Flubendazole (formerly also known as Flumoxanal, NSC 313680), an efficacious anti-helmintic drug widely used as an anti-helmintic for human, rodents and ruminants, is an autophagy inducer by targeting Atg4B, it is used to treat internal parasite and worm infection. Flubendazole results in morphological changes included contraction of the soma region, formation of blebs on the tegument, rostellar disorganization, loss of hooks and destruction of microtriches in Echinococcus granulosus. Flubendazole exerts anticancer activities by mechanisms including inhibition of microtubule function. Flubendazole induces p53-mediated apoptosis and arrests G2/M cell cycle.

Physicochemical Properties

Molecular Formula	C16H12FN3O3
Molecular Weight	313.28
Exact Mass	313.086
CAS #	31430-15-6
Related CAS #	Flubendazole-d3;1173021-08-3
PubChem CID	35802
Appearance	White to off-white solid powder
Density	1.4±0.1 g/cm3
Melting Point	290°C
Index of Refraction	1.685
LogP	3.05
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Heavy Atom Count	23
Complexity	454
Defined Atom Stereocenter Count	0
SMILES	O=C(OC)NC1=NC2=CC=C(C(C3=CC=C(F)C=C3)=O)C=C2N1
InChi Key	CPEUVMUXAHMANV-UHFFFAOYSA-N
InChi Code	InChI=1S/C16H12FN3O3/c1-23-16(22)20-15-18-12-7-4-10(8-13(12)19-15)14(21)9-2-5-11(17)6-3-9/h2-8H,1H3,(H2,18,19,20,22)
Chemical Name	methyl (5-(4-fluorobenzoyl)-1H-benzo[d]imidazol-2-yl)carbamate
Synonyms	Flumoxanal, NSC 313680; NSC 313680; NSC313680; NSC-313680; R 17899; R17899; R-17899
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In vitro activity: Flubendazole results in morphological changes included contraction of the soma region, formation of blebs on the tegument, rostellar disorganization, loss of hooks and destruction of microtriches in Echinococcus granulosus. Flubendazole have a bicyclic ring system in which a benzene has been fused to the -4 and -5 positions of the heterocycle (imidazole). Flubendazole and Albendazole shows similar potency in affecting rat embryonic development in vitro, inducing retardation of growth and dysmorphogenic effects at concentrations ≥0.5 μg/mL.
ln Vivo	Flubendazole (6.32 mg/kg/day) initially induces an arrest of embryonic development followed by a generalized cell death that leads to 100% embryolethality by gestation day (GD) 12.5. Flubendazole (3.46 mg/kg/day) markedly reduces embryonic development by GD 12.5 without causing cell death. Flubendazole in olive oil causes a statistically significant increase in embryolethality at doses of 7.83 mg/kg per day and higher, with complete resorption in all dams at 31.33 mg/kg per day in rats. Flubendazole treatment causes a slight increase of metyrapone and daunorubicin activities in hepatic as well as intestinal cytosol in birds. Flubendazole treatment leads to statistically significant inhibition of intestinal GST activity. Flubendazole treatment leads to slight but significant inhibition (decrease to 69%) of 7-ethoxyresorufin activity in hepatic microsomes.
Animal Protocol	6.32, 7.83, 31.33 mg/kg/day Birds
References	Parasitol Res.2006 Mar;98(4):317-23.
Additional Infomation	Flubendazole is a member of the class of mebendazole in which the benzoyl group is replaced by a p-fluorobenzoyl group. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections. It has a role as an antinematodal drug and a teratogenic agent. It is a member of benzimidazoles, a carbamate ester, an organofluorine compound and an aromatic ketone. Flubendazole is an anthelmintic that is used to treat worm infection in humans. It is available OTC in Europe.

Solubility Data

Solubility (In Vitro)

DMSO: 3 mg/mL (9.6 mM) Water:<1 mg/mL Ethanol:<1 mg/mL

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.1920 mL	15.9602 mL	31.9203 mL
	5 mM	0.6384 mL	3.1920 mL	6.3841 mL
	10 mM	0.3192 mL	1.5960 mL	3.1920 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.