기본 정보
- 표준 SMILES
CC(C)OC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)COc2cccc(C(F)(F)F)c2)[C@H](O)C[C@@H]1O- InChIKey
MKPLKVHSHYCHOC-AHTXBMBWSA-N- 분자식
- C26H35F3O6
- 평균 분자량
- 500.5 g/mol
- 단동위원소 질량
- 500.2385735
개요
Travoprost is the isopropyl ester of prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of travoprost are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. It is a pro-drug; the isopropyl ester group is hydrolysed by esterases in the cornea to the biologically active free acid, fluprostenol. It has a role as an antihypertensive agent, an antiglaucoma drug, a prodrug, a prostaglandin receptor agonist and an ophthalmology drug. It is an isopropyl ester, a prostaglandins Falpha and a member of (trifluoromethyl)benzenes. It is functionally related to a fluprostenol.
이름 및 식별자
- 우선 이름
- Travoprost
- IUPAC
- propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
- 영어명
- Travoprost
- 분자식
- C26H35F3O6
- 분자량
- 500.55
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
157283-68-6- PubChem CID
- 5282226
- DTXSID
DTXSID80896948- ChEMBL
CHEMBL1200799- ChEBI
CHEBI:746859- UNII
- WJ68R08KX9
- EC Number
- 682-028-9
- Nikkaji
- J1.152.432J
물성
구조 계산 물성
- XLogP
- 4.1
- 극성 표면적
- 96.2 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 13
- 무거운 원자 수
- 35
- 형식 전하
- 0
- 복잡도
- 693
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Sensory organs -> Ophthalmologicals
Solubility
>16 mg/ml at 25.0°C
7.59e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiglaucoma Agents; Prostaglandins
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
물리화학적 성질
- 끓는 점
- 584.8 · 584.8±50.0 °C(Predicted)
- 밀도
- 1.245 · 1.245±0.06 g/cm3(Predicted)
- 인화점
- 17 °C · 17 °C
- 저장 조건
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- 용해도
- 디클로로메탄(소량으로 용해, 초음파 처리함), 클로로포름(소량으로 용해), 메탄올(소량으로 용해)
- 물리적 상태
- 에탄올 용액에 용해됨
- 산도 계수 (pKa)
- 13.43 · 13.43±0.20(Predicted)
- 색상
- 무색~연한 베이지
- BCS Class
- 2 · 2
- 안정성
- 감광성
- InChIKey
- MKPLKVHSHYCHOC-AHTXBMBWSA-N
- SMILES
- C(OC(C)C)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1
화학적 성질
Colorless Oil
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 6.2% (1 of 16) of reports.
Warning
H302 (18.8%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P263, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 16 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
독성 정보
안전 데이터
- wgk
- 1
- ridadr
- UN 1170 3/PG 2
- HS 번호
- 2937500000
- risk_code
- 11-36/37/38
- hazard_code
- F,Xi
- safety_code
- 16-26-36-7
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- 스토리지 클래스
- 3 - Flammable liquids
화학 및 산업
약리 정보
ATC Code
S01EE04
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
Travoprost demonstrates preferential affinity and full agonist activity for the prostaglandin FP receptor in the nanomolar range. Travoprost shows no significant affinity for other prostanoid or non-prostanoid receptors. Travoprost-induced reduction of intraocular pressure is observed about two hours after administration, and the maximum effect is reached after 12 hours. Significant lowering of intraocular pressure can be maintained for periods exceeding 24 hours with a single dose.
Mechanism of Action
Travoprost is a prodrug. Upon administration, travoprost is absorbed through the cornea and hydrolyzed to its active metabolite, travoprost free acid. The ester moiety of the free acid allows for enhanced penetration into the aqueous humour. While the exact mechanism of travoprost is largely unknown, it is believed to be related to its full agonist activity for the prostaglandin FP receptor. By binding to the FP receptor, travoprost free acid increases the outflow of aqueous humour via the trabecular meshwork and uveoscleral pathways, thereby reducing the intraocular pressure.
Metabolism/Metabolites
Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is metabolized to inactive metabolites via beta-oxidation of the α (carboxylic acid) chain to give the 1,2-dinor and 1,2,3,4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13, 14 double bond.
FDA Pharmacological Classification
WJ68R08KX9
TRAVOPROST
Established Pharmacologic Class [EPC] - Prostaglandin Analog
Chemical Structure [CS] - Prostaglandins
Travoprost is a Prostaglandin Analog.
TRAVOPROST
MeSH Pharmacological Classification
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
Following ophthalmic administration, travoprost is absorbed through the cornea. In many patients in multiple-dose pharmacokinetic studies, the plasma concentrations of the free acid were below 0.01 ng/mL, which was the quantitation limit of the assay. In these studies, the mean plasma Cmax of travoprost free acid was 0.018 ± 0.007 ng/mL (ranging from 0.01 to 0.052 ng/mL), and the Tmax was about 30 minutes.
The elimination of travoprost free acid from plasma is rapid. The levels of travoprost free acid were generally below the limit of quantification within one hour after dosing. Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid.
No information is available.
No information is available.
응용 분야
개요Travoprost was launched in the US as Travatan, an ophthalmic solution (0.004%) administered topically for the treatment of elevated intraocular hypertension (lOP) through open-angle glaucoma, a common optic neuropathy and a leading cause of blindness. Travoprost is the isopropyl ester of (+)-fluprostenol, a new prostaglandin derivative belonging to the PGF2α, analog class. This compound can be prepared in 8 steps from a bicyclic lactone aldehyde by a Wittig alkylidenation followed, after 2 ketonic reductions, by a lactol opening to prostenoic acid while protecting and deprotecting appropriately. Travoprost is a full agonist of FP receptors with a greater affinity than PGF2α, (K1 = 52 nM). Pharmacologic studies in rabbits treated daily for a week demonstrated a significant increase of the microvascular optic nerve head blood flow without significant alterations in the systemic flow. In several placebo-controlled clinical studies with hundreds of patients suffering from open-angle glaucoma or ocular hypertension, travoprost (1 to 4 pm daily) dose-dependently reduced lOP (by about 30% at 4 pm); it was shown equal or superior to latanoprost, another prostaglandin analog (5 pm daily) or the adrenergic ~-blocker timolol (500 pm bid). In addition, travoprost was safe and well tolerated with a low incidence of conjunctival hyperaemia.
용도Travoprost is a selective FP prostaglandin receptor agonist used to treat glaucoma (1,2).
일반 설명Travoprost (Travatan and Travatan-Z) is supplied asa 2.5- or 5.0-mL sterile 0.004% ophthalmic solution in a4.0- or 7.5-mL size container. Travoprost is claimed to bethe most potent and FP-specific analog in this product category. Cautions and side effects are similar to those givenpreviously.
공급사50 곳
추가 설명
정의ChEBI: The isopropyl ester of prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophth lmic solutions of travoprost are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. It is a pro-drug; the isopropyl ester group is hydrolysed by esterases in the co nea to the biologically active free acid, fluprostenol.
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