Norucholic acid | CAS# 99697-24-2 | Biochemical

MedKoo Cat#: 574263 | Name: Norucholic acid

Description:

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

Norucholic acid is a Ursodeoxycholic Acid derivative. It is superior to Ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice.

Chemical Structure

Norucholic acid

CAS#99697-24-2

Theoretical Analysis

MedKoo Cat#: 574263

Name: Norucholic acid

CAS#: 99697-24-2

Chemical Formula: C23H38O4

Exact Mass: 378.2770

Molecular Weight: 378.55

Elemental Analysis: C, 72.98; H, 10.12; O, 16.91

Price and Availability

Size	Price	Availability
1mg	USD 250.00	2 Weeks
5mg	USD 450.00	2 Weeks
10mg	USD 850.00	2 Weeks
25mg	USD 1,850.00	2 Weeks

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Synonym

24-nor-Ursodeoxycholic acid; Norucholic acid; Norursodeoxycholic Acid; 24-Norursodeoxycholic acid

IUPAC/Chemical Name

(3R)-3-((3S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)butanoic acid

InChi Key

QYYDXDSPYPOWRO-PFFZYYQLSA-N

InChi Code

InChI=1S/C23H38O4/c1-13(10-20(26)27)16-4-5-17-21-18(7-9-23(16,17)3)22(2)8-6-15(24)11-14(22)12-19(21)25/h13-19,21,24-25H,4-12H2,1-3H3,(H,26,27)/t13-,14?,15+,16-,17+,18+,19+,21+,22+,23-/m1/s1

SMILES Code

O[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@H](C)CC(O)=O)CC[C@@]4([H])[C@]3([H])[C@@H](O)CC2C1

Appearance

Off-White to Pale Yellow Solid

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

DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

24-norursodeoxycholic acid (Norucholic acid) is a side chain-shortened C23 homologue of UDCA and has shown potent anti-cholestatic, anti-inflammatory and anti-fibrotic properties.

In vitro activity:

The role of norUDCA in inducing autophagy, autophagy-mediated degradation of α1ATZ and the role of AMPK in norUDCA-induced autophagy were examined in the current report. NorUDCA promoted disposal of α1ATZ via autophagy-mediated degradation of α1ATZ in HTOZ cells. Activation of AMPK was required for norUDCA-induced autophagy and α1ATZ degradation. Reference: PLoS One. 2018 Aug 1;13(8):e0200897. https://pubmed.ncbi.nlm.nih.gov/30067827/

In vivo activity:

Mdr2(-/-) mice were fed a diet containing 24-norUrsodeoxycholic acid (0.5% wt/wt) or ursodeoxycholic acid (0.5% wt/wt) as a clinical comparator for 4 weeks; controls received standard chow. 24-norUrsodeoxycholic acid markedly improved liver tests and liver histology and significantly reduced hydroxyproline content and the number of infiltrating neutrophils and proliferating hepatocytes and cholangiocytes. Reference: Gastroenterology. 2006 Feb;130(2):465-81. https://pubmed.ncbi.nlm.nih.gov/16472600/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	132.08

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 378.55 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.

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. Tang Y, Blomenkamp KS, Fickert P, Trauner M, Teckman JH. NorUDCA promotes degradation of α1-antitrypsin mutant Z protein by inducing autophagy through AMPK/ULK1 pathway. PLoS One. 2018 Aug 1;13(8):e0200897. doi: 10.1371/journal.pone.0200897. PMID: 30067827; PMCID: PMC6070232. 2. Sombetzki M, Fuchs CD, Fickert P, Österreicher CH, Mueller M, Claudel T, Loebermann M, Engelmann R, Langner C, Sahin E, Schwinge D, Guenther ND, Schramm C, Mueller-Hilke B, Reisinger EC, Trauner M. 24-nor-ursodeoxycholic acid ameliorates inflammatory response and liver fibrosis in a murine model of hepatic schistosomiasis. J Hepatol. 2015 Apr;62(4):871-8. doi: 10.1016/j.jhep.2014.11.020. Epub 2014 Nov 21. PMID: 25463533; PMCID: PMC4368108. 3. Truong JK, Li J, Li Q, Pachura K, Rao A, Gumber S, Fuchs CD, Feranchak AP, Karpen SJ, Trauner M, Dawson PA. Active enterohepatic cycling is not required for the choleretic actions of 24-norUrsodeoxycholic acid in mice. JCI Insight. 2023 Mar 22;8(6):e149360. doi: 10.1172/jci.insight.149360. PMID: 36787187. 4. Fickert P, Wagner M, Marschall HU, Fuchsbichler A, Zollner G, Tsybrovskyy O, Zatloukal K, Liu J, Waalkes MP, Cover C, Denk H, Hofmann AF, Jaeschke H, Trauner M. 24-norUrsodeoxycholic acid is superior to ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice. Gastroenterology. 2006 Feb;130(2):465-81. doi: 10.1053/j.gastro.2005.10.018. PMID: 16472600.

In vitro protocol:

In vivo protocol:

1. Truong JK, Li J, Li Q, Pachura K, Rao A, Gumber S, Fuchs CD, Feranchak AP, Karpen SJ, Trauner M, Dawson PA. Active enterohepatic cycling is not required for the choleretic actions of 24-norUrsodeoxycholic acid in mice. JCI Insight. 2023 Mar 22;8(6):e149360. doi: 10.1172/jci.insight.149360. PMID: 36787187. 2. Fickert P, Wagner M, Marschall HU, Fuchsbichler A, Zollner G, Tsybrovskyy O, Zatloukal K, Liu J, Waalkes MP, Cover C, Denk H, Hofmann AF, Jaeschke H, Trauner M. 24-norUrsodeoxycholic acid is superior to ursodeoxycholic acid in the treatment of sclerosing cholangitis in Mdr2 (Abcb4) knockout mice. Gastroenterology. 2006 Feb;130(2):465-81. doi: 10.1053/j.gastro.2005.10.018. PMID: 16472600.

This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Fri Oct 30 10:48:41 2020 Search: 24-Norursodeoxycholic acid 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: Zhangdi HJ, Su SB, Wang F, Liang ZY, Yan YD, Qin SY, Jiang HX. Crosstalk network among multiple inflammatory mediators in liver fibrosis. World J Gastroenterol. 2019 Sep 7;25(33):4835-4849. doi: 10.3748/wjg.v25.i33.4835. PMID: 31543677; PMCID: PMC6737310. 2: Traussnigg S, Schattenberg JM, Demir M, Wiegand J, Geier A, Teuber G, Hofmann WP, Kremer AE, Spreda F, Kluwe J, Petersen J, Boettler T, Rainer F, Halilbasic E, Greinwald R, Pröls M, Manns MP, Fickert P, Trauner M; Austrian/German NAFLD- norUDCA study group. Norursodeoxycholic acid versus placebo in the treatment of non-alcoholic fatty liver disease: a double-blind, randomised, placebo- controlled, phase 2 dose-finding trial. Lancet Gastroenterol Hepatol. 2019 Oct;4(10):781-793. doi: 10.1016/S2468-1253(19)30184-0. Epub 2019 Jul 22. PMID: 31345778. 3: Cabrera D, Arab JP, Arrese M. UDCA, NorUDCA, and TUDCA in Liver Diseases: A Review of Their Mechanisms of Action and Clinical Applications. Handb Exp Pharmacol. 2019;256:237-264. doi: 10.1007/164_2019_241. PMID: 31236688. 4: Blokker BA, Maijo M, Echeandia M, Galduroz M, Patterson AM, Ten A, Philo M, Schungel R, Gutierrez-de Juan V, Halilbasic E, Fuchs C, Le Gall G, Milkiewicz M, Milkiewicz P, Banales JM, Rushbrook SM, Mato JM, Trauner M, Müller M, Martínez- Chantar ML, Varela-Rey M, Beraza N. Fine-Tuning of Sirtuin 1 Expression Is Essential to Protect the Liver From Cholestatic Liver Disease. Hepatology. 2019 Feb;69(2):699-716. doi: 10.1002/hep.30275. PMID: 30229970; PMCID: PMC6492079. 5: Tang Y, Blomenkamp KS, Fickert P, Trauner M, Teckman JH. NorUDCA promotes degradation of α1-antitrypsin mutant Z protein by inducing autophagy through AMPK/ULK1 pathway. PLoS One. 2018 Aug 1;13(8):e0200897. doi: 10.1371/journal.pone.0200897. PMID: 30067827; PMCID: PMC6070232. 6: Jansen PLM. New therapies target the toxic consequences of cholestatic liver disease. Expert Rev Gastroenterol Hepatol. 2018 Mar;12(3):277-285. doi: 10.1080/17474124.2018.1424538. Epub 2018 Jan 10. PMID: 29310470. 7: Krones E, Pollheimer MJ, Rosenkranz AR, Fickert P. Cholemic nephropathy - Historical notes and novel perspectives. Biochim Biophys Acta Mol Basis Dis. 2018 Apr;1864(4 Pt B):1356-1366. doi: 10.1016/j.bbadis.2017.08.028. Epub 2017 Aug 26. PMID: 28851656. 8: Chazouillères O. 24-Norursodeoxycholic acid in patients with primary sclerosing cholangitis: A new "urso saga" on the horizon? J Hepatol. 2017 Sep;67(3):446-447. doi: 10.1016/j.jhep.2017.06.024. Epub 2017 Jul 1. PMID: 28676324. 9: Fickert P, Hirschfield GM, Denk G, Marschall HU, Altorjay I, Färkkilä M, Schramm C, Spengler U, Chapman R, Bergquist A, Schrumpf E, Nevens F, Trivedi P, Reiter FP, Tornai I, Halilbasic E, Greinwald R, Pröls M, Manns MP, Trauner M; European PSC norUDCA Study Group. norUrsodeoxycholic acid improves cholestasis in primary sclerosing cholangitis. J Hepatol. 2017 Sep;67(3):549-558. doi: 10.1016/j.jhep.2017.05.009. Epub 2017 May 18. PMID: 28529147. 10: Krones E, Eller K, Pollheimer MJ, Racedo S, Kirsch AH, Frauscher B, Wahlström A, Ståhlman M, Trauner M, Grahammer F, Huber TB, Wagner K, Rosenkranz AR, Marschall HU, Fickert P. NorUrsodeoxycholic acid ameliorates cholemic nephropathy in bile duct ligated mice. J Hepatol. 2017 Jul;67(1):110-119. doi: 10.1016/j.jhep.2017.02.019. Epub 2017 Feb 27. PMID: 28242240. 11: Zhang CY, Yuan WG, He P, Lei JH, Wang CX. Liver fibrosis and hepatic stellate cells: Etiology, pathological hallmarks and therapeutic targets. World J Gastroenterol. 2016 Dec 28;22(48):10512-10522. doi: 10.3748/wjg.v22.i48.10512. PMID: 28082803; PMCID: PMC5192262. 12: Tang Y, Fickert P, Trauner M, Marcus N, Blomenkamp K, Teckman J. Autophagy induced by exogenous bile acids is therapeutic in a model of α-1-AT deficiency liver disease. Am J Physiol Gastrointest Liver Physiol. 2016 Jul 1;311(1):G156-65. doi: 10.1152/ajpgi.00143.2015. Epub 2016 Apr 21. PMID: 27102560. 13: Wanek T, Halilbasic E, Visentin M, Mairinger S, Römermann K, Stieger B, Kuntner C, Müller M, Langer O, Trauner M. Influence of 24-Nor-Ursodeoxycholic Acid on Hepatic Disposition of [(18)F]Ciprofloxacin, a Positron Emission Tomography Study in Mice. J Pharm Sci. 2016 Jan;105(1):106-12. doi: 10.1016/j.xphs.2015.11.014. Epub 2016 Jan 13. PMID: 26852845. 14: Halilbasic E, Fuchs C, Hofer H, Paumgartner G, Trauner M. Therapy of Primary Sclerosing Cholangitis--Today and Tomorrow. Dig Dis. 2015;33 Suppl 2:149-63. doi: 10.1159/000440827. Epub 2015 Dec 7. PMID: 26641242. 15: Trauner M, Halilbasic E, Claudel T, Steinacher D, Fuchs C, Moustafa T, Pollheimer M, Krones E, Kienbacher C, Traussnigg S, Kazemi-Shirazi L, Munda P, Hofer H, Fickert P, Paumgartner G. Potential of nor-Ursodeoxycholic Acid in Cholestatic and Metabolic Disorders. Dig Dis. 2015;33(3):433-9. doi: 10.1159/000371904. Epub 2015 May 27. PMID: 26045280. 16: Sombetzki M, Fuchs CD, Fickert P, Österreicher CH, Mueller M, Claudel T, Loebermann M, Engelmann R, Langner C, Sahin E, Schwinge D, Guenther ND, Schramm C, Mueller-Hilke B, Reisinger EC, Trauner M. 24-nor-ursodeoxycholic acid ameliorates inflammatory response and liver fibrosis in a murine model of hepatic schistosomiasis. J Hepatol. 2015 Apr;62(4):871-8. doi: 10.1016/j.jhep.2014.11.020. Epub 2014 Nov 21. PMID: 25463533; PMCID: PMC4368108. 17: Trauner M, Halilbasic E, Kazemi-Shirazi L, Kienbacher C, Staufer K, Traussnigg S, Hofer H. Therapeutic role of bile acids and nuclear receptor agonists in fibrosing cholangiopathies. Dig Dis. 2014;32(5):631-6. doi: 10.1159/000360517. Epub 2014 Jul 14. PMID: 25034298. 18: García-Rodríguez JL, Barbier-Torres L, Fernández-Álvarez S, Gutiérrez-de Juan V, Monte MJ, Halilbasic E, Herranz D, Álvarez L, Aspichueta P, Marín JJ, Trauner M, Mato JM, Serrano M, Beraza N, Martínez-Chantar ML. SIRT1 controls liver regeneration by regulating bile acid metabolism through farnesoid X receptor and mammalian target of rapamycin signaling. Hepatology. 2014 May;59(5):1972-83. doi: 10.1002/hep.26971. Epub 2014 Mar 31. PMID: 24338587; PMCID: PMC3999184. 19: Belonovskaia EB, Naruta EE, Lukivskaia OIa, Abakumov VZ, Buko VU. [Preventive administration of new UDCA derivatives in experimental alcoholic steatohepatitis]. Eksp Klin Farmakol. 2013;76(1):25-9. Russian. PMID: 23461012. 20: Fickert P, Pollheimer MJ, Silbert D, Moustafa T, Halilbasic E, Krones E, Durchschein F, Thüringer A, Zollner G, Denk H, Trauner M. Differential effects of norUDCA and UDCA in obstructive cholestasis in mice. J Hepatol. 2013 Jun;58(6):1201-8. doi: 10.1016/j.jhep.2013.01.026. Epub 2013 Jan 29. PMID: 23369794; PMCID: PMC3650580.