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MedKoo Cat#: 599125 | Name: Lobenzarit sodium
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Description:

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

Lobenzarit sodium is an antirheumatic agent.

Chemical Structure

Lobenzarit sodium
Lobenzarit sodium
CAS#64808-48-6

Theoretical Analysis

MedKoo Cat#: 599125

Name: Lobenzarit sodium

CAS#: 64808-48-6

Chemical Formula: C14H8ClNNa2O4

Exact Mass: 0.0000

Molecular Weight: 335.65

Elemental Analysis: C, 50.10; H, 2.40; Cl, 10.56; N, 4.17; Na, 13.70; O, 19.07

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
500mg USD 1,450.00 2 Weeks
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Related CAS #
63329-53-3 (free) 64808-48-6 (sodium)
Synonym
Lobenzarit sodium; CCA;
IUPAC/Chemical Name
sodium 2-((2-carboxylatophenyl)amino)-4-chlorobenzoate
InChi Key
QPJBONAWFAURGB-UHFFFAOYSA-L
InChi Code
InChI=1S/C14H10ClNO4.2Na/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);;/q;2*+1/p-2
SMILES Code
O=C([O-])C1=CC=C(Cl)C=C1NC2=CC=CC=C2C([O-])=O.[Na+].[Na+]
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lobenzarit sodium is a antirheumatic agent.
In vitro activity:
In this study it was found that CCA (lobenzarit disodium) inhibits the production of guanosine 3',5'-cyclic monophosphate almost completely when present in concentrations of 1 mM. Further results demonstrated that such inhibition could also be explained by interference in constitutive nitric oxide generation. In addition to previous findings, more insight into the molecular mechanism of action of CCA is provided. Reference: Mediators Inflamm. 1995;4(5):364-7. https://pubmed.ncbi.nlm.nih.gov/18475666/
In vivo activity:
In the in vivo experiments, the daily administration of 10 mg/kg CCA (lobenzarit disodium) for 4 weeks augmented or inhibited Ts cell-induction when mice were immunized with a suboptimal (30 micrograms/body) or an optimal (100 micrograms/body) amount of KLH, respectively. CCA augmented the induction of helper T (Th) cells both in vitro and in vivo when Th cells were induced with a suboptimal amount of antigens. These results suggest that CCA is a compound showing immunomodulating properties that affect Ts and Th cell-induction depending on immunological conditions. Reference: Jpn J Pharmacol. 1983 Aug;33(4):859-66. https://pubmed.ncbi.nlm.nih.gov/6226816/

Preparing Stock Solutions

The following data is based on the product molecular weight 335.65 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. Padrón J, Rojas A, Glaría L, Caveda L, Delgado R, Torres M, Martínez O, López E, Beltrán A, Palacios M. Lobenzarit disodium inhibits the constitutive NO-cGMP metabolic pathways. Possible involvement as an immunomodulatory drug. Mediators Inflamm. 1995;4(5):364-7. doi: 10.1155/S0962935195000597. PMID: 18475666; PMCID: PMC2365655. 2. Sugawara I, Kitagawa H, Inagaki H, De Ley M, Fukuda A. Human interferon-gamma (IFN-gamma) containing cells bear various surface phenotypic markers. Microbiol Immunol. 1986;30(10):1049-59. doi: 10.1111/j.1348-0421.1986.tb03034.x. PMID: 2948099. 3. Yamamoto I, Ohmori H, Sasano M. Effect of N-(2-carboxyphenyl)-4-chloroanthranilic acid disodium salt (CCA) on the induction of helper and suppressor T cells in vitro and in vivo. Jpn J Pharmacol. 1983 Aug;33(4):859-66. doi: 10.1254/jjp.33.859. PMID: 6226816.
In vitro protocol:
1. Padrón J, Rojas A, Glaría L, Caveda L, Delgado R, Torres M, Martínez O, López E, Beltrán A, Palacios M. Lobenzarit disodium inhibits the constitutive NO-cGMP metabolic pathways. Possible involvement as an immunomodulatory drug. Mediators Inflamm. 1995;4(5):364-7. doi: 10.1155/S0962935195000597. PMID: 18475666; PMCID: PMC2365655. 2. Sugawara I, Kitagawa H, Inagaki H, De Ley M, Fukuda A. Human interferon-gamma (IFN-gamma) containing cells bear various surface phenotypic markers. Microbiol Immunol. 1986;30(10):1049-59. doi: 10.1111/j.1348-0421.1986.tb03034.x. PMID: 2948099.
In vivo protocol:
1. Yamamoto I, Ohmori H, Sasano M. Effect of N-(2-carboxyphenyl)-4-chloroanthranilic acid disodium salt (CCA) on the induction of helper and suppressor T cells in vitro and in vivo. Jpn J Pharmacol. 1983 Aug;33(4):859-66. doi: 10.1254/jjp.33.859. PMID: 6226816.
1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: Ohuchi K, Watanabe M, Fukui Y, Hirasawa N, Ozeki T, Tsurufuji S. The effect of diphenylamine derivatives on arachidonic acid metabolism in rat peritoneal macrophages. Prostaglandins Leukot Med. 1987 Jun;28(1):15-23. PubMed PMID: 3112805. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: 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. 17: 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. 18: Cynshi O, Saitoh M, Cynshi F, Tanemura M, Hata S, Nakano M. Anti-oxidative profile of lobenzarit disodium (CCA). Biochem Pharmacol. 1990 Nov 1;40(9):2117-22. PubMed PMID: 2242038. 19: 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. 20: Miranda A, Millán M, Caraballo I. Study of the critical points in lobenzarit disodium hydrophilic matrices for controlled drug delivery. Chem Pharm Bull (Tokyo). 2006 May;54(5):598-602. PubMed PMID: 16651752.

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