Ursodoxicoltaurine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 462512

CAS#: 14605-22-2

Description: Ursodoxicoltaurine is a neuroprotectant.


Chemical Structure

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Ursodoxicoltaurine
CAS# 14605-22-2

Theoretical Analysis

MedKoo Cat#: 462512
Name: Ursodoxicoltaurine
CAS#: 14605-22-2
Chemical Formula: C26H45NO6S
Exact Mass: 499.2968
Molecular Weight: 499.707
Elemental Analysis: C, 62.49; H, 9.08; N, 2.80; O, 19.21; S, 6.42

Price and Availability

Size Price Availability Quantity
500.0mg USD 225.0 Ready to ship
1.0g USD 380.0 Ready to ship
5.0g USD 760.0 2 Weeks
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Synonym: Ursodoxicoltaurine; Tauroursodeoxycholic Acid, TUDCA

IUPAC/Chemical Name: 2-(3α,7β-dihydroxy-5β-cholan-24-amido)ethane-1- sulfonic acid

InChi Key: BHTRKEVKTKCXOH-LBSADWJPSA-N

InChi Code: InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1

SMILES Code: O[C@@H]1CC[C@@]2(C)[C@@](C[C@H](O)[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCC(NCCS(=O)(O)=O)=O)([H])C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Safety Data Sheet (SDS):

Biological target: Tauroursodeoxycholate (Tauroursodeoxycholic acid) is an endoplasmic reticulum (ER) stress inhibitor. Tauroursodeoxycholate significantly reduces expression of apoptosis molecules, such as caspase-3 and caspase-12. Tauroursodeoxycholate also inhibits ERK.
In vitro activity: As shown in Fig. 3, the percentages of TUNEL-positive apoptotic cells were increased up to 60% in groups exposed to tunicamycin compared with the TUN only group; however, there was no change when cells were exposed to TUDCA alone. As expected, pretreatment with TUDCA reduced the occurrence of apoptosis in tunicamycin-treated DRG neurons (Fig. 3), indicating the neuroprotective role of TUDCA. Reference: Exp Ther Med. 2022 Jun 10;24(2):509. https://pubmed.ncbi.nlm.nih.gov/35837048/
In vivo activity: Compared with the CON group, TUDCA supplementation improved the intestinal morphology by increasing the V/C ratios in jejunum and ileum (P < 0.05) (Fig. 1A, B). In addition, PAS staining results showed that TUDCA supplementation increased the number of goblet cells secreting mucopolysaccharides in jejunum and ileum (P < 0.05, Fig. 1C and D). Furthermore, the expression of TJ proteins, such as OCC and Claudin-1, was higher in jejunum of piglets supplemented with TUDCA (P < 0.05, Fig. 2A, B). Accordingly, the intestinal permeability was reduced, which was manifested by the decreased serum LPS and DAO levels (P < 0.05, Fig. 2C, D). These above results suggested that dietary supplementation of TUDCA enhanced intestinal barrier function of weaned piglets. Reference: J Anim Sci Biotechnol. 2022 Jun 8;13(1):73. https://pubmed.ncbi.nlm.nih.gov/35672805/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 20.01
DMSO 53.0 106.06
DMSO:PBS (pH 7.2) (1:4) 0.2 0.4
Ethanol 50.0 100.06
Water 12.5 25.01

Preparing Stock Solutions

The following data is based on the product molecular weight 499.707 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Chen F, Ge Z, Li N, Yu Z, Wu R, Zhao Y, He X, Cai G. TUDCA protects against tunicamycin-induced apoptosis of dorsal root ganglion neurons by suppressing activation of ER stress. Exp Ther Med. 2022 Jun 10;24(2):509. doi: 10.3892/etm.2022.11436. PMID: 35837048; PMCID: PMC9257946. 2. Kim SY, Kwon YW, Jung IL, Sung JH, Park SG. Tauroursodeoxycholate (TUDCA) inhibits neointimal hyperplasia by suppression of ERK via PKCα-mediated MKP-1 induction. Cardiovasc Res. 2011 Nov 1;92(2):307-16. doi: 10.1093/cvr/cvr219. Epub 2011 Aug 11. PMID: 21840882. 3. Pasha M, Kirschenman R, Wooldridge A, Spaans F, Cooke CM, Davidge ST. The Effect of Tauroursodeoxycholic Acid (TUDCA) Treatment on Pregnancy Outcomes and Vascular Function in a Rat Model of Advanced Maternal Age. Antioxidants (Basel). 2022 Jun 28;11(7):1275. doi: 10.3390/antiox11071275. PMID: 35883766; PMCID: PMC9312116. 4. Song M, Zhang F, Fu Y, Yi X, Feng S, Liu Z, Deng D, Yang Q, Yu M, Zhu C, Zhu X, Wang L, Gao P, Shu G, Ma X, Jiang Q, Wang S. Tauroursodeoxycholic acid (TUDCA) improves intestinal barrier function associated with TGR5-MLCK pathway and the alteration of serum metabolites and gut bacteria in weaned piglets. J Anim Sci Biotechnol. 2022 Jun 8;13(1):73. doi: 10.1186/s40104-022-00713-3. PMID: 35672805; PMCID: PMC9175448.
In vitro protocol: 1. Chen F, Ge Z, Li N, Yu Z, Wu R, Zhao Y, He X, Cai G. TUDCA protects against tunicamycin-induced apoptosis of dorsal root ganglion neurons by suppressing activation of ER stress. Exp Ther Med. 2022 Jun 10;24(2):509. doi: 10.3892/etm.2022.11436. PMID: 35837048; PMCID: PMC9257946. 2. Kim SY, Kwon YW, Jung IL, Sung JH, Park SG. Tauroursodeoxycholate (TUDCA) inhibits neointimal hyperplasia by suppression of ERK via PKCα-mediated MKP-1 induction. Cardiovasc Res. 2011 Nov 1;92(2):307-16. doi: 10.1093/cvr/cvr219. Epub 2011 Aug 11. PMID: 21840882.
In vivo protocol: 1. Pasha M, Kirschenman R, Wooldridge A, Spaans F, Cooke CM, Davidge ST. The Effect of Tauroursodeoxycholic Acid (TUDCA) Treatment on Pregnancy Outcomes and Vascular Function in a Rat Model of Advanced Maternal Age. Antioxidants (Basel). 2022 Jun 28;11(7):1275. doi: 10.3390/antiox11071275. PMID: 35883766; PMCID: PMC9312116. 2. Song M, Zhang F, Fu Y, Yi X, Feng S, Liu Z, Deng D, Yang Q, Yu M, Zhu C, Zhu X, Wang L, Gao P, Shu G, Ma X, Jiang Q, Wang S. Tauroursodeoxycholic acid (TUDCA) improves intestinal barrier function associated with TGR5-MLCK pathway and the alteration of serum metabolites and gut bacteria in weaned piglets. J Anim Sci Biotechnol. 2022 Jun 8;13(1):73. doi: 10.1186/s40104-022-00713-3. PMID: 35672805; PMCID: PMC9175448.

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1: WHO Drug Information, Vol. 34, No. 2, 2020
2. Chen F, Ge Z, Li N, Yu Z, Wu R, Zhao Y, He X, Cai G. TUDCA protects against tunicamycin-induced apoptosis of dorsal root
ganglion neurons by suppressing activation of ER stress. Exp Ther Med. 2022 Jun 10;24(2):509. doi: 10.3892/etm.2022.11436. PMID:
35837048; PMCID: PMC9257946.
3. Kim SY, Kwon YW, Jung IL, Sung JH, Park SG. Tauroursodeoxycholate (TUDCA) inhibits neointimal hyperplasia by suppression
of ERK via PKCα-mediated MKP-1 induction. Cardiovasc Res. 2011 Nov 1;92(2):307-16. doi: 10.1093/cvr/cvr219. Epub 2011 Aug
11. PMID: 21840882.
4. Pasha M, Kirschenman R, Wooldridge A, Spaans F, Cooke CM, Davidge ST. The Effect of Tauroursodeoxycholic Acid (TUDCA)
Treatment on Pregnancy Outcomes and Vascular Function in a Rat Model of Advanced Maternal Age. Antioxidants (Basel). 2022 Jun
28;11(7):1275. doi: 10.3390/antiox11071275. PMID: 35883766; PMCID: PMC9312116.
5. Song M, Zhang F, Fu Y, Yi X, Feng S, Liu Z, Deng D, Yang Q, Yu M, Zhu C, Zhu X, Wang L, Gao P, Shu G, Ma X, Jiang Q,
Wang S. Tauroursodeoxycholic acid (TUDCA) improves intestinal barrier function associated with TGR5-MLCK pathway and the alteration of serum metabolites and gut bacteria in weaned piglets. J Anim Sci Biotechnol. 2022 Jun 8;13(1):73. doi: 10.1186/s40104-
022-00713-3. PMID: 35672805; PMCID: PMC9175448