Details of the Drug

General Information of Drug (ID: DMCUT21)

Drug Name
Ursodeoxycholic acid
Synonyms
Actigall; Antigall; Arsacol; Delursan; Destolit; Deursil; Litursol; Lyeton; Peptarom; Solutrat; UDCA; UDCS; UrSO; Urosiol; Ursacol; Ursobilin; Ursochol; Ursodamor; Ursodeoxycholate; Ursodiol; Ursofalk; Ursolvan; Ursosan; Acide ursodesoxycholique; Acido ursodeossicolico; Acido ursodeossicolico [Italian]; Acido ursodeoxicolico; Acidum ursodeoxycholicum; Deoxyursocholic Acid; Sodium Ursodeoxycholate; Ursacholic Acid; Urso DS; Urso Forte; Ursodeoxy cholic acid; Ursodesoxycholicacid; Ursodexycholic Acid; Ursodiol [USAN]; IU5; U0030; Urso 250; Acide ursodesoxycholique [INN-French]; Acido ursodeoxicolico [INN-Spanish]; Acidum ursodeoxycholicum [INN-Latin]; Actigall (TN); Cholit-ursan; Deursil (TN); Dom-ursodiol c; ISO-URSODEOXYCHOLIC ACID; PHL-ursodiol c; PMS-ursodiol c; U-9000; Urso (TN); Urso Forte (TN); Ursodiol (USP); Ursosan (TN); Ursodeoxycholic acid (JP15/INN); Ursodeoxycholic acid, UDCA, Ursosan, Ursofalk, Urso Forte, Udiliv, Ursodiol; Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)-(9CI); (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid; (3alpha,5beta,7beta,8xi)-3,7-dihydroxycholan-24-oic acid; (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid; 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol; 3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-oic Acid; 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; 3alpha,7beta-Dihydroxy-5beta-cholanic acid; 5beta-Cholan-24-oic acid-3alpha,7beta-diol; 5beta-Cholanic Acid-3alpha,7beta-diol; 7-beta-Hydroxylithocholic acid; 7beta-Hydroxylithocholic acid
Indication
Disease Entry ICD 11 Status REF
Cholelithiasis DC11 Approved [1]
Primary biliary cholangitis DB96.1 Approved [2]
Primary biliary cirrhosis DB96.1 Approved [3]
Colon cancer 2B90.Z Investigative [4]
Therapeutic Class
Cholagogues and Choleretics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 392.6
Logarithm of the Partition Coefficient (xlogp) 4.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [5]
Elimination
0.5% of drug is excreted from urine in the unchanged form [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 38.208 micromolar/kg/day [6]
Chemical Identifiers
Formula
C24H40O4
IUPAC Name
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Canonical SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
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
Cross-matching ID
PubChem CID
31401
ChEBI ID
CHEBI:9907
CAS Number
128-13-2
DrugBank ID
DB01586
TTD ID
D0G3SH
VARIDT ID
DR00615
INTEDE ID
DR2172
ACDINA ID
D00713
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Biliverdin reductase A (BLVRA) TTJBPN3 BIEA_HUMAN Activator [7]
Solute carrier family 23 member 2 (SLC23A2) TTOP832 S23A2_HUMAN Activator [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-hydroxysteroid dehydrogenase (hdhB)
Main DME 		DEOMLHG A4ECA9_9ACTN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
2',3'-cyclic-nucleotide 3'-phosphodiesterase (CNP) OTB8HCED CN37_HUMAN Gene/Protein Processing [10]
ADP/ATP translocase 2 (SLC25A5) OT1XIBMN ADT2_HUMAN Gene/Protein Processing [10]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [11]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [11]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [11]
Alpha-1-acid glycoprotein 2 (ORM2) OTRJGZP8 A1AG2_HUMAN Gene/Protein Processing [10]
AP-2 complex subunit mu (AP2M1) OTQCOSFN AP2M1_HUMAN Gene/Protein Processing [10]
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Gene/Protein Processing [12]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [13]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
Cetyl alcohol E00061 2682 Coating agent; Emollient; Emulsifying agent; Stiffening agent
D&C red no. 28 E00491 6097185 Colorant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF E00255 17730 Colorant
Butyl alcohol E00011 263 Flavoring agent; Solvent
Dibutyl sebacate E00160 7986 Plasticizing agent
Eisenoxyd E00585 56841934 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Hydrogen peroxide E00027 784 Antimicrobial preservative
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Medium-chain triglyceride E00640 Not Available Emollient; Lubricant; Surfactant
Polyethylene glycol 3350 E00652 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000 E00655 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 23 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Ursodeoxycholic acid 300 mg capsule 300 mg Oral Capsule Oral
Ursodeoxycholic acid 250 mg tablet 250 mg Oral Tablet Oral
Ursodeoxycholic acid 500 mg tablet 500 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Management of symptomatic cholelithiasis: a systematic review. Syst Rev. 2022 Dec 12;11(1):267.
2 Primary biliary cholangitis: pathogenesis and therapeutic opportunities. Nat Rev Gastroenterol Hepatol. 2020 Feb;17(2):93-110.
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7104).
4 Design and synthesis of bile acid derivatives and their activity against colon cancer. RSC Med Chem. 2022 Aug 19;13(11):1391-1409.
5 BDDCS applied to over 900 drugs
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Role of vitamin C transporters and biliverdin reductase in the dual pro-oxidant and anti-oxidant effect of biliary compounds on the placental-fetal... Toxicol Appl Pharmacol. 2008 Oct 15;232(2):327-36.
8 Transport of fluorescent chenodeoxycholic acid via the human organic anion transporters OATP1B1 and OATP1B3. J Lipid Res. 2006 Jun;47(6):1196-202.
9 Identification, cloning, heterologous expression, and characterization of a NADPH-dependent 7beta-hydroxysteroid dehydrogenase from Collinsella aerofaciens. Appl Microbiol Biotechnol. 2011 Apr;90(1):127-35.
10 Gene expression profiling of early primary biliary cirrhosis: possible insights into the mechanism of action of ursodeoxycholic acid. Liver Int. 2008 Aug;28(7):997-1010. doi: 10.1111/j.1478-3231.2008.01744.x. Epub 2008 Apr 15.
11 Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. Chem Biol Interact. 2003 Feb 1;143-144:503-13.
12 Hepatic apolipoprotein A-I gene expression in patients with cholesterol gallstones treated with ursodeoxycholic acid. Ann Hepatol. 2002 Apr-Jun;1(2):85-9.
13 Mechanism of apoptotic effects induced selectively by ursodeoxycholic acid on human hepatoma cell lines. World J Gastroenterol. 2007 Mar 21;13(11):1652-8. doi: 10.3748/wjg.v13.i11.1652.