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157283-68-6 molecular structure
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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

ChemBase ID: 172
Molecular Formular: C26H35F3O6
Molecular Mass: 500.5477096
Monoisotopic Mass: 500.2385735
SMILES and InChIs

SMILES:
FC(F)(F)c1cc(OC[C@H](O)/C=C/[C@@H]2[C@H]([C@@H](O)C[C@H]2O)C/C=C\CCCC(=O)OC(C)C)ccc1
Canonical SMILES:
CC(OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@H]([C@@H]1/C=C/[C@H](COc1cccc(c1)C(F)(F)F)O)O)C
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

Cite this record

CBID:172 http://www.chembase.cn/molecule-172.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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
IUPAC Traditional name
travoprost
Brand Name
Travatan
Travatan Z
Synonyms
Travoprost
Travatan
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester
AL 6221
Travaprost
CAS Number
157283-68-6
PubChem SID
46507637
160963635
PubChem CID
5282226

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.948069  H Acceptors
H Donor LogD (pH = 5.5) 3.839193 
LogD (pH = 7.4) 3.839193  Log P 3.839193 
Molar Refractivity 127.8575 cm3 Polarizability 48.49126 Å3
Polar Surface Area 96.22 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five false 
Log P 4.02  LOG S -4.82 
Solubility (Water) 7.59e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
>16 mg/ml at 25.0°C expand Show data source
Acetonitrile expand Show data source
Chloroform expand Show data source
Dichloromethane expand Show data source
Methanol expand Show data source
Apperance
Colorless Oil expand Show data source
Hydrophobicity(logP)
4.6 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC Selleck Chemicals Selleck Chemicals
DrugBank - DB00287 external link
Item Information
Drug Groups approved
Description 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 F2alpha analogue. [Wikipedia]
Indication Ophthalmic solution 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.
Pharmacology 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.
Toxicity Symptoms of overexposure include irritation to the skin, eyes, nose, throat, and respiratory tract.
Affected Organisms
Humans and other mammals
Biotransformation Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is metabolized to inactive metabolites via beta-oxidation of the α(carboxylic acid) chain to give the 1,2-dinor and 1,2,3,4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13,14 double bond.
Absorption Systemically absorbed when administered to the eye.
Half Life Terminal elimination half-life of travoprost free acid is 45 minutes.
Elimination Less than 2% of the topical ocular dose of travoprost was excreted in the urine within 4 hours as the travoprost free acid.
References
Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. [Pubmed]
Costagliola C, dell'Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. [Pubmed]
Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. [Pubmed]
Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. [Pubmed]
Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - T715600 external link
Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol. Antiglaucoma.
Selleck Chemicals - S1554 external link
Research Area: Cardiovascular Disease
Biological Activity:
Travoprost is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. [1]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lim KS, Nau CB, O'Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. Pubmed
  • • Costagliola C, dell'Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure - part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. Pubmed
  • • Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. Pubmed
  • • Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. Pubmed
  • • Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. Pubmed
  • • Hellberg, M.R., et al.: J. Ocul. Pharmacol. Ther., 17, 421 (2001)
  • • McCue, B.A., et al.: J. Pharm. Biomed. Anal., 28, 199 (2001)
  • • Schuman, J.S., et al.: Am. J. Ophthalmol., 140, 242 (2001)
  • • Carvalho, A.B., et al.: Vet. Ophthalmol., 9, 121 (2001)
  • • http://en.wikipedia.org/wiki/Travoprost
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PATENTS

PATENTS

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