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MedKoo Cat#: 326712 | Name: Benfotiamine
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Description:

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

Benfotiamine, or S-benzoylthiamine O-monophosphate, is a synthetic S-acyl derivative of thiamine (vitamin B1). It is prescribed there for treating sciatica and other painful nerve conditions. It is marketed as a medicine and/or dietary supplement, depending on the respective Regulatory Authority. Benfotiamine upregulates antioxidative system in activated BV-2 microglia cells. Benfotiamine enhances antioxidant defenses and protects against cisplatin-induced DNA damage in nephrotoxic rats.

Chemical Structure

Benfotiamine
Benfotiamine
CAS#22457-89-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 326712

Name: Benfotiamine

CAS#: 22457-89-2 (free acid)

Chemical Formula: C19H23N4O6PS

Exact Mass: 466.1076

Molecular Weight: 466.45

Elemental Analysis: C, 48.92; H, 4.97; N, 12.01; O, 20.58; P, 6.64; S, 6.87

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 weeks
10g USD 450.00 2 weeks
25g USD 750.00 2 weeks
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Related CAS #
22457-89-2 (free acid) Benfotiamine sodium 147317-17-7 (semihydrate)
Synonym
BRN-0771326; BTMP; CB-8088; CB8088; CB 8088; Berdi; Betivina; Biotamin; Benfotiamine; S-benzoylthiamine O-monophosphate; Benphothiamine; Betivina; Benzoylthiamine monophosphate
IUPAC/Chemical Name
(Z)-S-(2-(N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido)-5-(phosphonooxy)pent-2-en-3-yl) benzothioate
InChi Key
BTNNPSLJPBRMLZ-LGMDPLHJSA-N
InChi Code
InChI=1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13-
SMILES Code
O=C(S/C(CCOP(O)(O)=O)=C(N(CC1=CN=C(C)N=C1N)C=O)/C)C2=CC=CC=C2
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, not in water
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
Benfotiamine is primarily marketed as an antioxidant dietary supplement. In a clinical study with six patients, benfotiamine lowered AGE by 40%. Benfotiamine may be useful for the treatment of diabetic retinopathy, neuropathy, and nephropathy however "Most of the effects attributed to benfotiamine are extrapolated from in vitro and animal studies. Unfortunately apparent evidences from human studies are scarce and especially endpoint studies are missing. Therefore additional clinical studies are mandatory to explore the therapeutic potential of benfotiamine in both diabetic and non-diabetic pathological conditions". It is thought that treatment with benfotiamine leads to increased intracellular thiamine diphosphate levels, a cofactor of transketolase. This enzyme directs advanced glycation and lipoxidation end products (AGE's, ALE's) substrates to the pentose phosphate pathway, thus reducing tissue AGEs.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Benfotiamine is a lipid-soluble form of thiamine (vitamin B1).
In vitro activity:
Whether Benfotiamine (BFT) could activate the Nrf2/ARE pathway in WT and Nrf2-deficient fibroblasts was examined (Fig. 8). BFT administration induced transcription of four prototypical genes controlled by the Nrf2/ARE pathway: GSR, HO1, GCLM and NQO1 in WT but not in Nrf2 knock-out (KO) mouse embryonic fibroblasts (MEFs) (Fig. 8A). WT MEFs treated with 100 μM BFT for 3 h had significantly increased GSR and HO1 mRNA levels. Addition of 50 or 100 µM BFT for 8 h elevated GCLM and NQO1 mRNA levels compared with WT MEFs treated with vehicle, which remained unchanged in Nrf2 KO MEFs. None of the genes examined showed a response to thiamine except for GSR at the highest dose (100 μM) after 8 h treatment (Fig. 8B). These findings indicate that BFT can activate Nrf2/ARE genes in WT but not in Nrf2-deficient fibroblasts. Reference: Hum Mol Genet. 2018 Aug 15;27(16):2874-2892. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6077804/
In vivo activity:
To assess the effects of BFT on lifespan, TG mice were fed with BFT or control diet until natural death. BFT-treated P301S TG mice lived significantly longer than their TG littermates fed with a control diet (average of 390 versus 322 days; 21% increase in longevity) (Fig. 1B), although no changes in body weight were observed (Fig. 1A). To study behavioral deficits, P301S TG mice were assessed at 5, 7 and 9 months of age using the elevated plus maze (EPM) (to assess anxiety-like behavior) (Fig. 1C) and at 9 months of age using the contextual fear conditioning (to assess associative fear learning and memory) (Fig. 1D). TG mice showed enhanced hyperactivity and disinhibition as well as memory impairment relative to WT mice. Nevertheless, these behavioral deficits were rescued in TG mice treated with BFT. During the training period, all mice were able to learn the task and freeze after two electric shocks. Hind limb paralysis is a distinctive feature of TG mice at late-stage disease. To determine the effects of BFT on cell death, L3‒L6 regions of the spinal cord, which contain motor neuron pools for the hind limbs, were stained with cresyl violet and subjected to stereological neuron counting (Fig. 1E–G). The number of SMI32-positive neurons was also assessed (Fig. 1H–J). A significant preservation of motor neurons in TG mice treated with BFT relative to TG mice on a control diet was found. Reference: Hum Mol Genet. 2018 Aug 15;27(16):2874-2892. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6077804/
Solvent mg/mL mM
Solubility
DMSO 60.0 128.63
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 466.45 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. Tapias V, Jainuddin S, Ahuja M, Stack C, Elipenahli C, Vignisse J, Gerges M, Starkova N, Xu H, Starkov AA, Bettendorff L, Hushpulian DM, Smirnova NA, Gazaryan IG, Kaidery NA, Wakade S, Calingasan NY, Thomas B, Gibson GE, Dumont M, Beal MF. Benfotiamine treatment activates the Nrf2/ARE pathway and is neuroprotective in a transgenic mouse model of tauopathy. Hum Mol Genet. 2018 Aug 15;27(16):2874-2892. doi: 10.1093/hmg/ddy201. PMID: 29860433; PMCID: PMC6077804. 2. Bozic I, Savic D, Stevanovic I, Pekovic S, Nedeljkovic N, Lavrnja I. Benfotiamine upregulates antioxidative system in activated BV-2 microglia cells. Front Cell Neurosci. 2015 Sep 4;9:351. doi: 10.3389/fncel.2015.00351. eCollection 2015. PubMed PMID: 26388737; PubMed Central PMCID: PMC4559599. 3. Moraes RCM, Singulani MP, Gonçalves AC, Portari GV, Torrão ADS. Oral benfotiamine reverts cognitive deficit and increase thiamine diphosphate levels in the brain of a rat model of neurodegeneration. Exp Gerontol. 2020 Nov;141:111097. doi: 10.1016/j.exger.2020.111097. Epub 2020 Sep 25. PMID: 32987117.
In vitro protocol:
1. Tapias V, Jainuddin S, Ahuja M, Stack C, Elipenahli C, Vignisse J, Gerges M, Starkova N, Xu H, Starkov AA, Bettendorff L, Hushpulian DM, Smirnova NA, Gazaryan IG, Kaidery NA, Wakade S, Calingasan NY, Thomas B, Gibson GE, Dumont M, Beal MF. Benfotiamine treatment activates the Nrf2/ARE pathway and is neuroprotective in a transgenic mouse model of tauopathy. Hum Mol Genet. 2018 Aug 15;27(16):2874-2892. doi: 10.1093/hmg/ddy201. PMID: 29860433; PMCID: PMC6077804. 2. Bozic I, Savic D, Stevanovic I, Pekovic S, Nedeljkovic N, Lavrnja I. Benfotiamine upregulates antioxidative system in activated BV-2 microglia cells. Front Cell Neurosci. 2015 Sep 4;9:351. doi: 10.3389/fncel.2015.00351. eCollection 2015. PubMed PMID: 26388737; PubMed Central PMCID: PMC4559599.
In vivo protocol:
1. Tapias V, Jainuddin S, Ahuja M, Stack C, Elipenahli C, Vignisse J, Gerges M, Starkova N, Xu H, Starkov AA, Bettendorff L, Hushpulian DM, Smirnova NA, Gazaryan IG, Kaidery NA, Wakade S, Calingasan NY, Thomas B, Gibson GE, Dumont M, Beal MF. Benfotiamine treatment activates the Nrf2/ARE pathway and is neuroprotective in a transgenic mouse model of tauopathy. Hum Mol Genet. 2018 Aug 15;27(16):2874-2892. doi: 10.1093/hmg/ddy201. PMID: 29860433; PMCID: PMC6077804. 2. Moraes RCM, Singulani MP, Gonçalves AC, Portari GV, Torrão ADS. Oral benfotiamine reverts cognitive deficit and increase thiamine diphosphate levels in the brain of a rat model of neurodegeneration. Exp Gerontol. 2020 Nov;141:111097. doi: 10.1016/j.exger.2020.111097. Epub 2020 Sep 25. PMID: 32987117.
1: Bozic I, Savic D, Stevanovic I, Pekovic S, Nedeljkovic N, Lavrnja I. Benfotiamine upregulates antioxidative system in activated BV-2 microglia cells. Front Cell Neurosci. 2015 Sep 4;9:351. doi: 10.3389/fncel.2015.00351. eCollection 2015. PubMed PMID: 26388737; PubMed Central PMCID: PMC4559599. 2: Zhu Z, Varadi G, Carter SG. Pharmacokinetics of the transdermal delivery of benfotiamine. Acta Diabetol. 2016 Apr;53(2):317-22. doi: 10.1007/s00592-015-0776-2. Epub 2015 Jul 4. PubMed PMID: 26141141. 3: Manzardo AM, Pendleton T, Poje A, Penick EC, Butler MG. Change in psychiatric symptomatology after benfotiamine treatment in males is related to lifetime alcoholism severity. Drug Alcohol Depend. 2015 Jul 1;152:257-63. doi: 10.1016/j.drugalcdep.2015.03.032. Epub 2015 Apr 8. PubMed PMID: 25908323; PubMed Central PMCID: PMC4550087. 4: Sugimori N, Espinoza JL, Trung LQ, Takami A, Kondo Y, An DT, Sasaki M, Wakayama T, Nakao S. Paraptosis cell death induction by the thiamine analog benfotiamine in leukemia cells. PLoS One. 2015 Apr 7;10(4):e0120709. doi: 10.1371/journal.pone.0120709. eCollection 2015. PubMed PMID: 25849583; PubMed Central PMCID: PMC4388699. 5: Müller-Krebs S, Nissle K, Tsobaneli J, Zeier M, Kihm LP, Kender Z, Fleming T, Nawroth PP, Reiser J, Schwenger V. Effect of benfotiamine in podocyte damage induced by peritoneal dialysis fluid. Front Med (Lausanne). 2015 Mar 10;2:10. doi: 10.3389/fmed.2015.00010. eCollection 2015. PubMed PMID: 25806370; PubMed Central PMCID: PMC4354337. 6: Bozic I, Savic D, Laketa D, Bjelobaba I, Milenkovic I, Pekovic S, Nedeljkovic N, Lavrnja I. Benfotiamine attenuates inflammatory response in LPS stimulated BV-2 microglia. PLoS One. 2015 Feb 19;10(2):e0118372. doi: 10.1371/journal.pone.0118372. eCollection 2015. PubMed PMID: 25695433; PubMed Central PMCID: PMC4335016. 7: Hegazy MA, Abdelwahab NS, Fayed AS. A novel spectral resolution and simultaneous determination of multicomponent mixture of Vitamins B1, B6, B12, Benfotiamine and Diclofenac in tablets and capsules by derivative and MCR-ALS. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Apr 5;140:524-33. doi: 10.1016/j.saa.2014.12.108. Epub 2015 Jan 20. PubMed PMID: 25645231. 8: Jung KH, Lee JH, Park JW, Paik JY, Quach CH, Lee EJ, Lee KH. Annexin V imaging detects diabetes-accelerated apoptosis and monitors the efficacy of benfotiamine treatment in ischemic limbs of mice. Mol Imaging. 2014;13:1-7. PubMed PMID: 24824853. 9: Nacitarhan C, Minareci E, Sadan G. The effect of benfotiamine on mu-opioid receptor mediated antinociception in experimental diabetes. Exp Clin Endocrinol Diabetes. 2014 Mar;122(3):173-8. doi: 10.1055/s-0033-1363977. Epub 2014 Mar 18. PubMed PMID: 24643695. 10: Sergienko VA, Segin VB, Samir A, Sergienko AA. [The effect of long-chain polyunsaturated higher ω-3 fatty acids, benfotiamine and α-lipoic acid on the lipid metabolism in patients with diabetes mellitus type 2 and cardiovascular autonomic neuropathy]. Zh Nevrol Psikhiatr Im S S Korsakova. 2013;113(11):54-8. Russian. PubMed PMID: 24429949. 11: Xie F, Cheng Z, Li S, Liu X, Guo X, Yu P, Gu Z. Pharmacokinetic study of benfotiamine and the bioavailability assessment compared to thiamine hydrochloride. J Clin Pharmacol. 2014 Jun;54(6):688-95. doi: 10.1002/jcph.261. Epub 2014 Jan 22. PubMed PMID: 24399744. 12: Manzardo AM, He J, Poje A, Penick EC, Campbell J, Butler MG. Double-blind, randomized placebo-controlled clinical trial of benfotiamine for severe alcohol dependence. Drug Alcohol Depend. 2013 Dec 1;133(2):562-70. doi: 10.1016/j.drugalcdep.2013.07.035. Epub 2013 Aug 11. PubMed PMID: 23992649; PubMed Central PMCID: PMC3818307. 13: Stirban A, Pop A, Fischer A, Heckermann S, Tschoepe D. Variability of skin autofluorescence measurement over 6 and 12 weeks and the influence of benfotiamine treatment. Diabetes Technol Ther. 2013 Sep;15(9):733-7. doi: 10.1089/dia.2013.0103. Epub 2013 Aug 21. PubMed PMID: 23964994. 14: Kousar S, Sheikh MA, Asghar M. Antiglycation activity of thiamin-HCl and benfotiamine in diabetic condition. J Pak Med Assoc. 2012 Oct;62(10):1033-8. PubMed PMID: 23866441. 15: Harisa GI. Benfotiamine enhances antioxidant defenses and protects against cisplatin-induced DNA damage in nephrotoxic rats. J Biochem Mol Toxicol. 2013 Aug;27(8):398-405. doi: 10.1002/jbt.21501. Epub 2013 May 28. PubMed PMID: 23716490. 16: Stirban A, Pop A, Tschoepe D. A randomized, double-blind, crossover, placebo-controlled trial of 6 weeks benfotiamine treatment on postprandial vascular function and variables of autonomic nerve function in Type 2 diabetes. Diabet Med. 2013 Oct;30(10):1204-8. doi: 10.1111/dme.12240. Epub 2013 Jun 12. PubMed PMID: 23701274. 17: Portari GV, Vannucchi H, Jordao AA Jr. Liver, plasma and erythrocyte levels of thiamine and its phosphate esters in rats with acute ethanol intoxication: a comparison of thiamine and benfotiamine administration. Eur J Pharm Sci. 2013 Mar 12;48(4-5):799-802. doi: 10.1016/j.ejps.2013.01.010. Epub 2013 Jan 29. PubMed PMID: 23369791. 18: Hurt JK, Coleman JL, Fitzpatrick BJ, Taylor-Blake B, Bridges AS, Vihko P, Zylka MJ. Prostatic acid phosphatase is required for the antinociceptive effects of thiamine and benfotiamine. PLoS One. 2012;7(10):e48562. doi: 10.1371/journal.pone.0048562. Epub 2012 Oct 31. PubMed PMID: 23119057; PubMed Central PMCID: PMC3485352. 19: Ziegler D, Tesfaye S, Kempler P. Comment on: Fraser et al. The effects of long-term oral benfotiamine supplementation on peripheral nerve function and inflammatory markers in patients with type 1 diabetes: a 24-month, double-blind, randomized, placebo-controlled trial. Diabetes Care 2012;35:1095-1097. Diabetes Care. 2012 Nov;35(11):e79; author reply e80. doi: 10.2337/dc12-0817. PubMed PMID: 23093690; PubMed Central PMCID: PMC3476903. 20: Stirban A, Nandrean S, Kirana S, Götting C, Veresiu IA, Tschoepe D. Benfotiamine counteracts smoking-induced vascular dysfunction in healthy smokers. Int J Vasc Med. 2012;2012:968761. doi: 10.1155/2012/968761. Epub 2012 Oct 3. PubMed PMID: 23091724; PubMed Central PMCID: PMC3471443.