Structure of Etrasimod
CAS No.: 1206123-37-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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
4.5
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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 antibacterial agents. Inspired by our recent report on the antibacterial activity of etrasimod, an immunomodulating drug candidate, we prepared a series of etrasimod derivatives by varying substituents on the phenyl ring, altering the central tricyclic aromatic ring, and modifying the carboxyl group. From this series of compounds, indole derivative 24f was identified as the most potent antibacterial 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 etrasimod nor 24f affects S. aureus cell membranes. Importantly, 24f did not induce resistance in S. aureus, representing a significant improvement compared to etrasimod. Finally, the antibacterial activity of etrasimod 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 etrasimod and its derivatives as potential antibacterial candidates for combating infections caused by Gram-positive bacteria.
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Keywords: Antibacterial activity ; Derivatives ; Etrasimod ; MRSA ; Staphylococcus aureus
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Purchased from AmBeed: 1206123-37-6 ; 1360952-35-7 ; 1206124-13-1 ; 957208-65-0 ; 1206124-34-6 ; 957205-24-2 ; 1140461-83-1 ; 1261444-00-1
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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 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
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 << |
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 |
Tags: Etrasimod | APD334 | Carboxylic Acids | GPCR | Organic Building Blocks | Parkinson'S Disease and Alzheimer'S Disease | GPCR/G Protein | 1206123-37-6
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