| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg | |||
| Other Sizes |
| Targets |
Metabolite of Travoprost
15-Keto Travoprost specifically targets the prostaglandin F (FP) receptor, which is a G-protein-coupled receptor expressed in the ciliary body and trabecular meshwork of the eye. As a travoprost metabolite, it retains some degree of affinity for the FP receptor, though its potency is significantly reduced compared to the parent drug due to the oxidation of the 15-hydroxyl group to a ketone. Its primary use is not as a therapeutic agent but as a key biomarker and impurity marker for assessing travoprost stability, degradation, and metabolic profiling. |
|---|---|
| ln Vitro |
15-ketotravoprost (80 µgr/mL) is applied to treat idiopathic hypotrichosis of the eyelashes [1].
In vitro, 15-Keto Travoprost exhibits significantly reduced FP receptor agonist activity compared to travoprost. In functional assays using FP receptor-expressing cells, 15-Keto Travoprost has been shown to have more than 100-fold lower potency in stimulating intracellular calcium mobilization and activating downstream signaling pathways than the parent drug. This metabolite is considered to be largely inactive in terms of prostaglandin-mediated pharmacological effects. It is used primarily as an analytical standard for method validation. |
| ln Vivo |
15-Keto Travoprost is not administered therapeutically in vivo; it is an inactive metabolite formed endogenously by the rapid oxidation of travoprost following ocular administration. In vivo, travoprost is metabolized primarily in the cornea and liver via 15-hydroxyprostaglandin dehydrogenase (15-PGDH), which converts the 15-hydroxyl group to a 15-keto group, yielding 15-keto travoprost. This metabolic inactivation is responsible for the rapid clearance of prostaglandin analogs from the systemic circulation, minimizing systemic side effects.
|
| Enzyme Assay |
For non-cell-based assays, an HPLC-UV or LC-MS/MS method is used for the quantification of 15-Keto Travoprost as an analytical standard. A stock solution of 1 mg/mL is prepared in methanol or acetonitrile. Calibration standards (0.1-500 ng/mL) are prepared by serial dilution in mobile phase (water/acetonitrile, 50:50 with 0.1% formic acid). Samples are analyzed on a C18 reversed-phase column (150 × 4.6 mm, 3.5 um) with a flow rate of 1.0 mL/min at 40degC. Detection is performed by UV absorbance at 210 nm or by tandem mass spectrometry in positive ion mode (MRM transition: 497 → 179).
|
| Cell Assay |
For in vitro cell metabolism studies, human corneal epithelial cells or hepatocytes are cultured in 6-well plates at 37degC. Cells are treated with 1 uM travoprost for 0-24 hours. At specified time points (0, 1, 2, 4, 6, 12, 24 h), culture medium is collected and processed by protein precipitation with acetonitrile. The concentration of 15-Keto Travoprost is quantified by LC-MS/MS as a measure of the metabolic activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH). This assay is used to evaluate the metabolic stability of prostaglandin analogs.
|
| Animal Protocol |
For in vivo animal studies, the pharmacokinetics and metabolism of travoprost are evaluated in New Zealand White rabbits (the standard model for ocular drug delivery). Travoprost ophthalmic solution (0.004%, 50 uL) is topically administered to the eye. At predetermined time points (0.5, 1, 2, 4, 6, 12, 24 h post-dose), aqueous humor samples are collected by anterior chamber paracentesis, and plasma samples are obtained via ear vein puncture. Samples are analyzed by LC-MS/MS for both travoprost and its metabolite, 15-Keto Travoprost. The metabolite is used as a marker of ocular and systemic drug disposition.
|
| ADME/Pharmacokinetics |
15-Keto Travoprost is a major circulating metabolite of travoprost and serves as an important biomarker for the systemic exposure and clearance of the parent drug. As an analytical standard, it is used in method development, validation, and quality control (QC) applications for both the innovator product (Travatan Z) and generic formulations. The compound has low water solubility but is soluble in organic solvents such as ethanol, DMSO, and acetonitrile. It has no therapeutic applications and is supplied strictly for research and analytical testing.
|
| Toxicity/Toxicokinetics |
As an analytical standard for pharmaceutical quality control, toxicology data specific to 15-Keto Travoprost is not required, as it is not administered as a therapeutic agent. The parent drug, travoprost, is well tolerated in clinical use, with the most common adverse events being ocular hyperemia, eye irritation, and changes in eyelash growth. The metabolite is considered to be non-toxic at the concentrations achieved following therapeutic dosing. No specific toxicity data is available for this compound, which is classified as a research-grade impurity standard.
|
| References |
|
| Additional Infomation |
15-Ketofluoroprostol isopropyl ester is a prostaglandin.
15-Keto Travoprost is an important reference standard for regulatory pharmaceutical analysis and is used in the development and quality control of travoprost-containing ophthalmic products. The compound is listed as a specified impurity in the USP and EP monographs for travoprost drug substance, with acceptance criteria typically set at ≤1.0%. The presence of 15-Keto Travoprost in pharmaceutical formulations serves as an indicator of chemical degradation and product stability. This compound is not a therapeutic drug and is not approved for clinical administration. |
| Molecular Formula |
C26H33O6F3
|
|---|---|
| Molecular Weight |
498.53182
|
| Exact Mass |
498.222
|
| CAS # |
404830-45-1
|
| PubChem CID |
10207075
|
| Appearance |
Light yellow to yellow liquid
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
577.5±50.0 °C at 760 mmHg
|
| Flash Point |
303.1±30.1 °C
|
| Vapour Pressure |
0.0±1.7 mmHg at 25°C
|
| Index of Refraction |
1.541
|
| LogP |
3.82
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
9
|
| Rotatable Bond Count |
13
|
| Heavy Atom Count |
35
|
| Complexity |
733
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC(OC(CCC/C=C\C[C@@H]1[C@@H](/C=C/C(COC2C=CC=C(C(F)(F)F)C=2)=O)[C@H](O)C[C@@H]1O)=O)C
|
| InChi Key |
KSDDYCRRTVADFZ-OHDKTVHDSA-N
|
| InChi Code |
InChI=1S/C26H33F3O6/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/h3,5,7-9,12-14,17,21-24,31-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t21-,22-,23+,24-/m1/s1
|
| Chemical Name |
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
|
| Synonyms |
15-Keto Travoprost; 404830-45-1; 15-Oxo travoprost; 15-keto Fluprostenol isopropyl ester; 4U2P9U9Z66; (Z)-Isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxo-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoate; propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate; (5Z,13E)-(9S,11R)-9,11,-Dihydroxy-15-oxo-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-5,13-prostadienoic acid, isopropyl ester;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~200.59 mM)
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0059 mL | 10.0295 mL | 20.0590 mL | |
| 5 mM | 0.4012 mL | 2.0059 mL | 4.0118 mL | |
| 10 mM | 0.2006 mL | 1.0029 mL | 2.0059 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
