L902688
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532105

CAS#: 634193-54-7

Description: 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

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L902688
CAS# 634193-54-7

Theoretical Analysis

MedKoo Cat#: 532105
Name: L902688
CAS#: 634193-54-7
Chemical Formula: C21H27F2N5O2
Exact Mass: 419.21
Molecular Weight: 419.477
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 2 Weeks
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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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. 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

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.

Recalculate based on batch purity %
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: 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.
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.

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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.