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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
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 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
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- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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. Isosorbide mononitrate Alprostadil may increase the vasodilatory activities of Isosorbide mononitrate. Patent Blue The therapeutic efficacy of Alprostadil can be decreased when used in combination with Patent Blue. - 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 20.5 ug/1mL Intracavernous Pharmacia & Upjohn Company LLC 1995-07-06 Not applicable US 
Caverject Injection, powder, lyophilized, for solution 10.5 ug/1mL Intracavernous Pharmacia and Upjohn Company 1995-07-06 2009-08-25 US Caverject Injection, powder, lyophilized, for solution 41.1 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 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 Canada Ulc 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 / 8sx8
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Coronary Slow Flow Phenomenon / ST Segment Elevation Myocardial Infarction (STEMI) 1 4 Completed Treatment Diabetic Nephropathy 1 4 Completed Treatment Peripheral Arterial Occlusive Disease (PAOD) 1 4 Not Yet Recruiting Treatment Stroke 1 4 Unknown Status Prevention Acute Kidney Injury (AKI) / Diabetes Mellitus / Impaired Renal Function / Kidney Diseases / Renal Failure, Chronic Renal Failure 1
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 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 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 mcg Suppository Urethral 1000 ug/1 Suppository Urethral 125 ug/1 Suppository Urethral 125 mcg Suppository Urethral 250 ug/1 Suppository Urethral 250 mcg Suppository Urethral 500 mcg Suppository Urethral 500 ug/1 Suppository Rectal 1 mg Stick Urethral Suppository Rectal 0.125 mg 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 Injection Intravenous 0.5 mg/ml Injection, solution Intravascular; Intravenous 500 ug/1mL Solution Intravenous 0.5 mg 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Prostaglandin e receptor activity
- Specific Function
- Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
- Gene Name
- PTGER1
- Uniprot ID
- P34995
- Uniprot Name
- Prostaglandin E2 receptor EP1 subtype
- Molecular Weight
- 41800.655 Da
References
- 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
- 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
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
- Specific Function
- Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
- Gene Name
- PTGER3
- Uniprot ID
- P43115
- Uniprot Name
- Prostaglandin E2 receptor EP3 subtype
- Molecular Weight
- 43309.335 Da
References
- 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
- 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
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- Prostaglandin inactivation. Contributes to the regulation of events that are under the control of prostaglandin levels. Catalyzes the NAD-dependent dehydrogenation of lipoxin A4 to form 15-oxo-lipo...
- 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
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Acts as a multispecific organic anion pump which can transport nucleotide analogs.
- Gene Name
- ABCC5
- Uniprot ID
- O15440
- Uniprot Name
- Multidrug resistance-associated protein 5
- Molecular Weight
- 160658.8 Da
References
- Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- 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. [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
- 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
- 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
- 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
- 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
- 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
- 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 February 20, 2024 23:55