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Substance Name: Ursodiol [USAN:USP]
RN: 128-13-2
UNII: 724L30Y2QR
InChIKey: RUDATBOHQWOJDD-UZVSRGJWSA-N

Note

  • An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.

Molecular Formula

  • C24-H40-O4

Molecular Weight

  • 392.576
 

Classification Codes

  • Anticholelithogenic
  • Antiviral (COVID-19)
  • Cholagogues and Choleretics
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Ursodeoxycholic acid
  • Ursodeoxycholic acid [INN]
  • Ursodiol [USAN:USP]

MeSH Heading

  • Ursodeoxycholic acid

Synonyms

  • 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol
  • 3,7-Dihydroxycholan-24-oic acid
  • 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid
  • 3-alpha,7-beta-Dihydroxycholanic acid
  • 3-alpha,7-beta-Dioxycholanic acid
  • 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
  • 4-10-00-01604 (Beilstein Handbook Reference)
  • 7-beta-Hydroxylithocholic acid
  • Acide ursodesoxycholique
  • Acide ursodesoxycholique [INN-French]
  • Acido ursodeossicolico
  • Acido ursodeossicolico [Italian]
  • Acido ursodeoxicolico
  • Acido ursodeoxicolico [INN-Spanish]
  • Acidum ursodeoxycholicum
  • Acidum ursodeoxycholicum [INN-Latin]
  • Actigall
  • Arsacol
  • BRN 3219888
  • CCRIS 5502
  • Cholit-ursan
  • Delursan
  • Destolit
  • Deursil
  • EC 204-879-3
  • EINECS 204-879-3
  • Litursol
  • Lyeton
  • NSC 657950
  • NSC 683769
  • Peptarom
  • Solutrat
  • UNII-724L30Y2QR
  • Ursacol
  • UrSO
  • Urso 250
  • Urso DS
  • Urso Forte
  • Ursobilin
  • Ursochol
  • Ursocholic acid, deoxy-
  • Ursodamor
  • Ursodeoxycholate
  • Ursodeoxycholic acid
  • Ursodesoxycholic acid
  • Ursodiol
  • Ursofalk
  • Ursolvan

Systematic Names

  • 5-beta-Cholan-24-oic acid, 3-alpha,7-beta-dihydroxy-
  • Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)- (9CI)
  • Cholan-24-oic acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-
  • Ursodeoxycholic acid

Registry Numbers

CAS Registry Number

  • 128-13-2

FDA UNII

  • 724L30Y2QR

Other Registry Numbers

  • 50809-41-1
  • 80225-86-1

System Generated Number

  • 0000128132

Structure Descriptors

InChI

InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1

InChIKey

RUDATBOHQWOJDD-UZVSRGJWSA-N

Smiles

C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1200mg/kg (1200mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Kiso to Rinsho. Clinical Report. Vol. 9, Pg. 3159, 1975.
mouse LD50 intravenous 240mg/kg (240mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 9, Pg. 3159, 1975.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 9, Pg. 3159, 1975.
mouse LD50 subcutaneous 1gm/kg (1000mg/kg)   "Modern Pharmaceuticals of Japan, IV," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1972Vol. -, Pg. 109, 1972.
rat LD50 intraperitoneal 700mg/kg (700mg/kg)   Bollettino Chimico Farmaceutico. Vol. 126, Pg. 282, 1987.
rat LD50 intravenous 310mg/kg (310mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Kiso to Rinsho. Clinical Report. Vol. 9, Pg. 3159, 1975.
rat LD50 oral 4600mg/kg (4600mg/kg)   Bollettino Chimico Farmaceutico. Vol. 126, Pg. 282, 1987.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 9, Pg. 3159, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 203 deg C   EXP
log P (octanol-water) 3 (none)   EXP
Water Solubility 20 mg/L 20 EXP
Vapor Pressure 3.00E-13 mm Hg 25 EST
Henry's Law Constant 1.41E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.28E-11 cm3/molecule-sec 25 EST

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