Alprostadil

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentErectile dysfunction•••••••••••••••••••••
Management ofErectile dysfunction•••••••••••••••••••••• •••••••••••
Management ofPatent ductus arteriosus••••••••••••••••••••
Treatment ofRaynaud phenomenon••• •••••
Contraindications & Blackbox Warnings
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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

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

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.
DrugInteraction
AvanafilThe risk or severity of hypotension and priapism can be increased when Avanafil is combined with Alprostadil.
DipyridamoleThe risk or severity of hypotension and priapism can be increased when Dipyridamole is combined with Alprostadil.
FostamatinibThe risk or severity of hypotension and priapism can be increased when Fostamatinib is combined with Alprostadil.
IloprostIloprost may increase the hypotensive activities of Alprostadil.
Isosorbide mononitrateAlprostadil may increase the vasodilatory activities of Isosorbide mononitrate.
Food Interactions
No interactions found.

Products

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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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alprostadil Injection USPSolution500 mcg / mLIntravascularAdvanced Dosage Forms Inc.2009-01-06Not applicableCanada flag
Alprostadil Injection, USPLiquid500 mcg / mLIntra-arterial; IntravenousNovopharm Limited2000-10-262018-05-18Canada flag
CaverjectInjection, powder, lyophilized, for solution20.5 ug/1mLIntracavernousPharmacia &amp; Upjohn Company LLC1995-07-06Not applicableUS flag
CaverjectInjection, powder, lyophilized, for solution10.5 ug/1mLIntracavernousPharmacia and Upjohn Company1995-07-062009-08-25US flag
CaverjectInjection, powder, lyophilized, for solution5.4 ug/1mLIntracavernousPharmacia and Upjohn Company1995-07-062009-08-25US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlprostadilInjection500 ug/1mLIntravascular; IntravenousBedford Pharmaceuticals2005-03-042009-05-31US flag
AlprostadilInjection500 ug/1mLIntravascular; IntravenousBedford Pharmaceuticals2005-03-042009-07-31US flag
AlprostadilInjection, solution, concentrate500 ug/1mLIntravascularTeva Parenteral Medicines, Inc.1999-04-30Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Caverject Sterile Powder - Kit 11.9mcg /vialAlprostadil (11.9 mcg / vial) + Water (99.1 %)Kit; Liquid; Powder, for solutionIntracavernousPfizer Canada Ulc1996-07-302006-08-02Canada flag

Categories

ATC Codes
C01EA01 — AlprostadilG04BE01 — Alprostadil
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Degoute CS: Controlled hypotension: a guide to drug choice. Drugs. 2007;67(7):1053-76. [Article]
  6. FDA Approved Drug Products: CAVERJECT (alprostadil) injection for intracavernosal use [Link]
  7. FDA Approved Drug Products: Edex (alprostadil) injection for intracavernous use only [Link]
  8. DailyMed label: PROSTIN VR PEDIATRIC (alprostadil) injection solution for intravenous use [Link]
  9. Pfizer: Alprostadil SDS [Link]
  10. Health Canada Approved Drug Products: PROSTIN VR STERILE (alprostadil) solution for injection [Link]
  11. DailyMed Label: MUSE (alprostadil) suppository [Link]
  12. Medisca: Alprostadil SDS [Link]
Human Metabolome Database
HMDB0001442
KEGG Drug
D00180
KEGG Compound
C04741
PubChem Compound
149351
PubChem Substance
46508029
ChemSpider
4444306
BindingDB
50101853
RxNav
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

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
FormRouteStrength
SolutionParenteral500.000 µg
SolutionIntravenous20 mcg
Injection, solution, concentrateIntravenous
SolutionIntravenous20 mcg/ml
SolutionIntravenous
InjectionIntravascular; Intravenous500 ug/1mL
Injection, solution, concentrateIntravascular500 ug/1mL
Powder, for solutionIntravenous
Injection, solution, concentrateParenteral
Injection, powder, for solutionParenteral
Injection, powder, for solutionParenteral20 Mikrogramm
SolutionIntravascular500 mcg / mL
LiquidIntra-arterial; Intravenous500 mcg / mL
SolutionIntravenous50000000 mcg
Solution, concentrateIntravenous20 mcg
Solution, concentrateIntravenous2000000 mcg
Powder, for solutionIntra-arterial; Parenteral60 MICROGRAMMI
Powder, for solutionIntravenous; Parenteral20 MICROGRAMMI
SolutionIntravenous500.000 mcg/ml
SolutionIntravenous500 mcg
Injection, powder, for solutionIntracavernous10 MCG
Injection, powder, for solutionIntracavernous20 MCG
Injection, powder, for solutionIntracavernous5 MCG/ML
Injection, powder, lyophilized, for solutionIntracavernous10.5 ug/1mL
Injection, powder, lyophilized, for solutionIntracavernous20.5 ug/1mL
Injection, powder, lyophilized, for solutionIntracavernous41.1 ug/1mL
Injection, powder, lyophilized, for solutionIntracavernous5.4 ug/1mL
Injection, solutionIntravascular; Intravenous10 MICROGRAMMI/ML
Injection, solutionIntravascular; Intravenous20 MICROGRAMMI/ML
Injection, solutionIntravascular; Intravenous5 MICROGRAMMI/ML
SolutionParenteral10.000 mcg
Injection, powder, lyophilized, for solutionIntracavernous
Injection, powder, lyophilized, for solutionIntracavernous20 cg
Injection, powder, for solutionParenteral5 cg
Injection, powder, lyophilized, for solutionIntracavernous10 ug/0.5mL
Injection, powder, lyophilized, for solutionIntracavernous20 ug/0.5mL
Injection, powder, for solutionIntracavernous10 mcg/ml
Injection, powder, for solutionIntracavernous20 mcg/ml
Kit; liquid; powder, for solutionIntracavernous20 mcg / vial
Kit; liquid; powder, for solutionIntracavernous
Powder, for solutionIntracavernous11.9 mcg / vial
Powder, for solutionIntracavernous20 mcg / vial
InjectionIntravenous20 mcg
Injection, powder, lyophilized, for solutionIntracavernous10 ug/1mL
Injection, powder, lyophilized, for solutionIntracavernous20 ug/1mL
Injection, powder, lyophilized, for solutionIntracavernous40 ug/1mL
Injection, solution10 mcg
Injection, solution20 mcg
StickUrethral1000 MCG
StickUrethral125 MCG
StickUrethral250 MCG
StickUrethral500 MCG
SuppositoryUrethral1000 ug/1
SuppositoryUrethral1000 mcg
SuppositoryUrethral125 mcg
SuppositoryUrethral125 ug/1
SuppositoryUrethral250 mcg
SuppositoryUrethral250 ug/1
SuppositoryUrethral500 mcg
SuppositoryUrethral500 ug/1
SuppositoryRectal1 mg
StickUrethral
SuppositoryRectal0.125 mg
Injection, solution, concentrateIntravenous500 Mikrogramm
Powder, for solution
Injection, powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntra-arterial; Intravenous20 µg
SolutionIntravenous0.5 mg/ml
Solution0.5 mg/1ml
Injection, solutionIntravenous
InjectionIntravenous0.5 mg/ml
Injection, solutionIntravascular; Intravenous500 ug/1mL
SolutionIntravenous0.5 mg
SolutionIntra-arterial; Intravenous500 mcg / mL
Injection, powder, for solution
Injection, powder, for solutionIntracavernous
CreamTopical2 MG/G
CreamTopical220 mcg / 100 mg
CreamTopical3 MG/G
CreamTopical330 mcg / 100 mg
CreamTopical
Powder
Prices
Unit descriptionCostUnit
Alprostadil powder5049.0USD g
Edex Cartridge 6 Pack 40 mcg Kit Box412.4USD box
Caverject 6 40 mcg Solution Box341.78USD box
Edex 6 Pack 20 mcg Kit Box301.0USD box
Caverject 6 20 mcg Solution, 1 Box Contains 6 Vials Box272.05USD box
Prostin Vr 500 mcg/ml266.72USD ml
Edex Cartridge 6 Pack 10 mcg Kit Box233.65USD box
Edex Cartridge 2 Pack 40 mcg Kit Box135.23USD box
Edex 40 mcg cartridge kit132.18USD kit
Prostin vr 500 mcg/ml ampul108.0USD ml
Edex 2 Pack 20 mcg Kit Box97.47USD box
Edex 20 mcg cartridge kit96.47USD kit
Edex Cartridge 2 Pack 10 mcg Kit Box77.22USD box
Edex 10 mcg cartridge kit74.88USD kit
Alprostadil 500 mcg/ml vial66.0USD ml
Caverject Impulse 1 Box = 2 Blister Trays, 20 mcg47.77USD box
Caverject impulse 20 mcg kit46.66USD each
Caverject Impulse 1 Box = 2 Blister Trays, 10 mcg37.51USD box
Muse 1000 mcg Pellets36.97USD pellet
Caverject impulse 10 mcg kit36.23USD each
Muse 1000 mcg urethral suppository35.54USD suppository
Muse 500 mcg Pellets34.23USD pellet
Muse 500 mcg urethral suppository32.92USD suppository
Muse 250 mcg Pellets31.99USD pellet
Muse 250 mcg urethral suppository30.76USD suppository
Muse 125 mcg Pellets30.56USD pellet
Muse 125 mcg urethral suppository29.39USD suppository
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5773020No1998-06-302010-04-25US flag
CA1335346No1995-04-252012-04-25Canada flag
US5886039No1999-03-232016-03-23US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115-116 °CSDS
water solubility26.7 mg/LSDS
logP3.20AVDEEF,A ET AL. (1995)
pKa4.85 (at 25 °C)AVDEEF,A ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0788 mg/mLALOGPS
logP3.04ALOGPS
logP3.59Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.35Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity98.32 m3·mol-1Chemaxon
Polarizability42.13 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9815
Blood Brain Barrier+0.8704
Caco-2 permeable+0.5245
P-glycoprotein substrateSubstrate0.5554
P-glycoprotein inhibitor INon-inhibitor0.9202
P-glycoprotein inhibitor IINon-inhibitor0.8983
Renal organic cation transporterNon-inhibitor0.9064
CYP450 2C9 substrateNon-substrate0.8211
CYP450 2D6 substrateNon-substrate0.8834
CYP450 3A4 substrateNon-substrate0.5292
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9502
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9725
Ames testNon AMES toxic0.9387
CarcinogenicityNon-carcinogens0.9201
BiodegradationReady biodegradable0.6056
Rat acute toxicity2.9631 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9087
hERG inhibition (predictor II)Non-inhibitor0.9138
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-22bae8a8d8b142c38bdc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-2ef553dc16ff5cfaee35
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3379000000-d658b7ca709444ddc16f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0069000000-4fce126f398acdf03012
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00aj-6594000000-fe9c5a0f0763c0a1a0a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05tf-7900000000-aeffcc303416c0b1be4d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-22bae8a8d8b142c38bdc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-2ef553dc16ff5cfaee35
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-0069000000-4fce126f398acdf03012
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3379000000-d658b7ca709444ddc16f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00aj-6594000000-fe9c5a0f0763c0a1a0a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05tf-7900000000-aeffcc303416c0b1be4d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-220.7653631
predicted
DarkChem Lite v0.1.0
[M-H]-221.1128631
predicted
DarkChem Lite v0.1.0
[M-H]-207.6479631
predicted
DarkChem Lite v0.1.0
[M-H]-198.68137
predicted
DeepCCS 1.0 (2019)
[M-H]-220.7653631
predicted
DarkChem Lite v0.1.0
[M-H]-221.1128631
predicted
DarkChem Lite v0.1.0
[M-H]-207.6479631
predicted
DarkChem Lite v0.1.0
[M-H]-198.68137
predicted
DeepCCS 1.0 (2019)
[M+H]+220.5189631
predicted
DarkChem Lite v0.1.0
[M+H]+220.8638631
predicted
DarkChem Lite v0.1.0
[M+H]+210.3251631
predicted
DarkChem Lite v0.1.0
[M+H]+201.03937
predicted
DeepCCS 1.0 (2019)
[M+H]+220.5189631
predicted
DarkChem Lite v0.1.0
[M+H]+220.8638631
predicted
DarkChem Lite v0.1.0
[M+H]+210.3251631
predicted
DarkChem Lite v0.1.0
[M+H]+201.03937
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.9558978
predicted
DarkChem Standard v0.1.0
[M+Na]+219.9178631
predicted
DarkChem Lite v0.1.0
[M+Na]+207.95436
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.9558978
predicted
DarkChem Standard v0.1.0
[M+Na]+219.9178631
predicted
DarkChem Lite v0.1.0
[M+Na]+207.95436
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
Molecular Weight
41800.655 Da
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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]
  2. 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]
  3. 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
  1. 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
  1. 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
  1. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW: Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. Br J Pharmacol. 1998 Apr;123(7):1317-24. [Article]

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
  1. 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]
  2. 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
  1. 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
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [Article]
  2. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 an...
Gene Name
SLCO3A1
Uniprot ID
Q9UIG8
Uniprot Name
Solute carrier organic anion transporter family member 3A1
Molecular Weight
76552.135 Da
References
  1. Adachi H, Suzuki T, Abe M, Asano N, Mizutamari H, Tanemoto M, Nishio T, Onogawa T, Toyohara T, Kasai S, Satoh F, Suzuki M, Tokui T, Unno M, Shimosegawa T, Matsuno S, Ito S, Abe T: Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Nishio T, Adachi H, Nakagomi R, Tokui T, Sato E, Tanemoto M, Fujiwara K, Okabe M, Onogawa T, Suzuki T, Nakai D, Shiiba K, Suzuki M, Ohtani H, Kondo Y, Unno M, Ito S, Iinuma K, Nunoki K, Matsuno S, Abe T: Molecular identification of a rat novel organic anion transporter moat1, which transports prostaglandin D(2), leukotriene C(4), and taurocholate. Biochem Biophys Res Commun. 2000 Sep 7;275(3):831-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. 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]
  2. 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 May 29, 2024 19:09