Travoprost

S01E - Antiglaucoma preparations and miotics ATC S01EE04 Small molecule approved 2001 Topical Prodrug

Active form: Fluprostenol.

JFDA label: Travatan Eye Drops

Mechanism of Action

Agonist of Prostaglandin F2-alpha receptor — Prostanoid FP receptor agonist

Target	Action	Gene / class
Prostaglandin F2-alpha receptor efficacy	AGONIST	PTGFR

Indications

Approved

Elevated intraocular pressure

Contraindications

Source: Lexicomp

Additional contraindications (not in US labeling): Hypersensitivity to travoprost or any component of the formulation Absolute
There are no contraindications listed in the manufacturer’s labeling Absolute
pregnancy or women attempting to become pregnant Absolute

Adverse Reactions

Very Common >10%Common 1–10%Uncommon 0.1–1% Rare 0.01–0.1%Very Rare <0.01%Not Known

Cardiac disorders (5)

Common Angina pectoris · bradycardia · chest pain · hypertension · hypotension

Nervous system disorders (5)

Common anxiety · depression · Foreign body sensation of eye · headache · pain

Renal and urinary disorders (3)

Common Prostatic disease · urinary incontinence · urinary tract infection

Immune system disorders (1)

Common Hypersensitivity reaction

Metabolism and nutrition disorders (1)

Common Hypercholesterolemia

Gastrointestinal disorders (2)

Common Dyspepsia · gastrointestinal distress

Skin and subcutaneous tissue disorders (2)

Common Hyperpigmentation of eyelashes · increased growth in number of eyelashes

Musculoskeletal and connective tissue disorders (2)

Common Arthritis · back pain

Eye disorders (21)

Common blepharitis · blurred vision · cataract · conjunctivitis · corneal staining · crusting of eyelid · Decreased visual acuity · dry eye syndrome · eye discomfort · eye pain · eye pruritus · hyperpigmentation of eyelids · increased eyelash length · increased eyelash thickness · iris discoloration · keratitis · lacrimation · ophthalmic inflammation · photophobia · subconjunctival hemorrhage · visual disturbance

Infections and infestations (1)

Common Infection

Other (1)

Very Common Ophthalmic: Ocular hyperemia

Respiratory, thoracic and mediastinal disorders (3)

Common Bronchitis · flu-like symptoms · sinusitis

Dosing

Source: Lexicomp

Elevated intraocular pressure: Ophthalmic: Instill 1 drop into affected eye(s) once daily in the evening; do not exceed once-daily dosing (may decrease IOP-lowering effect).

(For additional information see "Travoprost: Pediatric drug information") Elevated intraocular pressure: Adolescents ≥16 years: Ophthalmic: Refer to adult dosing.

Refer to adult dosing.

There are no dosage adjustments provided in the manufacturer's labeling; dosage adjustments are unlikely due to low systemic absorption.

Warnings & Precautions

Source: Lexicomp

Bacterial keratitis

Inadvertent contamination of multiple-dose ophthalmic solutions has caused bacterial keratitis.

Ocular effects

May permanently change/increase brown pigmentation of the iris, the eyelid skin, and eyelashes. In addition, may increase the length, thickness, and/or number of eyelashes (may vary between eyes); changes occur slowly and may not be noticeable for months or years. Long-term consequences and potential injury to eye are not known. Disease-related concerns:

Ocular disease

Use with caution in patients with intraocular inflammation (eg, uveitis), aphakic patients, pseudophakic patients with a torn posterior lens capsule, or patients with risk factors for macular edema. Safety and efficacy have not been determined for use in patients with angle-closure-, inflammatory-, or neovascular glaucoma. Special populations:

Contact lens wearers

Remove contact lens prior to instillation; may reinsert 15 minutes following administration.

Pediatric

Use in pediatric patients (

Pregnancy & Lactation

Pregnancy

FDA category C

Adverse events have been observed in animal reproduction studies following systemic administration. If ophthalmic agents are needed during pregnancy, the minimum effective dose should be used in combination with punctual occlusion to decrease potential exposure to the fetus (Samples 1988).

Lactation

It is not known if travoprost is present in breast milk. The manufacturer recommends that caution be exercised when administering travoprost to nursing women.

Chemistry & Properties

Formula	C26H35F3O6
Molecular weight	500.55 g/mol
IUPAC name	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
CAS	157283-68-6
PubChem CID	5282226
InChIKey	`MKPLKVHSHYCHOC-AHTXBMBWSA-N`
logP	4.43 (XLogP 4.1)
Polar surface area	96.22 Å²
H-bond acceptors / donors	6 / 3
Drug-likeness (QED)	0.22
Lipinski violations	1

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

Biology & Pharmacokinetics

Pharmacokinetics predicted

Bioavailability	70.0%
Half-life	0.767 h
Volume of distribution	1.642 L/kg
Protein binding	92.9%
BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP1A2	Inhibitor	—
CYP2C8	Inhibitor	—
CYP2C9	Inhibitor	—
CYP3A4	Inhibitor	—

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP2B1 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)

Registered Products (3)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Travoprost Rafarm	Injection 40 mcg/ml	2.5 ml	Sun Set Drug Store	3.160
Travatan Eye Drops	Ophthalmic Solution 0.004 %	2.5 ml	The Jordan Drugstore Co	4.520
Duotrav	Injection 40 mcg/ml, 5 mg/ml	2.5 ml	The Jordan Drugstore Co	5.840