Bendazac
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MedKoo CAT#: 329308

CAS#: 20187-55-7

Description: Bendazac, also known as Bendazolic acid and AF-983, is an anticataract drug. It has been reported that Bendazac acts by preventing protein denaturation.

Chemical Structure

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Bendazac
CAS# 20187-55-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329308
Name: Bendazac
CAS#: 20187-55-7
Chemical Formula: C16H14N2O3
Exact Mass: 282.10
Molecular Weight: 282.299
Elemental Analysis: C, 68.08; H, 5.00; N, 9.92; O, 17.00

Price and Availability

Size Price Availability Quantity
1g USD 250 2 weeks
5g USD 450 2 weeks
10g USD 650 2 weeks
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Synonym: Bendazac; AF 983; AF-983; AF983; Bendazolic acid; Bindazac; Versus

IUPAC/Chemical Name: 2-((1-benzyl-1H-indazol-3-yl)oxy)acetic acid

InChi Key: BYFMCKSPFYVMOU-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H14N2O3/c19-15(20)11-21-16-13-8-4-5-9-14(13)18(17-16)10-12-6-2-1-3-7-12/h1-9H,10-11H2,(H,19,20)

SMILES Code: O=C(O)COC1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3

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: Bendazac is an oxyacetic acid with anti-inflammatory, antinecrotic, choleretic and antilipidaemic properties.
In vitro activity: The effect of bendazac lysine on the human lens epithelial cell line HLE-B3 adhesion to polymethylmethacrylate (PMMA) intraocular lenses (IOLs) was evaluated. After adherence to IOLs, cells were incubated in the presence of the drug for 24 h. Results obtained show that bendazac is able to induce a linear dose-dependent inhibition of HLE-B3 adhesiveness to PMMA IOLs. In particular, treatment with bendazac 33, 100 and 300 microM resulted in a 15, 32 and 54% inhibition, respectively. Statistical analysis shows that this effect is significant at 100 microM (p < 0.05) and 300 microM (p < 0.01). The analysis of the effects of bendazac on the viability and on the proliferative capacity of HLE-B3 cells did not show any drug-related toxicity up to the concentration of 400 microM. These results demonstrate that bendazac lysine is able to inhibit adhesion of lens epithelial cells to PMMA IOLs and suggests the potential beneficial use of this drug in preventing secondary cataract development. Reference: Ophthalmic Res. 2004 May-Jun;36(3):145-50. https://www.karger.com/Article/Abstract/77327
In vivo activity: The effects of bendazac lysine (BDL) on experimental diabetic peripheral neuropathy (DPN) in rats were evaluated. Diabetic rats without treatment showed hypopraxia, polydipsia, polyuria, slow weight gain, cataract, increased tail-flick threshold temperature, decreased motor nerve conduction velocity (nd induced pathological morphological changes of myelinated nerve fibres. All these symptoms were ameliorated in diabetic rats treated with BDL. Bendazac lysine ameliorated the blood glucose concentration, glycosylated haemoglobin levels and insulin levels in the plasma of diabetic rats, reduced aldose reductase activity in erythrocytes and advanced glycation end-products in both nerves and serum and increase the activity of glutathione peroxidase in the nerves and Na(+)/K(+)-ATPase in the nerves and erythrocytes. The results suggest that bendazac lysine exerts its protective effects against the progression of diabetic peripheral neuropathy in STZ-diabetic rats through multiple mechanisms and is a potential drug for the prevention of deterioration in DPN. Reference: Clin Exp Pharmacol Physiol. 2006 Dec;33(12):1231-8. https://onlinelibrary.wiley.com/doi/10.1111/j.1440-1681.2006.04515.x

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 250.0 885.58

Preparing Stock Solutions

The following data is based on the product molecular weight 282.30 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. Soldo L, Ruggieri A, Milanese C, Pinza M, Guglielmotti A. Bendazac lysine inhibition of human lens epithelial cell adhesion to polymethylmethacrylate intraocular lenses. Ophthalmic Res. 2004 May-Jun;36(3):145-50. doi: 10.1159/000077327. PMID: 15103205. 2. Yu JX, Yin XX, Shen JP, Qiu J, Yin HL, Jiang SJ. Protective effects of bendazac lysine on diabetic peripheral neuropathy in streptozotocin-induced diabetic rats. Clin Exp Pharmacol Physiol. 2006 Dec;33(12):1231-8. doi: 10.1111/j.1440-1681.2006.04515.x. PMID: 17184506.
In vitro protocol: 1. Soldo L, Ruggieri A, Milanese C, Pinza M, Guglielmotti A. Bendazac lysine inhibition of human lens epithelial cell adhesion to polymethylmethacrylate intraocular lenses. Ophthalmic Res. 2004 May-Jun;36(3):145-50. doi: 10.1159/000077327. PMID: 15103205.
In vivo protocol: 1. Yu JX, Yin XX, Shen JP, Qiu J, Yin HL, Jiang SJ. Protective effects of bendazac lysine on diabetic peripheral neuropathy in streptozotocin-induced diabetic rats. Clin Exp Pharmacol Physiol. 2006 Dec;33(12):1231-8. doi: 10.1111/j.1440-1681.2006.04515.x. PMID: 17184506.

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1: Balfour JA, Clissold SP. Bendazac lysine. A review of its pharmacological properties and therapeutic potential in the management of cataracts. Drugs. 1990 Apr;39(4):575-96. doi: 10.2165/00003495-199039040-00007. PMID: 2190795.


2: Rovei V, Campistron G, Dueymes JM, Ego D, Conte JJ, Houin G. Pharmacokinetics of bendazac-lysine and 5-hydroxybendazac in patients with renal insufficiency. Eur J Clin Pharmacol. 1987;33(3):303-10. doi: 10.1007/BF00637567. PMID: 3691618.


3: Soldo L, Ruggieri A, Milanese C, Pinza M, Guglielmotti A. Bendazac lysine inhibition of human lens epithelial cell adhesion to polymethylmethacrylate intraocular lenses. Ophthalmic Res. 2004 May-Jun;36(3):145-50. doi: 10.1159/000077327. PMID: 15103205.


4: Iwakiri K, Hata M, Miura Y, Numano K, Yuge M, Sasaki E. Allergic contact dermatitis due to bendazac and alclometasone dipropionate. Contact Dermatitis. 1999 Oct;41(4):218-39. doi: 10.1111/j.1600-0536.1999.tb06133.x. PMID: 10515101.


5: Hockwin O, Laser H, De Gregorio M, Carrieri MP. Bendazac lysine in selected types of human senile cataract. A long-term double-masked placebo-controlled clinical trial with multilinear densitometric image analysis of Scheimpflug photographs. Ophthalmic Res. 1989;21(3):141-54. doi: 10.1159/000266799. PMID: 2674821.


6: Rovei V, Escourrou J, Campistron G, Ego D, Thiola A, Ribet A, Houin G. The pharmacokinetics of bendazac-lysine and 5-hydroxybendazac, its main metabolite, in patients with hepatic cirrhosis. Eur J Clin Pharmacol. 1988;35(4):391-6. doi: 10.1007/BF00561370. PMID: 3197747.


7: Scorza Barcellona P, Campana A, Caranti S, D'Onofrio E, Silvestrini B. Pretreatment with bendazac attenuates retinal damage induced by intense light in rats. Pharmacol Res. 1991 Jul;24(1):105-12. doi: 10.1016/1043-6618(91)90070-e. PMID: 1946139.


8: Pandolfo L, Livrea MA, Bono A. Effects of bendazac L-lysine salt on X-ray- induced cataract in the rabbit lens. Exp Eye Res. 1986 Feb;42(2):167-75. doi: 10.1016/0014-4835(86)90040-0. PMID: 3699106.


9: Benitez del Castillo JM, Jimenez-Alfaro I, Ortega P, Castillo A, Diaz D, Toledano N, Garcia-Sanchez J. Effect of bendazac lysine on lens and retina in diabetics. Doc Ophthalmol. 1994;86(4):387-93. doi: 10.1007/BF01204597. PMID: 7835176.


10: Rodríguez Rodríguez E, Prieto de Paula JM, Cancelo Suárez P, Echevarría Iturbe C. Hepatitis crónica activa por bendazaco [Chronic active hepatitis due to bendazac]. Rev Clin Esp. 1994 Aug;194(8):657-8. Spanish. PMID: 7938854.


11: Testa M, Iuliano G, Marino E, Buongiovanni C, Paolercio F, Trapanese A, Mortow P. Bendazac and benzydamine for treatment of cataract: individualized therapy by the "BLOA test". J Ocul Pharmacol. 1986 Summer;2(3):251-66. doi: 10.1089/jop.1986.2.251. PMID: 3503111.


12: Guglielmotti A, Capezzone De Joannon A, Cazzolla N, Marchetti M, Soldo L, Cavallo G, Pinza M. Radical scavenger activity of bendazac, an anticataract non- steroidal anti-inflammatory agent. Pharmacol Res. 1995 Dec;32(6):369-73. doi: 10.1016/s1043-6618(05)80042-8. PMID: 8736488.


13: Yu JX, Yin XX, Shen JP, Qiu J, Yin HL, Jiang SJ. Protective effects of bendazac lysine on diabetic peripheral neuropathy in streptozotocin-induced diabetic rats. Clin Exp Pharmacol Physiol. 2006 Dec;33(12):1231-8. doi: 10.1111/j.1440-1681.2006.04515.x. PMID: 17184506.


14: Lewis BS, Harding JJ. The major metabolite of bendazac inhibits the glycosylation of soluble lens proteins: a possible mechanism for a delay in cataractogenesis. Exp Eye Res. 1988 Aug;47(2):217-25. doi: 10.1016/0014-4835(88)90005-x. PMID: 3409993.


15: Alcalde M, Garcia-Diaz M, Najarro F, Donoso MS, Cebria L, Pascasio JM. Hepatotoxicity due to lysine salt of bendazac. Scand J Gastroenterol. 1996 Feb;31(2):206-8. doi: 10.3109/00365529609031987. PMID: 8658045.


16: Valeri P, Palmery M, Martinelli B, Catanese B. Absorption of bendazac lysine after topical application to the rabbit eye. Pharmacol Res Commun. 1987 Aug;19(8):517-25. doi: 10.1016/0031-6989(87)90089-0. PMID: 3432319.


17: Shen H, Gou S, Shen J, Zhu Y, Zhang Y, Chen X. Synthesis and biological evaluations of novel bendazac lysine analogues as potent anticataract agents. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2115-8. doi: 10.1016/j.bmcl.2010.02.061. Epub 2010 Feb 19. PMID: 20223660.


18: Silva MP, Mira L, Lima J, Manso CF. Kinetics of the inhibition of xanthine dehydrogenase and of the reversible and irreversible forms of xanthine oxidase by silibinin and bendazac. Environ Toxicol Pharmacol. 1996 Jul 15;1(4):279-84. doi: 10.1016/1382-6689(96)00021-X. PMID: 21781693.


19: Ciancarelli-Tozzi MG, Silvestrini B, Finazzi-Agro A. Photosensitized haemolysis of human erythrocytes is reduced by bendazac. Drugs Exp Clin Res. 1989;15(5):219-22. PMID: 2791873.


20: Marques C, Ramalho JS, Pereira P, Mota MC. Bendazac decreases in vitro glycation of human lens crystallins. Decrease of in vitro protein glycation by bendazac. Doc Ophthalmol. 1995;90(4):395-404. doi: 10.1007/BF01268125. PMID: 8620822.