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Treprostinil

HCID 6918140
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
81846-19-7
표준 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
분자식
C23H34O5
평균 분자량
390.5 g/mol
단동위원소 질량
390.24062419

개요

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.

이름 및 식별자

우선 이름
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
영어명
Treprostinil
분자식
C23H34O5
분자량
390.51

이름 및 동의어

Treprostinil81846-19-7UniprostRumodolinTyvasoUT-15LRX-15treprostinilo15AU81treprostinilumTyvaso dpiRUM6K67ESG
이름 더 보기
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))-

데이터베이스 식별자

CAS
81846-19-7
PubChem CID
6918140
DTXSID

물성

구조 계산 물성보충 중

XLogP
4.5
극성 표면적
87 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
5
회전 가능 결합 수
10
무거운 원자 수
28
형식 전하
0
복잡도
495

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Antihypertensives

Pharmaceuticals -> Listed in ZINC15

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

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

물리화학적 성질

녹는점
121 · 121-123°
끓는 점
587.1 · 587.1±50.0 °C(Predicted)
밀도
1.158 · 1.158±0.06 g/cm3(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (100%)

독성 정보

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

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

안전 데이터

wgk
WGK 3
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 2건

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 · 1건

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 · 1건

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.

관련 반응

36건
반응 기록 만들기
HRID 39617 반응식
HRID 39617생성물로uspto-grants-2013_09
HRID 39618 반응식
HRID 39618생성물로uspto-grants-2013_09
HRID 43308 반응식
HRID 43308반응물로uspto-grants-2013_09
HRID 43309 반응식
HRID 43309반응물로uspto-grants-2013_09
HRID 131750 반응식
HRID 131750반응물로uspto-grants-2008_06
HRID 131751 반응식
HRID 131751반응물로uspto-grants-2008_06
HRID 245602 반응식
HRID 245602생성물로uspto-grants-2014_02
HRID 245603 반응식
HRID 245603생성물로uspto-grants-2014_02
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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새 노트새 반응견적 요청하기
DTXSID901021654
ChEMBL
CHEMBL1237119
ChEBI
CHEBI:50861
UNII
RUM6K67ESG
EC Number
808-233-7
Nikkaji
J430.982K
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
클로로포름(약간 용해됨, 가열), 메탄올(약간 용해됨, 가열)
물리적 상태
고체
산도 계수 (pKa)
3.19 · 3.19±0.10(Predicted)
색상
미색부터 베이지까지
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
Biological Half-LifeThe terminal elimination half-life of treprostinil is approximately 4 hours, following a two-compartment model.
Metabolism/Metabolites · 1건

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 · 6건

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 · 1건

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 · 4건

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

응용 분야

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

상·하류 제품 정보

상류 원료

2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile(S)-1-클로로헵탄-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-하이드록시벤잘데하이드Treprostinil Ethyl Ester(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol