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Substance Name: Probenecid [USP:INN:BAN:JAN]
RN: 57-66-9
UNII: PO572Z7917
InChIKey: DBABZHXKTCFAPX-UHFFFAOYSA-N

Note

  • The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.

Molecular Formula

  • C13-H19-N-O4-S

Molecular Weight

  • 285.3621
 

Classification Codes

  • Adjuvants, Pharmaceutic
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Gout Suppressants
  • Human Data
  • Mutation Data
  • Pharmaceutic Aids
  • Renal Agents
  • Renal Tubular Blocker
  • Tumor Data
  • Uricosuric
  • Uricosuric Agents

Names and Synonyms

Name of Substance

  • Probenecid
  • Probenecid [USP:INN:BAN:JAN]

MeSH Heading

  • Probenecid

Synonyms

  • 4-((Dipropylamino)sulfonyl)benzoic acid
  • 4-(Di-n-propylsulfamoyl)benzoesaeure
  • 4-(Dipropylsulfamoyl)benzoic acid
  • 4-(N,N-Dipropylsulfamoyl)benzoesaeure
  • 4-11-00-00691 (Beilstein Handbook Reference)
  • AI3-50078
  • Apurina
  • Benecid
  • Benemid
  • Benemide
  • Benuryl
  • Benzoic acid, 4-((dipropylamino)sulfonyl)-
  • Benzoic acid, p-(dipropylsulfamoyl)-
  • BRN 2815775
  • CCRIS 3643
  • Col-Probenecid
  • EINECS 200-344-3
  • Ethamide
  • HSDB 3387
  • NCI-C56097
  • NSC 18786
  • p-(Dipropylsulfamoyl)benzoic acid
  • Polycillin-BRB
  • Probalan
  • Probampacin
  • Probecid
  • Proben
  • Probenecid
  • Probenecid acid
  • Probenecida
  • Probenecida [INN-Spanish]
  • Probenecide
  • Probenecide [INN-French]
  • Probenecidum
  • Probenecidum [INN-Latin]
  • Probenemid
  • Probenid
  • Probexin
  • Prolongine
  • Robenecid
  • Synergid R
  • Tubophan
  • UNII-PO572Z7917
  • Uricosid

Systematic Names

  • Benzoic acid, 4-((dipropylamino)sulfonyl)-
  • Benzoic acid, p-(dipropylsulfamoyl)-
  • Probenecid

Superlist Name

  • Probenecid

Mixture Names

  • Colbenemid
  • Polycillin-PRB

Registry Numbers

CAS Registry Number

  • 57-66-9

FDA UNII

  • PO572Z7917

System Generated Number

  • 0000057669

Structure Descriptors

InChI

1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)

InChIKey

DBABZHXKTCFAPX-UHFFFAOYSA-N

Smiles

c1(S(=O)(=O)N(CCC)CCC)ccc(cc1)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 230mg/kg (230mg/kg)   Compilation of LD50 Values of New Drugs.
man TDLo oral 50mg/kg/1W-I (50mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA Journal of Rheumatology. Vol. 13, Pg. 208, 1986.
mouse LD50 oral 1666mg/kg (1666mg/kg)   Drugs in Japan Vol. 6, Pg. 735, 1982.
mouse LDLo intraperitoneal 1gm/kg (1000mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 16, Pg. 1655, 1968.
mouse LDLo intravenous 458mg/kg (458mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo subcutaneous 1156mg/kg (1156mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LD50 intravenous 304mg/kg (304mg/kg)   Drugs in Japan Vol. -, Pg. 1045, 1990.
rat LD50 oral 1600mg/kg (1600mg/kg)   "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 1230, 1989.
rat LDLo intraperitoneal 394mg/kg (394mg/kg)   Compilation of LD50 Values of New Drugs.
rat LDLo subcutaneous 611mg/kg (611mg/kg)   Compilation of LD50 Values of New Drugs.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 195 deg C   EXP
pKa Dissociation Constant 3.4 (none)   EXP
log P (octanol-water) 3.21 (none)   EXP
Water Solubility 27.1 mg/L 25 EST
Vapor Pressure 3.34E-08 mm Hg 25 EST
Henry's Law Constant 1.27E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.47E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.