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

Similar Structures

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

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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 Type	Indication	Combined Product Details	Approval Level	Age Group	Dose Form
Management of	Elevated intraocular pressure		••••••••••••
Management of	Elevated intraocular pressure		••••••••••••
Management of	Increased intra ocular pressure (iop)		••••••••••••	••••••••••• ••••••• •••••••••
Management of	Increased intra ocular pressure (iop)		••••••••••••
Used in combination to treat	Increased intraocular pressure	Combination 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

Target	Actions	Organism
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 C_max of travoprost free acid was 0.018 ± 0.007 ng/mL (ranging from 0.01 to 0.052 ng/mL), and the T_max 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

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Travoprost
- Travoprost free acid

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

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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
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Aceclofenac	The therapeutic efficacy of Travoprost can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Travoprost can be decreased when used in combination with Acemetacin.
Acetylsalicylic acid	The therapeutic efficacy of Travoprost can be decreased when used in combination with Acetylsalicylic acid.
Alclofenac	The therapeutic efficacy of Travoprost can be decreased when used in combination with Alclofenac.
Aminophenazone	The 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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Izba	Solution	0.003 % w/v	Ophthalmic	Novartis	2017-02-06	Not applicable
Izba	Solution / drops	30 μg/ml	Ophthalmic	Novartis Europharm Limited	2016-09-08	Not applicable
Izba	Solution	0.03 mg/1mL	Ophthalmic	Alcon, Inc.	2014-06-02	2014-06-02
Izba	Solution / drops	30 μg/ml	Ophthalmic	Novartis Europharm Limited	2016-09-08	Not applicable
Travatan	Solution / drops	40 μg/ml	Ophthalmic	Novartis Europharm Limited	2016-09-08	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-travoprost	Solution	0.003 % w/v	Ophthalmic	Apotex Corporation	Not applicable	Not applicable
Apo-travoprost Z	Solution	0.004 % w/v	Ophthalmic	Apotex Corporation	2014-08-14	Not applicable
Mylan-travoprost Z	Solution	0.004 % w/v	Ophthalmic	Mylan Pharmaceuticals	Not applicable	Not applicable
PMS-travoprost Z	Solution	0.004 % w/v	Ophthalmic	Pharmascience Inc	Not applicable	Not applicable
Sandoz Travoprost	Solution	0.004 % w/v	Ophthalmic	Sandoz Canada Incorporated	2014-08-15	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-travoprost-timolol Pq	Travoprost (0.004 % w/v) + Timolol maleate (0.5 % w/v)	Solution	Ophthalmic	Apotex Corporation	Not applicable	Not applicable
Apo-travoprost-timop Pq	Travoprost (0.004 % w/v) + Timolol maleate (0.5 % w/v)	Solution	Ophthalmic	Apotex Corporation	2018-12-06	Not applicable
BIOFOCUS®	Travoprost (0.04 mg) + Timolol maleate (5 mg)	Solution	Ophthalmic	LABORATORIOS SYNTHESIS S.A.S.	2015-05-15	2016-06-23
DRASOTER-T %0.004 + %0.5 GÖZ DAMLASI, ÇÖZELTİ, 1 ADET	Travoprost (0.004 %) + Timolol (0.5 %)	Solution / drops	Ophthalmic	Deva Holding A.S.	2019-01-11	Not applicable
DUOTRAV	Travoprost (40 MICROGRAMMI/ML) + Timolol (5 MG/ML)	Solution / drops	Ophthalmic	Novartis Europharm Limited	2015-10-15	Not applicable

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

Waugh J, Jarvis B: Travoprost. Drugs Aging. 2002;19(6):465-71; discussion 472-3. doi: 10.2165/00002512-200219060-00005. [Article]
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]
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]
EMA Approved Drug Products: Travatan (travoprost) Ophthalmic Solution [Link]
Healio: Alcon receives FDA approval for first-line use of Travatan Z [Link]
FDA Approved Drug Products: iDose TR (travoprost) intracameral implant, for intracameral administration [Link]
DailyMed Label: TRAVOPROST ophthalmic solution (ionic buffered solution) 0.004%, for topical ophthalmic use [Link]
Health Canada Approved Drug Products: APO-TRAVOPROST (Travoprost) Ophthalmic Solution [Link]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Glaucoma	2
4	Completed	Diagnostic	Glaucoma / Ocular Hypertension	1
4	Completed	Supportive Care	Dry Eye Syndrome (DES)	1
4	Completed	Treatment	Angle-Closure Glaucoma	1
4	Completed	Treatment	Anterior Uveitis (AU) / Macular Edema, Cystoid	1

Pharmacoeconomics

Manufacturers

Alcon inc

Packagers

Alcon Laboratories
Liberty Carton Co.
Physicians Total Care Inc.

Dosage Forms

Form	Route	Strength
Solution / drops	Ophthalmic	40 MCG/ML
Solution	Conjunctival; Ophthalmic
Solution / drops	Ophthalmic	40 MICROGRAMMI/ML
Solution	Ophthalmic	40.00 µg
Solution / drops	Ophthalmic
Solution	Ophthalmic	40.000 mcg
Solution	Conjunctival; Ophthalmic	0.04 mg
Solution / drops	Ophthalmic
Solution	Conjunctival; Ophthalmic	40 cg
Solution	Ophthalmic	0.003 % w/v
Solution	Ophthalmic	0.03 mg/1mL
Solution / drops	Ophthalmic	30 μg/ml
Solution / drops	Ophthalmic	30 MCG/ML
Solution	Ophthalmic
Solution	Ophthalmic	40.000 µg
Solution	Ophthalmic	0.004 % w/v
Liquid	Ophthalmic	0.04 mg/1ml
Solution	Ophthalmic	0.004 %
Solution	Ophthalmic	0.04 mg
Solution	Ophthalmic	0.04 mg/1mL
Solution / drops	Ophthalmic	40 μg/ml
Solution; solution / drops	Ophthalmic
Solution / drops; suspension / drops	Ophthalmic	40 UG
Solution	Ophthalmic	0.03 mg/ml
Solution	Ophthalmic	0.04 mg/ml
Solution	Conjunctival; Ophthalmic	40 mcg
Solution / drops	Ophthalmic	0.004 %
Solution / drops; suspension / drops	Ophthalmic	40 UG/ML
Solution / drops	Ophthalmic	40 Mikrogramm/ml
Solution / drops; suspension / drops	Ophthalmic
Solution	Ophthalmic
Solution / drops	Ophthalmic	0.04 mg/1mL
Solution	Ophthalmic	0.040 mg/ml
Solution	Ophthalmic	0.040 mg
Solution / drops	Ophthalmic	0.03 mg/1ml

Prices

Unit description	Cost	Unit
Travatan 0.004% Solution 5ml Bottle	190.82USD	bottle
Travatan Z 0.004% Solution 5ml Bottle	190.82USD	bottle
Travatan 0.004% Solution 2.5ml Bottle	95.41USD	bottle
Travatan Z 0.004% Solution 2.5ml Bottle	95.41USD	bottle
Travatan 0.004% eye drop	45.87USD	ml
Travatan z 0.004% eye drop	36.7USD	ml
Travatan 0.004 % Solution	12.18USD	ml
Travatan Z 0.004 % Solution	12.18USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5631287	No	1997-05-20	2014-12-22
US6503497	No	2003-01-07	2012-05-06
CA2181172	No	2003-04-29	2015-12-19
CA2129287	No	2002-05-14	2014-08-02
US8268299	No	2012-09-18	2029-10-13
US8323630	No	2012-12-04	2027-09-20
US8388941	No	2013-03-05	2027-09-20
US9144561	No	2015-09-29	2029-03-13
US8722735	No	2014-05-13	2029-10-10
US8178582	No	2012-05-15	2029-10-10
US8754123	No	2014-06-17	2029-05-19
US11426306	No	2010-10-17	2030-10-17
US10206813	No	2010-10-17	2030-10-17

Properties

State

Liquid

Experimental Properties

Property	Value	Source
water solubility	>16 mg/ml at 25.0°C	Not Available
logP	4.6	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00759 mg/mL	ALOGPS
logP	4.02	ALOGPS
logP	3.84	Chemaxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.95	Chemaxon
pKa (Strongest Basic)	-2.9	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	96.22 Å²	Chemaxon
Rotatable Bond Count	14	Chemaxon
Refractivity	127.86 m³·mol^-1	Chemaxon
Polarizability	50.93 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9857
Blood Brain Barrier	+	0.887
Caco-2 permeable	+	0.5
P-glycoprotein substrate	Substrate	0.5907
P-glycoprotein inhibitor I	Non-inhibitor	0.8237
P-glycoprotein inhibitor II	Non-inhibitor	0.6435
Renal organic cation transporter	Non-inhibitor	0.8856
CYP450 2C9 substrate	Non-substrate	0.8327
CYP450 2D6 substrate	Non-substrate	0.8383
CYP450 3A4 substrate	Substrate	0.652
CYP450 1A2 substrate	Non-inhibitor	0.728
CYP450 2C9 inhibitor	Non-inhibitor	0.7607
CYP450 2D6 inhibitor	Non-inhibitor	0.9125
CYP450 2C19 inhibitor	Non-inhibitor	0.6844
CYP450 3A4 inhibitor	Non-inhibitor	0.8546
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7657
Ames test	Non AMES toxic	0.7427
Carcinogenicity	Non-carcinogens	0.9088
Biodegradation	Not ready biodegradable	0.9726
Rat acute toxicity	3.5280 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9744
hERG inhibition (predictor II)	Non-inhibitor	0.6722

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-08gl-3324900000-5b14332e11a6e68b289b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00xu-0033900000-4107f8db4f801ca53fbf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03k9-0401900000-39d8515ad5f30722422c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0900400000-065a06cba5c3f275d406
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-02fx-0052900000-1dff3e21be93becdbdc1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0910200000-53f3423b78edfc8899bd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-3894200000-440bda33f72e0a0bff8f

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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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Details1. Prostaglandin F2-alpha receptor

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

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]
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]
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]
Neacsu AM: [Receptors involved in the mechanism of action of topical prostaglandines]. Oftalmologia. 2009;53(2):3-7. [Article]
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]
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]
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]
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]
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]
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]
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]
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 February 20, 2024 23:55

Travoprost

Identification

Structure for Travoprost (DB00287)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References