Travoprost

HCID 5282226CAS 157283-68-6

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

Travoprost157283-68-6TravatanTravatan ZIzbaAL-6221AL6221Otx-tptravoprostumIDOSE TRWJ68R08KX9CHEBI:746859
이름 더 보기
TrovoprostFLUPROSTENOL ISOPROPYL ESTER(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]buten-1-yl][cyclopentyl]hept-5-enoateTrivoFLU-IPRAL 6221ravoprosTrivoprostTravaprost
NSC-760366DTXSID80896948DTXCID401326382DUOTRAV COMPONENT TRAVOPROST(1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-7-(3,5-Dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic acid, 1-methylethyl esterpropan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-en-1-yl]cyclopentyl]hept-5-enoate5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3R)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl ester, (5Z)-isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[(alpha,alpha,alpha-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate

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

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Sensory organs -> Ophthalmologicals

LogP4.6
Solubility · 2건

>16 mg/ml at 25.0°C

7.59e-03 g/L

Human Drugs · 5건

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

Physical DescriptionLiquid

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

화학적 성질

Colorless Oil

안전 및 규제

GHS 분류

GHS Classification · 5건

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

Hazard Classes and CategoriesAcute Tox. 4 (18.8%)

독성 정보

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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

화학 및 산업

약리 정보

ATC Code · 3건

S01EE04

S - Sensory organs

QS - Sensory organs

Protein BindingNo information is available.
Pharmacodynamics · 1건

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 · 1건

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.

Biological Half-LifeThe terminal elimination half-life of travoprost free acid was estimated from fourteen subjects and ranged from 17 minutes to 86 minutes with the mean half-life of 45 minutes.
Metabolism/Metabolites · 1건

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.

응용 분야 · 3건

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

北京华美互利生物化工010-56205725 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
江苏恒盛药业有限公司0512-58726293
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
추가 설명 · 1건

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.

관련 반응

7건

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