Travoprost

Travoprost

Clinical data
Trade names	Travatan
AHFS/Drugs.com	Monograph
MedlinePlus	a602027
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (eye drops)
ATC code	S01EE04 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Activation by ester hydrolysis, deactivation by beta oxidation, OH-oxidation, double bond reduction
Onset of action	2 hours
Biological 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
ECHA InfoCard	100.207.141
Chemical and physical data
Formula	C26H35F3O6
Molar mass	500.548 g/mol
3D model (Jmol)	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?)

Travoprost ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a synthetic prostaglandin analog (or more specifically, an analog of prostaglandin F_2α) that works by increasing the outflow of aqueous fluid from the eyes. It is also known by the brand names of Travatan and Travatan Z, manufactured by Alcon.

Possible side effects are:

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.

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).

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 with a terminal half-life of 45 minutes.