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
• Drug Type: Small molecular drug
• #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: CHEBI:746859
  CAS Number: 157283-68-6
  DrugBank ID: DB00287
  TTD ID: D09CZA

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 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

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.