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Chemical Structure| 1206123-37-6 Chemical Structure| 1206123-37-6

Structure of Etrasimod
CAS No.: 1206123-37-6

Chemical Structure| 1206123-37-6

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Etrasimod is a potent, selective and orally available antagonist of the sphingosine-1-phosphate-1 (S1P1) receptor with an IC50 value of 1.88 nM in CHO cells.

Synonyms: APD334

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Product Citations

Product Citations

Zore, Matej ; San-Martin-Galindo, Paola ; Reigada, Ines ; Hanski, Leena ; Fallarero, Adyary ; Yli-Kauhaluoma, Jari , et al.

Abstract: The emergence of multidrug-resistant bacteria along with a declining pipeline of clinically useful antibiotics has led to the urgent need for the development of more effective agents. Inspired by our recent report on the activity of , an immunomodulating drug candidate, we prepared a series of derivatives by varying substituents on the phenyl ring, altering the central tricyclic aromatic ring, and modifying the carboxyl group. From this series of compounds, derivative 24f was identified as the most potent compound, with the minimum inhibitory concentration (MIC) values between 2.5 and 10 μM against various Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA), S. epidermidis and enterococci. Moreover, 24f exhibited rapid bactericidal activity against S. aureus, low toxicity and hemolytic activity, and a synergistic effect with gentamicin against S. aureus, MRSA, and Enterococcus faecalis. Furthermore, it was shown that neither nor 24f affects S. aureus cell membranes. Importantly, 24f did not induce resistance in S. aureus, representing a significant improvement compared to . Finally, the activity of and 24f against S. aureus and MRSA was confirmed in vivo in a Caenorhabditis elegans infection model. Taken together, our study highlights the value of and its derivatives as potential candidates for combating infections caused by Gram-positive bacteria.

Keywords: activity ; Derivatives ; ; MRSA ; Staphylococcus aureus

Alternative Products

Product Details of Etrasimod

CAS No. :1206123-37-6
Formula : C26H26F3NO3
M.W : 457.48
SMILES Code : O=C(O)C[C@H]1CCC2=C1NC3=C2C=C(OCC4=CC=C(C5CCCC5)C(C(F)(F)F)=C4)C=C3
Synonyms :
APD334
MDL No. :MFCD28502134
InChI Key :MVGWUTBTXDYMND-QGZVFWFLSA-N
Pubchem ID :44623998

Safety of Etrasimod

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Related Pathways of Etrasimod

GPCR

Isoform Comparison

Biological Activity

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT06294925 Colitis, Ulcerative RECRUITING 2027-05-13 Gastroenterologie OpernstraBe,... More >> Kassel, Hessen, 34117, Germany|Praxis Heil und Müller, Andernach, 56626, Germany|MVZ für Gastroenterologie am Bayerischen Platz, Berlin, 10825, Germany|Alb-Donau Klinikum, Blaubeuren, 89143, Germany|MVZ Dachau, Dachau, 85221, Germany|Interdisziplinares Crohn Colitis Centrum, Frankfurt am Main, 60594, Germany|Facharztpraxis für Gastroenterologie, Grevenbroich, 41515, Germany|Studiengesellschaft BSF UG., Halle (Saale), 06108, Germany|Praxis für Gasteroenterologie, Heidelberg, 69115, Germany|Evangelisches Krankenhaus Kalk, Koeln, 51103, Germany|Praxis für Gasteroenterologie Lübeck, Lübeck, 23560, Germany|Klinikum Lüneburg, Lüneburg, 21339, Germany|Internistische Praxengemeinschaft Oldenburg, Oldenburg, 10115, Germany|Magen-Darm-Zentrum Remscheid, Remscheid, 42859, Germany|CED am Rhein, Wesseling, 50389, Germany|Royal Devon and Exeter NHS Foundation Trust., Exeter, Devon, EX2 5DW, United Kingdom|NHS Greater Glasgow and Clyde, Glasgow, Lanarkshire, G4 0SF, United Kingdom|Nottingham University Hospitals NHS Trust, Queens Medical Centre, Nottingham, Nottinghamshire, NG7 2UH, United Kingdom|Oxford University Hospitals NHS Foundation Trust, Oxford, Oxfordshire, OX3 9DU, United Kingdom|Western General Hospital, Edinburgh, Scotland, EH4 2XU, United Kingdom|Cambridge University Hospitals NHS Foundation Trust Gastroenterology, Cambridge, 351404, United Kingdom|Northern Care Alliance NHS Foundation Trust, Greater Manchester, Crumpsall, M8 5RB, United Kingdom|University Hospitals Birmingham NHS Foundation Trust Gastroenterology, Edgbaston, B15 2QD, United Kingdom|Barts Health NHS Trust, The Royal London Hospital, London, E1 1BB, United Kingdom|St. Mark's Hospital, London, HA1 3UJ, United Kingdom|University College London Hospital, London, NW1 2PG, United Kingdom|St Thomas' Hospital - Guy's & St Thomas' NHS Foundation Trust, London, SE1 7EH, United Kingdom|St George's Hospital - St George's Healthcare Nhs Trust, London, SW17 0QT, United Kingdom|Imperial College Healthcare NHS, London, W2 1PG, United Kingdom Less <<
NCT03139032 Inflammatory Bowel Diseases|Sk... More >>in Extra-intestinal Manifestations Less << PHASE2 TERMINATED 2017-12-06 Arena 2001, Leuven, Belgium|Ar... More >>ena 1001, Hamburg, Germany|Arena 3001, Belgrade, Serbia Less <<
NCT05287126 Ulcerative Colitis PHASE2 RECRUITING 2031-08-07 Arkansas Children's (IP Addres... More >>s), Little Rock, Arkansas, 72202, United States|Arkansas Children's, Little Rock, Arkansas, 72202, United States|Valley View Wellness Medical Center, Garden Grove, California, 92845, United States|Loma Linda Children's Hospital, Loma Linda, California, 92354, United States|Loma Linda University Clinical Trial Center, Loma Linda, California, 92354, United States|Loma Linda University Eye Institute, Loma Linda, California, 92354, United States|Loma Linda University Medical Center, Loma Linda, California, 92354, United States|Loma Linda University Pediatric Clinics, Loma Linda, California, 92354, United States|Childrens Hospital of Orange County, Orange, California, 92868, United States|Loma Linda University Children's Hospital Pediatric Specialty Clinics, San Bernardino, California, 92408, United States|University of California San Francisco,, San Francisco, California, 94158, United States|University of California San Francisco, San Francisco, California, 94158, United States|University of California,San Francisco Pediatric ClinicalResearch Center (PCRC), San Francisco, California, 94158, United States|IHS Health Research, Kissimmee, Florida, 34741, United States|Arnold Palmer Hospital - Center for Digestive Health and Nutrition, Orlando, Florida, 32806, United States|Nemours Children's Hospital, Orlando, Florida, 32827, United States|Kissimmee Endoscopy Center, Windermere, Florida, 34741, United States|Children's Center for Digestive Health Care, LLC, Atlanta, Georgia, 30342, United States|University of Chicago Medical Center, Chicago, Illinois, 60637, United States|Boston Children's Hospital, Boston, Massachusetts, 02115, United States|Beaumont Hospital, Royal Oak, Michigan, 48073, United States|William Beaumont Hospital, Royal Oak, Michigan, 48073, United States|Dartmouth Hitchcock Medical Center, Lebanon, New Hampshire, 03756, United States|University of Rochester Medical Center Clinical Research Center, Rochester, New York, 14642, United States|University of Rochester Medical Center, Rochester, New York, 14642, United States|University Hospitals Cleveland Medical Center Rainbow Babies & Children's Hospital, Cleveland, Ohio, 44106, United States|University Hospitals Cleveland Medical Center, Cleveland, Ohio, 44106, United States|Tennessee Eye Care, Knoxville, Tennessee, 37909, United States|East Tennessee Children's Hospital, Knoxville, Tennessee, 37916, United States|Statcare Pulmonary, Knoxville, Tennessee, 37919, United States|GI for Kids, Knoxville, Tennessee, 37922, United States|Tennova, Knoxville, Tennessee, 37934, United States|Advance Clinical Trial PLLC, Abilene, Texas, 79606, United States|DCT - Midwest GI, Abilene, Texas, 79606, United States|Landeskrankenhaus Salzburg, Salzburg, 5020, Austria|University Hospitals Leuven, Leuven, 3000, Belgium|UZ Leuven, Leuven, 3000, Belgium|Tsujinaka Hospital - Kashiwanoha, Kashiwa, Chiba, 277-0871, Japan|Ishii Eye Clinic, Nagareyama-shi, Chiba, 270-0116, Japan|Gunma University Hospital, Maebashi, Gunma, 371-8511, Japan|Hyogo Medical University Hospital, Nishinomiya, Hyogo, 663-8501, Japan|Kinki University - Nara Hospital, Ikoma City, Nara, 630-0293, Japan|Saitama Prefectural Children's Medical Center, Saitama-shi, Saitama, 330-8777, Japan|Jichi Medical University Hospital, Shimotsuke, Tochigi, 329 0498, Japan|Juntendo University Hospital, Bunkyo-ku, Tokyo, 113-8431, Japan|Japanese Red Cross Kyoto Daini Hospital, Kyoto, 602-8026, Japan|Saga University Hospital, Saga, 849-8501, Japan|Toyama Prefectural Central Hospital, Toyama, 930-8550, Japan|Instytut "Pomnik - Centrum Zdrowia Dziecka" (IPCZD) (The Children's Memorial Health Institute), Warsaw, Mazowieckie, 04-730, Poland|Uniwersytecki Szpital Dzieci?cy w Krakowie, Krakow, 30-663, Poland|Twoja Przychodnia - Szczecińskie Centrum Medyczne, Szczecin, 71-434, Poland|Centrum Zdrowia MDM, Warsaw, 00-635, Poland|WIP Warsaw IBD Point Profesor Kierkus, Warsaw, 00-728, Poland|Centrum Zdrowia MDM, Warszawa, 00-189, Poland|Uniwersytecki Szpital Kliniczny im. Jana Mikulicza-Radeckiego we Wroclawiu, Wroclaw, 50-369, Poland|Instytut Centrum Zdrowia Matki Polki, Lodz, ?ódzkie, 93-338, Poland|Cliniq s.r.o., Bratislava, 811 09, Slovakia|Hospital Clinico Universitario de Santiago de Compostela, Santiago de Compostela, A Coruna, 15706, Spain|Consorci Corporacio Sanitaria Parc Tauli, Sabadell, Barcelona, 08208, Spain|Hospital Universitari Vall d'Hebron, Barcelona, 08035, Spain|Hospital Universitari Vall d'Hebron, Barcelona, 08035, Spain|Hospital Reina Sofia, Cordoba, 14004, Spain Less <<
NCT06398626 Colitis, Ulcerative RECRUITING 2027-09-15 Reddy GI Associates, Mesa, Ari... More >>zona, 85206, United States|Amicis Research Center, Valencia, California, 91355, United States|Rocky Mountain Gastroenterology, Littleton, Colorado, 80120, United States|Gastro Florida, Clearwater, Florida, 33756, United States|Gastro Florida, Lutz, Florida, 33558, United States|Best Choice Medical Research Service, Pembroke Pines, Florida, 33024, United States|EBGS Clinical Research Center, Snellville, Georgia, 30078, United States|MGG Group Co., Inc., Chevy Chase Clinical Research, Chevy Chase, Maryland, 20815, United States|Woodholme Gastroenterology Associates PA, Glen Burnie, Maryland, 21061, United States|NYU Langone Health, New York, New York, 10016, United States|University of North Carolina at Chapel Hill, Division of Gastroenterology and Hepatology, Chapel Hill, North Carolina, 27599, United States|Hightower Clinical Trial Services, Oklahoma City, Oklahoma, 73102, United States|BI Research Center, Houston, Texas, 77084, United States|Washington Gastroenterology, Tacoma, Washington, 98405, United States Less <<
NCT06025227 Colitis, Ulcerative AVAILABLE - -
NCT03072953 Pyoderma Gangrenosum PHASE2 TERMINATED 2018-05-22 Westmead Hospital, Westmead, N... More >>ew South Wales, 2145, Australia|Veracity Clinical Research, Woolloongabba, Queensland, 4102, Australia|Eastern Clinical Research Unit, Box Hill, Victoria, 3128, Australia|Royal Melbourne Hospital, Parkville, Victoria, 3050, Australia|Fremantle Dermatology, Fremantle, Western Australia, 6160, Australia|Braemar Day Hospital, Hamilton, New Zealand Less <<
NCT03155932 Primary Biliary Cholangitis PHASE2 TERMINATED 2019-01-31 Gastroenterology and Hepatolog... More >>y, UC Davis Medical Center, Sacramento, California, 95817, United States|Baylor College of Medicine, Houston, Texas, 77030, United States|Texas Liver Institute, San Antonio, Texas, 78215, United States|Swedish Medical Center, Seattle, Washington, 98104, United States|Royal Prince Alfred Hospital, Camperdown, New South Wales, 2050, Australia|Sunshine Coast University Hospital, Birtinya, Queensland, 4575, Australia|Alfred Health, Melbourne, Victoria, 3004, Australia|Auckland City Hospital, Grafton, Auckland, 1023, New Zealand|Christchurch Clinical Studies Trust, Christchurch, 8011, New Zealand Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.19mL

0.44mL

0.22mL

10.93mL

2.19mL

1.09mL

21.86mL

4.37mL

2.19mL

References

 

Historical Records

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