Name | 3'-Carbamoylbiphenyl-3-yl cyclohexylcarbamate |
Synonyms | URB597 URB-597 KDS-4103 URB 597 NEW FAAH inhibitor FAAH INHIBITOR II FATOSTATIN A, 125B11 3'-Carbamoylbiphenyl-3-yl cyclohexylcarbamate 3-(3-carbaMoylphenyl)phenyl N-cyclohexylcarbaMate 3'-CarbaMoyl-[1,1'-biphenyl]-3-yl cyclohexylcarbaMate N-cyclohexylcarbamic acid [3-(3-carbamoylphenyl)phenyl] ester N-Cyclohexylcarbamic acid 3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl ester carbamic acid, N-cyclohexyl-, 3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl ester KDS 4103 N-Cyclohexylcarbamic acid 3'-(aminocarbonyl)[1,1'-biphenyl]-3-yl ester |
CAS | 546141-08-6 |
EINECS | 637-274-1 |
InChI | InChI=1/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24) |
Molecular Formula | C20H22N2O3 |
Molar Mass | 338.4 |
Density | 1.23 |
Boling Point | 533.2±50.0 °C(Predicted) |
Flash Point | 276.3°C |
Solubility | Soluble in DMSO (~14 mg/ml), DMF (~10 mg/ml), 1:1 DMF:PBS(pH 7.2) (500 ug/ml), 1:2 DMS |
Vapor Presure | 1.9E-11mmHg at 25°C |
Appearance | powder |
Color | white |
pKa | 11.74±0.20(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
Refractive Index | 1.617 |
MDL | MFCD05863934 |
Use | A cell permeable carbamate and potent inhibitor of fatty acid amide hydrolase (FAHH) |
In vitro study | Urb 597 binds to the hydrophobic pocket and catalytic core region of the FAAH, attaching the active site residue to the FAAH's membrane surface. URB597 acts on rat meninges and Inhibits FAAH activity with an IC50 of 4.6 nM. URB597 acts on human liver microsomes and Inhibits FAAH activity with an IC50 of 3 nM. URB597 acts on primary rat microglia at concentrations of 10 µm or 20 µm, reducing the LPS-induced enzymes cyclooxygenase 2(COX2) and inducible nitric oxide synthase (iNOS; NOS2) the expression of the inflammatory mediators prostaglandin E2 (PGE2) and the release of nitric oxide (NO) are subsequently reduced. URB597 concentration of 100 μm, causing Ca |
In vivo study | URB597 was injected intraperitoneally at a dose of 0.3 mg/kg to treat the meninges of rats and inhibit [URB597 at a dose of 0.3 mg/kg to act on inflammatory and painful rats, reduces allodynia and hyperalgesia through analgesia mediated by cannabinoid CB1 and CB2 receptors. URB597 alleviated chronic mild stress-induced weight gain and decreased glucose uptake by inhibiting brain FAAH activity in rats treated intraperitoneally with 0.3 mg/kg daily for 5 weeks. URB597 administered intraperitoneally at a dose of 0.3 mg/kg in female rats reversed most of the depression-like symptoms induced by adolescent THC treatment. |
Hazard Symbols | N - Dangerous for the environment |
Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
UN IDs | UN 3077 9/PG 3 |
WGK Germany | 3 |
biological activity | URB597 is an oral bioeffective FAAH inhibitor with IC50 of 4.6 nM and no inhibitory activity on other ephedrine-related targets. Phase 1. URB597 (KDS-4103) is an oral bioeffective FAAH inhibitor with IC50 of 4.6 nM and no inhibitory activity on other ephedrine-related targets. Phase 1. |
Target | Value |
FAAH | 4.6 nM |