Cetaben | CAS#55986-43-1 (free base)

MedKoo Cat#: 531101 | Name: Cetaben

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Description:

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

Cetaben is a unique, peroxisome proliferator-activated receptor α (PPARα)-independent peroxisome proliferator with hypolipidemic activity, characterized by reduction in serum triglyceride and cholesterol concentrations in rats.

Chemical Structure

Cetaben

CAS#55986-43-1 (free base)

Theoretical Analysis

MedKoo Cat#: 531101

Name: Cetaben

CAS#: 55986-43-1 (free base)

Chemical Formula: C23H39NO2

Exact Mass: 361.2981

Molecular Weight: 361.57

Elemental Analysis: C, 76.40; H, 10.87; N, 3.87; O, 8.85

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

55986-43-1 (free base) 64059-66-1 (sodium)

Synonym

Cetaben (free base)

IUPAC/Chemical Name

4-(hexadecylamino)-benzoic acid

InChi Key

QXWKHSSBFQDQPR-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20-24-22-18-16-21(17-19-22)23(25)26/h16-19,24H,2-15,20H2,1H3,(H,25,26)

SMILES Code

O=C(O)C1=CC=C(NCCCCCCCCCCCCCCCC)C=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

>2 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:

Cetaben is a PPARα-independent peroxisome proliferator.

In vitro activity:

Human HepG2 and rat MH1C1 hepatoma cell lines were examined for their response to cetaben, an exceptional type of peroxisome proliferator. Shape change and proliferation of peroxisomes as well as induction of selected peroxisomal enzymes catalase, acyl-CoA oxidase, and peroxisomal bifunctional enzyme, were assessed in response to cetaben. In MH1C1 cells, peroxisomes were seen in clusters displaying typical features of microperoxisomes. Cetaben caused little but reversible proliferation and morphological heterogeneity with the occurrence of dumbbell-shaped and cup-shaped peroxisomal profiles. Peroxisomes in HepG2 cells showed marked variation in size and shape. Cetaben treatment of HepG2 cells caused disintegration of Golgi regions and augmented mitochondrial matrix. Interestingly, MH1C1 cells showed different subunit composition of acyl-CoA oxidase in immunoblot analysis: only subunit A at 72 kDa was detected but not the cleavage products. In situ hybridization underlined the marked morphological heterogeneity observed, and both cell lines revealed different stages of gene expression. These results indicate that cetaben represents an extraordinary type of peroxisomal proliferator with pleiotropic effects on human and rat hepatoma cells, and, at least in the human hepatoma cell line HepG2, these effects are not restricted to peroxisome proliferation. Reference: Histochem Cell Biol. 2001 Jun;115(6):509-19. https://dx.doi.org/10.1007/s004180100278

In vivo activity:

The effects of cetaben and clofibric acid were compared on the activities of peroxisomal enzymes in the liver and kidney of male Wistar rats. Cetaben at 200 mg/kg body wt increased the activities of all of the enzymes in the liver that were studied two to eight times, whereas the changes induced by the same dose of clofibric acid increased some of the enzymes and decreased others. In the kidney, cetaben increased the activities of all investigated peroxisomal enzymes, while clofibric acid only increased the activity of palmitoyl-CoA oxidase. The data obtained in the dose-response study of cetaben revealed a significant rise in the activities of peroxisomal enzymes in both the liver and kidney at doses of 50-100 mg/kg body wt administered over 10 days, but the maximal effect was observed at 250 mg/kg. Palmitoyl-CoA oxidase and D-amino acid oxidase respond most markedly to cetaben. Cetaben could represent an atypical peroxisomal proliferator, since it increased the activities of all peroxisomal enzymes investigated. The fact that the individual components localized in the peroxisomes do not change markedly could be of importance with respect to the function and physical properties of peroxisomes. Reference: Biochem Pharmacol. 1994 Feb 9;47(3):515-9. https://linkinghub.elsevier.com/retrieve/pii/0006-2952(94)90183-X

Preparing Stock Solutions

The following data is based on the product molecular weight 361.57 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:

In vitro protocol:

1. Kovacs W, Walter I, Stangl H. Cetaben-induced changes on the morphology and peroxisomal enzymes in MH1C1 rat hepatoma cells and HepG2 human hepatoblastoma cells. Histochem Cell Biol. 2001 Jun;115(6):509-19. doi: 10.1007/s004180100278. PMID: 11455451.

In vivo protocol:

1. Chandoga J, Rojeková I, Hampl L, Hocman G. Cetaben and fibrates both influence the activities of peroxisomal enzymes in different ways. Biochem Pharmacol. 1994 Feb 9;47(3):515-9. doi: 10.1016/0006-2952(94)90183-x. PMID: 8117320.

1: Lee JA, Shinn P, Jaken S, Oliver S, Willard FS, Heidler S, Peery RB, Oler J, Chu S, Southall N, Dexheimer TS, Smallwood J, Huang R, Guha R, Jadhav A, Cox K, Austin CP, Simeonov A, Sittampalam GS, Husain S, Franklin N, Wild DJ, Yang JJ, Sutherland JJ, Thomas CJ. Novel Phenotypic Outcomes Identified for a Public Collection of Approved Drugs from a Publicly Accessible Panel of Assays. PLoS One. 2015 Jul 15;10(7):e0130796. doi: 10.1371/journal.pone.0130796. PubMed PMID: 26177200; PubMed Central PMCID: PMC4503722. 2: Kovacs WJ, Schrader M, Walter I, Stangl H. The hypolipidemic compound cetaben induces changes in Golgi morphology and vesicle movement. Histochem Cell Biol. 2004 Aug;122(2):95-109. PubMed PMID: 15322860. 3: Kovacs W, Walter I, Stangl H. Cetaben-induced changes on the morphology and peroxisomal enzymes in MH1C1 rat hepatoma cells and HepG2 human hepatoblastoma cells. Histochem Cell Biol. 2001 Jun;115(6):509-19. PubMed PMID: 11455451. 4: Kovacs W, Stangl H, Völkl A, Schad A, Dariush Fahimi H, Baumgart E. Localization of mRNAs encoding peroxisomal proteins in cell culture by non-radioactive in situ hybridization. Comparison of rat and human hepatoma cells and their responses to two divergent hypolipidemic drugs. Histochem Cell Biol. 2001 Jun;115(6):499-508. PubMed PMID: 11455450. 5: Stangl H, Kovacs W, Böck P, Kremser K. Differential induction of peroxisomal enzymes by hypolipidaemics in human (HepG2) and rat (MH1C1) hepatoma cell lines. Eur J Clin Chem Clin Biochem. 1995 Nov;33(11):775-83. PubMed PMID: 8620053. 6: Chandoga J, Hampl L, Turecký L, Rojeková I, Uhliková E, Hocman G. Cetaben is an exceptional type of peroxisome proliferator. Int J Biochem. 1994 May;26(5):679-96. PubMed PMID: 8005353. 7: Chandoga J, Rojeková I, Hampl L, Hocman G. Cetaben and fibrates both influence the activities of peroxisomal enzymes in different ways. Biochem Pharmacol. 1994 Feb 9;47(3):515-9. PubMed PMID: 8117320. 8: Schön HJ, Grgurin M, Klune G, Prager C, Marz R, Legenstein E, Böck P, Kramar R. Effects of hypolipidaemics cetaben and clofibrate on mitochondrial and peroxisomal enzymes of rat liver. J Pharm Pharmacol. 1994 Feb;46(2):144-7. PubMed PMID: 8021805. 9: Yamaguchi Y, Yamada K, Kitagawa S, Kunitomo M. Atherosclerosis mouse model induced by a high-cholesterol diet supplemented with beta-aminopropionitrile: effects of various anti-atherosclerotic agents on the biochemical parameters. Jpn J Pharmacol. 1990 Oct;54(2):187-96. PubMed PMID: 2077185. 10: Fort FL, Stein HH, Langenberg K, Lewkowski JP, Heyman IA, Kesterson JW. Cetaben versus clofibrate: comparison of toxicity and peroxisome proliferation in rats. Toxicology. 1983 Nov;28(4):305-11. PubMed PMID: 6606240. 11: DeVries VG, Largis EE, Miner TG, Shepherd RG, Upeslacis J. Potential antiatherosclerotic agents. 4. [(Functionalized-alkyl)amino]benzoic acid analogues of cetaben. J Med Chem. 1983 Oct;26(10):1411-21. PubMed PMID: 6604818. 12: Albright JD, DeVries VG, Du MT, Largis EE, Miner TG, Reich MF, Shepherd RG. Potential antiatherosclerotic agents. 3. Substituted benzoic and non benzoic acid analogues of cetaben. J Med Chem. 1983 Oct;26(10):1393-411. PubMed PMID: 6604817. 13: Albright JD, DeVries VG, Largis EE, Miner TG, Reich MF, Schaffer SA, Shepherd RG, Upeslacis J. Potential antiatherosclerotic agents. 2. (Aralkylamino)- and (alkylamino) benzoic acid analogues of cetaben. J Med Chem. 1983 Oct;26(10):1378-93. PubMed PMID: 6604816. 14: Kunitomo M, Takaoka K, Matsumoto J, Iwai H, Bando Y. [Experimental induction of atherosclerosis in guinea pigs fed a cholesterol and vitamin D2-rich diet]. Nihon Yakurigaku Zasshi. 1983 Apr;81(4):275-83. Japanese. PubMed PMID: 6604004. 15: Katocs AS Jr, Schaffer SA. Antiatherogenic activity of cetaben sodium, sodium p-(hexadecylamino) benzoate, in the aortae of hypercholesteremic rabbits subjected to aortic endothelial cell desquamation. Artery. 1982;11(3):192-206. PubMed PMID: 6985202. 16: Chow SL, Sims BE. Micellar solubilization of cetaben sodium in surfactant and lipid solutions. J Pharm Sci. 1981 Aug;70(8):924-6. PubMed PMID: 6975813. 17: Oker-Blom C. Toxicological studies on 4-(hexadecylamino)benzoate (PHB), an agent with anti-atherosclerotic properties, in the rat. Toxicol Lett. 1981 Jan;7(3):273-7. PubMed PMID: 6971504. 18: Sirtori CR, Tremoli E, Paoletti R. New strategies in the development of anti-atherosclerotic drugs. Artery. 1980;8(6):507-18. Review. PubMed PMID: 7020650. 19: Albright JD, Schaffer SA, Shepherd RG. Cetaben sodium, an antiatherosclerotic agent. J Pharm Sci. 1979 Jul;68(7):936-7. PubMed PMID: 313437. 20: Hollander W, Prusty S, Nagraj S, Kirkpatrick B, Paddock J, Colombo M. Comparative effects of cetaben (PHB) and dichlormethylene diphosphonate (Cl2MDP) on the development of atherosclerosis in the cynomolgus monkey. Atherosclerosis. 1978 Nov;31(3):307-25. PubMed PMID: 152632.