Ensiklopedia Dunia

Technopedia Center

Faculty of Engineering and Computer Science
S1 Informatics S1 Information Systems S1 Information Technology S1 Computer Engineering S1 Electrical Engineering S1 Civil Engineering

faculty of Economics and Business
S1 Management S1 Accountancy

Faculty of Letters and Educational Sciences
S1 English literature S1 English language education S1 Mathematics education S1 Sports Education

Travoprost - Wikipedia

From Wikipedia, the free encyclopedia

Travoprost
Clinical data

Trade names	Travatan, Izba, others
AHFS/Drugs.com	Monograph
MedlinePlus	a602027
License data	US DailyMed: Travoprost
Pregnancy category	AU: B3^[1]
Routes of administration	Topical eye drops
ATC code	S01EE04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only^[2] EU: Rx-only^[3] In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Activation by ester hydrolysis, deactivation by beta oxidation, OH-oxidation, double bond reduction
Onset of action	2 hours
Elimination half-life	1.5 hours (in aqueous fluid) 45 minutes (terminal)
Duration of action	≥ 24 hours
Excretion	Mainly via kidney
Identifiers
IUPAC name Propan-2-yl 7-[3,5-dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl) phenoxy]-but-1-enyl]-cyclopentyl]hept-5-enoate
CAS Number	157283-68-6^Y
PubChem CID	5282226
IUPHAR/BPS	7102
DrugBank	DB00287^Y
ChemSpider	4445407^Y
UNII	WJ68R08KX9
KEGG	D01964^Y
ChEBI	CHEBI:746859^Y
ChEMBL	ChEMBL1200799^N
CompTox Dashboard (EPA)	DTXSID80896948
ECHA InfoCard	100.207.141
Chemical and physical data
Formula	C₂₆H₃₅F₃O₆
Molar mass	500.555 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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 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^Y Key:MKPLKVHSHYCHOC-AHTXBMBWSA-N^Y
^NY (what is this?) (verify)

Travoprost, sold under the brand name Travatan among others, is a medication used to treat high pressure inside the eye including glaucoma.^[4] Specifically it is used for open 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 include cataracts.^[5] Use during pregnancy or breastfeeding is generally not recommended.^[5] It is a prostaglandin analog and works by increasing the outflow of aqueous 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 a generic 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

Travoprost is used to treat high pressure inside the eye including glaucoma.^[4] Specifically it is used for open angle glaucoma when other agents are not sufficient.^[5]^[4]

Side effects

Possible side effects are:^[8]

blurred vision
eyelid redness
permanent darkening of eyelashes
eye discomfort
permanent darkening of the iris to brown (heterochromia)
burning sensation during use
thickening of the eyelashes
inflammation of the prostate 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

Mechanism of action

It is a synthetic prostaglandin analog (or more specifically, an analog of prostaglandin F_2α)^[10]^[11] that works by increasing the outflow of aqueous fluid from the eyes.^[12]

Like other analogs of prostaglandin F_2α such as tafluprost and latanoprost, travoprost is an ester prodrug of the free acid, which acts as an agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eye and thus lowering intraocular pressure.^[8]

Pharmacokinetics

Travoprost is absorbed through the cornea, where it is hydrolysed 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 25 pg/ml (compared to 20 ng/ml in the eye, which is higher by nearly a factor of 1000).^[8]

Metabolites are formed by beta oxidation of the acidic chain (compare Tafluprost#Pharmacokinetics), oxidation of the OH-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]

References

^ "Travoprost ophthalmic Use During Pregnancy". Drugs.com. 8 October 2019. Retrieved 16 May 2020.
^ "iDose TR- travoprost intracameral implant". DailyMed. 20 December 2023. Retrieved 26 February 2024.
^ ^a ^b "Travatan EPAR". European Medicines Agency (EMA). Retrieved 3 January 2021.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Travoprost Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 26 March 2019.
^ ^a ^b ^c ^d ^e ^f British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1152. ISBN 9780857113382.
^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
^ "Travoprost - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
^ ^a ^b ^c ^d ^e Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Travatan 40 Mikrogramm/ml Augentropfen.
^ 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.
^ Alcon Laboratories, Inc. (September 2011). "Travatan - travoprost solution". DailyMed. Bethesda, MD: U.S. National Library of Medicine. Retrieved 30 September 2011.
^ Alcon Laboratories, Inc. (September 2011). "Travatan Z (travoprost) solution". DailyMed. Bethesda, MD: U.S. National Library of Medicine. Retrieved 30 September 2011.
^ AHFS Consumer Medication Information (1 January 2011). "Travoprost Ophthalmic". MedlinePlus. Bethesda, MD: U.S. National Library of Medicine. Retrieved 30 September 2011.
^ Drugs.com: Travoprost Monograph.

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Parasympathomimetics

muscarinic	Aceclidine Pilocarpine
muscarinic/nicotinic	Acetylcholine Carbachol
acetylcholinesterase inhibitors	Demecarium Ecothiopate Stigmine (Fluostigmine Neostigmine Physostigmine) Paraoxon

Carbonic anhydrase inhibitors/
(sulfonamides)

Beta blocking agents

Prostaglandin analogues (F_2α)

Other agents

Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG)

Precursor

H₂

Active

D/J	D₂
E/F	E₂ (Dinoprostone) E₁ (Alprostadil) F_2α (Dinoprost):
I	I₂ (Prostacyclin/Epoprostenol):

Thromboxanes (TX)

A₂
B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide
Initial	A₄ B₄
SRS-A	C₄ D₄ E₄

Eoxins (EX)

Precursor	Arachidonic acid 15-hydroperoxide
Eoxins	A₄ C₄ D₄ E₄

Nonclassic

Lipoxins (LX) (A₄, B₄)
Virodhamine

By function

bronchoconstriction
- PGD₂
- TXA₂
- LTC₄
- LTD₄
- LTE₄

vasoconstriction
- PGF_2α
- TXA₂
- TXB₂
vasodilation
- PGE₂
- PGI₂
- LTC₄
- LTD₄
- LTE₄

platelets: induce
- TXA₂
inhibit
- PGD₂
- PGI₂
leukocytes: induce
- TXA₂
- LTB₄
inhibit
- PGD₂
- PGE₂

fever stimulation:
- PGE₂

labor stimulation:
- PGE₂ (Dinoprostone)
- PGF_2α (Dinoprost)

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)

DP₁Tooltip Prostaglandin D2 receptor 1	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant
DP₂Tooltip Prostaglandin D2 receptor 2	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 QAV-680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant

EP (E₂)

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators