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57-66-9

57-66-9 structure
57-66-9 structure
  • Name: probenecid
  • Chemical Name: probenecid
  • CAS Number: 57-66-9
  • Molecular Formula: C13H19NO4S
  • Molecular Weight: 285.359
  • Catalog: API Antipyretic analgesics Anti-gout medicine
  • Create Date: 2018-02-07 08:00:00
  • Modify Date: 2024-01-02 08:41:44
  • Probenecid is a potent and selective agonist of transient receptor potential vanilloid 2 (TRPV2) channels.
Name probenecid
Synonyms Proben
benacen
Benuryl
EINECS 200-344-3
4-[(di-n-propylamino)sulphonyl]benzoic Acid
4-(Dipropylsulfamoyl)benzoic acid
Apurina
MFCD00038402
probalan
Probecid
4-dipropylsulfamoyl-benzoic acid
Probexin
probenid
4-(N,N-dipropylaminosulphonyl)benzoic acid
benemide
Benzoic acid, 4-[(dipropylamino)sulfonyl]-
Benemid
Probenecid
Description Probenecid is a potent and selective agonist of transient receptor potential vanilloid 2 (TRPV2) channels.
Related Catalog
Target

TRPV2[1]

In Vitro Probenecid efficiently inhibits ATP-dependent active vesicular N-ethylmaleimide glutathione (NEM-GS) uptake by both MRP1 and MRP2. A significant inhibition of the MRP1-ATPase is observed at higher organic anion concentrations. In contrast, the ATPase activity of MRP2 is strongly stimulated by both Probenecid (approximate KACT=250 μM), sulfinpyrazone (KACT=300 μM), and indomethacin (KACT=150 μM), and ATPase activation is even stronger than in the case of NEM-GS. The organic anion activation of the MRP2-ATPase followed bell-shaped curves, with maximum values obtained at about 2 mM for Probenecid, 800 μM for sulfinpyrazone, and 400 μM for indomethacin[2]. Probenecid is an inhibitor of the hTAS2R16, hTAS2R38, and hTAS2R43 bitter taste receptors. Probenecid acts on a subset of TAS2Rs and inhibits through a novel, allosteric mechanism of action. Probenecid is also commonly used to enhance cellular signals in GPCR calcium mobilization assays. Probenecid specifically inhibits the cellular response mediated by the bitter taste receptor hTAS2R16 and provide molecular and pharmacological evidence for direct interaction with this GPCR using a non-competitive (allosteric) mechanism[3].
In Vivo Administration of Probenecid to WT mice results in increased contractility as measured via ejection fraction (EF) relative to EF in control mice given saline. The increased contractility is noted within 5 minutes of the bolus injection with all doses at or above 75 mg/kg (peak change of 5.26±3.35, 8.40±2.80, 7.32±2.52 for 75mg/kg, 100mg/kg and 200mg/kg, respectively). The measured change in contractility as measured at 5 minute intervals (for 30 minutes total) revealed a dose dependent increase in contractility with an estimated EC50 of 49.33 mg/kg. The EF remained at an elevated state for at least 1 hour on subjects (n=5, dose of 200 mg/kg IV) that are evaluated for a longer period of time (average increase in EF over baseline of 8.9±2.57)[1].
Cell Assay HEK-293T cells are transfected with hTAS2R expression constructs using Lipofectamine 2000 in poly-lysine coated, black 384-well plates with clear bottoms and incubated for 22 hours at 37°C. Growth media is removed and cells are washed twice with HBSS containing 20 mM HEPES, then loaded with a calcium indicator dye in HBSS containing 20 mM HEPES (Calcium 4 Assay kit) with or without 1 mM Probenecid. Cells are incubated at 37°C for 1 hour in the presence of both dye and Probenecid, then moved to a Flexstation II-384 set for 32°C. After a 15-minute temperature equilibration (without washout), indicated compounds are injected (at t=~25 seconds) and fluorescence is measured for 100 to 180 seconds, reading every 3 seconds. Data sets are analyzed and represented as % over baseline signal using Prism 5.0 software. For Schild plots, replicates of raw calcium flux values are expressed as % over baseline signal. The mean value at 36 seconds (corresponding to the maximum flux signal) for each concentration of TAS2R ligand in the presence of the indicated concentration of Probenecid is plotted against the log of ligand concentration. Data points are fit using non-linear regression in GraphPad Prism[1].
Animal Admin Mice[1] In order to obtain a dose response curve, male C57 WT (n=39) mice 12-16 weeks of age are anesthetized with isoflurane while intravenous jugular access (IV) is obtained under a microscope. Subsequently, an echocardiographic study with both M-mode and B-mode is obtained in parasternal long axis (PSLAX) as described below. Either saline or different doses of Probenecid (increasing from 2 to 200mg/kg) are injected (bolus IV) for the initial contractility studies in WT mice.
References

[1]. Koch SE, et al. Probenecid: novel use as a non-injurious positive inotrope acting via cardiac TRPV2 stimulation. J Mol Cell Cardiol. 2012 Jul;53(1):134-44.

[2]. Bakos E, et al. Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8.

[3]. Greene TA, et al. Probenecid inhibits the human bitter taste receptor TAS2R16 and suppresses bitter perception of salicin. PLoS One. 2011;6(5):e20123.
Density 1.2±0.1 g/cm3
Boiling Point 438.0±47.0 °C at 760 mmHg
Melting Point 194-196°C
Molecular Formula C13H19NO4S
Molecular Weight 285.359
Flash Point 218.7±29.3 °C
Exact Mass 285.103485
PSA 83.06000
LogP 3.30
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.542
Storage condition Store at RT
Stability Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
Water Solubility <0.1 g/100 mL at 20 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DG9400000
CHEMICAL NAME :
Benzoic acid, p-(dipropylsulfamoyl)-
CAS REGISTRY NUMBER :
57-66-9
BEILSTEIN REFERENCE NO. :
2815775
LAST UPDATED :
199710
DATA ITEMS CITED :
23
MOLECULAR FORMULA :
C13-H19-N-O4-S
MOLECULAR WEIGHT :
285.39
WISWESSER LINE NOTATION :
QVR DSWN3&3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
50 mg/kg/1W-I
TOXIC EFFECTS :
Blood - other hemolysis with or without anemia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
394 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
611 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1666 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1156 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
458 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
230 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
304 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9600 mg/kg/14D-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 gm/kg/13W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38400 mg/kg/14D-C
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
52 gm/kg/13W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
206 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Liver - tumors

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
5 mg/L
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-395,1991 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4171 No. of Facilities: 66 (estimated) No. of Industries: 2 No. of Occupations: 9 No. of Employees: 4059 (estimated) No. of Female Employees: 1675 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R40
Safety Phrases S36/37
RIDADR 3249
WGK Germany 3
RTECS DG9400000
HS Code 2935009090
HS Code 2935009090
Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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title: CAS No. 57-66-9 | Chemsrc address: https://www.chemsrc.com/en/baike/242920.html

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