Treprostinil (CED0005189)

Record Information

Version

1.0

Creation Date

2016-05-25 18:20:00 UTC

Update Date

2026-05-14 16:36:56 UTC

Accession Number

CHEM022100

Identification

Common Name

Treprostinil

Class

Small Molecule

Description

Treprostinil is an organic compound with the chemical formula C23H34O5 and an average molecular weight of 390.51 g/mol. Treprostinil belongs to the phenoxyacetic acid derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is categorized under the superclass of benzenoids. The compound is identified in five recorded sources, including antithrombotic agents within healthcare, pharmaceuticals, and veterinary products. Other sources include electrically stimulated smoking devices, as well as household cleaning and consumer products such as non-electric simulated smoking devices, cigar cigarettes, and other smoking requisites. Exposure to this compound occurs through oral, intravenous, subcutaneous, and respiratory routes. Treprostinil interacts with five recorded protein targets. It acts as an agonist or weak inhibitor of the P2Y purinoceptor 12 (P2RY12) and targets the prostacyclin receptor (PTGIR), the prostaglandin E2 receptor EP2 subtype (PTGER2), and the peroxisome proliferator-activated receptor delta (PPARD), in addition to one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Treprostinilo	ChEBI
Treprostinilum	ChEBI
Remodulin	Kegg
Orenitram	HMDB
Trepostinil sodium	HMDB
Treprostinil diolamine	HMDB
Treprostinil sodium	HMDB
UT-15	HMDB
UT-15C	HMDB
((1R,2R,3AS,9as)-2-hydroxy-1-((3S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cylopent(b)naphthalen-5-yl)oxy)acetate	HMDB
Treprostinil diethanolamine	HMDB
Treprostinil diolamin	HMDB

Chemical Formula

C₂₃H₃₄O₅

Average Molecular Mass

390.513 g/mol

Monoisotopic Mass

390.241 g/mol

CAS Registry Number

81846-19-7

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

Traditional Name

treprostinil

SMILES

[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

InChI Identifier

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

InChI Key

PAJMKGZZBBTTOY-ZFORQUDYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives 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

Substituents

Phenoxyacetate
Tetralin
Fatty alcohol
Alkyl aryl ether
Fatty acyl
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

carboxylic acid (CHEBI:50861 )
carbotricyclic compound (CHEBI:50861 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0073 g/L	ALOGPS
logP	3.53	ALOGPS
logP	4	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108 m³·mol⁻¹	ChemAxon
Polarizability	45.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0fxw-4197000000-f2c1b87e66efdc91b50e	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0076-7210190000-21ff7ee6208bb7b64a7d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fu-0019000000-07524b6871c3cbeb6247	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-4259000000-db102057e93677a67e3f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abc-9384000000-69f5a3403f3e6092f791	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0009000000-69eb101db3001417d4da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-009i-1009000000-b4d4f7ffb8b39aec097f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fs-7396000000-b9875923704c71aa676a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0029000000-23c56b7cb115f5b54c17	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0079-3089000000-21aeb3a71382c50e5572	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-4092000000-14472fa2804e67f69f32	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abc-0019000000-b56cc01da374c6cef594	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2069000000-1c37a2baaf68029ce216	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-4092000000-e68c8ee6cce6cffc29ab	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
728.0	Log mg/kg	[410:1300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
273	Antithrombotic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

2 pathways

Treprostinil Action Pathway

Treprostinil Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P34995	Humans	Predicted (SEA)	4.12601
Click to view 3D structure	Prostacyclin receptor	P43119	Humans	Predicted (SEA)	2.17978
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	P43116	Humans	Predicted (SEA)	4.7488
Click to view 3D structure	Prostaglandin D2 receptor	Q13258	Humans	Predicted (SEA)	4.82665
Click to view 3D structure	Solute carrier organic anion transporter family member 2A1	Q92959	Humans	Predicted (SEA)	1.40129
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P43115	Humans	Predicted (SEA)	33.2416
Click to view 3D structure	Prostaglandin F2-alpha receptor	P43088	Humans	Predicted (SEA)	15.8812
Click to view 3D structure	Thromboxane A2 receptor	P21731	Humans	Predicted (SEA)	41.3379
Click to view 3D structure	Solute carrier organic anion transporter family member 2B1	Q9JHI3	Rattus norvegicus	Predicted (SEA)	2.41333
Click to view 3D structure	Solute carrier organic anion transporter family member 2A1	Q9EPT5	Mus musculus	Predicted (SEA)	3.34752
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P35408	Humans	Predicted (SEA)	61.1895
Click to view 3D structure	Prostaglandin F2-alpha receptor	P37289	Bos taurus	Predicted (SEA)	2.10193
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	807.997
Click to view 3D structure	Nuclear receptor subfamily 4 group A member 2	Q07917	Rattus norvegicus	Predicted (SEA)	5.83869
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	1553.56
Click to view 3D structure	Prostaglandin F2-alpha receptor	P43117	Mus musculus	Predicted (SEA)	5.2159
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	1125.78
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	1940.16
Click to view 3D structure	Prostaglandin E2 receptor EP1 subtype	P35375	Mus musculus	Predicted (SEA)	39.6253
Click to view 3D structure	Prostaglandin E2 receptor EP3 subtype	P30557	Mus musculus	Predicted (SEA)	53.7938
Click to view 3D structure	Prostaglandin E2 receptor EP4 subtype	P32240	Mus musculus	Predicted (SEA)	57.2192
Click to view 3D structure	Prostaglandin E2 receptor EP2 subtype	Q62053	Mus musculus	Predicted (SEA)	31.3732
Click to view 3D structure	DNA-directed DNA/RNA polymerase mu	Q9NP87	Humans	Predicted (SEA)	20.7857
Click to view 3D structure	DNA nucleotidylexotransferase	P06526	Bos taurus	Predicted (SEA)	20.7857
Click to view 3D structure	DNA polymerase iota	Q6R3M4	Mus musculus	Predicted (SEA)	18.9952