Lobenzarit | CAS#63329-53-3 | immunomodulator

MedKoo Cat#: 599124 | Name: Lobenzarit

Description:

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

Lobenzarit is an immunomodulator, which is most frequently used to treat arthritis. Its chemical scaffold has also been repurposed to target tryptophan biosynthesis in Mycobacterium tuberculosis

Chemical Structure

Lobenzarit

CAS#63329-53-3

Theoretical Analysis

MedKoo Cat#: 599124

Name: Lobenzarit

CAS#: 63329-53-3

Chemical Formula: C14H10ClNO4

Exact Mass: 291.0298

Molecular Weight: 291.68

Elemental Analysis: C, 57.65; H, 3.46; Cl, 12.15; N, 4.80; O, 21.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

63329-53-3 (free) 64808-48-6 (sodium)

Synonym

Lobenzarit; Lobenzaritum;

IUPAC/Chemical Name

2-((2-carboxyphenyl)amino)-4-chlorobenzoic acid

InChi Key

UGDPYGKWIHHBMB-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H10ClNO4/c15-8-5-6-10(14(19)20)12(7-8)16-11-4-2-1-3-9(11)13(17)18/h1-7,16H,(H,17,18)(H,19,20)

SMILES Code

O=C(O)C1=CC=C(Cl)C=C1NC2=CC=CC=C2C(O)=O

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 291.68 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

1: Evans GL, Gamage SA, Bulloch EM, Baker EN, Denny WA, Lott JS. Repurposing the chemical scaffold of the anti-arthritic drug Lobenzarit to target tryptophan biosynthesis in Mycobacterium tuberculosis. Chembiochem. 2014 Apr 14;15(6):852-64. doi: 10.1002/cbic.201300628. Epub 2014 Mar 12. Erratum in: Chembiochem. 2015 Mar 23;16(5):706. Chembiochem. 2015 Mar 23;16(5):706. PubMed PMID: 24623674. 2: Evans GL, Gamage SA, Bulloch EM, Baker EN, Denny WA, Lott JS. Corrigendum: Repurposing the Chemical Scaffold of the Anti-Arthritic Drug Lobenzarit to Target Tryptophan Biosynthesis in Mycobacterium tuberculosis. Chembiochem. 2015 Mar 23;16(5):706. doi: 10.1002/cbic.201500098. Epub 2015 Mar 11. PubMed PMID: 26177917. 3: Remirez D, Commandeur JN, Groot E, Vermeulen NP. Mechanism of protection of lobenzarit against paracetamol-induced toxicity in rat hepatocytes. Eur J Pharmacol. 1995 Dec 7;293(4):301-8. PubMed PMID: 8748682. 4: Sakane N, Yoshida T, Umekawa T, Miyazaki R, Kondo M. Nephrogenic diabetes insipidus induced by lobenzarit disodium treatment in patients with rheumatoid arthritis. Intern Med. 1996 Feb;35(2):119-22. Review. PubMed PMID: 8680099. 5: Remirez D, Commandeur JN, Groot E, Gonzalez R, Rodriguez S, Ancheta O, Rojas E, Ramos ME, Vermeulen NP. Protective effects of lobenzarit against allyl alcohol-induced hepatotoxicity in mice and rats. Environ Toxicol Pharmacol. 1997 Jun 6;3(2):129-35. PubMed PMID: 21781770. 6: González R, Pascual C, Ancheta O, Carreras B, Remírez D, Pellón R. Hepatoprotective effects of lobenzarit disodium on acetaminophen-induced liver damage in mice. Agents Actions. 1992 Sep;37(1-2):114-20. PubMed PMID: 1456172. 7: Shiokawa Y, Horiuchi Y, Mizushima Y, Kageyama T, Shichikawa K, Ofuji T, Honma M, Yoshizawa H, Abe C, Ogawa N. A multicenter double-blind controlled study of lobenzarit, a novel immunomodulator, in rheumatoid arthritis. J Rheumatol. 1984 Oct;11(5):615-23. PubMed PMID: 6392550. 8: Kishimoto C, Takada H, Kuroki Y, Matsushita I, Hiraoka Y, Kurokawa M, Ochiai H, Sasayama S. Enhancement of coxsackievirus B3 myocarditis in mice by lobenzarit disodium through inhibition of splenic pan T cells. Cardiovasc Res. 1993 Feb;27(2):243-8. PubMed PMID: 8386064. 9: Castellanos Gil E, Iraizoz Colarte A, Bataille B, Brouillet F, Caraballo I. Estimation of the percolation thresholds in ternary lobenzarit disodium-dextran-HPMC hydrophilic matrices tablets: effects of initial porosity. Eur J Pharm Sci. 2009 Nov 5;38(4):312-9. doi: 10.1016/j.ejps.2009.07.013. Epub 2009 Aug 8. PubMed PMID: 19666114. 10: Hirohata S, Ohnishi K, Sagawa A. Treatment of systemic lupus erythematosus with lobenzarit: an open clinical trial. Clin Exp Rheumatol. 1994 May-Jun;12(3):261-5. PubMed PMID: 8070158. 11: Hirohata S, Shinohara S, Inoue T, Miyamoto T, Lipsky PE. Regulation of B cell function by lobenzarit, a novel disease-modifying antirheumatic drug. Arthritis Rheum. 1992 Feb;35(2):168-75. PubMed PMID: 1734906. 12: Andou S, Fujii S, Harada Y, Ooi J, Nomiyama J, Mori K, Ookubo M, Azuno Y, Fujii Y, Kaku K, et al. Alpha-methyldopa-type autoimmune hemolytic anemia caused by lobenzarit disodium of a mefenamic acid derivative and immunomodulator. Blood. 1994 May 15;83(10):3097. PubMed PMID: 8180406. 13: González R, Remírez D. Current views on the pharmacological properties of the immunomodulator, lobenzarit disodium. J Investig Allergol Clin Immunol. 1997 Mar-Apr;7(2):77-82. Review. PubMed PMID: 9161931. 14: Yamashita Y, Nakano T, Ohsugi Y. New immunomodulator lobenzarit disodium (CCA): activation of IgE class-specific suppressor T lymphocytes and regulation of IgE antibody response enhanced by sublethal X-irradiation in SJL/J mice. Int Arch Allergy Appl Immunol. 1987;83(3):296-302. PubMed PMID: 2954916. 15: Nishinarita S, Hayakawa J, Suzuki R, Hayama T, Hiranuma M, Sawada S, Horie T. [Lobenzarit disodium (CCA)--induced diabetes insipidus in a patient with rheumatoid arthritis]. Ryumachi. 1992 Aug;32(4):333-7; discussion 337-9. Japanese. PubMed PMID: 1411795. 16: Haynes DR, Gadd SJ, Whitehouse MW, Mayrhofer G, Vernon-Roberts B. Complete prevention of the clinical expression of adjuvant-induced arthritis in rats by cyclosporin-A and lobenzarit: the regulation of lymph node cell populations and cytokine production. Inflamm Res. 1996 Apr;45(4):159-65. PubMed PMID: 8741004. 17: Yokoyama T, Kanda T, Suzuki T, Murata K. Effects of lobenzarit on murine acute viral myocarditis. Cardiovasc Drugs Ther. 1992 Aug;6(4):403-7. PubMed PMID: 1325832. 18: Armesto J, Frutos N, Gonzalez R, Pascual C. In vitro activation of hepatic glutathione reductase from mice by lobenzarit disodium. Agents Actions. 1993 May;39(1-2):69-71. PubMed PMID: 8285143. 19: Kawakami A, Eguchi K, Ueki Y, Migita K, Ida H, Nakao H, Kurata A, Fukuda T, Ishimaru T, Kurouji K, et al. Effects of lobenzarit disodium on human endothelial cells. Lobenzarit disodium inhibits proliferative response, HLA-DR antigen expression, and T cell adherence toward endothelial cells. Arthritis Rheum. 1991 Mar;34(3):296-303. PubMed PMID: 1900689. 20: Takada H, Kishimoto C, Kuroki Y, Matsushita I, Hiraoka Y, Kurokawa M, Ochiai H, Sasayama S. The effects of lobenzarit disodium, a novel immunomodulator, upon murine coxsackievirus B3 myocarditis. Heart Vessels. 1993;8(2):59-66. PubMed PMID: 8390975.