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Identification
- Summary
Alprostadil is a prostaglandin E1 agonist used for the treatment of erectile dysfunction and as an adjunct for its diagnosis.
- Brand Names
- Caverject, Edex, Muse, Prostin Vr
- Generic Name
- Alprostadil
- DrugBank Accession Number
- DB00770
- Background
Alprostadil is a chemically-identical synthetic form of prostaglandin E1 (PGE1), a potent vasodilator produced endogenously. In 1996, the FDA approved the use of alprostadil, administered either with an intracavernosal injection or an intraurethral suppository, for the treatment of erectile dysfunction, and it is used in men for whom oral treatment is either contraindicated or ineffective. After administration, alprostadil promotes smooth muscle relaxation of the corpus cavernosal.1,3
Alprostadil is also used in neonatal patients with congenital heart defects that depend on a patent ductus for survival until corrective or palliative surgery can be performed. This drug causes vasodilation by directly affecting vascular and ductus arteriosus (DA) smooth muscle, preventing or reversing the functional closure of the DA that occurs shortly after birth. This results in increased pulmonary or systemic blood flow in infants.4,8,10
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Alprostadil (DB00770)
- Weight
- Average: 354.487
Monoisotopic: 354.240624195 - Chemical Formula
- C20H34O5
- Synonyms
- (11α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid
- (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
- 11α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid
- Alprostadil
- Alprostadilum
- PGE-1
- PGE1
- Prostaglandin E1
- External IDs
- ONO-1608
- U 10136
- U-10,136
- U-10136
Pharmacology
- Indication
Alprostadil is indicated for palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival.8 It is also indicated for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology,6,7 and as an adjunct to other diagnostic tests in the diagnosis of erectile dysfunction.6
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Erectile dysfunction •••••••••••• ••••••••• Management of Erectile dysfunction •••••••••••• •••••••••• ••••••••••• Management of Patent ductus arteriosus •••••••••••• •••••••• Treatment of Raynaud phenomenon ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Prostaglandin E1 is produced endogenously to relax vascular smooth muscle and cause vasodilation. As a synthetic form of prostaglandin E1, alprostadil has the same pharmacodynamic effects.1 Alprostadil inhibits platelet aggregation, has anti-inflammatory effects, interferes with immune responses, and stimulates factor X, a blood coagulation enzyme.5
In adult males, the use of alprostadil may lead to prolonged erection and priapism, penile fibrosis, hypotension, and injection site bleeding.6 In patients treated up to 24 months with alprostadil, the incidence of prolonged erections (>4 hours long) was 4% of all, and the incidence of priapism (erections greater than 6 hours in duration) was <1%.7 Patients with preexisting cardiovascular disease treated with alprostadil may also have higher cardiac risk.6 Neonates with congenital heart defects treated with alprostadil may experience apnea. Apnea is experienced by 10-12% of neonates and is more common in those weighing less than 2 kg at birth. The administration of alprostadil to neonates may also result in gastric outlet obstruction secondary to antral hyperplasia.8
- Mechanism of action
Alprostadil is a smooth muscle relaxant that promotes vasodilation and platelet aggregation inhibition. In neonatal patients with ductus arteriosus patency, alprostadil relaxes the ductus arteriosus (DA) smooth muscle, preventing or reversing the functional closure of the DA that occurs shortly after birth. This results in increased pulmonary or systemic blood flow in infants. Alprostadil appears to be most effective within 96 hours after birth since the DA rapidly loses its responsiveness to alprostadil.10
When administered by intracavernosal injection or as an intraurethral suppository, alprostadil acts locally to relax the trabecular smooth muscle of the corpora cavernosa and the cavernosal arteries. Swelling, elongation, and rigidity of the penis result when arterial blood rapidly flows into the corpus cavernosum to expand the lacunar spaces. The entrapped blood reduces the venous blood outflow as sinusoids compress against the tunica albuginea leading to penile rigidity. This is referred to as the corporal veno-occlusive mechanism.2,7,11
Target Actions Organism AThromboxane A2 receptor modulatorHumans AProstaglandin E2 receptor EP1 subtype agonistHumans AProstaglandin E2 receptor EP2 subtype agonistHumans AProstaglandin E2 receptor EP3 subtype agonistHumans AProstaglandin E2 receptor EP4 subtype agonistHumans UProstaglandin D2 receptor 2 agonistHumans - Absorption
In patients with erectile dysfunction given 20 μg of alprostadil intracavernously, the systemic plasma concentrations of prostaglandin E1 increased from a baseline of 0.8 pg/mL to a Cmax of 16.8 pg/mL (corrected for baseline). The tmax and AUC for this group of patients were 4.8 min and 173 pg⋅min/mL, respectively.7 In patients given 20 μg of alprostadil intravenously, AUC was similar to the one detected in patients that received alprostadil intracavernously (174 pg⋅min/mL); however, they had a higher tmax (25.5 min) and a lower Cmax (7.09 pg/mL). Compared to the same dose given by a short-term intravenous infusion, the absolute bioavailability of alprostadil estimated from systemic exposure was about 98%.7
- Volume of distribution
The volume of distribution of alprostadil has yet to be determined.6
- Protein binding
Alprostadil is bound in plasma primarily to albumin (81% bound) and, to a lesser extent, alpha-globulin IV-4 fraction (55% bound).6
- Metabolism
Alprostadil is rapidly metabolized in the human body. Following intracavernous administration, alprostadil is metabolized in the corpus cavernosum, and a smaller portion is absorbed from the penis into systemic circulation.7 After intravenous or arterial administration, alprostadil is metabolized and distributed throughout the entire body except for the central nervous system.10 As much as 60-90% of the circulating alprostadil may be metabolized in the lungs through first-pass pulmonary elimination, in a process known as beta- and omega-oxidation.7
The enzymatic oxidation of the C15-hydroxy group of alprostadil leads to the formation of 15-keto-PGE1, while the reduction of the C13, 14-double bond produces 15-keto-PGE0, and 13,14-dihydro-PGE1 (PGE0). The 15-keto metabolites are inactive, but the PGE0 metabolite has a similar potency to alprostadil in isolated animal organs.7 The major metabolite of alprostadil is 15-keto-PGE0.1
Hover over products below to view reaction partners
- Route of elimination
Following the degradation of alprostadil by beta- and omega-oxidation, metabolites are excreted primarily by the kidney, and excretion is essentially complete within 24 hours after administration (92%).10 Approximately 88% and 12% of alprostadil metabolites are excreted through urine and feces, respectively, over 72 hours. Alprostadil and its metabolites are not retained in tissues, and unchanged alprostadil has not been detected in urine.7,10
- Half-life
In healthy adults and neonates given a single intravenous dose of alprostadil, half-life goes from 5 to 10 minutes.10
- Clearance
In patients with erectile dysfunction given an intravenous infusion of alprostadil (20 μg), the total body clearance was 115 L/min.7
- Adverse Effects
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In neonatal patients given alprostadil intravenously, apnea, bradycardia, pyrexia, hypotension, and flushing may be signs of drug overdosage. In patients with apnea or bradycardia, discontinue the infusion, and provide appropriate medical treatment. Caution should be used in restarting the infusion. In patients with pyrexia or hypotension, reduce the infusion rate until these symptoms subside. Flushing is usually a result of incorrect intraarterial catheter placement, and the catheter should be repositioned.8
For patients given alprostadil intracavernosally for the treatment of erectile dysfunction, there is limited data on overdosage. Systemic reactions are uncommon with the intracavernous use of alprostadil, and hypotension occurrs in less than 1% of patients treated with this drug. A prolonged erection or priapism is the main symptom of an alprostadil overdose in this group of patients. Erections lasting more than 6 hours should be treated due to the potential for tissue hypoxia and possible necrosis. In the event of an intracavernous overdose, the patient is strongly encouraged to go to the nearest emergency room if his personal physician is not available. Supportive therapy according to the presence of other symptoms is recommended.6,7
The oral LD50 of alprostadil in mice and rats is 186 mg/kg and 228 mg/kg, respectively.9,12
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAvanafil The risk or severity of hypotension and priapism can be increased when Avanafil is combined with Alprostadil. Dipyridamole The risk or severity of hypotension and priapism can be increased when Dipyridamole is combined with Alprostadil. Fostamatinib The risk or severity of hypotension and priapism can be increased when Fostamatinib is combined with Alprostadil. Iloprost Iloprost may increase the hypotensive activities of Alprostadil. Isosorbide mononitrate Alprostadil may increase the vasodilatory activities of Isosorbide mononitrate. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Alista / Alprostan (Zentiva) / Alprostapint (Closter) / Alprostar (Recordati) / Alprostin (Pfizer) / Alprox-TD / Altesil (Taiyo Pharmaceutical) / Alyprost (Fuji Yakuhin) / Apistandin (Fuji Yakuhin) / Aplicav (Libbs) / Befar (Nexmed) / Bolesi (Yaoyou Pharmaceutical) / Bondil (Meda) / Cardiobron (Fada) / Caverject DC (Pfizer) / Caverject Dual (Pfizer) / Eglandin (Welfide) / Femprox / Kai Tong (Jilin Yuhua Pharmaceutical Co.) / Kaishi (Tide Pharmaceutical) / Karon (Zentiva) / Liple (Tanabe Mitsubishi Pharma) / Minprog (Pfizer) / Palux (Taisho Yakuhin) / Pridax (Gebro) / Prink (Taiyo Pharmaceutical) / Prolisina VR (Pfizer) / Prostandin (Ono Yakuhin) / Prostavasin (Schwarz) / Prostin VR (Pfizer) / Prostivas (Pfizer) / Sugiran (Esteve) / Tandetron (Takata Seiyaku) / Topiglan / Vasaprostan (Bayer) / Vasoprost (UCB) / Vasostenoon (Kevelt) / Viridal (UCB)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alprostadil Injection USP Solution 500 mcg / mL Intravascular Advanced Dosage Forms Inc. 2009-01-06 Not applicable Canada 
Alprostadil Injection, USP Liquid 500 mcg / mL Intra-arterial; Intravenous Novopharm Limited 2000-10-26 2018-05-18 Canada Caverject Injection, powder, lyophilized, for solution 41.1 ug/1mL Intracavernous Pharmacia & Upjohn Company LLC 1995-07-06 Not applicable US 
Caverject Injection, powder, lyophilized, for solution 5.4 ug/1mL Intracavernous Pharmacia & Upjohn Company LLC 1995-07-06 2009-08-25 US Caverject Injection, powder, lyophilized, for solution 20.5 ug/1mL Intracavernous Pharmacia & Upjohn Company LLC 1995-07-06 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alprostadil Injection 500 ug/1mL Intravascular; Intravenous Bedford Pharmaceuticals 2005-03-04 2009-05-31 US Alprostadil Injection, solution, concentrate 500 ug/1mL Intravascular Meitheal Pharmaceuticals Inc. 2024-09-15 Not applicable US Alprostadil Injection 500 ug/1mL Intravascular; Intravenous Bedford Pharmaceuticals 2005-03-04 2009-07-31 US Alprostadil Injection, solution, concentrate 500 ug/1mL Intravascular Teva Parenteral Medicines, Inc. 1999-04-30 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Caverject Sterile Powder - Kit 11.9mcg /vial Alprostadil (11.9 mcg / vial) + Water (99.1 %) Kit; Liquid; Powder, for solution Intracavernous Pfizer Italia S.R.L. 1996-07-30 2006-08-02 Canada
Categories
- ATC Codes
- C01EA01 — Alprostadil
- C01EA — Prostaglandins
- C01E — OTHER CARDIAC PREPARATIONS
- C01 — CARDIAC THERAPY
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Autacoids
- Biological Factors
- Cardiac Therapy
- Cardiovascular Agents
- Drugs Used in Erectile Dysfunction
- Eicosanoids
- Fatty Acids
- Fatty Acids, Monounsaturated
- Fatty Acids, Unsaturated
- Genito Urinary System and Sex Hormones
- Genitourinary Agents
- Genitourinary Arterial Vasodilation
- Hematologic Agents
- Inflammation Mediators
- Lipids
- Miscellaneous Vasodilatating Agents
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Substrates
- OATP2B1/SLCO2B1 substrates
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Prostaglandin E1 Agonist
- Prostaglandin Receptor Agonists
- Prostaglandins
- Prostaglandins E
- Prostaglandins, Synthetic
- Urological Agents
- Urologicals
- Vasodilating Agents
- Venous Vasodilation
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- F5TD010360
- CAS number
- 745-65-3
- InChI Key
- GMVPRGQOIOIIMI-DWKJAMRDSA-N
- InChI
- InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
- IUPAC Name
- 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
- SMILES
- CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O
References
- Synthesis Reference
Rodríguez, A., et al. (1999), An Efficient Asymmetric Synthesis of Prostaglandin E1. Eur. J. Org. Chem., 1999: 2655-2662. https://doi.org/10.1002/(SICI)1099-0690(199910)1999:102655::AID-EJOC26553.0.CO;2-2
- General References
- Hanchanale V, Eardley I: Alprostadil for the treatment of impotence. Expert Opin Pharmacother. 2014 Feb;15(3):421-8. doi: 10.1517/14656566.2014.873789. Epub 2013 Dec 26. [Article]
- Lea AP, Bryson HM, Balfour JA: Intracavernous alprostadil. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic potential in erectile dysfunction. Drugs Aging. 1996 Jan;8(1):56-74. doi: 10.2165/00002512-199608010-00009. [Article]
- Costabile RA, Mammen T, Hwang K: An overview and expert opinion on the use of alprostadil in the treatment of sexual dysfunction. Expert Opin Pharmacother. 2008 Jun;9(8):1421-9. doi: 10.1517/14656566.9.8.1421. [Article]
- Heymann MA, Clyman RI: Evaluation of alprostadil (prostaglandin E1) in the management of congenital heart disease in infancy. Pharmacotherapy. 1982 May-Jun;2(3):148-55. [Article]
- Degoute CS: Controlled hypotension: a guide to drug choice. Drugs. 2007;67(7):1053-76. [Article]
- FDA Approved Drug Products: CAVERJECT (alprostadil) injection for intracavernosal use [Link]
- FDA Approved Drug Products: Edex (alprostadil) injection for intracavernous use only [Link]
- DailyMed label: PROSTIN VR PEDIATRIC (alprostadil) injection solution for intravenous use [Link]
- Pfizer: Alprostadil SDS [Link]
- Health Canada Approved Drug Products: PROSTIN VR STERILE (alprostadil) solution for injection [Link]
- DailyMed Label: MUSE (alprostadil) suppository [Link]
- Medisca: Alprostadil SDS [Link]
- External Links
- Human Metabolome Database
- HMDB0001442
- KEGG Drug
- D00180
- KEGG Compound
- C04741
- PubChem Compound
- 149351
- PubChem Substance
- 46508029
- ChemSpider
- 4444306
- BindingDB
- 50101853
- 598
- ChEBI
- 15544
- ChEMBL
- CHEMBL495
- ZINC
- ZINC000003813088
- Therapeutic Targets Database
- DAP001490
- PharmGKB
- PA448334
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- XPG
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Prostaglandin_E1
- PDB Entries
- 3whx / 8iz9 / 8sx8
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Diabetes 1 somestatus stop reason just information to hide Not Available Completed Not Available Non-Occlusive Mesenteric Ischaemia (NOMI) 1 somestatus stop reason just information to hide Not Available Completed Health Services Research Anembryonic Pregnancy 1 somestatus stop reason just information to hide Not Available Completed Treatment Acute Respiratory Distress Syndrome (ARDS) / Pulmonary Hypertension (PH) 1 somestatus stop reason just information to hide Not Available Completed Treatment Cervical Ripening and Induction of Labor 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Bedford laboratories div ben venue laboratories inc
- Teva parenteral medicines inc
- Pfizer inc
- Pharmacia and upjohn co
- Schwarz pharma ag
- Vivus inc
- Packagers
- Bedford Labs
- Ben Venue Laboratories Inc.
- Medisca Inc.
- Nutrimol De Mexico Sa De Cv
- Paladin Laboratories Usa Inc.
- Pfizer Inc.
- Pharmacia Inc.
- Physicians Total Care Inc.
- Schwarz Pharma Inc.
- Sicor Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Vetter Pharma Fertigung GmbH and Co. KG
- Vivus
- Dosage Forms
Form Route Strength Solution Parenteral 500.000 µg Solution Intravenous 20 mcg Injection, solution, concentrate Intravenous Solution Intravenous 20 mcg/ml Solution Intravenous 500 mcg/ml Injection Intravascular; Intravenous 500 ug/1mL Injection, solution, concentrate Intravascular 500 ug/1mL Powder, for solution Intravenous Injection, solution, concentrate Parenteral Injection, powder, for solution Parenteral Injection, powder, for solution Parenteral 20 Mikrogramm Solution Intravenous 0.5 mg Solution Intravascular 500 mcg / mL Liquid Intra-arterial; Intravenous 500 mcg / mL Solution Intravenous 50000000 mcg Solution, concentrate Intravenous 20 mcg Solution, concentrate Intravenous 2000000 mcg Powder, for solution Intra-arterial; Parenteral 60 MICROGRAMMI Powder, for solution Intravenous; Parenteral 20 MICROGRAMMI Solution Intravenous 500.000 mcg/ml Solution Intravenous 500 mcg Injection, powder, for solution Intracavernous 10 MCG Injection, powder, for solution Intracavernous 20 MCG Injection, powder, for solution Intracavernous 5 MCG/ML Injection, powder, lyophilized, for solution Intracavernous 10.5 ug/1mL Injection, powder, lyophilized, for solution Intracavernous 20.5 ug/1mL Injection, powder, lyophilized, for solution Intracavernous 41.1 ug/1mL Injection, powder, lyophilized, for solution Intracavernous 5.4 ug/1mL Injection, solution Intravascular; Intravenous 10 MICROGRAMMI/ML Injection, solution Intravascular; Intravenous 20 MICROGRAMMI/ML Injection, solution Intravascular; Intravenous 5 MICROGRAMMI/ML Solution Parenteral 10.000 mcg Injection, powder, lyophilized, for solution Intracavernous Injection, powder, lyophilized, for solution Intracavernous 20 cg Injection, powder, for solution Parenteral 5 cg Injection, powder, lyophilized, for solution Intracavernous 10 ug/0.5mL Injection, powder, lyophilized, for solution Intracavernous 20 ug/0.5mL Injection, powder, for solution Intracavernous 10 mcg/ml Injection, powder, for solution Intracavernous 20 mcg/ml Kit; liquid; powder, for solution Intracavernous 20 mcg / vial Kit; liquid; powder, for solution Intracavernous Powder, for solution Intracavernous 11.9 mcg / vial Powder, for solution Intracavernous 20 mcg / vial Injection Intravenous 20 mcg Injection, powder, lyophilized, for solution Intracavernous 10 ug/1mL Injection, powder, lyophilized, for solution Intracavernous 20 ug/1mL Injection, powder, lyophilized, for solution Intracavernous 40 ug/1mL Injection, solution 10 mcg Injection, solution 20 mcg Stick Urethral 1000 MCG Stick Urethral 125 MCG Stick Urethral 250 MCG Stick Urethral 500 MCG Suppository Urethral 1000 ug/1 Suppository Urethral 1000 mcg Suppository Urethral 125 mcg Suppository Urethral 125 ug/1 Suppository Urethral 250 ug/1 Suppository Urethral 250 mcg Suppository Urethral 500 ug/1 Suppository Urethral 500 mcg Suppository Rectal 1 mg Stick Urethral Suppository Rectal 0.125 mg Injection, solution, concentrate Intravenous 500 Mikrogramm Powder, for solution Injection, powder, for solution Intravenous Injection, powder, lyophilized, for solution Intra-arterial; Intravenous 20 µg Solution Intravenous 0.5 mg/ml Solution 0.5 mg/1ml Injection, solution Intravenous 500 mcg Injection Intravenous 0.5 mg/ml Injection, solution Intravascular; Intravenous 500 ug/1mL Solution Intra-arterial; Intravenous 500 mcg / mL Injection, powder, for solution Injection, powder, for solution Intracavernous Cream Topical 2 MG/G Cream Topical 220 mcg / 100 mg Cream Topical 3 MG/G Cream Topical 330 mcg / 100 mg Cream Topical Powder - Prices
Unit description Cost Unit Alprostadil powder 5049.0USD g Edex Cartridge 6 Pack 40 mcg Kit Box 412.4USD box Caverject 6 40 mcg Solution Box 341.78USD box Edex 6 Pack 20 mcg Kit Box 301.0USD box Caverject 6 20 mcg Solution, 1 Box Contains 6 Vials Box 272.05USD box Prostin Vr 500 mcg/ml 266.72USD ml Edex Cartridge 6 Pack 10 mcg Kit Box 233.65USD box Edex Cartridge 2 Pack 40 mcg Kit Box 135.23USD box Edex 40 mcg cartridge kit 132.18USD kit Prostin vr 500 mcg/ml ampul 108.0USD ml Edex 2 Pack 20 mcg Kit Box 97.47USD box Edex 20 mcg cartridge kit 96.47USD kit Edex Cartridge 2 Pack 10 mcg Kit Box 77.22USD box Edex 10 mcg cartridge kit 74.88USD kit Alprostadil 500 mcg/ml vial 66.0USD ml Caverject Impulse 1 Box = 2 Blister Trays, 20 mcg 47.77USD box Caverject impulse 20 mcg kit 46.66USD each Caverject Impulse 1 Box = 2 Blister Trays, 10 mcg 37.51USD box Muse 1000 mcg Pellets 36.97USD pellet Caverject impulse 10 mcg kit 36.23USD each Muse 1000 mcg urethral suppository 35.54USD suppository Muse 500 mcg Pellets 34.23USD pellet Muse 500 mcg urethral suppository 32.92USD suppository Muse 250 mcg Pellets 31.99USD pellet Muse 250 mcg urethral suppository 30.76USD suppository Muse 125 mcg Pellets 30.56USD pellet Muse 125 mcg urethral suppository 29.39USD suppository DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5773020 No 1998-06-30 2010-04-25 US CA1335346 No 1995-04-25 2012-04-25 Canada US5886039 No 1999-03-23 2016-03-23 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 115-116 °C SDS water solubility 26.7 mg/L SDS logP 3.20 AVDEEF,A ET AL. (1995) pKa 4.85 (at 25 °C) AVDEEF,A ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0788 mg/mL ALOGPS logP 3.04 ALOGPS logP 3.59 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.35 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 13 Chemaxon Refractivity 98.32 m3·mol-1 Chemaxon Polarizability 42.13 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 220.7653631 predictedDarkChem Lite v0.1.0 [M-H]- 221.1128631 predictedDarkChem Lite v0.1.0 [M-H]- 207.6479631 predictedDarkChem Lite v0.1.0 [M-H]- 198.68137 predictedDeepCCS 1.0 (2019) [M-H]- 220.7653631 predictedDarkChem Lite v0.1.0 [M-H]- 221.1128631 predictedDarkChem Lite v0.1.0 [M-H]- 207.6479631 predictedDarkChem Lite v0.1.0 [M-H]- 198.68137 predictedDeepCCS 1.0 (2019) [M+H]+ 220.5189631 predictedDarkChem Lite v0.1.0 [M+H]+ 220.8638631 predictedDarkChem Lite v0.1.0 [M+H]+ 210.3251631 predictedDarkChem Lite v0.1.0 [M+H]+ 201.03937 predictedDeepCCS 1.0 (2019) [M+H]+ 220.5189631 predictedDarkChem Lite v0.1.0 [M+H]+ 220.8638631 predictedDarkChem Lite v0.1.0 [M+H]+ 210.3251631 predictedDarkChem Lite v0.1.0 [M+H]+ 201.03937 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.9558978 predictedDarkChem Standard v0.1.0 [M+Na]+ 219.9178631 predictedDarkChem Lite v0.1.0 [M+Na]+ 207.95436 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.9558978 predictedDarkChem Standard v0.1.0 [M+Na]+ 219.9178631 predictedDarkChem Lite v0.1.0 [M+Na]+ 207.95436 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C
- Specific Function
- guanyl-nucleotide exchange factor activity
- Gene Name
- TBXA2R
- Uniprot ID
- P21731
- Uniprot Name
- Thromboxane A2 receptor
- Molecular Weight
- 37430.69 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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
- Specific Function
- D1 dopamine receptor binding
- Gene Name
- PTGER1
- Uniprot ID
- P34995
- Uniprot Name
- Prostaglandin E2 receptor EP1 subtype
- Molecular Weight
- 41800.655 Da
References
- Norel X, de Montpreville V, Brink C: Vasoconstriction induced by activation of EP1 and EP3 receptors in human lung: effects of ONO-AE-248, ONO-DI-004, ONO-8711 or ONO-8713. Prostaglandins Other Lipid Mediat. 2004 Oct;74(1-4):101-12. [Article]
- Takahashi HK, Iwagaki H, Tamura R, Xue D, Sano M, Mori S, Yoshino T, Tanaka N, Nishibori M: Unique regulation profile of prostaglandin e1 on adhesion molecule expression and cytokine production in human peripheral blood mononuclear cells. J Pharmacol Exp Ther. 2003 Dec;307(3):1188-95. Epub 2003 Oct 15. [Article]
- Ito Y, Murai Y, Ishibashi H, Onoue H, Akaike N: The prostaglandin E series modulates high-voltage-activated calcium channels probably through the EP3 receptor in rat paratracheal ganglia. Neuropharmacology. 2000 Jan 4;39(2):181-90. [Article]
- Matlhagela K, Taub M: Involvement of EP1 and EP2 receptors in the regulation of the Na,K-ATPase by prostaglandins in MDCK cells. Prostaglandins Other Lipid Mediat. 2006 Mar;79(1-2):101-13. Epub 2006 Jan 27. [Article]
- Tokuda H, Kozawa O, Miwa M, Uematsu T: p38 mitogen-activated protein (MAP) kinase but not p44/p42 MAP kinase is involved in prostaglandin E1-induced vascular endothelial growth factor synthesis in osteoblasts. J Endocrinol. 2001 Sep;170(3):629-38. [Article]
- Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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
- Specific Function
- prostaglandin E receptor activity
- Gene Name
- PTGER2
- Uniprot ID
- P43116
- Uniprot Name
- Prostaglandin E2 receptor EP2 subtype
- Molecular Weight
- 39759.945 Da
References
- Dijkstra BG, Schneemann A, Hoyng PF: Flow after prostaglandin E1 is mediated by receptor-coupled adenylyl cyclase in human anterior segments. Invest Ophthalmol Vis Sci. 1999 Oct;40(11):2622-6. [Article]
- Takahashi HK, Iwagaki H, Tamura R, Katsuno G, Xue D, Sugita S, Mori S, Yoshino T, Tanaka N, Nishibori M: Differential effect of prostaglandins E1 and E2 on lipopolysaccharide-induced adhesion molecule expression on human monocytes. Eur J Pharmacol. 2005 Apr 11;512(2-3):223-30. [Article]
- Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for prostaglandin E2 (PGE2) (PubMed:7883006, PubMed:7981210, PubMed:8117308, PubMed:8135729, PubMed:8307176). The activity of this receptor can couple to both the inhibition of adenylate cyclase mediated by G(i) proteins, and to an elevation of intracellular calcium (PubMed:7883006, PubMed:7981210, PubMed:8117308, PubMed:8135729). Required for normal development of fever in response to pyrinogens, including IL1B, prostaglandin E2 and bacterial lipopolysaccharide (LPS). Required for normal potentiation of platelet aggregation by prostaglandin E2, and thus plays a role in the regulation of blood coagulation. Required for increased HCO3(-) secretion in the duodenum in response to mucosal acidification, and thereby contributes to the protection of the mucosa against acid-induced ulceration. Not required for normal kidney function, normal urine volume and osmolality (By similarity)
- Specific Function
- prostaglandin E receptor activity
- Gene Name
- PTGER3
- Uniprot ID
- P43115
- Uniprot Name
- Prostaglandin E2 receptor EP3 subtype
- Molecular Weight
- 43309.335 Da
References
- Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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
- Specific Function
- prostaglandin E receptor activity
- Gene Name
- PTGER4
- Uniprot ID
- P35408
- Uniprot Name
- Prostaglandin E2 receptor EP4 subtype
- Molecular Weight
- 53118.845 Da
References
- Kiriyama M, Ushikubi F, Kobayashi T, Hirata M, Sugimoto Y, Narumiya S: Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br J Pharmacol. 1997 Sep;122(2):217-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General 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, GRK2, GPRK5/GRK5 and GRK6. Receptor activation is responsible, at least in part, in immune regulation and allergic/inflammation responses
- Specific Function
- G protein-coupled receptor activity
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the NAD-dependent dehydrogenation (oxidation) of a broad array of hydroxylated polyunsaturated fatty acids (mainly eicosanoids and docosanoids, including prostaglandins, lipoxins and resolvins), yielding their corresponding keto (oxo) metabolites (PubMed:10837478, PubMed:16757471, PubMed:16828555, PubMed:21916491, PubMed:25586183, PubMed:8086429). Decreases the levels of the pro-proliferative prostaglandins such as prostaglandin E2 (whose activity is increased in cancer because of an increase in the expression of cyclooxygenase 2) and generates oxo-fatty acid products that can profoundly influence cell function by abrogating pro-inflammatory cytokine expression (PubMed:15574495, PubMed:25586183). Converts resolvins E1, D1 and D2 to their oxo products, which represents a mode of resolvin inactivation. Resolvin E1 plays important roles during the resolution phase of acute inflammation, while resolvins D1 and D2 have a unique role in obesity-induced adipose inflammation (PubMed:16757471, PubMed:22844113)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (NAD+) activity
- Gene Name
- HPGD
- Uniprot ID
- P15428
- Uniprot Name
- 15-hydroxyprostaglandin dehydrogenase [NAD(+)]
- Molecular Weight
- 28977.105 Da
References
- Lea AP, Bryson HM, Balfour JA: Intracavernous alprostadil. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic potential in erectile dysfunction. Drugs Aging. 1996 Jan;8(1):56-74. doi: 10.2165/00002512-199608010-00009. [Article]
- Bailey J. (1991). Prostaglandins, leukotrienes, lipoxins and PAF. Springer. [ISBN:978-1-4899-0729-5]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- FDA Approved Drug Products: CAVERJECT (alprostadil) injection for intracavernosal use [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (NAD+) activity
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- ATP-binding cassette sub-family C member 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Mediates ATP-dependent transport of endogenous metabolites such as cAMP and cGMP, folic acid and N-lactoyl-amino acids (in vitro) (PubMed:10893247, PubMed:12637526, PubMed:12695538, PubMed:15899835, PubMed:17229149, PubMed:25964343). Acts also as a general glutamate conjugate and analog transporter that can limit the brain levels of endogenous metabolites, drugs, and toxins (PubMed:26515061). Confers resistance to the antiviral agent PMEA (PubMed:12695538). Able to transport several anticancer drugs including methotrexate, and nucleotide analogs in vitro, however it does with low affinity, thus the exact role of ABCC5 in mediating resistance still needs to be elucidated (PubMed:10840050, PubMed:12435799, PubMed:12695538, PubMed:15899835). Acts as a heme transporter required for the translocation of cytosolic heme to the secretory pathway (PubMed:24836561). May play a role in energy metabolism by regulating the glucagon-like peptide 1 (GLP-1) secretion from enteroendocrine cells (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCC5
- Uniprot ID
- O15440
- Uniprot Name
- ATP-binding cassette sub-family C member 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Mediates the transport of prostaglandins (PGs, mainly PGE2, PGE1, PGE3, PGF2alpha, PGD2, PGH2) and thromboxanes (thromboxane B2) across the cell membrane (PubMed:11997326, PubMed:26692285, PubMed:8787677). PGs and thromboxanes play fundamental roles in diverse functions such as intraocular pressure, gastric acid secretion, renal salt and water transport, vascular tone, and fever (PubMed:15044627). Plays a role in the clearance of PGs from the circulation through cellular uptake, which allows cytoplasmic oxidation and PG signal termination (PubMed:8787677). PG uptake is dependent upon membrane potential and involves exchange of a monovalent anionic substrate (PGs exist physiologically as an anionic monovalent form) with a stoichiometry of 1:1 for divalent anions or of 1:2 for monovalent anions (PubMed:29204966). Uses lactate, generated by glycolysis, as a counter-substrate to mediate PGE2 influx and efflux (PubMed:11997326). Under nonglycolytic conditions, metabolites other than lactate might serve as counter-substrates (PubMed:11997326). Although the mechanism is not clear, this transporter can function in bidirectional mode (PubMed:29204966). When apically expressed in epithelial cells, it facilitates transcellular transport (also called vectorial release), extracting PG from the apical medium and facilitating transport across the cell toward the basolateral side, whereupon the PG exits the cell by simple diffusion (By similarity). In the renal collecting duct, regulates renal Na+ balance by removing PGE2 from apical medium (PGE2 EP4 receptor is likely localized to the luminal/apical membrane and stimulates Na+ resorption) and transporting it toward the basolateral membrane (where PGE2 EP1 and EP3 receptors inhibit Na+ resorption) (By similarity). Plays a role in endometrium during decidualization, increasing uptake of PGs by decidual cells (PubMed:16339169). Involved in critical events for ovulation (PubMed:27169804). Regulates extracellular PGE2 concentration for follicular development in the ovaries (By similarity). Expressed intracellularly, may contribute to vesicular uptake of newly synthesized intracellular PGs, thereby facilitating exocytotic secretion of PGs without being metabolized (By similarity). Essential core component of the major type of large-conductance anion channel, Maxi-Cl, which plays essential roles in inorganic anion transport, cell volume regulation and release of ATP and glutamate not only in physiological processes but also in pathological processes (By similarity). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- lipid transporter activity
- Gene Name
- SLCO2A1
- Uniprot ID
- Q92959
- Uniprot Name
- Solute carrier organic anion transporter family member 2A1
- Molecular Weight
- 70043.33 Da
References
- Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [Article]
- Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Putative organic anion antiporter with apparent broad substrate specificity. Recognizes various substrates including thyroid hormone L-thyroxine, prostanoids such as prostaglandin E1 and E2, bile acids such as taurocholate, glycolate and glycochenodeoxycholate and peptide hormones such as L-arginine vasopressin, likely operating in a tissue-specific manner (PubMed:10873595, PubMed:14631946, PubMed:16971491, PubMed:19129463, PubMed:30063921). The transport mechanism, its electrogenicity and potential tissue-specific counterions remain to be elucidated (Probable)
- Specific Function
- organic anion transmembrane transporter activity
- Gene Name
- SLCO3A1
- Uniprot ID
- Q9UIG8
- Uniprot Name
- Solute carrier organic anion transporter family member 3A1
- Molecular Weight
- 76552.135 Da
References
- Adachi H, Suzuki T, Abe M, Asano N, Mizutamari H, Tanemoto M, Nishio T, Onogawa T, Toyohara T, Kasai S, Satoh F, Suzuki M, Tokui T, Unno M, Shimosegawa T, Matsuno S, Ito S, Abe T: Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76697.93 Da
References
- Nishio T, Adachi H, Nakagomi R, Tokui T, Sato E, Tanemoto M, Fujiwara K, Okabe M, Onogawa T, Suzuki T, Nakai D, Shiiba K, Suzuki M, Ohtani H, Kondo Y, Unno M, Ito S, Iinuma K, Nunoki K, Matsuno S, Abe T: Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate. Biochem Biophys Res Commun. 2000 Sep 7;275(3):831-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Liu HC, Jamshidi N, Chen Y, Eraly SA, Cho SY, Bhatnagar V, Wu W, Bush KT, Abagyan R, Palsson BO, Nigam SK: An Organic Anion Transporter 1 (OAT1)-centered Metabolic Network. J Biol Chem. 2016 Sep 9;291(37):19474-86. doi: 10.1074/jbc.M116.745216. Epub 2016 Jul 20. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 13, 2024 03:38