関: sodium taurocholate、taurocholic acid

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/27 18:01:11」(JST)

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Taurocholic acid, known also as cholaic acid, cholyltaurine, or acidum cholatauricum, is a deliquescent yellowish crystalline bile acid involved in the emulsification of fats. It occurs as a sodium salt in the bile of mammals. It is a conjugate of cholic acid with taurine. In medical use, it is administered as a cholagogue and choleretic.

Hydrolysis of taurocholic acid yields taurine.

For commercial use, taurocholic acid is manufactured from cattle bile, a byproduct of the meat-processing industry.^[1]

This acid is also one of the many molecules in the body that has cholesterol as its precursor.

Toxicity

LD50 in newborn rats is 380 mg/kg.

References

^ Taurocholic acid, sodium salt at GlycoFineChem.com

UpToDate Contents

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1. B型肝炎ウイルスの特性および感染の病因characteristics of the hepatitis b virus and pathogenesis of infection [show details]
…receptor for HBV (and hepatitis D virus) has been identified as a bile salt transporter, sodium taurocholate cotransporting polypeptide (NTCP), which binds to the pre-S1 region of the HBV envelope . The…
2. D型肝炎ウイルス感染の病因、疫学、自然経過、および臨床症状 pathogenesis epidemiology natural history and clinical manifestations of hepatitis d virus infection [show details]
…the level of HBV replication . HDV replicates at very high levels in hepatocytes . The sodium taurocholate cotransporting polypeptide (NTCP), which is the receptor for hepatitis B virus, has also been…
3. アマトキシンを含むきのこ中毒（タマゴテングダケなど）：臨床症状、診断、治療amatoxin containing mushroom poisoning eg amanita phalloides clinical manifestations diagnosis and treatment [show details]
…hepatocyte membrane proteins such as organic anion transporting polypeptide (OATP) and sodium taurocholate co-transporter (NTCP) concentrates the toxin within the liver cells . Amatoxins have a low volume …
4. D型肝炎ウイルス感染の治療および予防treatment and prevention of hepatitis d virus infection [show details]
…although this needs to be confirmed. HDV entry inhibitors − These agents act upon the sodium taurocholate cotransporting polypeptide (NTCP), which is a receptor shared by HBV and HDV . Myrcludex B…
5. コレラ：臨床的特徴、診断、治療、予防cholera clinical features diagnosis treatment and prevention [show details]
…isolated from stool using selective media such as thiosulfate citrate bile sucrose (TCBS) agar or taurocholate tellurite gelatin agar (TTGA). Once cultured, V. cholerae can be identified by biochemical tests;…

English Journal

Oral delivery of taurocholic acid linked heparin-docetaxel conjugates for cancer therapy.

Khatun Z, Nurunnabi M, Reeck GR, Cho KJ, Lee YK.SourceDepartment of Chemical & Biological Engineering, Korea National University of Transportation, Chungju 380-702, Republic of Korea.
Journal of controlled release : official journal of the Controlled Release Society.J Control Release.2013 Aug 28;170(1):74-82. doi: 10.1016/j.jconrel.2013.04.024. Epub 2013 May 9.
We have synthesized taurocholic acid (TCA) linked heparin-docetaxel (DTX) conjugates for oral delivery of anticancer drug. The ternary biomolecular conjugates formed self-assembly nanoparticles where docetaxel was located inside the core and taurocholic acid was located on the surface of the nanopar
PMID 23665255

Organic anion-transporting polypeptide 1a4 (Oatp1a4) is important for secondary bile acid metabolism.

Zhang Y, Csanaky IL, Selwyn FP, Lehman-McKeeman LD, Klaassen CD.SourceDepartment of Internal Medicine, University of Kansas Medical Center, 3901 Rainbow Boulevard, Kansas City, KS, 66160, USA. Electronic address: yzhang2.kumc@gmail.com.
Biochemical pharmacology.Biochem Pharmacol.2013 Aug 1;86(3):437-45. doi: 10.1016/j.bcp.2013.05.020. Epub 2013 Jun 6.
Organic anion transporting polypeptides (human: OATPs; rodent: Oatps) were thought to have important functions in bile acid (BA) transport. Oatp1a1, 1a4, and 1b2 are the three major Oatp1 family members in rodent liver. Our previous studies have characterized the BA homeostasis in Oatp1a1-null and O
PMID 23747753

Hepatocellular Organic Anion-Transporting Polypeptides (OATPs) and Multidrug Resistance-Associated Protein 2 (MRP2) Are Inhibited by Silibinin.

Wlcek K, Koller F, Ferenci P, Stieger B.SourceDepartment of Clinical Pharmacology and Toxicology, University Hospital Zurich, Rämistrasse 100, 8091 Zurich, Switzerland. katrin.wlcek@usz.ch.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2013 Aug;41(8):1522-8. doi: 10.1124/dmd.113.051037. Epub 2013 May 21.
Silibinin has been reported to be a promising compound for hepatitis C treatment of nonresponders to standard treatment. Although administered silibinin is well tolerated, increased serum bilirubin levels have been observed during high-dose i.v. silibinin therapy. The mechanism of silibinin-induced
PMID 23695864

Japanese Journal

Evaluation of the Effects of Absorption Enhancers on Caco-2 Cell Monolayers by Using a Pore Permeation Model Involving Two Different Sizes

Seki Toshinobu,Hamada Airi,Egawa Yuya [他]
Biological & pharmaceutical bulletin 36(11), 1862-1866, 2013-11
NAID 40019843029

Evaluation of the Effects of Absorption Enhancers on Caco-2 Cell Monolayers by Using a Pore Permeation Model Involving Two Different Sizes

関俊暢,濱田愛里,江川祐哉,八巻努,内田昌希,夏目秀視,木村聡一郎,上田秀雄
Biological and Pharmaceutical Bulletin 36(11), 1862-1866, 2013-11
… We applied a parallel pore permeation model based on the Renkin molecular sieving function by using two different-sized pathways to analyze the permeation-enhancing effects of poly-L-arginine (PLA) or a mixed system of spermine (SPM) and sodium taurocholate (STC). …
NAID 120005368921

Evaluation of the Effects of Absorption Enhancers on Caco-2 Cell Monolayers by Using a Pore Permeation Model Involving Two Different Sizes

Seki Toshinobu,Hamada Airi,Egawa Yuya,Yamaki Tsutomu,Uchida Masaki,Natsume Hideshi,Kimura Soichiro,Ueda Hideo
Biological and Pharmaceutical Bulletin 36(11), 1862-1866, 2013
… We applied a parallel pore permeation model based on the Renkin molecular sieving function by using two different-sized pathways to analyze the permeation-enhancing effects of poly-<span style="font-variant: small-caps;">L</span>-arginine (PLA) or a mixed system of spermine (SPM) and sodium taurocholate (STC). …
NAID 130003382042

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★リンクテーブル★

リンク元	「タウロコール酸」「taurocholic acid」「タウロコール酸塩」
拡張検索	「sodium taurocholate」

「タウロコール酸」

Taurocholic acid
Names
	IUPAC name 2-{[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]amino}ethanesulfonic acid
Identifiers
CAS Registry Number	81-24-3
ChEBI	CHEBI:28865
ChEMBL	ChEMBL224867
ChemSpider	6423
	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 ; Key: WBWWGRHZICKQGZ-HZAMXZRMSA-N ; InChI=1/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; Key: WBWWGRHZICKQGZ-HZAMXZRMBW ;
IUPHAR/BPS	4547
Jmol-3D images	Image
PubChem	6675
	SMILES C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C ;
Properties
Chemical formula	C26H45NO7S
Molar mass	515.7058 g/mol
Melting point	125.0 °C (257.0 °F; 398.1 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references