Organism
Human
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. Efficiently transports the major species of bile acids. Modulates SLC51A glycosylation, membrane trafficking and stability activities.
Gene Name:
SLC51B
Uniprot ID:
Q86UW2
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. [PubMed:12719432 ]
Details
13. Solute carrier organic anion transporter family member 2A1
Kind
Protein
Organism
Human
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, as well as PGE1, PGE2 and PGF2A.
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
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 ]
  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. [PubMed:7754369 ]
Details
14. Solute carrier organic anion transporter family member 4A1
Kind
Protein
Organism
Human
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
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. [PubMed:10873595 ]
Details
15. Solute carrier organic anion transporter family member 1C1
Kind
Protein
Organism
Human
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-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency. May play a signifiant role in regulating T4 flux into and out of the brain (By similarity).
Gene Name:
SLCO1C1
Uniprot ID:
Q9NYB5
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. [PubMed:12351693 ]
Details
16. Solute carrier organic anion transporter family member 3A1
Kind
Protein
Organism
Human
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 and vasopressin, but not DPDPE (a derivative of enkephalin lacking an N-terminal tyrosine residue), estrone-3-sulfate, taurocholate, digoxin nor DHEAS (PubMed:16971491).
Gene Name:
SLCO3A1
Uniprot ID:
Q9UIG8
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. [PubMed:10873595 ]
  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. [PubMed:14631946 ]
Details
17. Solute carrier organic anion transporter family member 1B1
Kind
Protein
Organism
Human
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, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
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. [PubMed:10873595 ]
  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. [PubMed:10358072 ]
  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. [PubMed:11159893 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:54