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Treprostinil

HCID 6918140
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
81846-19-7
Standard SMILES
CCCCC[C@H](O)CC[C@@H]1[C@H]2Cc3cccc(OCC(=O)O)c3C[C@H]2C[C@H]1O
InChIKey
PAJMKGZZBBTTOY-ZFORQUDYSA-N
Molecular formula
C23H34O5
Average molar mass
390.5 g/mol
Monoisotopic mass
390.24062419

Overview

Treprostinil is a carboxylic acid and a carbotricyclic compound. It has a role as a cardiovascular drug, a vasodilator agent, an antihypertensive agent, a platelet aggregation inhibitor, a vitamin K antagonist and a human blood serum metabolite.

Names & identifiers

Preferred name
Treprostinil
IUPAC
2-[[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalen-5-yl]oxy]acetic acid
English name
Treprostinil
Molecular formula
C23H34O5
Molecular weight
390.51

Names & synonyms

Treprostinil81846-19-7UniprostRumodolinTyvasoUT-15LRX-15treprostinilo15AU81treprostinilumTyvaso dpiRUM6K67ESG
Show more names
REMODULIN2-(((1R,2R,3aS,9aS)-2-hydroxy-1-((S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl)oxy)acetic acidOrenitramTreprostinil-13C2-d1LRX 15BW 15AUU 6284015AU-81
15-AU-81CHEBI:50861L-606DTXSID901021654((1R,2R,3aS,9aS)-2-hydroxy-1-((3S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cylopent(b)naphthalen-5-yl)oxy)acetate2-{[(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({(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yl}oxy)acetic acidAcetic acid, ((2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-(3-hydroxyoctyl)-1H-benz(f)inden-5-yl)oxy)-, (1R-(1alpha(S*),2beta,3aalpha,9aalpha))-

Database identifiers

CAS
81846-19-7
PubChem CID
6918140
DTXSID

Properties

Computed structural properties

XLogP
4.5
Topological polar surface area
87 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
10
Heavy atoms
28
Formal charge
0
Complexity
495

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antihypertensives

Pharmaceuticals -> Listed in ZINC15

LogP4.1
Solubility7.31e-03 g/L
Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Cardiovascular Agents; Prostaglandins; Vasodilator Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine (Orphan designations)

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point90-100°C
Physical DescriptionSolid

Physicochemical properties

Melting point
121 · 121-123°

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Adverse EffectsLocal adverse effects are the most common side effects related to either the SQ or inhaled routes of administration:
Toxicity Summary · 1 item

Researchers did encounter treprostinil overdose during the trials, which presented with signs and symptoms of vasodilatation such as flushing, hypotension, and headache. It can also result from pump dysfunction, accidental bolus administration, or prescribing the wrong dose. These symptoms are self-limited and will be resolved by temporarily discontinuing the medication or reducing the dosage.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
WGK 3
Signal word
Danger

Chemistry & industry

Pharmacology

ATC Code · 2 items

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein BindingAt _in vitro_ concentrations ranging from 330 to 10,000 μg/L, the human plasma protein binding of treprostinil is approximately 91%. This concentration is above what is considered to be clinically relevant.
Pharmacodynamics · 1 item

As an analogue of prostacyclin, treprostinil promotes the vasodilation of pulmonary and systemic arterial vascular beds and the inhibition of platelet aggregation. In animals, the vasodilatory effects of treprostinil lead to a reduction of right and left ventricular afterload and an increase in cardiac output and stroke volume. Treprostinil also causes a dose-related negative inotropic and lusitropic effect, and no major effects on cardiac conduction have been detected. Short-lasting effects on QTc were detected in healthy volunteers (n=240) given inhaled single doses of 54 and 84 μg of treprostinil. These effects dissipated rapidly as treprostinil concentrations lowered. When given subcutaneously or intravenously, treprostinil has the potential to reach higher concentrations. The effect of oral treprostinil on QTc has not been evaluated. Due to its ability to inhibit platelet aggregation, treprostinil can increase the risk of bleeding, and patients with low systemic arterial pressure taking treprostinil may experience symptomatic hypotension. The abrupt withdrawal of treprostinil or drastic changes in dose may worsen the symptoms of pulmonary arterial hypertension (PAH). The inhalation of treprostinil can also cause bronchospasms in patients with asthma, chronic obstructive pulmonary disease (COPD), or bronchial hyperreactivity. When given intravenously, treprostinil can lead to infusion complications and increase the risk of bloodstream infections.

Mechanism of Action · 1 item

Treprostinil is a stable analogue of prostacyclin, a prostaglandin that acts as an anti-thrombotic agent and a potent vasodilator. Prostacyclin analogues are useful in the treatment of pulmonary arterial hypertension (PAH), a disease characterized by abnormally high blood pressure in the arteries between the heart and lungs. PAH leads to right heart failure due to the remodelling of pulmonary arteries, and patients with this condition have a poor prognosis. Treprostinil binds and activates the prostacyclin receptor, the prostaglandin D2 receptor 1, and the prostaglandin E2 receptor 2. The activation of these receptors leads to the elevation of intracellular cyclic adenosine monophosphate (cAMP) levels, which consequently promotes the opening of calcium-activated potassium channels that lead to cell hyperpolarization. This mechanism promotes the direct vasodilation of pulmonary and systemic arterial vascular beds and the inhibition of platelet aggregation. In addition to its direct vasodilatory effects, treprostinil inhibits inflammatory pathways.

Related reactions

36 records
New reaction record
HRID 39617 reaction equation
HRID 39617As productuspto-grants-2013_09
HRID 39618 reaction equation
HRID 39618As productuspto-grants-2013_09
HRID 43308 reaction equation
HRID 43308As reactantuspto-grants-2013_09
HRID 43309 reaction equation
HRID 43309As reactantuspto-grants-2013_09
HRID 131750 reaction equation
HRID 131750As reactantuspto-grants-2008_06
HRID 131751 reaction equation
HRID 131751As reactantuspto-grants-2008_06
HRID 245602 reaction equation
HRID 245602As productuspto-grants-2014_02
HRID 245603 reaction equation
HRID 245603As productuspto-grants-2014_02
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
DTXSID901021654
ChEMBL
CHEMBL1237119
ChEBI
CHEBI:50861
UNII
RUM6K67ESG
EC Number
808-233-7
Nikkaji
J430.982K
Boiling point
587.1 · 587.1±50.0 °C(Predicted)
Density
1.158 · 1.158±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
form
Solid
pka
3.19 · 3.19±0.10(Predicted)
color
Off-White to Beige
optical activity
40 to · [α]/D 40 to 50°, c =0.5 in methanol
InChIKey
PAJMKGZZBBTTOY-ZFORQUDYSA-N
SMILES
C(O)(=O)COC1=C2C(=CC=C1)C[C@@]1([H])[C@@]([H])(C2)C[C@@H](O)[C@@H]1CC[C@@H](O)CCCCC
FDA UNII
6 K67ESG · RUM6K67ESG
ATC code
1 AC21 · B01AC21
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
301 · H301-H311-H331-H361
Precautionary statements
501 · P501-P270-P202-P201-P264-P280-P308+P313-P362+P364-P301+P310+P330-P302+P352+P312-P405
WGK Germany
3 · WGK 3
Storage Class
11 · 11 - Combustible Solids
Symbol(GHS)
GHS06,GHS08
Storage Class
11 - Combustible Solids
Hazard statements
H301-H311-H331-H361
Precautionary statements
P501-P270-P202-P201-P264-P280-P308+P313-P362+P364-P301+P310+P330-P302+P352+P312-P405
Biological Half-LifeThe terminal elimination half-life of treprostinil is approximately 4 hours, following a two-compartment model.
Metabolism/Metabolites · 1 item

Treprostinil is mostly metabolized by the liver, mainly by CYP2C8, and by CYP2C9 to a lesser extent. Treprostinil does not have a single major metabolite. The five metabolites detected in urine (HU1 through HU5) accounted for 13.8, 14.3, 15.5, 10.6 and 10.2% of the dose, respectively. One of the metabolites (HU5) is the glucuronide conjugate of treprostinil. HU1, HU2, HU3 and HU4 are formed through the oxidation of the 3-hydroxyloctyl side chain. None of the metabolites of treprostinil appear to be active. _In vitro_ studies suggest that treprostinil does not inhibit or induce any major CYP enzymes.

FDA Pharmacological Classification · 6 items

RUM6K67ESG

TREPROSTINIL

Established Pharmacologic Class [EPC] - Prostacycline Vasodilator

Chemical Structure [CS] - Prostaglandins I

Physiologic Effects [PE] - Vasodilation

Treprostinil is a Prostacycline Vasodilator. The physiologic effect of treprostinil is by means of Vasodilation.

MeSH Pharmacological Classification · 1 item

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Absorption, Distribution and Excretion · 4 items

After subcutaneous infusion, treprostinil is completely absorbed, with a bioavailability of about 100%, and it reaches steady-state concentrations in approximately 10 hours. The pharmacokinetics of treprostinil follow a two-compartment model and are linear between 2.5 and 125 ng/kg/min. Subcutaneous and intravenous doses of treprostinil are bioequivalent at 10 ng/kg/min. Compared to healthy subjects, patients with mild and moderate hepatic insufficiency had a corresponding Cmax 2- and 4-times higher and an AUC0-∞ 3- and 5-times higher when given a subcutaneous treprostinil dose of 10 ng/kg/min for 150 min. When given orally at doses between 0.5 and 15 mg twice a day, treprostinil follows a dose-proportional pharmacokinetic profile. The oral bioavailability of treprostinil is 17%, and drug concentration reaches its highest level between 4 and 6 hours after oral administration. The oral absorption of treprostinil is affected by food. The AUC and Cmax of oral treprostinil increase 49% and 13%, respectively, when this drug is administered with a high-fat, high-calorie meal. The AUC and Cmax of inhaled treprostinil were proportional to the doses administered (18 to 90 μg). The bioavailability of inhaled treprostinil was 64% in patients receiving 2 doses of 18 μg, and 72% in patients receiving two doses of 36 μg. Two separate studies that evaluated the pharmacokinetics of inhaled treprostinil at a maintenance dose of 54 μg found that the mean Cmax was 0.91 and 1.32 ng/mL, respectively, with a corresponding Tmax of 0.25 and 0.12 hr and a mean AUC of 0.81 and 0.97 hr⋅ng/mL.

Treprostinil metabolites are excreted through urine (79%) and feces (13%) over 10 days. Only a small proportion of treprostinil is excreted unchanged. When administered orally, 1.13% and 0.19% of unchanged treprostinil diolamine are found in urine and feces, respectively. When administered subcutaneously, intravenously or by inhalation, 4% of unchanged treprostinil is found in urine.

The volume of distribution of treprostinil is 14 L/70 kg.

The clearance of treprostinil is 30 L/hr in a 70 kg person. In patients with mild to moderate hepatic insufficiency, clearance is reduced up to 80%.

Cellular LocationsCytoplasm

Applications

UsesSynthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

Upstream & downstream products

Upstream raw materials

2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile(S)-1-Chloroheptan-2-ol2-[[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalen-5-yl]oxy]acetic acid,2-(2-hydroxyethylamino)ethanol101692-03-9Treprostinil Methyl Ester2-Allyl-3-hydroxybenzaldehydeTreprostinil Ethyl Ester(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol

Suppliers100 total

济南百隆化学有限公司[email protected] · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
HubeiwidelychemicaltechnologyCo.,Ltd18627774460 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
湖南瑞威尔生物科技有限公司15608648206 13297919155 · [email protected]
江西瑞威尔生物科技有限公司18502728206 · [email protected]
上海波以尔化工有限公司[email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
苏州莱忆科生物科技有限公司13771999217 13771999217 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
InvivoChem中国13549236410 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海厚博生物科技有限公司+21-18501659228 18501659228
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
嘉兴诺华化工有限公司18957373295
杭州杰恒化工有限公司0571-87396432 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
池州凯隆进出口贸易有限公司[email protected]
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
上海众强药业有限公司13951772964 · [email protected]
上海泽涵生物医药科技有限公司021-61350663 13052117465 · [email protected]
南京伶亚生物医药科技有限公司18068075658 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
开封明仁药业有限公司0371-65741762 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
台州市瑞欣化工有限公司0576-89085261 15867635987 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Treprostinil is a carboxylic acid and a carbotricyclic compound. It has a role as a platelet aggregation inhibitor, a vasodilator agent, an antihypertensive agent, a cardiovascular drug, a vitamin K antagonist and a human blood serum metabolite.