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
Primary biliary cirrhosis	DB96.1	Approved	[1], [2]

Therapeutic Class

Cholagogues and Choleretics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

392.6

Topological Polar Surface Area (xlogp)

4.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Elimination: 0.5% of drug is excreted from urine in the unchanged form [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 38.208 micromolar/kg/day [4]

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

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	[5], [6]
Solute carrier family 23 member 2 (SLC23A2)	TTOP832	S23A2_HUMAN	Activator	[5], [6]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporting polypeptide 1B1 (SLCO1B1)	DT3D8F0	SO1B1_HUMAN	Substrate	[7]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Beta-hydroxysteroid dehydrogenase (hdhB)_{Main DME}	DEOMLHG	A4ECA9_9ACTN	Substrate	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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
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⏷ 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	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).
2	Drug information of Ursodeoxycholic acid, 2008. eduDrugs.
3	BDDCS applied to over 900 drugs
4	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
5	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.
6	Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: a population-based cohort study. Hepatology. 2007 Oct;46(4):1131-7.
7	Transport of fluorescent chenodeoxycholic acid via the human organic anion transporters OATP1B1 and OATP1B3. J Lipid Res. 2006 Jun;47(6):1196-202.
8	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.
9	Preclinical Mouse Models To Study Human OATP1B1- and OATP1B3-Mediated Drug-Drug Interactions in Vivo. Mol Pharm. 2015 Dec 7;12(12):4259-69.
10	Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
11	Contribution of OATP1B1 and OATP1B3 to the disposition of sorafenib and sorafenib-glucuronide. Clin Cancer Res. 2013 Mar 15;19(6):1458-66.
12	Identification of drugs and drug metabolites as substrates of multidrug resistance protein 2 (MRP2) using triple-transfected MDCK-OATP1B1-UGT1A1-MRP2 cells. Br J Pharmacol. 2012 Mar;165(6):1836-1847.
13	The effect of SLCO1B115 on the disposition of pravastatin and pitavastatin is substrate dependent: the contribution of transporting activity changes by SLCO1B115. Pharmacogenet Genomics. 2008 May;18(5):424-33.
14	Influence of SLCO1B1, 1B3, 2B1 and ABCC2 genetic polymorphisms on mycophenolic acid pharmacokinetics in Japanese renal transplant recipients. Eur J Clin Pharmacol. 2007 Dec;63(12):1161-9.
15	Rifampicin alters atorvastatin plasma concentration on the basis of SLCO1B1 521T>C polymorphism. Clin Chim Acta. 2009 Jul;405(1-2):49-52.
16	FDA Drug Development and Drug Interactions
17	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. (Target id: 1042).
18	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.