Details of the Drug

General Information of Drug (ID: DM20K91)

Drug Name
Travoprost
Synonyms
Travatan; Travatanz; Travatan Alcon; Travatan Z; Travoprost [USAN]; AL6221; AL-6221; Travatan (TN); Travatan Z (TN); Travatan, Travoprost; Travoprost (JAN/USAN/INN); 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; 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; 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; (((1R)-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic acid, 1-methylethyl ester; (+)-Fluprostenol isopropyl ester; (1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-7-(3,5-Dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-5-heptenoic acid, 1-methylethyl ester; (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3R)-3-hydroxy-4-((alpha,alpha,alpha-trifluoro-m-isopropyl-tolyl)oxy)-1-butenyl)cyclopentyl)-5-heptenoate; 5-Heptenoic acid,7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3R)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-,1-methylethyl ester,(5Z)
Indication
Disease Entry ICD 11 Status REF
Ocular hypertension 9C61.01 Approved [1]
Open-angle glaucoma 9C61 Approved [2]
Therapeutic Class
Ophthalmologicals
Affected Organisms
Humans and other mammals
ATC Code
S01EE04: Travoprost
S01EE: Prostaglandin analogues
S01E: ANTIGLAUCOMA PREPARATIONS AND MIOTICS
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 500.5
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 13
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 25 ng/L [3]
Elimination
Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid []
Half-life
The concentration or amount of drug in body reduced by one-half in 45 minutes []
Metabolism
The drug is metabolized via the esterases in the cornea to its biologically active free acid []
Vd
The volume of distribution (Vd) of drug is 2.6 L/kg []
Chemical Identifiers
Formula
C26H35F3O6
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
Canonical SMILES
CC(C)OC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O
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
InChIKey
MKPLKVHSHYCHOC-AHTXBMBWSA-N
Cross-matching ID
PubChem CID
5282226
ChEBI ID
CHEMBL1200799
CAS Number
157283-68-6
UNII
WJ68R08KX9
DrugBank ID
DB00287
TTD ID
D09CZA
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin F2-alpha receptor (PTGFR) TTT2ZAR PF2R_HUMAN Agonist [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Ocular hypertension
ICD Disease Classification 9C61.01
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin F2-alpha receptor (PTGFR) DTT PTGFR 8.25E-02 -0.05 -0.14
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Travoprost FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7102).
3 Electronic Medicines Compendium: Travatan (travoprost) Monograph
4 Prostaglandin subtype-selective and non-selective IOP-lowering comparison in monkeys. J Ocul Pharmacol Ther. 2009 Feb;25(1):1-8.