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Identification
NameTreprostinil
Accession NumberDB00374  (APRD01272)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Treprostinil is a synthetic analogue of prostacyclin, used to treat pulmonary hypertension. Treprostinil is marketed as Remodulin®. [Wikipedia]

Structure
Thumb
Synonyms
(1R,2R,3aS,9aS)-[[2,3,3a,4,9,9a-hexahydro-2-hydroxy- 1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl] oxy]acetic acid
[[(1R,2R,3aS,9aS)-2-Hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphtalen-5-yl]oxy]acetic acid
Treprostinil
Treprostinilo
Treprostinilum
Uniprost
External Identifiers
  • 15AU81
  • BW 15AU
  • LRX 15
  • U 62840
  • UT 15
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Orenitramtablet, extended release2.5 mg/1oralUnited Therapeutics Corp.2013-12-20Not applicableUs
Orenitramtablet, extended release1 mg/1oralUnited Therapeutics Corp.2013-12-20Not applicableUs
Orenitramtablet, extended release.25 mg/1oralUnited Therapeutics Corp.2013-12-20Not applicableUs
Orenitramtablet, extended release.125 mg/1oralUnited Therapeutics Corp.2013-12-20Not applicableUs
Remodulininjection, solution20 mg/20mLintravenous; subcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUs
Remodulinsolution10 mgintravenous; subcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada
Remodulinsolution5 mgintravenous; subcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada
Remodulininjection, solution200 mg/20mLintravenous; subcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUs
Remodulinsolution2.5 mgintravenous; subcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada
Remodulininjection, solution100 mg/20mLintravenous; subcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUs
Remodulinsolution1 mgintravenous; subcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada
Remodulininjection, solution50 mg/20mLintravenous; subcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUs
Tyvasoinhalant1.74 mg/2.9mLoralUnited Therapeutics Corp.2009-08-14Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Treprostinil diolamine
ThumbNot applicableDBSALT001333
Categories
UNIIRUM6K67ESG
CAS number81846-19-7
WeightAverage: 390.5131
Monoisotopic: 390.240624198
Chemical FormulaC23H34O5
InChI KeyInChIKey=PAJMKGZZBBTTOY-ZFORQUDYSA-N
InChI
InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1
IUPAC Name
2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid
SMILES
[H][C@]12C[C@@H](O)[[email protected]](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • Tetralin
  • Fatty alcohol
  • Alkyl aryl ether
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor use as a continuous subcutaneous infusion or intravenous infusion (for those not able to tolerate a subcutaneous infusion) for the treatment of pulmonary arterial hypertension in patients with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.
PharmacodynamicsPulmonary arterial hypertension (PAH) is a disease in which blood pressure is abnormally high in the arteries between the heart and lungs. PAH is characterized by symptoms of shortness of breath during physical exertion. The condition can ultimately lead to heart failure. Treprostinil is a potent oral antiplatelet agent. The major pharmacologic actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In animals, the vasodilatory effects reduce right and left ventricular afterload and increase cardiac output and stroke volume. Other studies have shown that treprostinil causes a dose-related negative inotropic and lusitropic effect. No major effects on cardiac conduction have been observed.
Mechanism of actionThe major pharmacological actions of treprostinil are direct vasodilation of pulmonary and systemic arterial vascular beds and inhibition of platelet aggregation. In addition to treprostinil's direct vasodilatory effects, it also inhibits inflammatory cytokine. As a synthetic analogue of prostacyclin, it binds to the prostacyclin receptor, which subsequently induces the aforementioned downstream effects.
Related Articles
AbsorptionRelatively rapid and complete after subcutaneous infusion, with an absolute bioavailability approximately 100%. In patients with mild (n=4) or moderate (n=5) hepatic insufficiency and portopulmonary hypertension following a subcutaneous dose of 10 ng per kg of body weight per min for 150 mins the AUC 0-∞ was increased 3-fold and 5-fold respectively.
Volume of distribution
  • 14 L/70 kg
Protein bindingHuman plasma protein binding is approximately 91% in in vitro concentrations ranging from 330 to 10,000 µ/L.
Metabolism

Substantially metabolized by the liver, but the precise enzymes responsible are unknown. Five metabolites have been described (HU1 through HU5) however, the biological activity and metabolic fate of these are unknown. The chemical structure of HU1 is unknown. The metabolite HU5 is the glucuronide conjugate of treprostinil. The other metabolites are formed by oxidation of the 3-hydroxyoctyl side chain (HU2) and subsequent additional oxidation (HU3) or dehydration (HU4). Study results of in vitro human hepatic cytochrome P450 demonstrates that treprostinil does not inhibit CYP-1A2, 2C9, 2C19, 2D6, 2E1, or 3A. Whether treprostinil induces these enzymes has not been studied.

Route of eliminationNot Available
Half lifeTerminal elimination half-life is approximately 2 to 4 hours. Plasma half-life is 34 and 85 minutes for intravenous and subcutaneous infusion of the drug, respectively.
ClearanceNot Available
ToxicitySymptoms of overdose are extensions of its dose-limiting pharmacologic effects and include flushing, headache, hypotension, nausea, vomiting, and diarrhea. Most events were self-limiting and resolved with reduction or withholding of treprostinil.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.994
Blood Brain Barrier+0.5541
Caco-2 permeable+0.5838
P-glycoprotein substrateSubstrate0.7733
P-glycoprotein inhibitor INon-inhibitor0.719
P-glycoprotein inhibitor IINon-inhibitor0.7518
Renal organic cation transporterNon-inhibitor0.8064
CYP450 2C9 substrateNon-substrate0.7811
CYP450 2D6 substrateNon-substrate0.8144
CYP450 3A4 substrateSubstrate0.6538
CYP450 1A2 substrateInhibitor0.7312
CYP450 2C9 inhibitorNon-inhibitor0.8496
CYP450 2D6 inhibitorNon-inhibitor0.9127
CYP450 2C19 inhibitorNon-inhibitor0.6214
CYP450 3A4 inhibitorNon-inhibitor0.6587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6885
Ames testNon AMES toxic0.8716
CarcinogenicityNon-carcinogens0.9452
BiodegradationNot ready biodegradable0.7495
Rat acute toxicity2.0749 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9588
hERG inhibition (predictor II)Inhibitor0.7664
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • United therapeutics corp
Packagers
Dosage forms
FormRouteStrength
Tablet, extended releaseoral.125 mg/1
Tablet, extended releaseoral.25 mg/1
Tablet, extended releaseoral1 mg/1
Tablet, extended releaseoral2.5 mg/1
Injection, solutionintravenous; subcutaneous100 mg/20mL
Injection, solutionintravenous; subcutaneous20 mg/20mL
Injection, solutionintravenous; subcutaneous200 mg/20mL
Injection, solutionintravenous; subcutaneous50 mg/20mL
Solutionintravenous; subcutaneous1 mg
Solutionintravenous; subcutaneous10 mg
Solutionintravenous; subcutaneous2.5 mg
Solutionintravenous; subcutaneous5 mg
Inhalantoral1.74 mg/2.9mL
Prices
Unit descriptionCostUnit
Remodulin 10 mg/ml vial737.0USD ml
Remodulin 5 mg/ml vial368.5USD ml
Tyvaso inhalation starter kit185.8USD ml
Remodulin 2.5 mg/ml vial184.25USD ml
Tyvaso 1.74 mg/2.9 ml solution174.55USD ml
Tyvaso inhalation refill kit165.68USD ml
Remodulin 1 mg/ml vial73.7USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5153222 No1994-10-062014-10-06Us
US6521212 No1998-11-132018-11-13Us
US6756033 No1998-11-132018-11-13Us
US6765117 No1997-10-242017-10-24Us
US7417070 No2006-07-302026-07-30Us
US7544713 No2004-07-142024-07-14Us
US7999007 No2009-03-292029-03-29Us
US8252839 No2004-05-242024-05-24Us
US8349892 No2011-01-222031-01-22Us
US8410169 No2010-02-132030-02-13Us
US8497393 No2008-12-152028-12-15Us
US8653137 No2008-09-052028-09-05Us
US8658694 No2008-09-052028-09-05Us
US8747897 No2009-10-082029-10-08Us
US9050311 No2004-05-242024-05-24Us
US9199908 No2004-05-242024-05-24Us
US9278901 No2004-05-242024-05-24Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityInsoluble at 25°CNot Available
logP4.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00731 mg/mLALOGPS
logP3.53ALOGPS
logP4ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108 m3·mol-1ChemAxon
Polarizability45.74 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Hitesh Batra, Raju Penmasta, Vijay Sharma, Sudersan M. Tuladhar, David A. Walsh, “TREPROSTINIL PRODUCTION.” U.S. Patent US20110319641, issued December 29, 2011.

US20110319641
General ReferencesNot Available
External Links
ATC CodesB01AC21
AHFS Codes
  • 24:12.92
PDB EntriesNot Available
FDA labelDownload (223 KB)
MSDSDownload (17.4 KB)
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Treprostinil.
AcebutololTreprostinil may increase the hypotensive activities of Acebutolol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Treprostinil is combined with Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Acetylsalicylic acid.
AliskirenTreprostinil may increase the hypotensive activities of Aliskiren.
AlteplaseAlteplase may increase the anticoagulant activities of Treprostinil.
AmilorideTreprostinil may increase the hypotensive activities of Amiloride.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Aminosalicylic Acid.
AmlodipineTreprostinil may increase the hypotensive activities of Amlodipine.
AnagrelideAnagrelide may increase the anticoagulant activities of Treprostinil.
AnistreplaseThe risk or severity of adverse effects can be increased when Anistreplase is combined with Treprostinil.
ApixabanApixaban may increase the anticoagulant activities of Treprostinil.
ArgatrobanTreprostinil may increase the anticoagulant activities of Argatroban.
AtenololTreprostinil may increase the hypotensive activities of Atenolol.
Azilsartan medoxomilTreprostinil may increase the hypotensive activities of Azilsartan medoxomil.
BenazeprilTreprostinil may increase the hypotensive activities of Benazepril.
BendroflumethiazideTreprostinil may increase the hypotensive activities of Bendroflumethiazide.
BetaxololTreprostinil may increase the hypotensive activities of Betaxolol.
Bismuth SubsalicylateThe risk or severity of adverse effects can be increased when Treprostinil is combined with Bismuth Subsalicylate.
BisoprololTreprostinil may increase the hypotensive activities of Bisoprolol.
BivalirudinTreprostinil may increase the anticoagulant activities of Bivalirudin.
BumetanideTreprostinil may increase the hypotensive activities of Bumetanide.
CaffeineCaffeine may increase the anticoagulant activities of Treprostinil.
CandesartanTreprostinil may increase the hypotensive activities of Candesartan.
CangrelorCangrelor may increase the anticoagulant activities of Treprostinil.
CaptoprilTreprostinil may increase the hypotensive activities of Captopril.
CarbamazepineThe serum concentration of Treprostinil can be decreased when it is combined with Carbamazepine.
CarvedilolTreprostinil may increase the hypotensive activities of Carvedilol.
CelecoxibThe risk or severity of adverse effects can be increased when Treprostinil is combined with Celecoxib.
ChlorothiazideTreprostinil may increase the hypotensive activities of Chlorothiazide.
ChlorthalidoneTreprostinil may increase the hypotensive activities of Chlorthalidone.
CilazaprilTreprostinil may increase the hypotensive activities of Cilazapril.
CilostazolCilostazol may increase the anticoagulant activities of Treprostinil.
CitalopramCitalopram may increase the anticoagulant activities of Treprostinil.
Citric AcidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Citric Acid.
ClevidipineTreprostinil may increase the hypotensive activities of Clevidipine.
ClonidineTreprostinil may increase the hypotensive activities of Clonidine.
ClopidogrelClopidogrel may increase the anticoagulant activities of Treprostinil.
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Treprostinil is combined with Collagenase clostridium histolyticum.
Cyproterone acetateThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Cyproterone acetate.
Dabigatran etexilateDabigatran etexilate may increase the anticoagulant activities of Treprostinil.
DalteparinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Dalteparin.
DanaparoidTreprostinil may increase the anticoagulant activities of Danaparoid.
DasatinibDasatinib may increase the anticoagulant activities of Treprostinil.
DeferasiroxThe risk or severity of adverse effects can be increased when Treprostinil is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Deoxycholic Acid.
DesirudinTreprostinil may increase the anticoagulant activities of Desirudin.
DesogestrelDesogestrel may decrease the anticoagulant activities of Treprostinil.
DesvenlafaxineDesvenlafaxine may increase the anticoagulant activities of Treprostinil.
DiclofenacThe risk or severity of adverse effects can be increased when Treprostinil is combined with Diclofenac.
DicoumarolThe risk or severity of adverse effects can be increased when Treprostinil is combined with Dicoumarol.
DienogestThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Dienogest.
DiflunisalThe risk or severity of adverse effects can be increased when Treprostinil is combined with Diflunisal.
DihydrocodeineDihydrocodeine may increase the anticoagulant activities of Treprostinil.
DiltiazemTreprostinil may increase the hypotensive activities of Diltiazem.
DipyridamoleDipyridamole may increase the anticoagulant activities of Treprostinil.
DofetilideTreprostinil may increase the QTc-prolonging activities of Dofetilide.
DoxazosinTreprostinil may increase the hypotensive activities of Doxazosin.
DrospirenoneDrospirenone may decrease the anticoagulant activities of Treprostinil.
DuloxetineDuloxetine may increase the anticoagulant activities of Treprostinil.
Edetic AcidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Edetic Acid.
EdoxabanEdoxaban may increase the anticoagulant activities of Treprostinil.
EnalaprilTreprostinil may increase the hypotensive activities of Enalapril.
EnalaprilatTreprostinil may increase the hypotensive activities of Enalaprilat.
EnoxaparinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Enoxaparin.
EplerenoneTreprostinil may increase the hypotensive activities of Eplerenone.
EpoprostenolThe risk or severity of adverse effects can be increased when Epoprostenol is combined with Treprostinil.
EprosartanTreprostinil may increase the hypotensive activities of Eprosartan.
EptifibatideEptifibatide may increase the anticoagulant activities of Treprostinil.
EscitalopramEscitalopram may increase the anticoagulant activities of Treprostinil.
EsmololTreprostinil may increase the hypotensive activities of Esmolol.
EstradiolEstradiol may decrease the anticoagulant activities of Treprostinil.
Estrone sulfateEstropipate may decrease the anticoagulant activities of Treprostinil.
Etacrynic acidTreprostinil may increase the hypotensive activities of Ethacrynic acid.
EthanolEthanol can cause an increase in the absorption of Treprostinil resulting in an increased serum concentration and potentially a worsening of adverse effects.
Ethinyl EstradiolEthinyl Estradiol may decrease the anticoagulant activities of Treprostinil.
Ethyl biscoumacetateThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ethyl biscoumacetate.
Ethynodiol diacetateEthynodiol may decrease the anticoagulant activities of Treprostinil.
EtodolacThe risk or severity of adverse effects can be increased when Treprostinil is combined with Etodolac.
EtonogestrelThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Etonogestrel.
FelodipineTreprostinil may increase the hypotensive activities of Felodipine.
FenoprofenThe risk or severity of adverse effects can be increased when Treprostinil is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Treprostinil is combined with Floctafenine.
FluoxetineFluoxetine may increase the anticoagulant activities of Treprostinil.
FlurbiprofenThe risk or severity of adverse effects can be increased when Treprostinil is combined with Flurbiprofen.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Treprostinil.
Fondaparinux sodiumThe risk or severity of adverse effects can be increased when Treprostinil is combined with Fondaparinux sodium.
FosinoprilTreprostinil may increase the hypotensive activities of Fosinopril.
FosphenytoinThe serum concentration of Treprostinil can be decreased when it is combined with Fosphenytoin.
FurosemideTreprostinil may increase the hypotensive activities of Furosemide.
GemfibrozilThe serum concentration of Treprostinil can be increased when it is combined with Gemfibrozil.
GoserelinTreprostinil may increase the QTc-prolonging activities of Goserelin.
GuanfacineTreprostinil may increase the hypotensive activities of Guanfacine.
HeparinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Heparin.
HydralazineTreprostinil may increase the hypotensive activities of Hydralazine.
HydrochlorothiazideTreprostinil may increase the hypotensive activities of Hydrochlorothiazide.
Hydroxyprogesterone caproateThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Hydroxyprogesterone caproate.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Treprostinil.
IbuprofenThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ibuprofen.
IcosapentIcosapent may increase the anticoagulant activities of Treprostinil.
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Treprostinil.
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Treprostinil.
IndapamideTreprostinil may increase the hypotensive activities of Indapamide.
IndomethacinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Indomethacin.
InfliximabThe risk or severity of adverse effects can be increased when Treprostinil is combined with Infliximab.
IrbesartanTreprostinil may increase the hypotensive activities of Irbesartan.
IsradipineTreprostinil may increase the hypotensive activities of Isradipine.
KetoprofenThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Treprostinil is combined with Ketorolac.
LabetalolTreprostinil may increase the hypotensive activities of Labetalol.
LeuprolideTreprostinil may increase the QTc-prolonging activities of Leuprolide.
LevomilnacipranLevomilnacipran may increase the anticoagulant activities of Treprostinil.
LevonorgestrelThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Levonorgestrel.
LisinoprilTreprostinil may increase the hypotensive activities of Lisinopril.
LosartanTreprostinil may increase the hypotensive activities of Losartan.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Treprostinil is combined with Magnesium salicylate.
MannitolTreprostinil may increase the hypotensive activities of Mannitol.
MecamylamineTreprostinil may increase the hypotensive activities of Mecamylamine.
Medroxyprogesterone acetateThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Medroxyprogesterone Acetate.
Mefenamic acidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Mefenamic acid.
Megestrol acetateThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Megestrol acetate.
MeloxicamThe risk or severity of adverse effects can be increased when Treprostinil is combined with Meloxicam.
MestranolMestranol may decrease the anticoagulant activities of Treprostinil.
MethyclothiazideTreprostinil may increase the hypotensive activities of Methyclothiazide.
MethyldopaTreprostinil may increase the hypotensive activities of Methyldopa.
MetolazoneTreprostinil may increase the hypotensive activities of Metolazone.
MetoprololTreprostinil may increase the hypotensive activities of Metoprolol.
MifepristoneMifepristone may increase the QTc-prolonging activities of Treprostinil.
MilnacipranMilnacipran may increase the anticoagulant activities of Treprostinil.
MinoxidilTreprostinil may increase the hypotensive activities of Minoxidil.
MoexiprilTreprostinil may increase the hypotensive activities of Moexipril.
MoxonidineTreprostinil may increase the hypotensive activities of Moxonidine.
NabumetoneThe risk or severity of adverse effects can be increased when Treprostinil is combined with Nabumetone.
NadololTreprostinil may increase the hypotensive activities of Nadolol.
NadroparinTreprostinil may increase the anticoagulant activities of Nadroparin.
NaproxenThe risk or severity of adverse effects can be increased when Treprostinil is combined with Naproxen.
NebivololTreprostinil may increase the hypotensive activities of Nebivolol.
NicardipineTreprostinil may increase the hypotensive activities of Nicardipine.
NifedipineTreprostinil may increase the hypotensive activities of Nifedipine.
NimodipineTreprostinil may increase the hypotensive activities of Nimodipine.
NintedanibThe risk or severity of adverse effects can be increased when Treprostinil is combined with Nintedanib.
NisoldipineTreprostinil may increase the hypotensive activities of Nisoldipine.
NitroprussideTreprostinil may increase the hypotensive activities of Nitroprusside.
NorethisteroneThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Norethindrone.
NorgestimateNorgestimate may decrease the anticoagulant activities of Treprostinil.
ObinutuzumabThe risk or severity of adverse effects can be increased when Treprostinil is combined with Obinutuzumab.
OlmesartanTreprostinil may increase the hypotensive activities of Olmesartan.
Omega-3 fatty acidsOmega-3 fatty acids may increase the anticoagulant activities of Treprostinil.
Omega-3-acid ethyl estersOmega-3-acid ethyl esters may increase the anticoagulant activities of Treprostinil.
OxaprozinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Oxaprozin.
ParoxetineParoxetine may increase the anticoagulant activities of Treprostinil.
PenbutololTreprostinil may increase the hypotensive activities of Penbutolol.
Pentosan PolysulfatePentosan Polysulfate may increase the anticoagulant activities of Treprostinil.
PerindoprilTreprostinil may increase the hypotensive activities of Perindopril.
PhenindioneThe risk or severity of adverse effects can be increased when Treprostinil is combined with Phenindione.
PhenobarbitalThe serum concentration of Treprostinil can be decreased when it is combined with Phenobarbital.
PhenoxybenzamineTreprostinil may increase the hypotensive activities of Phenoxybenzamine.
PhenprocoumonThe risk or severity of adverse effects can be increased when Treprostinil is combined with Phenprocoumon.
PhentolamineTreprostinil may increase the hypotensive activities of Phentolamine.
PhenytoinThe serum concentration of Treprostinil can be decreased when it is combined with Phenytoin.
PindololTreprostinil may increase the hypotensive activities of Pindolol.
PiroxicamThe risk or severity of adverse effects can be increased when Treprostinil is combined with Piroxicam.
PrasugrelPrasugrel may increase the anticoagulant activities of Treprostinil.
PrazosinTreprostinil may increase the hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Treprostinil can be decreased when it is combined with Primidone.
ProgesteroneThe therapeutic efficacy of Treprostinil can be decreased when used in combination with Progesterone.
PropranololTreprostinil may increase the hypotensive activities of Propranolol.
QuinaprilTreprostinil may increase the hypotensive activities of Quinapril.
RamiprilTreprostinil may increase the hypotensive activities of Ramipril.
ReserpineTreprostinil may increase the hypotensive activities of Reserpine.
ReteplaseReteplase may increase the anticoagulant activities of Treprostinil.
RidogrelThe risk or severity of adverse effects can be increased when Ridogrel is combined with Treprostinil.
RifampicinThe serum concentration of Treprostinil can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Treprostinil can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Treprostinil can be increased when it is combined with Ritonavir.
RivaroxabanTreprostinil may increase the anticoagulant activities of Rivaroxaban.
SalsalateThe risk or severity of adverse effects can be increased when Treprostinil is combined with Salsalate.
SecobarbitalThe serum concentration of Treprostinil can be decreased when it is combined with Secobarbital.
SertralineSertraline may increase the anticoagulant activities of Treprostinil.
SotalolTreprostinil may increase the hypotensive activities of Sotalol.
SpironolactoneTreprostinil may increase the hypotensive activities of Spironolactone.
StiripentolThe serum concentration of Treprostinil can be increased when it is combined with Stiripentol.
StreptokinaseThe risk or severity of adverse effects can be increased when Streptokinase is combined with Treprostinil.
SulindacThe risk or severity of adverse effects can be increased when Treprostinil is combined with Sulindac.
SulodexideThe risk or severity of adverse effects can be increased when Treprostinil is combined with Sulodexide.
TelmisartanTreprostinil may increase the hypotensive activities of Telmisartan.
TenecteplaseTenecteplase may increase the anticoagulant activities of Treprostinil.
TerazosinTreprostinil may increase the hypotensive activities of Terazosin.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Treprostinil is combined with Tiaprofenic acid.
TicagrelorTicagrelor may increase the anticoagulant activities of Treprostinil.
TiclopidineTiclopidine may increase the anticoagulant activities of Treprostinil.
TimololTreprostinil may increase the hypotensive activities of Timolol.
TinzaparinTreprostinil may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the anticoagulant activities of Treprostinil.
TirofibanTirofiban may increase the anticoagulant activities of Treprostinil.
TolmetinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Tolmetin.
TorasemideTreprostinil may increase the hypotensive activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Treprostinil is combined with Tositumomab.
TrandolaprilTreprostinil may increase the hypotensive activities of Trandolapril.
TriamtereneTreprostinil may increase the hypotensive activities of Triamterene.
UrokinaseThe risk or severity of adverse effects can be increased when Urokinase is combined with Treprostinil.
ValsartanTreprostinil may increase the hypotensive activities of Valsartan.
VenlafaxineVenlafaxine may increase the anticoagulant activities of Treprostinil.
VerapamilTreprostinil may increase the hypotensive activities of Verapamil.
VilazodoneVilazodone may increase the anticoagulant activities of Treprostinil.
Vitamin EVitamin E may increase the anticoagulant activities of Treprostinil.
VorapaxarThe risk or severity of adverse effects can be increased when Vorapaxar is combined with Treprostinil.
VortioxetineVortioxetine may increase the anticoagulant activities of Treprostinil.
WarfarinThe risk or severity of adverse effects can be increased when Treprostinil is combined with Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase.
Gene Name:
PTGIR
Uniprot ID:
P43119
Molecular Weight:
40955.485 Da
References
  1. Falcetti E, Hall SM, Phillips PG, Patel J, Morrell NW, Haworth SG, Clapp LH: Smooth muscle proliferation and role of the prostacyclin (IP) receptor in idiopathic pulmonary arterial hypertension. Am J Respir Crit Care Med. 2010 Nov 1;182(9):1161-70. doi: 10.1164/rccm.201001-0011OC. Epub 2010 Jul 9. [PubMed:20622039 ]
  2. Sprague RS, Bowles EA, Hanson MS, DuFaux EA, Sridharan M, Adderley S, Ellsworth ML, Stephenson AH: Prostacyclin analogs stimulate receptor-mediated cAMP synthesis and ATP release from rabbit and human erythrocytes. Microcirculation. 2008 Jul;15(5):461-71. doi: 10.1080/10739680701833804. [PubMed:18574748 ]
  3. Olschewski H, Rose F, Schermuly R, Ghofrani HA, Enke B, Olschewski A, Seeger W: Prostacyclin and its analogues in the treatment of pulmonary hypertension. Pharmacol Ther. 2004 May;102(2):139-53. [PubMed:15163595 ]
  4. 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:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as ...
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular Weight:
49902.99 Da
References
  1. Ali FY, Egan K, FitzGerald GA, Desvergne B, Wahli W, Bishop-Bailey D, Warner TD, Mitchell JA: Role of prostacyclin versus peroxisome proliferator-activated receptor beta receptors in prostacyclin sensing by lung fibroblasts. Am J Respir Cell Mol Biol. 2006 Feb;34(2):242-6. Epub 2005 Oct 20. [PubMed:16239641 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation.
Gene Name:
P2RY12
Uniprot ID:
Q9H244
Molecular Weight:
39438.355 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Gotzkowsky SK, Dingemanse J, Lai A, Mottola D, Laliberte K: Lack of a pharmacokinetic interaction between oral treprostinil and bosentan in healthy adult volunteers. J Clin Pharmacol. 2010 Jul;50(7):829-34. doi: 10.1177/0091270009351173. Epub 2010 Feb 4. [PubMed:20133511 ]
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Drug created on June 13, 2005 07:24 / Updated on June 28, 2016 02:00