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

MedKoo CAT#: 326712

CAS#: 22457-89-2

Description: 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.


Price and Availability

Size
Price

1g
USD 90
10g
USD 450
100g
USD 1750
Size
Price

2g
USD 150
20g
USD 650
200g
Ask price
Size
Price

5g
USD 250
50g
USD 950

Benfotiamine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326712
Name: Benfotiamine
CAS#: 22457-89-2
Chemical Formula: C19H23N4O6PS
Exact Mass: 466.1076
Molecular Weight: 466.4488
Elemental Analysis: C, 48.92; H, 4.97; N, 12.01; O, 20.58; P, 6.64; S, 6.87


Synonym: BRN-0771326; BTMP; CB-8088; CB8088; CB 8088; Berdi; Betivina; Biotamin; Benfotiamine; S-benzoylthiamine O-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


Technical Data

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).

Harmonized System Code:
293490


Additional Information

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.


References

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.