TRAVOPROST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H35F3O6
Molecular Weight	500.5487
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)CCC/C(/[H])=C(/[H])\C[C@]1([H])[C@@]([H])(/C(/[H])=C(\[H])/[C@]([H])(COc2cccc(c2)C(F)(F)F)O)[C@@]([H])(C[C@]1([H])O)O

InChI

InChIKey=MKPLKVHSHYCHOC-AHTXBMBWSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB00287
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_LBL.pdf

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analogue that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoporst free acid is potent and highly selective for the FP prostanoid receptor. Travoprost free acid is a selective FP prostanoid receptor agonist and is believed to reduce intraocular pressure by increasing the drainage of aqueous humor, which is done primarily through increased uveoscleral outflow and to a lesser extent, trabecular outflow facility. Travoprost ophthalmic solution is used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication. Travoprost is known by the brand names of Travatan and Travatan Z, manufactured by Alcon.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid FP receptor 23 Target ID: CHEMBL1987 Sources: http://www.drugbank.ca/drugs/DB00287 \| http://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_LBL.pdf	Agonist 2456		1.4 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_LBL.pdf	Primary		Approved 7997	TRAVATAN Z Approved Use TRAVATAN Z® (travoprost ophthalmic solution) 0.004% is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date 1.15871043E12

C_max

Value	Dose	Co-administered	Analyte	Population
0.018 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021994lbl.pdf	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		FLUPROSTENOL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
0.049 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28437175	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		FLUPROSTENOL plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.039 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28437175	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		FLUPROSTENOL plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
45 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021994lbl.pdf	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		FLUPROSTENOL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
31.8 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28437175	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		FLUPROSTENOL plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% REVIEW https://www.ema.europa.eu/en/documents/scientific-discussion/travatan-epar-scientific-discussion_en.pdf			FLUPROSTENOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.004 % 1 times / 15 min multiple, ophthalmic Overdose Dose: 0.004 %, 1 times / 15 min Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/25259759	unhealthy n = 1 Health Status: unhealthy Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25259759	Disc. AE: Abdominal cramps, Bleeding menstrual heavy... AEs leading to discontinuation/dose reduction: Abdominal cramps (severe, 1 patient) Bleeding menstrual heavy (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25259759
0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf	Disc. AE: Conjunctival hyperemia... AEs leading to discontinuation/dose reduction: Conjunctival hyperemia (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	unhealthy n = 336 Health Status: unhealthy Population Size: 336 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	Disc. AE: Hyperemia eye, Iritis... AEs leading to discontinuation/dose reduction: Hyperemia eye (2 patients) Iritis (1 patient) Dermatitis (1 patient) Upper respiratory infection (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf

AEs

AE	Significance	Dose	Population
Abdominal cramps	severe, 1 patient Disc. AE	0.004 % 1 times / 15 min multiple, ophthalmic Overdose Dose: 0.004 %, 1 times / 15 min Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/25259759	unhealthy n = 1 Health Status: unhealthy Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25259759
Bleeding menstrual heavy	severe, 1 patient Disc. AE	0.004 % 1 times / 15 min multiple, ophthalmic Overdose Dose: 0.004 %, 1 times / 15 min Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / 15 min Sources: https://pubmed.ncbi.nlm.nih.gov/25259759	unhealthy n = 1 Health Status: unhealthy Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25259759
Conjunctival hyperemia	3% Disc. AE	0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/21257lbl.pdf
Dermatitis	1 patient Disc. AE	0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	unhealthy n = 336 Health Status: unhealthy Population Size: 336 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
Iritis	1 patient Disc. AE	0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	unhealthy n = 336 Health Status: unhealthy Population Size: 336 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
Upper respiratory infection	1 patient Disc. AE	0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	unhealthy n = 336 Health Status: unhealthy Population Size: 336 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf
Hyperemia eye	2 patients Disc. AE	0.004 % 1 times / day multiple, ophthalmic Recommended Dose: 0.004 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.004 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf	unhealthy n = 336 Health Status: unhealthy Population Size: 336 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021994s000_MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	esterase 63

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
esterase 63	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21257_Travatan_biopharmr.pdf#page=10	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:746859	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:746859
ChemicalBook	CB5703458	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5703458
MolPort	MolPort-006-167-507	https://www.molport.com/shop/molecule-link/MolPort-006-167-507
ZINC	ZINC000004474682	http://zinc15.docking.org/substances/ZINC000004474682
eMolecules	26757104	https://www.emolecules.com/cgi-bin/more?vid=26757104

PubMed

Title	Date	PubMed
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.	2004 Aug	15321024
Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study.	2008 May	18452763
Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction.	2008 Nov	19038618
A case of melancholic depression induced by beta-blocker antiglaucoma agents.	2008 Oct 6	18837686

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is one drop in the affected eye(s) once daily in the evening. TRAVATAN Z® (travoprost ophthalmic solution) should not be administered more than once daily

Route of Administration: Topical

In Vitro Use Guide

Travoprost stimulated the contraction of isolated non-pregnant female rat uterus in a concentration-dependent manner with the agonist potency EC(50)=1.3+/-0.07 nM

Name

Type

Language

TRAVOPROST

Official Name

English

TRAVOPROST [INN]

Common Name

English

TRAVOPROST [JAN]

Common Name

English

TRAVOPROST [ORANGE BOOK]

Common Name

English

TRAVOPROST [USP MONOGRAPH]

Common Name

English

TRAVATAN

Brand Name

English

NSC-760366

Code

English

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

Systematic Name

English

IZBA

Brand Name

English

TRAVOPROST [MART.]

Common Name

English

(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

Common Name

English

TRAVOPROST [VANDF]

Common Name

English

TRAVOPROST COMPONENT OF DUOTRAV

Brand Name

English

TRAVOPROST [USAN]

Common Name

English

TRAVOPROST [MI]

Common Name

English

AL-6221

Code

English

TRAVOPROST [WHO-DD]

Common Name

English

OTX-TP

Common Name

English

DUOTRAV COMPONENT TRAVOPROST

Brand Name

English

TRAVOPROST [USP-RS]

Common Name

English

TRAVOPROST [EMA EPAR]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175454