Identification

Name
Treprostinil
Accession Number
DB00374
Description

Treprostinil is a synthetic analogue of prostacyclin, used to treat pulmonary hypertension.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 390.5131
Monoisotopic: 390.240624198
Chemical Formula
C23H34O5
Synonyms
  • Treprostinil
  • Tréprostinil
  • Treprostinilo
  • Treprostinilum
External IDs
  • 15AU81
  • BW 15AU
  • LRX 15
  • LRX-15
  • U 62840
  • UT 15
  • UT-15

Pharmacology

Indication

For 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.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Pulmonary 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 action

The 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.

TargetActionsOrganism
AProstacyclin receptor
agonist
Humans
APeroxisome proliferator-activated receptor delta
agonist
Humans
AP2Y purinoceptor 12
agonist
Humans
Absorption

Relatively 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 binding

Human 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. There have been no studies that evaluate the potential of treprostinil to induce these enzymes.

Route of elimination
Not Available
Half-life

Terminal 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.

Clearance
Not Available
Adverse Effects
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Toxicity

Symptoms 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Treprostinil can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Abciximab is combined with Treprostinil.
AbirateroneThe metabolism of Treprostinil can be decreased when combined with Abiraterone.
AcebutololTreprostinil may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of bleeding can be increased when Treprostinil is combined with Aceclofenac.
AcemetacinThe risk or severity of bleeding can be increased when Treprostinil is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Treprostinil.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Treprostinil.
Acetyl sulfisoxazoleThe metabolism of Treprostinil can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Treprostinil is combined with Acetylsalicylic acid.
Additional Data Available
  • Extended Description
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with food. Taking treprostinil with food increases oral absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Treprostinil diolamineH1FKG90039830354-48-8RHWRWEUCEXUUAV-ZSESPEEFSA-N
Treprostinil sodium7JZ75N2NT6289480-64-4IQKAWAUTOKVMLE-ZSESPEEFSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OrenitramTablet, extended release5 mg/1OralUnited Therapeutics Corporation2013-12-20Not applicableUS flag
OrenitramTablet, extended release0.25 mg/1OralUnited Therapeutics Corporation2013-12-20Not applicableUS flag
OrenitramTablet, extended release2.5 mg/1OralUnited Therapeutics Corporation2013-12-20Not applicableUS flag
OrenitramTablet, extended release0.125 mg/1OralUnited Therapeutics Corporation2013-12-20Not applicableUS flag
OrenitramTablet, extended release2.5 mg/1OralAvera McKennan Hospital2016-07-202017-05-24US flag
OrenitramTablet, extended release1 mg/1OralUnited Therapeutics Corporation2013-12-20Not applicableUS flag
RemodulinInjection, solution50 mg/20mLIntravenous; SubcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUS flag
RemodulinSolution2.5 mgIntravenous; SubcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada flag
RemodulinInjection, solution200 mg/20mLIntravenous; SubcutaneousUnited Therapeutics Corporation2002-05-22Not applicableUS flag
RemodulinSolution10 mgIntravenous; SubcutaneousUnited Therapeutics Corporation2004-04-30Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TreprostinilInjection, solution20 mg/20mLIntravenous; SubcutaneousTeva Parenteral Medicines, Inc.2019-09-30Not applicableUS flag
TreprostinilInjection, solution5 mg/1mLIntravenous; SubcutaneousPar Pharmaceutical, Inc.2019-09-25Not applicableUS flag
TreprostinilInjection50 mg/20mLIntravenous; SubcutaneousSandoz Inc2019-03-25Not applicableUS flag
TreprostinilInjection, solution100 mg/20mLIntravenous; SubcutaneousTeva Parenteral Medicines, Inc.2019-09-30Not applicableUS flag
TreprostinilInjection, solution1 mg/1mLIntravenous; SubcutaneousPar Pharmaceutical, Inc.2019-09-25Not applicableUS flag
TreprostinilInjection200 mg/20mLIntravenous; SubcutaneousSandoz Inc2019-03-25Not applicableUS flag
TreprostinilInjection, solution10 mg/1mLIntravenous; SubcutaneousPar Pharmaceutical, Inc.2019-09-25Not applicableUS flag
TreprostinilInjection20 mg/20mLIntravenous; SubcutaneousSandoz Inc2019-03-25Not applicableUS flag
TreprostinilInjection, solution50 mg/20mLIntravenous; SubcutaneousTeva Parenteral Medicines, Inc.2019-09-30Not applicableUS flag
TreprostinilInjection, solution2.5 mg/1mLIntravenous; SubcutaneousPar Pharmaceutical, Inc.2019-09-25Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
B01AC21 — Treprostinil
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenoxyacetic acid derivatives
Direct Parent
Phenoxyacetic acid derivatives
Alternative Parents
Tetralins / Fatty alcohols / Alkyl aryl ethers / Secondary alcohols / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Alkyl aryl ether / Aromatic homopolycyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic alcohol / Ether / Fatty acyl / Fatty alcohol
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
carboxylic acid, carbotricyclic compound (CHEBI:50861)

Chemical Identifiers

UNII
RUM6K67ESG
CAS number
81846-19-7
InChI Key
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][[email protected]]12C[[email protected]@H](O)[[email protected]](CC[[email protected]@H](O)CCCCC)[[email protected]@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

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 References
Not Available
Human Metabolome Database
HMDB0014518
PubChem Compound
6918140
PubChem Substance
46504572
ChemSpider
5293353
RxNav
343048
ChEBI
50861
ChEMBL
CHEMBL1237119
ZINC
ZINC000003800475
Therapeutic Targets Database
DAP001214
PharmGKB
PA164768801
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Treprostinil
AHFS Codes
  • 48:48.00 — Vasodilating Agents
FDA label
Download (223 KB)
MSDS
Download (17.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPulmonary Arterial Hypertension (PAH)4
4CompletedTreatmentPulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH)1
4CompletedTreatmentPulmonary Hypertension (PH)2
4RecruitingOtherPulmonary Hypertension (PH)1
4RecruitingTreatmentPulmonary Arterial Hypertension (PAH)1
4TerminatedTreatmentPulmonary Arterial Hypertension (PAH)2
4TerminatedTreatmentPulmonary Hypertension (PH)2
4WithdrawnTreatmentPulmonary Arterial Hypertension (PAH)3
3Active Not RecruitingTreatmentNon-operable Chronic Thromboembolic Pulmonary Hypertension1
3Active Not RecruitingTreatmentPrimary Pulmonary Hypertension1

Pharmacoeconomics

Manufacturers
  • United therapeutics corp
Packagers
  • Baxter International Inc.
  • United Therapeutics Corp.
Dosage Forms
FormRouteStrength
Tablet, extended releaseOral0.125 mg/1
Tablet, extended releaseOral0.25 mg/1
Tablet, extended releaseOral1 mg/1
Tablet, extended releaseOral2.5 mg/1
Tablet, extended releaseOral5 mg/1
Injection, solutionIntravenous; Subcutaneous100 mg/20mL
Injection, solutionIntravenous; Subcutaneous20 mg/20mL
Injection, solutionIntravenous; Subcutaneous200 mg/20mL
Injection, solutionIntravenous; Subcutaneous50 mg/20mL
Injection, solutionParenteral5 MG/ML
SolutionIntravenous; Subcutaneous1 mg
SolutionIntravenous; Subcutaneous10 mg
SolutionIntravenous; Subcutaneous5 mg
SolutionParenteral1 mg/ml
SolutionParenteral10 mg/ml
SolutionParenteral2.5 mg/ml
SolutionParenteral5 mg/ml
SolutionIntravenous; Subcutaneous2.5 mg
InjectionIntravenous; Subcutaneous100 mg/20mL
InjectionIntravenous; Subcutaneous20 mg/20mL
InjectionIntravenous; Subcutaneous200 mg/20mL
InjectionIntravenous; Subcutaneous50 mg/20mL
Injection, solutionIntravenous; Subcutaneous1 mg/1mL
Injection, solutionIntravenous; Subcutaneous10 mg/1mL
Injection, solutionIntravenous; Subcutaneous2.5 mg/1mL
Injection, solutionIntravenous; Subcutaneous5 mg/1mL
Injection, solutionParenteral1 MG/ML
Injection, solutionParenteral10 MG/ML
Injection, solutionParenteral2.5 MG/ML
Injection, solutionParenteral4 MG/ML
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)Region
US5153222No1992-10-062014-10-06US flag
US8653137No2014-02-182028-09-05US flag
US8658694No2014-02-252028-09-05US flag
US7999007No2011-08-162029-03-29US flag
US9199908No2015-12-012024-05-24US flag
US6765117No2004-07-202017-10-24US flag
US8497393No2013-07-302028-12-15US flag
US6521212No2003-02-182018-11-13US flag
US6756033No2004-06-292018-11-13US flag
US7544713No2009-06-092024-07-14US flag
US9278901No2016-03-082024-05-24US flag
US7417070No2008-08-262026-07-30US flag
US8410169No2013-04-022030-02-13US flag
US9050311No2015-06-092024-05-24US flag
US8252839No2012-08-282024-05-24US flag
US8747897No2014-06-102029-10-08US flag
US8349892No2013-01-082031-01-22US flag
US9593066No2017-03-142028-12-15US flag
US9604901No2017-03-282028-12-15US flag
US9339507No2016-05-172028-03-10US flag
US9358240No2016-06-072028-05-05US flag
US9422223No2016-08-232024-05-24US flag
US9393203No2016-07-192026-04-27US flag
US9713599No2017-07-252024-12-16US flag
US10076505No2018-09-182024-12-16US flag
US10376525No2007-05-142027-05-14US flag
US10716793No2007-05-142027-05-14US flag
US10695308No2004-12-162024-12-16US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

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

Targets

Kind
Protein
Organism
Humans
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
Uniprot Name
Prostacyclin receptor
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
Humans
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-lin...
Gene Name
PPARD
Uniprot ID
Q03181
Uniprot Name
Peroxisome proliferator-activated receptor delta
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
Humans
Pharmacological action
Yes
Actions
Agonist
Curator comments
The resource suggests an interaction with P2Y12, conferring anti thrombotic activity, however this remains to be validated
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
Uniprot Name
P2Y purinoceptor 12
Molecular Weight
39438.355 Da
References
  1. Bacha NC, Levy M, Guerin CL, Le Bonniec B, Harroche A, Szezepanski I, Renard JM, Gaussem P, Israel-Biet D, Boulanger CM, Smadja DM: Treprostinil treatment decreases circulating platelet microvesicles and their procoagulant activity in pediatric pulmonary hypertension. Pediatr Pulmonol. 2019 Jan;54(1):66-72. doi: 10.1002/ppul.24190. Epub 2018 Nov 28. [PubMed:30485728]

Enzymes

Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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]

Drug created on June 13, 2005 07:24 / Updated on November 23, 2020 09:08

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