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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Dinoprostone
- Accession Number
- DB00917 (APRD00927)
- Type
- Small Molecule
- Groups
- Approved
- 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
Structure for DB00917 (Dinoprostone)
- 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
- Propess
- Prostaglandin E2
- External IDs
- U-12,062 / U-12062
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Cervidil Insert 10 mg/241mg Vaginal Ferring Pharmaceuticals 1995-03-30 Not applicable US 
Cervidil Insert, extended release 10 mg/1 Vaginal Forest Laboratories 1995-05-19 2015-12-31 US Cervidil Insert 10 mg Vaginal Ferring Pharmaceuticals 1997-06-17 Not applicable Canada 
Dinoprostone Insert 10 mg/241mg Vaginal Ferring Pharmaceuticals 2014-02-01 Not applicable US Prepidil Gel .5 mg/3g Vaginal Pharmacia & Upjohn Inc 1992-12-09 Not applicable US Prepidil Gel Gel 0.5 mg Endocervical Pfizer 1990-12-31 Not applicable Canada Prostin E2 Suppository 20 mg/1 Vaginal Pharmacia & Upjohn Inc 1978-01-18 Not applicable US Prostin E2 Tablets Tablet 0.5 mg Oral Pfizer 1977-12-31 Not applicable Canada Prostin E2 Vaginal Gel Gel 2 mg Vaginal Pfizer 1991-12-31 Not applicable Canada Prostin E2 Vaginal Gel Gel 1 mg Vaginal Pfizer 1991-12-31 Not applicable Canada - International/Other Brands
- Prepidil / Propess (Ferring Pharmaceuticals) / Prostarmon E (DCPC) / PROSTIN / Prostin e2
- Categories
- Autacoids
- Biological Factors
- Cytochrome P-450 CYP1A2 Substrates
- Eicosanoids
- Fatty Acids
- Fatty Acids, Unsaturated
- Genito Urinary System and Sex Hormones
- Inflammation Mediators
- Lipids
- OAT3 Inhibitors
- OAT3 Substrates
- OATP1B1/SLCO1B1 Substrates
- OCT2 Inhibitors
- Prostaglandins
- Prostaglandins E
- Prostaglandins, Synthetic
- Reproductive Control Agents
- Uterotonic agents
- Uterotonics
- UNII
- K7Q1JQR04M
- CAS number
- 363-24-6
- Weight
- Average: 352.4651
Monoisotopic: 352.224974134 - Chemical Formula
- C20H32O5
- 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
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.
- Associated Conditions
- Associated Therapies
- 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.
Target Actions Organism AProstaglandin E2 receptor EP2 subtype agonistHuman AProstaglandin E2 receptor EP1 subtype agonistHuman AProstaglandin E2 receptor EP3 subtype agonistHuman AProstaglandin E2 receptor EP4 subtype agonistHuman UProstaglandin D2 receptor 2 agonistHuman - 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
- Toxicity
Oral, mouse: LD50 = 750 mg/kg; Oral, rat: LD50 = 500 mg/kg.
- Affected organisms
- Humans and other mammals
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group (4R)-limonene The therapeutic efficacy of Dinoprostone can be decreased when used in combination with (4R)-limonene. Investigational Abiraterone The serum concentration of Dinoprostone can be increased when it is combined with Abiraterone. Approved Aceclofenac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Aceclofenac. Approved, Investigational Acemetacin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Acemetacin. Approved, Experimental, Investigational Acetylsalicylic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Acetylsalicylic acid. Approved, Vet Approved Adapalene The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Adapalene. Approved Agmatine The serum concentration of Agmatine can be increased when it is combined with Dinoprostone. Experimental, Investigational Alclofenac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Alclofenac. Approved, Withdrawn Alminoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Alminoprofen. Experimental Andrographolide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Andrographolide. Investigational Anisodamine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Anisodamine. Investigational Antipyrine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Antipyrine. Approved, Investigational Apalutamide The serum concentration of Dinoprostone can be decreased when it is combined with Apalutamide. Approved, Investigational Apocynin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Apocynin. Investigational Apremilast The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Apremilast. Approved, Investigational Azapropazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Azapropazone. Withdrawn Azelastine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Azelastine. Approved Azithromycin The metabolism of Dinoprostone can be decreased when combined with Azithromycin. Approved Balsalazide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Balsalazide. Approved, Investigational Bendazac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bendazac. Experimental Benorilate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Benorilate. Experimental Benoxaprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Benoxaprofen. Withdrawn Benzydamine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Benzydamine. Approved Bevonium The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bevonium. Experimental Bortezomib The metabolism of Dinoprostone can be decreased when combined with Bortezomib. Approved, Investigational Bromfenac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bromfenac. Approved Bucillamine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bucillamine. Investigational Bufexamac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bufexamac. Approved, Experimental Bumadizone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Bumadizone. Experimental Caffeine The metabolism of Dinoprostone can be decreased when combined with Caffeine. Approved Carbamazepine The metabolism of Dinoprostone can be increased when combined with Carbamazepine. Approved, Investigational Carbaspirin calcium The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Carbaspirin calcium. Experimental, Investigational Carbetocin The risk or severity of adverse effects can be increased when Dinoprostone is combined with Carbetocin. Approved, Investigational Carboprost Tromethamine The risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Dinoprostone. Approved Carprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Carprofen. Approved, Vet Approved, Withdrawn Castanospermine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Castanospermine. Experimental Celecoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Celecoxib. Approved, Investigational Chloroquine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Chloroquine. Approved, Investigational, Vet Approved Choline magnesium trisalicylate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Choline magnesium trisalicylate. Approved Cimetidine The serum concentration of Cimetidine can be increased when it is combined with Dinoprostone. Approved, Investigational Ciprofloxacin The metabolism of Dinoprostone can be decreased when combined with Ciprofloxacin. Approved, Investigational Citalopram The metabolism of Dinoprostone can be decreased when combined with Citalopram. Approved Clonixin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Clonixin. Approved Curcumin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Curcumin. Approved, Investigational Cyproterone acetate The serum concentration of Dinoprostone can be decreased when it is combined with Cyproterone acetate. Approved, Investigational Deferasirox The serum concentration of Dinoprostone can be increased when it is combined with Deferasirox. Approved, Investigational Diclofenac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Diclofenac. Approved, Vet Approved Difenpiramide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Difenpiramide. Experimental Diflunisal The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Diflunisal. Approved, Investigational Dosulepin The metabolism of Dinoprostone can be decreased when combined with Dosulepin. Approved Droxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Droxicam. Withdrawn Duvelisib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Duvelisib. Investigational E-6201 The therapeutic efficacy of Dinoprostone can be decreased when used in combination with E-6201. Investigational Eltrombopag The serum concentration of Dinoprostone can be increased when it is combined with Eltrombopag. Approved Epirizole The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Epirizole. Approved Estradiol The excretion of Estradiol can be decreased when combined with Dinoprostone. Approved, Investigational, Vet Approved Etanercept The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etanercept. Approved, Investigational Ethenzamide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ethenzamide. Experimental Etodolac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etodolac. Approved, Investigational, Vet Approved Etofenamate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etofenamate. Approved, Investigational Etoricoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Etoricoxib. Approved, Investigational Evening primrose oil The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Evening primrose oil. Investigational, Nutraceutical Exisulind The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Exisulind. Investigational Felbinac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Felbinac. Experimental Fenbufen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Fenbufen. Approved Fenoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Fenoprofen. Approved Fentiazac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Fentiazac. Experimental Feprazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Feprazone. Experimental Ferulic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ferulic acid. Experimental Floctafenine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Floctafenine. Approved, Withdrawn Flunixin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Flunixin. Vet Approved Flunoxaprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Flunoxaprofen. Experimental Flurbiprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Flurbiprofen. Approved, Investigational Fluvoxamine The metabolism of Dinoprostone can be decreased when combined with Fluvoxamine. Approved, Investigational Furosemide The excretion of Dinoprostone can be decreased when combined with Furosemide. Approved, Vet Approved Guacetisal The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Guacetisal. Experimental Higenamine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Higenamine. Investigational Histamine The serum concentration of Histamine can be increased when it is combined with Dinoprostone. Approved, Investigational Ibuprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ibuprofen. Approved Ibuproxam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ibuproxam. Withdrawn Icatibant The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Icatibant. Approved, Investigational Imidazole salicylate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Imidazole salicylate. Experimental Indobufen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Indobufen. Investigational Indomethacin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Indomethacin. Approved, Investigational Indoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Indoprofen. Withdrawn Irinotecan The excretion of Dinoprostone can be decreased when combined with Irinotecan. Approved, Investigational Isoxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Isoxicam. Withdrawn Kebuzone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Kebuzone. Experimental Ketoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ketoprofen. Approved, Vet Approved Ketorolac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Ketorolac. Approved Lamivudine The serum concentration of Lamivudine can be increased when it is combined with Dinoprostone. Approved, Investigational Leflunomide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Leflunomide. Approved, Investigational Lidocaine The metabolism of Dinoprostone can be decreased when combined with Lidocaine. Approved, Vet Approved Lisofylline The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lisofylline. Investigational Lobeglitazone The metabolism of Dinoprostone can be decreased when combined with Lobeglitazone. Approved, Investigational Lonazolac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lonazolac. Experimental Lornoxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lornoxicam. Approved, Investigational Loxoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Loxoprofen. Approved, Investigational Lumiracoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Lumiracoxib. Approved, Investigational Magnesium salicylate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Magnesium salicylate. Approved Masoprocol The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Masoprocol. Approved, Investigational Meclofenamic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Meclofenamic acid. Approved, Vet Approved Mefenamic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mefenamic acid. Approved Meloxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Meloxicam. Approved, Vet Approved Mesalazine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mesalazine. Approved Metamizole The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Metamizole. Approved, Investigational, Withdrawn Metformin The serum concentration of Metformin can be increased when it is combined with Dinoprostone. Approved Mexiletine The metabolism of Dinoprostone can be decreased when combined with Mexiletine. Approved, Investigational Midostaurin The metabolism of Dinoprostone can be decreased when combined with Midostaurin. Approved, Investigational Mizoribine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mizoribine. Investigational Mofebutazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mofebutazone. Experimental Mycophenolate mofetil The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mycophenolate mofetil. Approved, Investigational Mycophenolic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Mycophenolic acid. Approved Nabumetone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nabumetone. Approved Nafamostat The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nafamostat. Approved, Investigational Naftifine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Naftifine. Approved Naproxen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Naproxen. Approved, Vet Approved Nepafenac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nepafenac. Approved, Investigational Nevirapine The metabolism of Dinoprostone can be decreased when combined with Nevirapine. Approved Nifenazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nifenazone. Experimental Niflumic Acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Niflumic Acid. Approved Nimesulide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nimesulide. Approved, Investigational, Withdrawn Nitroaspirin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Nitroaspirin. Investigational Nystatin The excretion of Dinoprostone can be decreased when combined with Nystatin. Approved, Vet Approved Olopatadine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Olopatadine. Approved Olsalazine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Olsalazine. Approved Orgotein The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Orgotein. Vet Approved Osimertinib The serum concentration of Dinoprostone can be decreased when it is combined with Osimertinib. Approved Oxaprozin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Oxaprozin. Approved Oxyphenbutazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Oxyphenbutazone. Approved, Withdrawn Oxytocin The risk or severity of adverse effects can be increased when Dinoprostone is combined with Oxytocin. Approved, Vet Approved Palmidrol The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Palmidrol. Experimental, Nutraceutical Parecoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Parecoxib. Approved Parthenolide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Parthenolide. Approved, Investigational Peginterferon alfa-2b The serum concentration of Dinoprostone can be increased when it is combined with Peginterferon alfa-2b. Approved Phenobarbital The metabolism of Dinoprostone can be increased when combined with Phenobarbital. Approved, Investigational Phenylbutazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Phenylbutazone. Approved, Vet Approved Pimecrolimus The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pimecrolimus. Approved, Investigational Pirfenidone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pirfenidone. Approved, Investigational Piroxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Piroxicam. Approved, Investigational Pirprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pirprofen. Experimental Pramipexole The serum concentration of Pramipexole can be increased when it is combined with Dinoprostone. Approved, Investigational Pranoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Pranoprofen. Experimental, Investigational Proglumetacin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Proglumetacin. Experimental Propacetamol The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Propacetamol. Approved, Investigational Propyphenazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Propyphenazone. Experimental Proquazone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Proquazone. Experimental PTC299 The therapeutic efficacy of Dinoprostone can be decreased when used in combination with PTC299. Investigational Ranitidine The serum concentration of Ranitidine can be increased when it is combined with Dinoprostone. Approved Resveratrol The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Resveratrol. Approved, Experimental, Investigational Rifampicin The metabolism of Dinoprostone can be increased when combined with Rifampicin. Approved Rofecoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Rofecoxib. Approved, Investigational, Withdrawn Ropinirole The metabolism of Dinoprostone can be decreased when combined with Ropinirole. Approved, Investigational Rucaparib The metabolism of Dinoprostone can be decreased when combined with Rucaparib. Approved, Investigational Salicylamide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salicylamide. Approved Salicylic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salicylic acid. Approved, Investigational, Vet Approved Salsalate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Salsalate. Approved Semapimod The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Semapimod. Investigational Seratrodast The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Seratrodast. Approved Serrapeptase The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Serrapeptase. Investigational Simeprevir The metabolism of Dinoprostone can be decreased when combined with Simeprevir. Approved SRT501 The therapeutic efficacy of Dinoprostone can be decreased when used in combination with SRT501. Investigational Sulfasalazine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Sulfasalazine. Approved Sulindac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Sulindac. Approved, Investigational Suprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Suprofen. Approved, Withdrawn Suxibuzone The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Suxibuzone. Experimental Tarenflurbil The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tarenflurbil. Investigational Tenidap The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tenidap. Experimental Tenofovir disoproxil The metabolism of Dinoprostone can be decreased when combined with Tenofovir disoproxil. Approved, Investigational Tenoxicam The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tenoxicam. Approved Tepoxalin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tepoxalin. Vet Approved Teriflunomide The serum concentration of Dinoprostone can be increased when it is combined with Teriflunomide. Approved Tetracycline The excretion of Dinoprostone can be decreased when combined with Tetracycline. Approved, Vet Approved Theophylline The metabolism of Dinoprostone can be decreased when combined with Theophylline. Approved Tiaprofenic acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tiaprofenic acid. Approved Ticlopidine The metabolism of Dinoprostone can be decreased when combined with Ticlopidine. Approved Tinoridine The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tinoridine. Investigational Tolfenamic Acid The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tolfenamic Acid. Approved, Investigational Tolmetin The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tolmetin. Approved Tribenoside The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Tribenoside. Experimental Triptolide The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Triptolide. Investigational Trolamine salicylate The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Trolamine salicylate. Approved Valdecoxib The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Valdecoxib. Approved, Investigational, Withdrawn Vemurafenib The serum concentration of Dinoprostone can be increased when it is combined with Vemurafenib. Approved Zaltoprofen The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zaltoprofen. Approved, Investigational Zidovudine The excretion of Zidovudine can be decreased when combined with Dinoprostone. Approved Zileuton The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zileuton. Approved, Investigational, Withdrawn Zomepirac The therapeutic efficacy of Dinoprostone can be decreased when used in combination with Zomepirac. Withdrawn Zucapsaicin The metabolism of Dinoprostone can be decreased when combined with Zucapsaicin. Approved, Investigational - Food Interactions
- Not 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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001220
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- D00079
- KEGG Compound
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- Wikipedia
- Dinoprostone
- ATC Codes
- G02AD02 — Dinoprostone
- AHFS Codes
- 76:00.00 — Oxytocics
- PDB Entries
- 3wfh
- 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
Form Route Strength Insert Vaginal 10 mg Insert, extended release Vaginal 10 mg/1 Insert Vaginal 10 mg/241mg Gel Vaginal .5 mg/3g Gel Endocervical 0.5 mg Suppository Vaginal 20 mg/1 Tablet Oral 0.5 mg Gel Vaginal 1 mg Gel Vaginal 2 mg - Prices
Unit description Cost Unit Prostin e2 vaginal 20 mg sup 1177.04USD each Cervidil 10 mg vaginal insrt 256.13USD each Prepidil 0.5 mg/3 gm gel 104.94USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5269321 No 1995-07-14 2012-07-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 67 °C PhysProp water solubility 58.1 mg/L Not Available logP 2.82 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.044 mg/mL ALOGPS logP 3.31 ALOGPS logP 3.23 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 4.3 ChemAxon pKa (Strongest Basic) -1.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 94.83 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 99.44 m3·mol-1 ChemAxon Polarizability 41 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9815 Blood Brain Barrier + 0.8704 Caco-2 permeable + 0.5245 P-glycoprotein substrate Substrate 0.5554 P-glycoprotein inhibitor I Non-inhibitor 0.9202 P-glycoprotein inhibitor II Non-inhibitor 0.8983 Renal organic cation transporter Non-inhibitor 0.9064 CYP450 2C9 substrate Non-substrate 0.8211 CYP450 2D6 substrate Non-substrate 0.8834 CYP450 3A4 substrate Non-substrate 0.5292 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9502 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9725 Ames test Non AMES toxic 0.9387 Carcinogenicity Non-carcinogens 0.9201 Biodegradation Ready biodegradable 0.6056 Rat acute toxicity 2.9631 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9087 hERG inhibition (predictor II) Non-inhibitor 0.9138
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Eicosanoids
- Direct Parent
- Prostaglandins and related compounds
- Alternative Parents
- Long-chain fatty acids / Hydroxy fatty acids / Unsaturated fatty acids / Cyclopentanols / Cyclic ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Prostaglandin skeleton / Long-chain fatty acid / Hydroxy fatty acid / Cyclopentanol / Fatty acid / Unsaturated fatty acid / Cyclic alcohol / Ketone / Cyclic ketone / Secondary alcohol
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- prostaglandins E (CHEBI:15551) / Prostaglandins (C00584) / Prostaglandins (LMFA03010003)
Targets
- 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 ...
- Gene Name
- PTGER2
- Uniprot ID
- P43116
- Uniprot Name
- Prostaglandin E2 receptor EP2 subtype
- Molecular Weight
- 39759.945 Da
References
- 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]
- 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]
- 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]
- Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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 importa...
- Gene Name
- PTGER1
- Uniprot ID
- P34995
- Uniprot Name
- Prostaglandin E2 receptor EP1 subtype
- Molecular Weight
- 41800.655 Da
References
- 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]
- 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]
- 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]
- Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241]
- 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 ...
- Gene Name
- PTGER3
- Uniprot ID
- P43115
- Uniprot Name
- Prostaglandin E2 receptor EP3 subtype
- Molecular Weight
- 43309.335 Da
References
- 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]
- 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]
- 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]
- Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241]
- 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...
- Gene Name
- PTGER4
- Uniprot ID
- P35408
- Uniprot Name
- Prostaglandin E2 receptor EP4 subtype
- Molecular Weight
- 53118.845 Da
References
- 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]
- 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]
- 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]
- 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]
- Sugimoto Y, Narumiya S: Prostaglandin E receptors. J Biol Chem. 2007 Apr 20;282(16):11613-7. Epub 2007 Feb 28. [PubMed:17329241]
- 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 al...
- Gene Name
- PTGDR2
- Uniprot ID
- Q9Y5Y4
- Uniprot Name
- Prostaglandin D2 receptor 2
- Molecular Weight
- 43267.15 Da
References
- 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
- 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
- Uniprot Name
- Cholesterol side-chain cleavage enzyme, mitochondrial
- Molecular Weight
- 60101.87 Da
References
- 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]
- 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
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- 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]
- 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 un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- 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
- 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, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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
- Uniprot Name
- Multidrug resistance-associated protein 5
- Molecular Weight
- 160658.8 Da
References
- 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]
- 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 ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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]
- 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]
- 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, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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]
- 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]
- 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
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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 sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Kimura H, Takeda M, Narikawa S, Enomoto A, Ichida K, Endou H: Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8. [PubMed:11907186]
- 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]
- 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]
- 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]
- 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
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- 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]
- 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
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- 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]
- 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]
- 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 inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- 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]
- 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]
- 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]
- 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. Efficie...
- Gene Name
- SLC51A
- Uniprot ID
- Q86UW1
- Uniprot Name
- Organic solute transporter subunit alpha
- Molecular Weight
- 37734.575 Da
References
- 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]
- 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. Efficie...
- Gene Name
- SLC51B
- Uniprot ID
- Q86UW2
- Uniprot Name
- Organic solute transporter subunit beta
- Molecular Weight
- 14346.195 Da
References
- 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]
- 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, a...
- Gene Name
- SLCO2A1
- Uniprot ID
- Q92959
- Uniprot Name
- Solute carrier organic anion transporter family member 2A1
- Molecular Weight
- 70043.33 Da
References
- Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [PubMed:8787677]
- 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]
- 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
- Uniprot Name
- Solute carrier organic anion transporter family member 4A1
- Molecular Weight
- 77192.505 Da
References
- 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]
- 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-gluc...
- Gene Name
- SLCO1C1
- Uniprot ID
- Q9NYB5
- Uniprot Name
- Solute carrier organic anion transporter family member 1C1
- Molecular Weight
- 78695.625 Da
References
- 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]
- 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 an...
- Gene Name
- SLCO3A1
- Uniprot ID
- Q9UIG8
- Uniprot Name
- Solute carrier organic anion transporter family member 3A1
- Molecular Weight
- 76552.135 Da
References
- 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]
- 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]
- 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, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- 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]
- 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]
- 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 August 14, 2018 04:32