15-keto-17-phenyl trinor Prostaglandin F2α (15-keto-17-phenyl trinor PGF2α) is an F-series prostaglandin (PG) analog that has been approved for use as an ocular antihypertensive agent. Oxidation of the C-15 hydroxyl group and amide hydrolysis of 15-keto-17-phenyl trinor PGF2α produces 15-keto-17-phenyl trinor PGF2α. 15-keto-17-phenyl trinor PGF2α is a potential metabolite of 15-keto-17-phenyl trinor Prostaglandin F2α (15-keto-17-phenyl trinor PGF2α) when administered to animals. 15-keto PG analogs are potential trace impurities in commercial formulations of their corresponding API compounds. Although 15-ketoPG is much less potent than the parent compound, it still produces a small but measurable decrease in IOP (1 mm Hg) in normal cynomolgus monkeys when given at a dose of 1 μg/eye. 15-Ketolatanoprost (15-keto-17-phenyl-13,14-dihydrotrimethyl PGF2α isopropyl ester) is a miotic agent in normal cat eyes, reducing pupil diameter by 8 mm at a dose of 5 μg/eye. Again, it is less potent than many other F-type PGs; for example, PGF2α produces this degree of miosis at doses below 1 μg/eye.

Physicochemical Properties

Molecular Formula	C23H30O5
Molecular Weight	386.48
Exact Mass	386.209
CAS #	949564-89-0
PubChem CID	52193985
Appearance	Typically exists as solid at room temperature
Density	1.2±0.1 g/cm3
Boiling Point	594.2±50.0 °C at 760 mmHg
Flash Point	327.2±26.6 °C
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.608
LogP	1.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	11
Heavy Atom Count	28
Complexity	547
Defined Atom Stereocenter Count	4
SMILES	C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/C(=O)CCC2=CC=CC=C2)C/C=C\CCCC(=O)O)O
InChi Key	HHEYLKRDELKWGI-RKJYIPPQSA-N
InChi Code	InChI=1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,19-22,25-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t19-,20-,21+,22-/m1/s1
Chemical Name	(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid
Synonyms	15-keto-17-phenyl trinor PGF2α
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)

Biological Activity

References

[1]. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17(8), 691-704 (1992).

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.5875 mL	12.9373 mL	25.8746 mL
	5 mM	0.5175 mL	2.5875 mL	5.1749 mL
	10 mM	0.2587 mL	1.2937 mL	2.5875 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.