Drug Information

General Information
Drug ID
DR01121
Drug Name
Taurocholic acid
Synonyms
2-((3-alpha,7-alpha,12-alpha-Trihydroxy-24-oxo-5-be ta-cholan-24-yl)amino)ethanesulfonic acid; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurine; 81-24-3; Acidum cholatauricum; C26H45NO7S; Cholaic acid; Cholic acid taurine conjugate; Cholyltaurine; EINECS 201-336-2; Ethanesulfonic acid, 2-(((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)amino)-; HSDB 832; N-Choloyltaurine; NSC 25505; NSC25505; TAUROCHOLIC ACID; Taurine Cholate; Taurine, N-choloyl-; Taurocholate; Taurocholic acid; UNII-5E090O0G3Z; [3H]taurocholic acid
Drug Type
Small molecular drug
Indication Type 2 diabetes [ICD11:5A11] Terminated [1]
Structure
3D MOL 2D MOL
Formula
C26H45NO7S
Canonical SMILES
CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
InChI
InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1
InChIKey
WBWWGRHZICKQGZ-HZAMXZRMSA-N
CAS Number
CAS 81-24-3
Pharmaceutical Properties Molecular Weight 515.7 Topological Polar Surface Area 153
Heavy Atom Count 35 Rotatable Bond Count 7
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
XLogP
2.2
PubChem CID
6675
PubChem SID
103512877 ,104312745 ,119526221 ,125311155 ,125311164 ,134972658 ,135750992 ,137102321 ,137202600 ,138724705 ,144080928 ,14717827 ,15805741 ,160854684 ,162224002 ,163138205 ,164779365 ,17422067 ,176484548 ,178101267 ,178101268 ,179323898 ,198948969 ,224772447 ,226395830 ,252497719 ,29225628 ,4266393 ,47439969 ,49748546 ,50065243 ,50397873 ,53789715 ,57323632 ,605316 ,8138084 ,8154316 ,828139 ,841389 ,86672 ,92309274 ,93167213
ChEBI ID
CHEBI:28865
TTD Drug ID
D09NTG
DT(s) Transporting This Drug ASBT Transporter Info Apical sodium-dependent bile acid transporter Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
BSEP Transporter Info Bile salt export pump Substrate [4]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [5]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [6]
NTCP Transporter Info Sodium/taurocholate cotransporting polypeptide Substrate [7]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [8]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [9]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [10]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [11]
OATP4A1 Transporter Info Organic anion transporting polypeptide 4A1 Substrate [12]
OSTalpha Transporter Info Organic solute transporter subunit alpha Substrate [13]
OSTbeta Transporter Info Organic solute transporter subunit beta Substrate [13]
Drug-Transporter Activity Data
Drug-Transporter Activity Data ASBT Transporter Info Km =9.4 microM Human embryonic kidney cells (HEK293)-ASBT [2]
ASBT Transporter Info Km =13.3 microM Monkey kidney fibroblast-like cell (COS)1-ASBT [14]
BSEP Transporter Info Km =4.25 microM High five cells-BSEP [15]
NTCP Transporter Info Km =7.9 microM Human cervical cancer cell line (Hela)-NTCP [7]
NTCP Transporter Info Km =6.2 microM Oocytes-NTCP [16]
OATP1A2 Transporter Info Km =15.9 microM Human embryonic kidney cells (HEK293)-OATP1A2 [8]
OATP1A2 Transporter Info Km =64 microM Human liver cancer cells (HepG2)-OATP1A2 [17]
OATP1A2 Transporter Info Km =60 microM Oocytes-OATP1A2 [18]
OATP1B1 Transporter Info Km =33.8 microM Human embryonic kidney cells (HEK293)-OATP1B1 [19]
OATP1B1 Transporter Info Km =13.6 microM Oocytes-OATP1B1 [9]
OATP2B1 Transporter Info Km =71.8 microM Human embryonic kidney cells (HEK293)-OATP2B1 [11]
OATP4A1 Transporter Info Km =14.9 microM Oocytes-OATP4A1 [12]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800033000)
2 Identification of a region of the ileal-type sodium/bile acid cotransporter interacting with a competitive bile acid transport inhibitor. Biochemistry. 2002 Dec 17;41(50):14916-24.
3 Characterization of the role of ABCG2 as a bile acid transporter in liver and placenta. Mol Pharmacol. 2012 Feb;81(2):273-83.
4 Inhibition of transport across the hepatocyte canalicular membrane by the antibiotic fusidate. Biochem Pharmacol. 2002 Jul 1;64(1):151-8.
5 Characterization of the role of polar amino acid residues within predicted transmembrane helix 17 in determining the substrate specificity of multidrug resistance protein 3. Biochemistry. 2003 Aug 26;42(33):9989-10000.
6 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
7 Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J Pharmacol Exp Ther. 1999 Dec;291(3):1204-9.
8 Identification of multiple binding sites for substrate transport in bovine organic anion transporting polypeptide 1a2. Drug Metab Dispos. 2013 Mar;41(3):602-7.
9 Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J Biol Chem. 1999 Jun 11;274(24):17159-63.
10 Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65.
11 Functional characterization of pH-sensitive organic anion transporting polypeptide OATP-B in human. J Pharmacol Exp Ther. 2004 Feb;308(2):438-45.
12 Identification of thyroid hormone transporters in humans: different molecules are involved in a tissue-specific manner. Endocrinology. 2001 May;142(5):2005-12.
13 Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82.
14 Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am J Physiol. 1998 Jan;274(1 Pt 1):G157-69.
15 The human bile salt export pump: characterization of substrate specificity and identification of inhibitors. Gastroenterology. 2002 Nov;123(5):1649-58.
16 Molecular cloning, chromosomal localization, and functional characterization of a human liver Na+/bile acid cotransporter. J Clin Invest. 1994 Mar;93(3):1326-31.
17 Molecular and functional characterization of bile acid transport in human hepatoblastoma HepG2 cells. Hepatology. 1996 May;23(5):1053-60.
18 Molecular and functional characterization of an organic anion transporting polypeptide cloned from human liver. Gastroenterology. 1995 Oct;109(4):1274-82.
19 A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J Biol Chem. 1999 Dec 24;274(52):37161-8.

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