L902688 | CAS#634193-54-7 | PGE2 receptor Agonist

MedKoo Cat#: 532105 | Name: L902688

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-902,688 is a highly potent agonist of the human PGE2 receptor, EP4. L902688 demonstrates a Ki value of 0.38 nM and an EC50 value of 0.6 nM and is >4,000-fold selective for EP4 over other EP and prostanoid receptors. Note: This product is supplied as methanol solution

Chemical Structure

L902688

CAS#634193-54-7

Theoretical Analysis

MedKoo Cat#: 532105

Name: L902688

CAS#: 634193-54-7

Chemical Formula: C21H27F2N5O2

Exact Mass: 419.2133

Molecular Weight: 419.48

Elemental Analysis: C, 60.13; H, 6.49; F, 9.06; N, 16.70; O, 7.63

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 415.00	2 Weeks

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Related CAS #

No Data

Synonym

L902688; L-902688; L 902688.

IUPAC/Chemical Name

(5R)-5-[(1E,3R)-4,4-difluoro-3-hydroxy-4-phenylbut-1-en-1-yl]-1-[6-(1H-1,2,3,4-tetrazol-5-yl)hexyl]pyrrolidin-2-one

InChi Key

WPTLQOYLIXWRNN-SLKVGHROSA-N

InChi Code

InChI=1S/C21H27F2N5O2/c22-21(23,16-8-4-3-5-9-16)18(29)13-11-17-12-14-20(30)28(17)15-7-2-1-6-10-19-24-26-27-25-19/h3-5,8-9,11,13,17-18,29H,1-2,6-7,10,12,14-15H2,(H,24,25,26,27)/b13-11+/t17-,18+/m0/s1

SMILES Code

O=C1N(CCCCCCC2=NN=NN2)[C@@H](/C=C/[C@@H](O)C(F)(F)C3=CC=CC=C3)CC1

Appearance

supplied as methanol solution.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-902688 is a potent, selective and orally active EP4 receptor agonist with a Ki of 0.38 nM and an EC50 of 0.6 nM.

In vitro activity:

This study demonstrates that the selective EP4 agonist L-902,688 increased the number and suppressive activity of MDSCs (myeloid-derived suppressor cells) through arginase-1 and nitric oxide synthase-2. Reference: Front Immunol. 2021 Jul 12;12:695933. https://pubmed.ncbi.nlm.nih.gov/34322123/

In vivo activity:

L-902,688 attenuated pulmonary arterial remodeling in hypoxic PAH (pulmonary arterial hypertension) mice and MCT-induced PAH rats; therefore, we conclude that the selective EP4 agonist L-902,688 reverses vascular remodeling by activating PPARγ. Reference: Am J Physiol Lung Cell Mol Physiol. 2018 Mar 1;314(3):L349-L359. https://pubmed.ncbi.nlm.nih.gov/29146573/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	71.52
	DMSO	30.0	71.52
	Ethanol	30.0	71.52
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.19

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 419.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. van Geffen C, Deißler A, Beer-Hammer S, Nürnberg B, Handgretinger R, Renz H, Hartl D, Kolahian S. Myeloid-Derived Suppressor Cells Dampen Airway Inflammation Through Prostaglandin E2 Receptor 4. Front Immunol. 2021 Jul 12;12:695933. doi: 10.3389/fimmu.2021.695933. PMID: 34322123; PMCID: PMC8311661. 2. Gill SK, Yao Y, Kay LJ, Bewley MA, Marriott HM, Peachell PT. The anti-inflammatory effects of PGE2 on human lung macrophages are mediated by the EP4 receptor. Br J Pharmacol. 2016 Nov;173(21):3099-3109. doi: 10.1111/bph.13565. Epub 2016 Sep 6. PMID: 27460634; PMCID: PMC5056231. 3. Li HH, Hsu HH, Chang GJ, Chen IC, Ho WJ, Hsu PC, Chen WJ, Pang JS, Huang CC, Lai YJ. Prostanoid EP4 agonist L-902,688 activates PPARγ and attenuates pulmonary arterial hypertension. Am J Physiol Lung Cell Mol Physiol. 2018 Mar 1;314(3):L349-L359. doi: 10.1152/ajplung.00245.2017. Epub 2017 Nov 16. PMID: 29146573. 4. Lai YJ, Chen IC, Li HH, Huang CC. EP4 Agonist L-902,688 Suppresses EndMT and Attenuates Right Ventricular Cardiac Fibrosis in Experimental Pulmonary Arterial Hypertension. Int J Mol Sci. 2018 Mar 3;19(3):727. doi: 10.3390/ijms19030727. PMID: 29510514; PMCID: PMC5877588.

In vitro protocol:

In vivo protocol:

1. Li HH, Hsu HH, Chang GJ, Chen IC, Ho WJ, Hsu PC, Chen WJ, Pang JS, Huang CC, Lai YJ. Prostanoid EP4 agonist L-902,688 activates PPARγ and attenuates pulmonary arterial hypertension. Am J Physiol Lung Cell Mol Physiol. 2018 Mar 1;314(3):L349-L359. doi: 10.1152/ajplung.00245.2017. Epub 2017 Nov 16. PMID: 29146573. 2. Lai YJ, Chen IC, Li HH, Huang CC. EP4 Agonist L-902,688 Suppresses EndMT and Attenuates Right Ventricular Cardiac Fibrosis in Experimental Pulmonary Arterial Hypertension. Int J Mol Sci. 2018 Mar 3;19(3):727. doi: 10.3390/ijms19030727. PMID: 29510514; PMCID: PMC5877588.

1: Malty RH, Hudmon A, Fehrenbacher JC, Vasko MR. Long-term exposure to PGE2 causes homologous desensitization of receptor-mediated activation of protein kinase A. J Neuroinflammation. 2016 Jul 11;13(1):181. doi: 10.1186/s12974-016-0645-0. PubMed PMID: 27400965; PubMed Central PMCID: PMC4940832.