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Travoprost

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Travoprost
Clinical data
Trade namesTravatan, Izba, others
AHFS/Drugs.comMonograph
MedlinePlusa602027
License data
Pregnancy
category
Routes of
administration
Topicaleye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismActivation by esterhydrolysis, deactivation bybeta oxidation, OH-oxidation, double bond reduction
Onset of action2 hours
Eliminationhalf-life1.5 hours (inaqueous fluid)
45 minutes (terminal)
Duration of action≥ 24 hours
ExcretionMainly via kidney
Identifiers
  • Propan-2-yl 7-[3,5-dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl)
    phenoxy]-but-1-enyl]-cyclopentyl]hept-5-enoate
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.207.141Edit this at Wikidata
Chemical and physical data
FormulaC26H35F3O6
Molar mass500.555 g·mol−1
3D model (JSmol)
  • FC(F)(F)c2cc(OC[C@H](O)/C=C/[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(=O)OC(C)C)ccc2
  • InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1 checkY
  • Key:MKPLKVHSHYCHOC-AHTXBMBWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Travoprost, sold under the brand nameTravatan among others, is amedication used to treathigh pressure inside the eye includingglaucoma.[4] Specifically it is used foropen angle glaucoma when other agents are not sufficient.[5][4] It is used as an eye drop.[4] Effects generally occur within two hours.[4]

Common side effects include red eyes, blurry vision, eye pain, dry eyes, and change in color of the eyes.[4][5] Other significant side effects may includecataracts.[5] Use duringpregnancy orbreastfeeding is generally not recommended.[5] It is aprostaglandin analog and works by increasing the outflow ofaqueous fluid from the eyes.[4]

Travoprost was approved for medical use in the United States and in the European Union in 2001.[4][3] It is available as ageneric medication in the United Kingdom.[5] In 2020, it was the 304th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[6][7]

Medical uses

[edit]

Travoprost is used to treathigh pressure inside the eye includingglaucoma.[4] Specifically it is used foropen angle glaucoma when other agents are not sufficient.[5][4]

Side effects

[edit]
One 2.5 ml dropperette of Travatan

Possible side effects are:[8]

  • blurred vision
  • eyelid redness
  • permanent darkening of eyelashes
  • eye discomfort
  • permanent darkening of theiris to brown (heterochromia)
  • burning sensation during use
  • thickening of the eyelashes
  • inflammation of theprostate gland, restricting urine flow (BPH)[citation needed]

Research suggests that wiping the eye with an absorbent pad after the administration of eye drops can result in shorter eyelashes and a lesser chance of hyperpigmentation in the eyelid, compared to not wiping off excess fluid.[9]

Pharmacology

[edit]

Mechanism of action

[edit]

It is a syntheticprostaglandin analog (or more specifically, ananalog ofprostaglandin F)[10][11] that works by increasing the outflow ofaqueous fluid from theeyes.[12]

Like other analogs of prostaglandin F such astafluprost andlatanoprost, travoprost is anesterprodrug of the free acid, which acts as anagonist at theprostaglandin F receptor, increasing outflow of aqueous fluid from the eye and thus lowering intraocular pressure.[8]

Pharmacokinetics

[edit]

Travoprost is absorbed through thecornea, where it ishydrolysed to the free travoprost acid. Highest concentrations of the acid in the eye are reached one to two hours after application, and its half-life in the aqueous fluid is 1.5 hours. Once it reaches the bloodstream, it is quickly metabolised, so that concentrations in the system do not exceed 25pg/ml (compared to 20 ng/ml in the eye, which is higher by nearly a factor of 1000).[8]

Metabolites are formed bybeta oxidation of the acidic chain (compareTafluprost#Pharmacokinetics),oxidation of theOH-group in the other side chain, and reduction of the double bond next to this OH-group. Travoprost acid and its metabolites are mainly excreted via the kidney[8] with a terminal half-life of 45 minutes.[13]

Metabolism. From left to right: travoprost, travoprost acid (theactive metabolite), 1,2-dinortravoprost acid, 1,2,3,4-tetranortravoprost acid. Below: reduction of the 13,14-double bond (red) and oxidation of the 15-hydroxy group (blue)[8]

References

[edit]
  1. ^"Travoprost ophthalmic Use During Pregnancy".Drugs.com. 8 October 2019. Retrieved16 May 2020.
  2. ^"iDose TR- travoprost intracameral implant".DailyMed. 20 December 2023. Retrieved26 February 2024.
  3. ^ab"Travatan EPAR".European Medicines Agency (EMA). 10 July 2007. Retrieved3 January 2021.
  4. ^abcdefghi"Travoprost Monograph for Professionals".Drugs.com. American Society of Health-System Pharmacists. Retrieved26 March 2019.
  5. ^abcdefBritish national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1152.ISBN 978-0-85711-338-2.
  6. ^"The Top 300 of 2020".ClinCalc. Retrieved7 October 2022.
  7. ^"Travoprost - Drug Usage Statistics".ClinCalc. Retrieved7 October 2022.
  8. ^abcdeHaberfeld, H, ed. (2015).Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Travatan 40 Mikrogramm/ml Augentropfen.
  9. ^Xu L, Wang X, Wu M (February 2017)."Topical medication instillation techniques for glaucoma".The Cochrane Database of Systematic Reviews.2017 (2) CD010520.doi:10.1002/14651858.CD010520.pub2.PMC 5419432.PMID 28218404.
  10. ^Alcon Laboratories, Inc. (September 2011)."Travatan - travoprost solution".DailyMed. Bethesda, MD: U.S. National Library of Medicine. Retrieved30 September 2011.
  11. ^Alcon Laboratories, Inc. (September 2011)."Travatan Z (travoprost) solution".DailyMed. Bethesda, MD: U.S. National Library of Medicine. Retrieved30 September 2011.
  12. ^AHFS Consumer Medication Information (1 January 2011)."Travoprost Ophthalmic".MedlinePlus. Bethesda, MD: U.S. National Library of Medicine. Retrieved30 September 2011.
  13. ^Drugs.com: TravoprostMonograph.
Drugs used forglaucoma preparations andmiosis (S01E)
Sympathomimetics
Parasympathomimetics
muscarinic
muscarinic/nicotinic
acetylcholinesterase inhibitors
Carbonic anhydrase inhibitors/
(sulfonamides)
Beta blocking agents
Prostaglandin analogues (F)
Other agents
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
Active
D/J
E/F
I
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Initial
SRS-A
Eoxins (EX)
Precursor
Eoxins
Nonclassic
By function
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
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