Identification

Name
Alprostadil
Accession Number
DB00770  (APRD00785)
Type
Small Molecule
Groups
Approved, Investigational
Description

Alprostadil is produced endogenously and causes vasodilation by means of a direct effect on 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. In infants, it is used 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. In adults, it is used for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.

Structure
Thumb
Synonyms
  • (11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid
  • (13e)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate
  • 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid
  • Alprostadil
  • Alprostadil Alfadex
  • Alprostadilum
  • Befar
  • PGE-1
  • PGE₁
  • PGE1 α-CD
  • Prostaglandin e1
External IDs
ONO-1608 / U 10136 / U-10,136 / U-10136
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alprostadil Injection USPSolution500 mcgIntravascularAdvanced Dosage Forms Inc.2009-01-06Not applicableCanada
Alprostadil Injection, USPLiquid500 mcgIntra-arterial; IntravenousNovopharm Limited2000-10-26Not applicableCanada
CaverjectInjection, powder, lyophilized, for solution10.5 ug/mLIntracavernousPharmacia & Upjohn Inc1995-07-062016-10-13Us
CaverjectInjection, powder, lyophilized, for solution5.4 ug/mLIntracavernousPharmacia & Upjohn Inc1995-07-062016-10-13Us
CaverjectInjection, powder, lyophilized, for solution20.5 ug/mLIntracavernousPharmacia & Upjohn Inc1995-07-06Not applicableUs
CaverjectInjection, powder, lyophilized, for solution41.1 ug/mLIntracavernousPharmacia & Upjohn Inc1995-07-06Not applicableUs
Caverject ImpulseInjection, powder, lyophilized, for solution10 ug/.5mLIntracavernousPharmacia & Upjohn Inc2002-06-11Not applicableUs
Caverject ImpulseInjection, powder, lyophilized, for solution10 ug/.5mLIntracavernousU.S. Pharmaceuticals2014-05-04Not applicableUs
Caverject ImpulseInjection, powder, lyophilized, for solution20 ug/.5mLIntracavernousPharmacia & Upjohn Inc2002-06-11Not applicableUs
Caverject ImpulseInjection, powder, lyophilized, for solution20 ug/.5mLIntracavernousU.S. Pharmaceuticals2014-05-04Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlprostadilInjection, solution, concentrate500 ug/mLIntravascularTeva Parenteral Medicines, Inc.1999-04-30Not applicableUs
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 / Caverject DC (Pfizer) / Caverject Dual (Pfizer) / Edex / Eglandin (Welfide) / Femprox / Kai Tong (Jilin Yuhua Pharmaceutical Co.) / Kaishi (Tide Pharmaceutical) / Karon (Zentiva) / Liple (Tanabe Mitsubishi Pharma) / Minprog (Pfizer) / Muse / 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)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Caverject Sterile Powder - Kit 11.9mcg /vialAlprostadil (11.9 mcg) + Water (99.1 %)Kit; Liquid; Powder, for solutionIntracavernousPfizer1996-07-302006-08-02Canada
Caverject Sterile Powder - Kit 23.2mcg/vialAlprostadil (23.2 mcg) + Water (99.1 %)Kit; Liquid; Powder, for solutionIntracavernousPfizer1996-07-30Not applicableCanada
Categories
UNII
F5TD010360
CAS number
745-65-3
Weight
Average: 354.481
Monoisotopic: 354.240624198
Chemical Formula
C20H34O5
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-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
SMILES

Pharmacology

Indication

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. Also for the treatment of erectile dysfunction due to neurogenic, vasculogenic, psychogenic, or mixed etiology.

Structured Indications
Pharmacodynamics

Alprostadil (prostaglandin E1) is produced endogenously to relax vascular smooth muscle and cause vasodilation. In adult males, the vasodilatory effects of alprostadil on the cavernosal arteries and the trabecular smooth muscle of the corpora cavernosa result in rapid arteriolar inflow and expansion of the lacunar spaces within the corpora. As the expanded corporal sinusoids are compressed against the tunica albuginea, venous outflow through the subtunical vessels is impeded and penile rigidity develops. This is referred to as the corporal veno-occlusive mechanism. In infants, the vasodilatory effects of alprostadil increase pulmonary or systemic blood flow.

Mechanism of action

Alprostadil causes vasodilation by means of a direct effect on vascular and ductus arteriosus (DA) smooth muscle, preventing or reversing the functional closure of the DA that occurs shortly after birth. This is because, as a form of prostaglandinE1 (PGE1) it has multiple effects on blood flow. This results in increased pulmonary or systemic blood flow in infants. In cyanotic congenital heart disease, alprostadil's actions result in an increased oxygen supply to the tissues. In infants with interrupted aortic arch or very severe aortic coarctation, alprostadil maintains distal aortic perfusion by permitting blood flow through the DA from the pulmonary artery to the aorta. In infants with aortic coarctation, alprostadil reduces aortic obstruction either by relaxing ductus tissue in the aortic wall or by increasing effective aortic diameter by dilating the DA. In infants with these aortic arch anomalies, systemic blood flow to the lower body is increased, improving tissue oxygen supply and renal perfusion. 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.

TargetActionsOrganism
AProstaglandin E2 receptor EP2 subtype
agonist
Human
AProstaglandin E2 receptor EP1 subtype
agonist
Human
UProstaglandin D2 receptor 2
agonist
Human
Absorption

The absolute bioavailability of alprostadil has not been determined.

Volume of distribution
Not Available
Protein binding

Bound in plasma primarily to albumin (81% bound) and to a lesser extent alpha-globulin IV-4 fraction (55% bound).

Metabolism

Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by beta- and omega-oxidation.

Route of elimination

Alprostadil must be infused continuously because it is very rapidly metabolized. As much as 80% of the circulating alprostadil may be metabolized in one pass through the lungs, primarily by β- and ω-oxidation. The metabolites are excreted primarily by the kidney, and excretion is essentially complete within 24 hours after administration.

Half life

5 to 10 minutes (after a single dose), in healthy adults and neonates.

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 186 mg/kg; Oral, rat: LD50 = 228 mg/kg. Apnea, bradycardia, pyrexia, hypotension, and flushing may be signs of drug overdosage.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbciximabAlprostadil may increase the anticoagulant activities of Abciximab.Approved
AceclofenacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Aceclofenac.Approved, Investigational
AcemetacinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Acemetacin.Approved
AcenocoumarolAlprostadil may increase the anticoagulant activities of Acenocoumarol.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Alprostadil is combined with Acetylsalicylic acid.Approved, Vet Approved
AdapaleneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Adapalene.Approved
AlclofenacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Alclofenac.Approved, Withdrawn
AlminoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Alminoprofen.Experimental
AloxiprinThe risk or severity of adverse effects can be increased when Alprostadil is combined with Aloxiprin.Experimental
AlteplaseAlprostadil may increase the anticoagulant activities of Alteplase.Approved
ALX-0081Alprostadil may increase the anticoagulant activities of ALX-0081.Investigational
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Alprostadil is combined with Aminosalicylic Acid.Approved
AnagrelideAlprostadil may increase the anticoagulant activities of Anagrelide.Approved
AncrodAlprostadil may increase the anticoagulant activities of Ancrod.Investigational
AndrographolideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Andrographolide.Investigational
AnisodamineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Anisodamine.Investigational
AnistreplaseAlprostadil may increase the anticoagulant activities of Anistreplase.Approved
AntipyrineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Antipyrine.Approved
Antithrombin III humanAlprostadil may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanThe risk or severity of adverse effects can be increased when Alprostadil is combined with Apixaban.Approved
ApocyninThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Apocynin.Investigational
ApremilastThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Apremilast.Approved, Investigational
ArdeparinAlprostadil may increase the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanAlprostadil may increase the anticoagulant activities of Argatroban.Approved, Investigational
AstaxanthinAlprostadil may increase the anticoagulant activities of Astaxanthin.Investigational
AvanafilThe risk or severity of adverse effects can be increased when Avanafil is combined with Alprostadil.Approved
AzapropazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Azapropazone.Withdrawn
AzelastineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Azelastine.Approved
BalsalazideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Balsalazide.Approved, Investigational
BatroxobinAlprostadil may increase the anticoagulant activities of Batroxobin.Experimental
BecaplerminAlprostadil may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BemiparinAlprostadil may increase the anticoagulant activities of Bemiparin.Approved, Investigational
BendazacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bendazac.Experimental
BenorilateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Benorilate.Experimental
BenoxaprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Benoxaprofen.Withdrawn
BenzydamineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Benzydamine.Approved
BeraprostAlprostadil may increase the anticoagulant activities of Beraprost.Investigational
BevoniumThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bevonium.Experimental
BivalirudinAlprostadil may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BrinaseAlprostadil may increase the anticoagulant activities of Brinase.Experimental
BromfenacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bromfenac.Approved
BucillamineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bucillamine.Investigational
BufexamacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bufexamac.Experimental
BuflomedilAlprostadil may increase the antiplatelet activities of Buflomedil.Experimental
BumadizoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Bumadizone.Experimental
ButylphthalideAlprostadil may increase the antiplatelet activities of Butylphthalide.Investigational
CangrelorAlprostadil may increase the anticoagulant activities of Cangrelor.Approved
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Alprostadil is combined with Carbaspirin calcium.Experimental, Investigational
CarprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Castanospermine.Experimental
CelecoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Celecoxib.Approved, Investigational
CertoparinAlprostadil may increase the anticoagulant activities of Certoparin.Approved, Investigational
ChloroquineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Chloroquine.Approved, Vet Approved
Choline magnesium trisalicylateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Choline magnesium trisalicylate.Approved
CilostazolAlprostadil may increase the anticoagulant activities of Cilostazol.Approved
Citric AcidAlprostadil may increase the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClonixinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Clonixin.Approved
ClopidogrelAlprostadil may increase the anticoagulant activities of Clopidogrel.Approved, Nutraceutical
CloricromenAlprostadil may increase the anticoagulant activities of Cloricromen.Experimental
ClorindioneAlprostadil may increase the anticoagulant activities of Clorindione.Experimental
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Alprostadil is combined with Collagenase clostridium histolyticum.Approved, Investigational
CurcuminThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Curcumin.Investigational
D-LimoneneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with D-Limonene.Investigational
Dabigatran etexilateAlprostadil may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinAlprostadil may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidAlprostadil may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanAlprostadil may increase the anticoagulant activities of Darexaban.Investigational
DasatinibDasatinib may increase the anticoagulant activities of Alprostadil.Approved, Investigational
DefibrotideAlprostadil may increase the anticoagulant activities of Defibrotide.Approved, Investigational
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Alprostadil is combined with Deoxycholic Acid.Approved
dersalazineThe risk or severity of adverse effects can be increased when Alprostadil is combined with dersalazine.Investigational
DesirudinAlprostadil may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseAlprostadil may increase the anticoagulant activities of Desmoteplase.Investigational
DextranAlprostadil may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Alprostadil may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Alprostadil may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Alprostadil may increase the anticoagulant activities of Dextran 75.Approved
DiclofenacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Diclofenac.Approved, Vet Approved
DicoumarolAlprostadil may increase the anticoagulant activities of Dicoumarol.Approved
DifenpiramideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Difenpiramide.Experimental
DiflunisalThe risk or severity of adverse effects can be increased when Alprostadil is combined with Diflunisal.Approved
DiphenadioneAlprostadil may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleAlprostadil may increase the anticoagulant activities of Dipyridamole.Approved
DitazoleAlprostadil may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
Drotrecogin alfaAlprostadil may increase the anticoagulant activities of Drotrecogin alfa.Approved, Investigational, Withdrawn
DroxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Droxicam.Approved
DuvelisibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Duvelisib.Investigational
E-6201The therapeutic efficacy of Alprostadil can be decreased when used in combination with E-6201.Investigational
Edetic AcidAlprostadil may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanAlprostadil may increase the anticoagulant activities of Edoxaban.Approved
EnoxaparinAlprostadil may increase the anticoagulant activities of Enoxaparin.Approved
EpinastineEpinastine may increase the antiplatelet activities of Alprostadil.Approved, Investigational
EpirizoleThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Epirizole.Approved
EplivanserinAlprostadil may increase the anticoagulant activities of Eplivanserin.Investigational
eplivanserineAlprostadil may increase the anticoagulant activities of eplivanserine.Investigational
EpoprostenolEpoprostenol may increase the antiplatelet activities of Alprostadil.Approved
EptifibatideAlprostadil may increase the anticoagulant activities of Eptifibatide.Approved, Investigational
EtanerceptThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Etanercept.Approved, Investigational
EthenzamideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ethenzamide.Experimental
Ethyl biscoumacetateAlprostadil may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Etofenamate.Approved, Investigational
EtoricoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Etoricoxib.Approved, Investigational
Evening primrose oilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Evening primrose oil.Approved, Investigational
exisulindThe therapeutic efficacy of Alprostadil can be decreased when used in combination with exisulind.Investigational
FelbinacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Felbinac.Experimental
FenbufenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Fenbufen.Approved
FenoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Fenoprofen.Approved
FentiazacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Fentiazac.Experimental
FeprazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Feprazone.Experimental
Ferulic acidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ferulic acid.Experimental
FibrinolysinAlprostadil may increase the anticoagulant activities of Fibrinolysin.Investigational
FloctafenineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Floctafenine.Approved, Withdrawn
FluindioneAlprostadil may increase the anticoagulant activities of Fluindione.Investigational
FlunixinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Flunixin.Vet Approved
FlunoxaprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Flunoxaprofen.Experimental
FlurbiprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Flurbiprofen.Approved, Investigational
FondaparinuxAlprostadil may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumAlprostadil may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
GabexateAlprostadil may increase the anticoagulant activities of Gabexate.Investigational
GlucosamineGlucosamine may increase the antiplatelet activities of Alprostadil.Approved
GuacetisalThe risk or severity of adverse effects can be increased when Alprostadil is combined with Guacetisal.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Alprostadil is combined with Hemoglobin crosfumaril.Experimental
HeparinAlprostadil may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenamineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Higenamine.Investigational
HydroxytyrosolAlprostadil may increase the antiplatelet activities of Hydroxytyrosol.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Alprostadil is combined with Ibritumomab tiuxetan.Approved
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Alprostadil.Approved
IbudilastAlprostadil may increase the antiplatelet activities of Ibudilast.Approved, Investigational
IbuprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ibuprofen.Approved
IbuproxamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ibuproxam.Withdrawn
IcatibantThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Icatibant.Approved
Icosapent ethylAlprostadil may increase the antiplatelet activities of Icosapent ethyl.Approved, Nutraceutical
IdraparinuxAlprostadil may increase the anticoagulant activities of Idraparinux.Investigational
IfenprodilAlprostadil may increase the antiplatelet activities of Ifenprodil.Approved, Investigational, Withdrawn
IfetrobanAlprostadil may increase the antiplatelet activities of Ifetroban.Investigational
IloprostIloprost may increase the antiplatelet activities of Alprostadil.Approved, Investigational
Imidazole salicylateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Imidazole salicylate.Experimental
IndobufenAlprostadil may increase the anticoagulant activities of Indobufen.Investigational
IndomethacinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Indomethacin.Approved, Investigational
IndoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Indoprofen.Withdrawn
IsoxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Isoxicam.Withdrawn
KebuzoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Kebuzone.Experimental
KetanserinAlprostadil may increase the antiplatelet activities of Ketanserin.Investigational
KetoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ketoprofen.Approved, Vet Approved
KetorolacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Ketorolac.Approved
LeflunomideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Leflunomide.Approved, Investigational
LepirudinAlprostadil may increase the anticoagulant activities of Lepirudin.Approved
LetaxabanAlprostadil may increase the anticoagulant activities of Letaxaban.Investigational
LimaprostLimaprost may increase the antiplatelet activities of Alprostadil.Approved, Investigational
LinsidomineAlprostadil may increase the antiplatelet activities of Linsidomine.Experimental
LisofyllineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Lisofylline.Investigational
LonazolacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Lonazolac.Experimental
LornoxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Lornoxicam.Approved, Investigational
LoxoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Loxoprofen.Approved, Investigational
LumiracoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Magnesium salicylate.Approved
MasoprocolThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Masoprocol.Approved, Investigational
Meclofenamic acidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Mefenamic acid.Approved
MelagatranAlprostadil may increase the anticoagulant activities of Melagatran.Experimental
MeloxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Meloxicam.Approved, Vet Approved
MesalazineThe risk or severity of adverse effects can be increased when Alprostadil is combined with Mesalazine.Approved
MetamizoleThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Metamizole.Investigational, Withdrawn
Methyl salicylateThe risk or severity of adverse effects can be increased when Alprostadil is combined with Methyl salicylate.Approved, Vet Approved
MilrinoneMilrinone may increase the antiplatelet activities of Alprostadil.Approved
MirodenafilThe risk or severity of adverse effects can be increased when Mirodenafil is combined with Alprostadil.Investigational
MizoribineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Mizoribine.Investigational
MofebutazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Mofebutazone.Experimental
Mycophenolate mofetilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Mycophenolic acid.Approved
NabumetoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Nabumetone.Approved
NadroparinAlprostadil may increase the anticoagulant activities of Nadroparin.Approved
NafamostatThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Nafamostat.Approved, Investigational
NaftifineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Naftifine.Approved
NaftopidilAlprostadil may increase the antiplatelet activities of Naftopidil.Investigational
NaproxenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Naproxen.Approved, Vet Approved
NepafenacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Nepafenac.Approved
NifenazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Nifenazone.Experimental
Niflumic AcidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Niflumic Acid.Approved
NimesulideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Alprostadil is combined with Nitroaspirin.Investigational
ObinutuzumabThe risk or severity of adverse effects can be increased when Alprostadil is combined with Obinutuzumab.Approved
OlopatadineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Olopatadine.Approved
OlsalazineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Olsalazine.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Alprostadil.Approved, Nutraceutical
OrgoteinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Orgotein.Vet Approved
OtamixabanAlprostadil may increase the anticoagulant activities of Otamixaban.Investigational
OxaprozinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Oxaprozin.Approved
OxyphenbutazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Oxyphenbutazone.Approved, Withdrawn
OzagrelAlprostadil may increase the anticoagulant activities of Ozagrel.Investigational
ParecoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Parecoxib.Approved
ParnaparinAlprostadil may increase the anticoagulant activities of Parnaparin.Approved, Investigational
ParthenolideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Parthenolide.Investigational
Pentaerythritol TetranitrateAlprostadil may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Alprostadil.Approved
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Alprostadil.Approved, Investigational
PhenindioneAlprostadil may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonAlprostadil may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenylbutazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
PicotamideAlprostadil may increase the anticoagulant activities of Picotamide.Experimental
PimecrolimusThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Pimecrolimus.Approved, Investigational
PirfenidoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Pirfenidone.Approved, Investigational
PiroxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Piroxicam.Approved, Investigational
PirprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Pirprofen.Experimental
PranoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Pranoprofen.Experimental, Investigational
PrasugrelAlprostadil may increase the anticoagulant activities of Prasugrel.Approved
ProglumetacinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Proglumetacin.Experimental
PropacetamolThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Propacetamol.Approved, Investigational
PropyphenazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Propyphenazone.Experimental
ProquazoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Proquazone.Experimental
Protein CAlprostadil may increase the anticoagulant activities of Protein C.Approved
Protein S humanAlprostadil may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeAlprostadil may increase the anticoagulant activities of Protocatechualdehyde.Approved
PTC299The therapeutic efficacy of Alprostadil can be decreased when used in combination with PTC299.Investigational
RamatrobanAlprostadil may increase the antiplatelet activities of Ramatroban.Investigational
ResveratrolThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Resveratrol.Approved, Experimental, Investigational
ReteplaseAlprostadil may increase the anticoagulant activities of Reteplase.Approved
ReviparinAlprostadil may increase the anticoagulant activities of Reviparin.Approved, Investigational
RidogrelAlprostadil may increase the antiplatelet activities of Ridogrel.Approved
RivaroxabanAlprostadil may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Rofecoxib.Investigational, Withdrawn
RosiglitazoneAlprostadil may increase the anticoagulant activities of Rosiglitazone.Approved, Investigational
SalicylamideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Salicylamide.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Alprostadil is combined with Salicylic acid.Approved, Vet Approved
SalsalateThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Salsalate.Approved
SarpogrelateAlprostadil may increase the anticoagulant activities of Sarpogrelate.Investigational
SaruplaseAlprostadil may increase the anticoagulant activities of Saruplase.Experimental
SelexipagAlprostadil may increase the anticoagulant activities of Selexipag.Approved
SemapimodThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Semapimod.Investigational
SeratrodastThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Seratrodast.Approved
SerrapeptaseThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Serrapeptase.Investigational
SevofluraneAlprostadil may increase the antiplatelet activities of Sevoflurane.Approved, Vet Approved
SildenafilThe risk or severity of adverse effects can be increased when Sildenafil is combined with Alprostadil.Approved, Investigational
SRT501The therapeutic efficacy of Alprostadil can be decreased when used in combination with SRT501.Investigational
StreptokinaseAlprostadil may increase the anticoagulant activities of Streptokinase.Approved, Investigational
SulfasalazineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Sulfasalazine.Approved
SulindacThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Sulindac.Approved
SulodexideAlprostadil may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SuprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Suprofen.Approved, Withdrawn
SuxibuzoneThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Suxibuzone.Experimental
TadalafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Alprostadil.Approved, Investigational
TarenflurbilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tarenflurbil.Investigational
TenecteplaseAlprostadil may increase the anticoagulant activities of Tenecteplase.Approved
TenidapThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tenidap.Experimental
TenoxicamThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tenoxicam.Approved
TepoxalinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tepoxalin.Vet Approved
TeriflunomideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Teriflunomide.Approved
TesmilifeneAlprostadil may increase the antiplatelet activities of Tesmilifene.Investigational
Tiaprofenic acidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tiaprofenic acid.Approved
TicagrelorAlprostadil may increase the anticoagulant activities of Ticagrelor.Approved
TiclopidineAlprostadil may increase the anticoagulant activities of Ticlopidine.Approved
TinoridineThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tinoridine.Investigational
TinzaparinAlprostadil may increase the anticoagulant activities of Tinzaparin.Approved
TioclomarolAlprostadil may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirTipranavir may increase the antiplatelet activities of Alprostadil.Approved, Investigational
TirofibanAlprostadil may increase the anticoagulant activities of Tirofiban.Approved
Tolfenamic AcidThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tolfenamic Acid.Approved
TolmetinThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tolmetin.Approved
TositumomabThe risk or severity of adverse effects can be increased when Alprostadil is combined with Tositumomab.Approved, Investigational
TranilastThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tranilast.Approved, Investigational
TrapidilAlprostadil may increase the antiplatelet activities of Trapidil.Approved
TreprostinilTreprostinil may increase the antiplatelet activities of Alprostadil.Approved, Investigational
TribenosideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Tribenoside.Experimental
TriflusalAlprostadil may increase the anticoagulant activities of Triflusal.Approved, Investigational
TriptolideThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Triptolide.Investigational
Trolamine salicylateThe risk or severity of adverse effects can be increased when Alprostadil is combined with Trolamine salicylate.Approved
TroxerutinAlprostadil may increase the anticoagulant activities of Troxerutin.Investigational
UdenafilThe risk or severity of adverse effects can be increased when Udenafil is combined with Alprostadil.Approved, Investigational
UrokinaseAlprostadil may increase the anticoagulant activities of Urokinase.Approved, Investigational, Withdrawn
ValdecoxibThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Valdecoxib.Investigational, Withdrawn
VardenafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Alprostadil.Approved
Vitamin EVitamin E may increase the antiplatelet activities of Alprostadil.Approved, Nutraceutical, Vet Approved
VorapaxarAlprostadil may increase the anticoagulant activities of Vorapaxar.Approved
WarfarinAlprostadil may increase the anticoagulant activities of Warfarin.Approved
XimelagatranAlprostadil may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
ZaltoprofenThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Zaltoprofen.Approved, Investigational
ZileutonThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Zomepirac.Withdrawn
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D00180
KEGG Compound
C04741
PubChem Compound
149351
PubChem Substance
46508029
ChemSpider
4444306
BindingDB
50101853
ChEBI
15544
ChEMBL
CHEMBL495
Therapeutic Targets Database
DAP001490
PharmGKB
PA448334
IUPHAR
1882
Guide to Pharmacology
GtP Drug Page
HET
XPG
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alprostadil
ATC Codes
C01EA01 — AlprostadilG04BE01 — Alprostadil
AHFS Codes
  • 24:12.92 — Miscellaneous Vasodilatating Agents
PDB Entries
3whx
FDA label
Download (283 KB)
MSDS
Download (74.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedBasic ScienceRaynaud's Phenomenon Secondary to Systemic Sclerosis1
2CompletedSupportive CareProstate Cancer1
2CompletedTreatmentSexual Dysfunction, Physiological1
2RecruitingTreatmentArteriosclerosis Obliterans1
2RecruitingTreatmentEvidence of Liver Transplantation1
2RecruitingTreatmentExtracorporeal Membrane Oxygenation / Respiratory Distress Syndrome, Adult1
2WithdrawnTreatmentNewborn Infants / Pulmonary Hypertension (PH) / Respiratory Distress Syndrome, Newborn / Respiratory Insufficiency / Streptococcal Infections1
2, 3Unknown StatusTreatmentBMI >30 kg/m2 / Labor Complications1
3CompletedTreatmentIntermittent Claudication Fontaine Stage II PAOD / Stage II Peripheral Arterial Occlusive Disease1
3SuspendedTreatmentHeart Failure, Unspecified1
3TerminatedTreatmentMacular Degeneration1
4CompletedTreatmentCoronary Slow Flow Phenomenon / ST Segment Elevation Myocardial Infarction (STEMI)1
4CompletedTreatmentDiabetic Nephropathies1
4CompletedTreatmentPeripheral Obliterative Arteriopathy1
4Not Yet RecruitingTreatmentST Segment Elevation Myocardial Infarction (STEMI)1
4Not Yet RecruitingTreatmentStrokes1
4Unknown StatusPreventionAcute Kidney Injury (AKI) / Diabetes Mellitus (DM) / Impaired Renal Function / Kidney Diseases / Kidney Failure,Chronic1
4Unknown StatusTreatmentComplications / Head and Neck / Microsurgery / Prostaglandin E1 / Thrombosis1
4WithdrawnTreatmentErectile Dysfunction (ED)1
Not AvailableCompletedSupportive CareErectile Dysfunction (ED) / Prostate Cancer / Stage I Prostate Cancer / Stage II Prostate Cancer1
Not AvailableCompletedTreatmentAcute Respiratory Distress Syndrome (ARDS) / Pulmonary Hypertension (PH)1
Not AvailableRecruitingNot AvailableDiabetes1
Not AvailableUnknown StatusPreventionRaynaud's Phenomenon / Skin Necrosis1
Not AvailableUnknown StatusTreatmentErectile Dysfunction (ED)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
Dosage forms
FormRouteStrength
Injection, solution, concentrateIntravascular500 ug/mL
SolutionIntravascular500 mcg
LiquidIntra-arterial; Intravenous500 mcg
Injection, powder, lyophilized, for solutionIntracavernous10.5 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous20.5 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous41.1 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous5.4 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous10 ug/.5mL
Injection, powder, lyophilized, for solutionIntracavernous20 ug/.5mL
Kit; liquid; powder, for solutionIntracavernous
Powder, for solutionIntracavernous11.9 mcg
Powder, for solutionIntracavernous23.2 mcg
Injection, powder, lyophilized, for solutionIntracavernous10 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous20 ug/mL
Injection, powder, lyophilized, for solutionIntracavernous40 ug/mL
SuppositoryUrethral1000 mcg
SuppositoryUrethral1000 ug/1
SuppositoryUrethral125 mcg
SuppositoryUrethral125 ug/1
SuppositoryUrethral250 mcg
SuppositoryUrethral250 ug/1
SuppositoryUrethral500 ug/1
SuppositoryUrethral500 mcg
Injection, solutionIntravascular; Intravenous500 ug/mL
SolutionIntra-arterial; Intravenous500 mcg
CreamTopical220 mcg
CreamTopical330 mcg
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)
US5773020No1993-04-252010-04-25Us
CA1335346No1995-04-252012-04-25Canada
US5886039No1996-03-232016-03-23Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)115-116 °CNot Available
water solubility26.7 mg/LNot Available
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
Polarizability41.88 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Long-chain fatty acids / Fatty alcohols / Hydroxy fatty acids / Cyclopentanols / Cyclic ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
Substituents
Prostaglandin skeleton / Long-chain fatty acid / Fatty alcohol / Hydroxy fatty acid / Cyclopentanol / Cyclic alcohol / Cyclic ketone / Ketone / Secondary alcohol / Carboxylic acid
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the ...
Gene Name
PTGER2
Uniprot ID
P43116
Uniprot Name
Prostaglandin E2 receptor EP2 subtype
Molecular Weight
39759.945 Da
References
  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. [PubMed:10509658]
  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. [PubMed:15840408]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an importa...
Gene Name
PTGER1
Uniprot ID
P34995
Uniprot Name
Prostaglandin E2 receptor EP1 subtype
Molecular Weight
41800.655 Da
References
  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. [PubMed:15560119]
  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. [PubMed:14561849]
  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. [PubMed:10670413]
  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. [PubMed:16516814]
  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. [PubMed:11524243]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Prostaglandin j receptor activity
Specific Function
Receptor for prostaglandin D2 (PGD2). Coupled to the G(i)-protein. Receptor activation may result in pertussis toxin-sensitive decreases in cAMP levels and Ca(2+) mobilization. PI3K signaling is al...
Gene Name
PTGDR2
Uniprot ID
Q9Y5Y4
Uniprot Name
Prostaglandin D2 receptor 2
Molecular Weight
43267.15 Da
References
  1. Wright DH, Metters KM, Abramovitz M, Ford-Hutchinson AW: Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. Br J Pharmacol. 1998 Apr;123(7):1317-24. [PubMed:9579725]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. [PubMed:10973807]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. [PubMed:14631946]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Lu R, Kanai N, Bao Y, Schuster VL: Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9. [PubMed:8787677]
  2. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, Schuster VL: Identification and characterization of a prostaglandin transporter. Science. 1995 May 12;268(5212):866-9. [PubMed:7754369]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34