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Substance Name: Carbenoxolone [INN:BAN]
RN: 5697-56-3
UNII: MM6384NG73
InChIKey: OBZHEBDUNPOCJG-WBXJDKIVSA-N

Note

  • An agent derived from licorice root. It is used for the treatment of digestive tract ulcers, especially in the stomach. Antidiuretic side effects are frequent, but otherwise the drug is low in toxicity.

Molecular Formula

  • C34-H50-O7

Molecular Weight

  • 570.762
 

Classification Codes

  • Anti-Ulcer Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Carbenoxolone
  • Carbenoxolone [INN:BAN]

MeSH Heading

  • Carbenoxolone

Synonyms

  • 3-beta-(3-Carboxypropionyloxy)-11-oxo-olean-12-en-30-oic acid
  • 3beta-(3-Carboxypropionyloxy)-11-oxo-olean-12-en-30-saeure
  • 3beta-Hydroxy-11-oxoolean-12-en-30-saeure hydogensuccinat
  • Biogastrone
  • Bioral
  • Carbenoxolona
  • Carbenoxolona [INN-Spanish]
  • Carbenoxolone
  • Carbenoxolonum
  • Carbenoxolonum [INN-Latin]
  • EINECS 227-174-2
  • UNII-MM6384NG73

Systematic Names

  • Carbenoxolone
  • Olean-12-en-29-oic acid, 3-(3-carboxy-1-oxopropoxy)-11-oxo-, (3beta,20beta)-
  • Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-, hydrogen succinate

Registry Numbers

CAS Registry Number

  • 5697-56-3

FDA UNII

  • MM6384NG73

Other Registry Numbers

  • 108064-10-4
  • 13020-80-9
  • 60093-85-8
  • 885512-34-5
  • 906421-35-0

Related Registry Number

  • 7421-40-1 (di-hydrochloride salt)

System Generated Number

  • 0005697563

Structure Descriptors

InChI

1S/C34H50O7/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40)/t21-,23-,24-,27+,30+,31-,32-,33+,34+/m0/s1

InChIKey

OBZHEBDUNPOCJG-WBXJDKIVSA-N

Smiles

C1([C@H]2[C@@]([C@@]3(C([C@@H]4[C@@](CC[C@@](C4)(C(O)=O)C)(C)CC3)=C1)C)(CC[C@@H]1[C@@]2(CC[C@@H](C1(C)C)OC(CCC(O)=O)=O)C)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 371mg/kg (371mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 323, 1980.
dog LD50 subcutaneous 1060mg/kg (1060mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 323, 1980.
man TDLo oral 120mg/kg/56D- (120mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: MUSCLE WEAKNESS
British Medical Journal. Vol. 2, Pg. 150, 1976.
mouse LD50 intravenous 290mg/kg (290mg/kg)   United States Patent Document. Vol. #4363816,
mouse LD50 oral 1400mg/kg (1400mg/kg)   United States Patent Document. Vol. #4224327,
rat LD50 intraperitoneal 128mg/kg (128mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 323, 1980.
rat LD50 oral 2450mg/kg (2450mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 323, 1980.
rat LD50 subcutaneous 1720mg/kg (1720mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 19, Pg. 323, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 292.5 deg C   EXP
log P (octanol-water) 7.060 (none)   EST
Atmospheric OH Rate Constant 1.08E-10 cm3/molecule-sec 25 EST

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