Structure of W146
CAS No.: 909725-61-7
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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.
W146 is a selective antagonist of sphingosine-1-phosphate receptor 1 (S1PR1) with an EC50 value of 398 nM.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 909725-61-7 |
Formula : | C16H27N2O4P |
M.W : | 342.37 |
SMILES Code : | O=C(NC1=CC=CC(CCCCCC)=C1)[C@H](N)CCP(O)(O)=O |
MDL No. : | MFCD16875441 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
BV-2 microglial cells | 250 nM | 1 hour | To investigate the effect of W146 on LPS-induced pSTAT3 expression in BV-2 microglial cells. Results showed that W146 pretreatment could inhibit LPS-induced increase in pSTAT3 expression. | J Headache Pain. 2022 Feb 10;23(1):25 |
DF-1 chicken fibroblasts | 10 µM/mL | 1-hour pretreatment followed by 24-hours infection | To investigate the inhibitory effect of W146 on NDV-induced IL-1β expression, results showed that W146 significantly reduced GM-induced IL-1β protein expression. | Vet Res. 2022 Jul 19;53(1):58 |
Mouse glomerular endothelial cells | 1 µM | 3 days | Chronic S1P1R antagonism significantly reduced HSP27 mRNA expression | Kidney Int. 2014 Apr;85(4):807-23 |
Human umbilical vein endothelial cells | 1 µM | 3 days | Chronic S1P1R antagonism significantly reduced HSP27 mRNA expression | Kidney Int. 2014 Apr;85(4):807-23 |
Rat sensory neurons | 1 µM | 30 minutes | W146, as a selective antagonist for S1PR1, in combination with CAY10444 (S1PR3 antagonist), blocked the S1P-induced enhancement of neuronal excitability. | J Neuroinflammation. 2015 Apr 12;12:70 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Mice | C57BL/6 mice | Intraperitoneal injection | 0.1 mg/kg | Once daily for 3 days | Chronic S1P1R antagonism exacerbated renal and hepatic injury and reduced endothelial HSP27 expression | Kidney Int. 2014 Apr;85(4):807-23 |
C57BL/6J mice | LPS/GalN-induced acute liver failure model | Intraperitoneal injection | 0.1 mg/kg | 10 minutes before and 30 minutes after the LPS/GalN injection | To evaluate the effect of S1PR1 inhibition on acute liver failure. Results showed that S1PR1 inhibition did not significantly improve liver damage but reduced serum TNF-α and IL-6 levels and partially attenuated the phosphorylation of MAPKs signaling. | United European Gastroenterol J. 2016 Oct;4(5):677-685 |
Sprague Dawley rats | Thermal hyperalgesia model | Intraplantar injection | 0.1–0.6 μg | Single injection, 15 minutes before S1P injection | W146 dose-dependently blocked S1P-induced thermal hyperalgesia, while its inactive enantiomer W140 had no such effect | Pain. 2011 Mar;152(3):643-648 |
Rats | Paclitaxel-induced neuropathic pain model | Intrathecal injection | 0.2-2.2 nmol/day | Daily administration for 15 days | W146 blocked and reversed paclitaxel-induced neuropathic pain by inhibiting spinal neuroinflammatory processes | J Biol Chem. 2014 Jul 25;289(30):21082-97 |
Sprague-Dawley rats | BPH model | Intraprostatic injection | 0.5 nmol | 4 weeks | W-146 suppresses testosterone-induced BPH | iScience. 2024 Oct 30;27(12):111290 |
C57BL/6 J mice | Chronic migraine model | Intraperitoneal injection | 1 mg/kg | Once daily for 9 days | To investigate the effect of W146 on chronic NTG-induced hyperalgesia. Results showed that W146 alleviated NTG-induced mechanical and thermal hyperalgesia and suppressed the upregulation of CGRP and c-fos in the TCC. | J Headache Pain. 2022 Feb 10;23(1):25 |
C57BL/6J mice | Pilocarpine-induced status epilepticus model and pentylenetetrazol-induced epilepsy model | Intraperitoneal injection | 1 mg/kg | Once daily for 48 hours | W146 increased the level of tight junction protein, attenuated blood-brain barrier disruption, and reduced seizure severity. | Neural Regen Res. 2023 Aug;18(8):1763-1769 |
Mice | Experimental Autoimmune Encephalomyelitis (EAE) model | Intraperitoneal injection | 1 mg/kg | Daily administration for 14 days | W146 is a selective S1PR1 antagonist used to study the analgesic mechanism of fingolimod. The experiments showed that W146 could block the inhibitory effect of fingolimod on EAE-induced hyperalgesia. | Pain. 2018 Feb;159(2):224-238 |
Syrian hamster | Hibernation model | Intracardial injection | 5 mg/kg | Single dose | Blockade of S1P1 receptor precludes restoration of lymphocyte numbers upon arousal | Proc Natl Acad Sci U S A. 2011 Feb 1;108(5):2052-7 |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
2.92mL 0.58mL 0.29mL |
14.60mL 2.92mL 1.46mL |
29.21mL 5.84mL 2.92mL |
Tags: W146 | W 146 | W-146 | LPL Receptor | Apoptosis | Lysophospholipid Receptor | inhibitor | 909725-61-7 |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
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P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
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P231 | Handle under inert gas. |
P232 | Protect from moisture. |
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P234 | Keep only in original container. |
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P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
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P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
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P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
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P333 | If skin irritation or rash occurs: |
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P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
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P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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