Travoprost

Identification

Summary

Travoprost is a prostaglandin analog used in the treatment of elevated intraocular pressure due to open angle glaucoma or ocular hypertension.

Brand Names
Duotrav, Izba, Travatan
Generic Name
Travoprost
DrugBank Accession Number
DB00287
Background

Travoprost is a synthetic isopropyl ester prodrug of a prostaglandin F2alpha (F2α) analogue and selective FP prostanoid receptor agonist. It is used to decrease intraocular pressure in open-angle glaucoma and ocular hypertension.7 Unlike other prostaglandin analogues, travoprost demonstrates full agonism and high selectivity at the prostanoid receptor, reporting a higher efficacy in reducing intraocular pressure and a reduced risk for developing off-target side effects.2

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 500.5477
Monoisotopic: 500.238573467
Chemical Formula
C26H35F3O6
Synonyms
  • (1R-(1.ALPHA.(Z),2.BETA.(1E,3R*),3.ALPHA.,5.ALPHA.))-7-(3,5-DIHYDROXY-2-(3-HYDROXY-4-(3-(TRIFLUOROMETHYL)PHENOXY)-1-BUTENYL)CYCLOPENTYL)-5-HEPTENOIC ACID, 1-METHYLETHYL ESTER
  • 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
  • isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[(α,α,α-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate
  • OTX-TP
  • Travoprost
  • TRAVOPROST COMPONENT OF DUOTRAV
  • Travoprostum
External IDs
  • AL-6221
  • NSC-760366

Pharmacology

Indication

Travoprost is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension.7,6,8 It is also used in pediatric patients aged two months to less than 18 years.4

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofElevated intraocular pressure••••••••••••
Management ofElevated intraocular pressure••••••••••••
Management ofIncreased intra ocular pressure (iop)••••••••••••••••••••••• ••••••• •••••••••
Management ofIncreased intra ocular pressure (iop)••••••••••••
Used in combination to treatIncreased intraocular pressureCombination Product in combination with: Timolol (DB00373)••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Travoprost demonstrates preferential affinity and full agonist activity for the prostaglandin FP receptor in the nanomolar range.3 Travoprost shows no significant affinity for other prostanoid or non-prostanoid receptors.2

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.4

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.1 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.7 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.1,4,7

TargetActionsOrganism
AProstaglandin F2-alpha receptor
agonist
Humans
Absorption

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.7

Volume of distribution

No information is available.

Protein binding

No information is available.

Metabolism

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.4,7

Hover over products below to view reaction partners

Route of elimination

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.7

Half-life

The 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.7

Clearance

No information is available.

Adverse Effects
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Toxicity

No cases of overdose have been reported for travoprost, as overdose from topical or ophthalmic administration is not likely to occur. Overdose from topical administration should be responded to with flushing of the eyes with lukewarm water. Treatment of an oral overdose should be symptomatic and supportive.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AceclofenacThe therapeutic efficacy of Travoprost can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Travoprost can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidThe therapeutic efficacy of Travoprost can be decreased when used in combination with Acetylsalicylic acid.
AlclofenacThe therapeutic efficacy of Travoprost can be decreased when used in combination with Alclofenac.
AminophenazoneThe therapeutic efficacy of Travoprost can be decreased when used in combination with Aminophenazone.
Food Interactions
No interactions found.

Products

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International/Other Brands
Travo-Z
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IzbaSolution0.003 % w/vOphthalmicNovartis2017-02-06Not applicableCanada flag
IzbaSolution0.03 mg/1mLOphthalmicAlcon, Inc.2014-06-022014-06-02US flag
IzbaSolution / drops30 μg/mlOphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
IzbaSolution / drops30 μg/mlOphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
TravatanSolution / drops40 μg/mlOphthalmicNovartis Europharm Limited2016-09-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-travoprostSolution0.003 % w/vOphthalmicApotex CorporationNot applicableNot applicableCanada flag
Apo-travoprost ZSolution0.004 % w/vOphthalmicApotex Corporation2014-08-14Not applicableCanada flag
Mylan-travoprost ZSolution0.004 % w/vOphthalmicMylan PharmaceuticalsNot applicableNot applicableCanada flag
PMS-travoprost ZSolution0.004 % w/vOphthalmicPharmascience IncNot applicableNot applicableCanada flag
Sandoz TravoprostSolution0.004 % w/vOphthalmicSandoz Canada Incorporated2014-08-15Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-travoprost-timolol PqTravoprost (0.004 % w/v) + Timolol maleate (0.5 % w/v)SolutionOphthalmicApotex CorporationNot applicableNot applicableCanada flag
Apo-travoprost-timop PqTravoprost (0.004 % w/v) + Timolol maleate (0.5 % w/v)SolutionOphthalmicApotex Corporation2018-12-06Not applicableCanada flag
BIOFOCUS®Travoprost (0.04 mg) + Timolol maleate (5 mg)SolutionOphthalmicLABORATORIOS SYNTHESIS S.A.S.2015-05-152016-06-23Colombia flag
DRASOTER-T %0.004 + %0.5 GÖZ DAMLASI, ÇÖZELTİ, 1 ADETTravoprost (0.004 %) + Timolol (0.5 %)Solution / dropsOphthalmicDeva Holding A.S.2019-01-11Not applicableTurkey flag
DUOTRAVTravoprost (40 MICROGRAMMI/ML) + Timolol (5 MG/ML)Solution / dropsOphthalmicNovartis Europharm Limited2015-10-15Not applicableItaly flag

Categories

ATC Codes
S01EE04 — Travoprost
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Trifluoromethylbenzenes / Phenoxy compounds / Phenol ethers / Fatty acid esters / Alkyl aryl ethers / Cyclopentanols / Cyclic alcohols and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organofluorides
show 4 more
Substituents
Alcohol / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxylic ester, prostaglandins Falpha, (trifluoromethyl)benzenes (CHEBI:746859)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WJ68R08KX9
CAS number
157283-68-6
InChI Key
MKPLKVHSHYCHOC-AHTXBMBWSA-N
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
IUPAC Name
propan-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-enoate
SMILES
CC(C)OC(=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(=C1)C(F)(F)F

References

General References
  1. Waugh J, Jarvis B: Travoprost. Drugs Aging. 2002;19(6):465-71; discussion 472-3. doi: 10.2165/00002512-200219060-00005. [Article]
  2. Whitson JT: Travoprost--a new prostaglandin analogue for the treatment of glaucoma. Expert Opin Pharmacother. 2002 Jul;3(7):965-77. doi: 10.1517/14656566.3.7.965. [Article]
  3. Al-Jazzaf AM, DeSantis L, Netland PA: Travoprost: a potent ocular hypotensive agent. Drugs Today (Barc). 2003 Jan;39(1):61-74. doi: 10.1358/dot.2003.39.1.799432. [Article]
  4. EMA Approved Drug Products: Travatan (travoprost) Ophthalmic Solution [Link]
  5. Healio: Alcon receives FDA approval for first-line use of Travatan Z [Link]
  6. FDA Approved Drug Products: iDose TR (travoprost) intracameral implant, for intracameral administration [Link]
  7. DailyMed Label: TRAVOPROST ophthalmic solution (ionic buffered solution) 0.004%, for topical ophthalmic use [Link]
  8. Health Canada Approved Drug Products: APO-TRAVOPROST (Travoprost) Ophthalmic Solution [Link]
Human Metabolome Database
HMDB0014432
KEGG Drug
D01964
PubChem Compound
5282226
PubChem Substance
46507637
ChemSpider
4445407
BindingDB
50248302
RxNav
283809
ChEBI
746859
ChEMBL
CHEMBL1200799
ZINC
ZINC000004474682
Therapeutic Targets Database
DAP000274
PharmGKB
PA164781371
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Travoprost

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableGlaucoma2
4CompletedDiagnosticGlaucoma / Ocular Hypertension1
4CompletedSupportive CareDry Eye Syndrome (DES)1
4CompletedTreatmentAngle-Closure Glaucoma1
4CompletedTreatmentAnterior Uveitis (AU) / Macular Edema, Cystoid1

Pharmacoeconomics

Manufacturers
  • Alcon inc
Packagers
  • Alcon Laboratories
  • Liberty Carton Co.
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
Solution / dropsOphthalmic40 MCG/ML
SolutionConjunctival; Ophthalmic
Solution / dropsOphthalmic40 MICROGRAMMI/ML
SolutionOphthalmic40.00 µg
Solution / dropsOphthalmic
SolutionOphthalmic40.000 mcg
SolutionConjunctival; Ophthalmic0.04 mg
Solution / dropsOphthalmic
SolutionConjunctival; Ophthalmic40 cg
SolutionOphthalmic0.003 % w/v
SolutionOphthalmic0.03 mg/1mL
Solution / dropsOphthalmic30 MCG/ML
Solution / dropsOphthalmic30 μg/ml
SolutionOphthalmic
SolutionOphthalmic40.000 µg
SolutionOphthalmic0.004 % w/v
LiquidOphthalmic0.04 mg/1ml
SolutionOphthalmic0.004 %
SolutionOphthalmic0.04 mg
SolutionOphthalmic0.04 mg/1mL
Solution / dropsOphthalmic40 μg/ml
Solution; solution / dropsOphthalmic
Solution / drops; suspension / dropsOphthalmic40 UG
SolutionOphthalmic0.03 mg/ml
SolutionOphthalmic0.04 mg/ml
SolutionConjunctival; Ophthalmic40 mcg
Solution / dropsOphthalmic0.004 %
Solution / drops; suspension / dropsOphthalmic40 UG/ML
Solution / dropsOphthalmic40 Mikrogramm/ml
Solution / drops; suspension / dropsOphthalmic
SolutionOphthalmic
Solution / dropsOphthalmic0.04 mg/1mL
SolutionOphthalmic0.040 mg/ml
SolutionOphthalmic0.040 mg
Solution / dropsOphthalmic0.03 mg/1ml
Prices
Unit descriptionCostUnit
Travatan 0.004% Solution 5ml Bottle190.82USD bottle
Travatan Z 0.004% Solution 5ml Bottle190.82USD bottle
Travatan 0.004% Solution 2.5ml Bottle95.41USD bottle
Travatan Z 0.004% Solution 2.5ml Bottle95.41USD bottle
Travatan 0.004% eye drop45.87USD ml
Travatan z 0.004% eye drop36.7USD ml
Travatan 0.004 % Solution12.18USD ml
Travatan Z 0.004 % Solution12.18USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5631287No1997-05-202014-12-22US flag
US6503497No2003-01-072012-05-06US flag
CA2181172No2003-04-292015-12-19Canada flag
CA2129287No2002-05-142014-08-02Canada flag
US8268299No2012-09-182029-10-13US flag
US8323630No2012-12-042027-09-20US flag
US8388941No2013-03-052027-09-20US flag
US9144561No2015-09-292029-03-13US flag
US8722735No2014-05-132029-10-10US flag
US8178582No2012-05-152029-10-10US flag
US8754123No2014-06-172029-05-19US flag
US11426306No2010-10-172030-10-17US flag
US10206813No2010-10-172030-10-17US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubility>16 mg/ml at 25.0°CNot Available
logP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00759 mg/mLALOGPS
logP4.02ALOGPS
logP3.84Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.95Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area96.22 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity127.86 m3·mol-1Chemaxon
Polarizability50.93 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9857
Blood Brain Barrier+0.887
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.5907
P-glycoprotein inhibitor INon-inhibitor0.8237
P-glycoprotein inhibitor IINon-inhibitor0.6435
Renal organic cation transporterNon-inhibitor0.8856
CYP450 2C9 substrateNon-substrate0.8327
CYP450 2D6 substrateNon-substrate0.8383
CYP450 3A4 substrateSubstrate0.652
CYP450 1A2 substrateNon-inhibitor0.728
CYP450 2C9 inhibitorNon-inhibitor0.7607
CYP450 2D6 inhibitorNon-inhibitor0.9125
CYP450 2C19 inhibitorNon-inhibitor0.6844
CYP450 3A4 inhibitorNon-inhibitor0.8546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7657
Ames testNon AMES toxic0.7427
CarcinogenicityNon-carcinogens0.9088
BiodegradationNot ready biodegradable0.9726
Rat acute toxicity3.5280 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9744
hERG inhibition (predictor II)Non-inhibitor0.6722
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-08gl-3324900000-5b14332e11a6e68b289b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xu-0033900000-4107f8db4f801ca53fbf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03k9-0401900000-39d8515ad5f30722422c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900400000-065a06cba5c3f275d406
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02fx-0052900000-1dff3e21be93becdbdc1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0910200000-53f3423b78edfc8899bd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-3894200000-440bda33f72e0a0bff8f
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-251.2891664
predicted
DarkChem Lite v0.1.0
[M-H]-217.36302
predicted
DeepCCS 1.0 (2019)
[M+H]+251.2162664
predicted
DarkChem Lite v0.1.0
[M+H]+219.18791
predicted
DeepCCS 1.0 (2019)
[M+Na]+250.7504664
predicted
DarkChem Lite v0.1.0
[M+Na]+224.79373
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Prostaglandin f receptor activity
Specific Function
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis...
Gene Name
PTGFR
Uniprot ID
P43088
Uniprot Name
Prostaglandin F2-alpha receptor
Molecular Weight
40054.1 Da
References
  1. Ota T, Aihara M, Narumiya S, Araie M: The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63. [Article]
  2. Thieme H, Schimmat C, Munzer G, Boxberger M, Fromm M, Pfeiffer N, Rosenthal R: Endothelin antagonism: effects of FP receptor agonists prostaglandin F2alpha and fluprostenol on trabecular meshwork contractility. Invest Ophthalmol Vis Sci. 2006 Mar;47(3):938-45. [Article]
  3. Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [Article]
  4. Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines]. Oftalmologia. 2009;53(2):3-7. [Article]
  5. Costagliola C, dell'Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. doi: 10.1517/14656560903300129. [Article]
  6. Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. [Article]
  7. Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. doi: 10.1016/j.survophthal.2008.08.010. [Article]
  8. Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. doi: 10.1517/14740330802465474 . [Article]
  9. Whitson JT: Travoprost--a new prostaglandin analogue for the treatment of glaucoma. Expert Opin Pharmacother. 2002 Jul;3(7):965-77. doi: 10.1517/14656566.3.7.965. [Article]
  10. Sharif NA, Kelly CR, Crider JY, Williams GW, Xu SX: Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J Ocul Pharmacol Ther. 2003 Dec;19(6):501-15. [Article]
  11. Al-Jazzaf AM, DeSantis L, Netland PA: Travoprost: a potent ocular hypotensive agent. Drugs Today (Barc). 2003 Jan;39(1):61-74. doi: 10.1358/dot.2003.39.1.799432. [Article]
  12. DailyMed Label: TRAVOPROST ophthalmic solution (ionic buffered solution) 0.004%, for topical ophthalmic use [Link]

Drug created at June 13, 2005 13:24 / Updated at April 21, 2024 05:26