Benfotiamine sodium

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MedKoo CAT#: 565590

CAS#: 22457-89-2

Description: Benfotiamine (rINN, or S-benzoylthiamine O-monophosphate) is a synthetic S-acyl derivative of thiamine (vitamin B1) that is marketed as a pharmaceutical drug in most countries, and as a thiamine derivative supplement for treating diabetic neuropathy.


Price and Availability

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Pricing updated 2020-08-15. Prices are subject to change without notice.

Benfotiamine sodium is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565590
Name: Benfotiamine sodium
CAS#: 22457-89-2
Chemical Formula: C19H21N4Na2O6PS
Exact Mass: 466.1076
Molecular Weight: 510.4123
Elemental Analysis: C, 44.71; H, 4.15; N, 10.98; Na, 9.01; O, 18.81; P, 6.07; S, 6.28


Related CAS #: 147317-17-7 (semihydrate)   22457-89-2 (free acid)    

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

IUPAC/Chemical Name: sodium (Z)-4-(N-((4-amino-2-methylpyrimidin-5-yl)methyl)formamido)-3-((phenylcarbonothioyl)oxy)pent-3-en-1-yl phosphate

InChi Key: VPBYYNRBNZZSBF-IHLCSVPUSA-L

InChi Code: InChI=1S/C19H23N4O6PS.2Na/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-28-30(25,26)27)29-19(31)15-6-4-3-5-7-15;;/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,25,26,27);;/q;2*+1/p-2/b17-13-;;

SMILES Code: S=C(O/C(CCOP(O[Na])(O[Na])=O)=C(C)\N(C=O)CC1=CN=C(N=C1N)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

Shelf Life:
>3 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


References

1: Yu L, Chen Y, Xu Y, He T, Wei Y, He R. D-ribose is elevated in T1DM patients and can be involved in the onset of encephalopathy. Aging (Albany NY). 2019 Jul 15;11. doi: 10.18632/aging.102089. [Epub ahead of print] PubMed PMID: 31307014.

2: Dalwadi P, Joshi AS, Thakur DS, Bhagwat NM. Neonatal diabetes mellitus: remission induced by novel therapy. BMJ Case Rep. 2019 Jun 25;12(6). pii: e228806. doi: 10.1136/bcr-2018-228806. PubMed PMID: 31243025.

3: Sambon M, Napp A, Demelenne A, Vignisse J, Wins P, Fillet M, Bettendorff L. Thiamine and benfotiamine protect neuroblastoma cells against paraquat and β-amyloid toxicity by a coenzyme-independent mechanism. Heliyon. 2019 May 14;5(5):e01710. doi: 10.1016/j.heliyon.2019.e01710. eCollection 2019 May. PubMed PMID: 31193162; PubMed Central PMCID: PMC6520661.

4: Gorlova A, Pavlov D, Anthony DC, Ponomarev ED, Sambon M, Proshin A, Shafarevich I, Babaevskaya D, Lesсh KP, Bettendorff L, Strekalova T. Thiamine and benfotiamine counteract ultrasound-induced aggression, normalize AMPA receptor expression and plasticity markers, and reduce oxidative stress in mice. Neuropharmacology. 2019 Sep 15;156. pii: S0028-3908(19)30058-9. doi: 10.1016/j.neuropharm.2019.02.025. Epub 2019 Feb 25. PubMed PMID: 30817932.

5: Tuncer S, Atilgan R, Pala Ş, Kuloğlu T, Artaş G, Aydın S. N-Acetylcysteine and Benfotiamine Protect Autotransplanted Ovarian Tissue From Ischemia-Reperfusion Injury: An Experimental Study. Exp Clin Transplant. 2018 Oct 5. doi: 10.6002/ect.2017.0320. [Epub ahead of print] PubMed PMID: 30295588.

6: Xu C, Liu WB, Zhang DD, Shi HJ, Zhang L, Li XF. Benfotiamine, a Lipid-Soluble Analog of Vitamin B(1), Improves the Mitochondrial Biogenesis and Function in Blunt Snout Bream (Megalobrama amblycephala) Fed High-Carbohydrate Diets by Promoting the AMPK/PGC-1β/NRF-1 Axis. Front Physiol. 2018 Sep 3;9:1079. doi: 10.3389/fphys.2018.01079. eCollection 2018. PubMed PMID: 30233383; PubMed Central PMCID: PMC6129842.

7: Yu Q, Liu H, Sang S, Chen L, Zhao Y, Wang Y, Zhong C. Thiamine deficiency contributes to synapse and neural circuit defects. Biol Res. 2018 Sep 19;51(1):35. doi: 10.1186/s40659-018-0184-5. PubMed PMID: 30231926; PubMed Central PMCID: PMC6145320.

8: Raj V, Ojha S, Howarth FC, Belur PD, Subramanya SB. Therapeutic potential of benfotiamine and its molecular targets. Eur Rev Med Pharmacol Sci. 2018 May;22(10):3261-3273. doi: 10.26355/eurrev_201805_15089. PubMed PMID: 29863274.

9: 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. PubMed PMID: 29860433; PubMed Central PMCID: PMC6077804.

10: Ustuner MA, Kaman D, Colakoglu N. Effects of benfotiamine and coenzyme Q10 on kidney damage induced gentamicin. Tissue Cell. 2017 Dec;49(6):691-696. doi: 10.1016/j.tice.2017.10.001. Epub 2017 Oct 12. PubMed PMID: 29066103.

11: Chen X, Su T, Chen Y, He Y, Liu Y, Xu Y, Wei Y, Li J, He R. d-Ribose as a Contributor to Glycated Haemoglobin. EBioMedicine. 2017 Nov;25:143-153. doi: 10.1016/j.ebiom.2017.10.001. Epub 2017 Oct 5. PubMed PMID: 29033370; PubMed Central PMCID: PMC5704047.

12: Várkonyi T, Körei A, Putz Z, Martos T, Keresztes K, Lengyel C, Nyiraty S, Stirban A, Jermendy G, Kempler P. Advances in the management of diabetic neuropathy. Minerva Med. 2017 Oct;108(5):419-437. doi: 10.23736/S0026-4806.17.05257-0. Epub 2017 May 25. Review. PubMed PMID: 28541026.

13: Vignisse J, Sambon M, Gorlova A, Pavlov D, Caron N, Malgrange B, Shevtsova E, Svistunov A, Anthony DC, Markova N, Bazhenova N, Coumans B, Lakaye B, Wins P, Strekalova T, Bettendorff L. Thiamine and benfotiamine prevent stress-induced suppression of hippocampal neurogenesis in mice exposed to predation without affecting brain thiamine diphosphate levels. Mol Cell Neurosci. 2017 Jul;82:126-136. doi: 10.1016/j.mcn.2017.05.005. Epub 2017 May 12. PubMed PMID: 28506637.

14: Spallone V. Might genetics play a role in understanding and treating diabetic polyneuropathy? Diabetes Metab Res Rev. 2017 May;33(4). doi: 10.1002/dmrr.2882. Epub 2017 Feb 23. PubMed PMID: 28032668.

15: Markova N, Bazhenova N, Anthony DC, Vignisse J, Svistunov A, Lesch KP, Bettendorff L, Strekalova T. Thiamine and benfotiamine improve cognition and ameliorate GSK-3β-associated stress-induced behaviours in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2017 Apr 3;75:148-156. doi: 10.1016/j.pnpbp.2016.11.001. Epub 2016 Nov 5. PubMed PMID: 27825907.

16: Gupta M, Verma P, Rastogi R, Arora S, Elwadhi D. Randomized open-label trial of baclofen for relapse prevention in alcohol dependence. Am J Drug Alcohol Abuse. 2017 May;43(3):324-331. doi: 10.1080/00952990.2016.1240797. Epub 2016 Nov 3. PubMed PMID: 27808555.

17: Bhattacharjee N, Barma S, Konwar N, Dewanjee S, Manna P. Mechanistic insight of diabetic nephropathy and its pharmacotherapeutic targets: An update. Eur J Pharmacol. 2016 Nov 15;791:8-24. doi: 10.1016/j.ejphar.2016.08.022. Epub 2016 Aug 25. Review. PubMed PMID: 27568833.

18: Park WS, Lee J, Hong T, Park G, Youn S, Seo Y, Lee S, Han S. Comparative Pharmacokinetic Analysis of Thiamine and Its Phosphorylated Metabolites Administered as Multivitamin Preparations. Clin Ther. 2016 Oct;38(10):2277-2285. doi: 10.1016/j.clinthera.2016.08.009. Epub 2016 Oct 1. PubMed PMID: 27707509.

19: Fayed AS, Hegazy MA, Wahab NS. Chromatographic Analysis of a Multicomponent Mixture of B1, B6, B12, Benfotiamine, and Diclofenac; Part I: HPLC and UPLC Methods for the Simultaneous Quantification of These Five Components in Tablets and Capsules. J AOAC Int. 2016 Nov 1;99(6):1513-1521. doi: 10.5740/jaoacint.16-0023. Epub 2016 Oct 1. PubMed PMID: 27697097.

20: Pan X, Chen Z, Fei G, Pan S, Bao W, Ren S, Guan Y, Zhong C. Long-Term Cognitive Improvement After Benfotiamine Administration in Patients with Alzheimer's Disease. Neurosci Bull. 2016 Dec;32(6):591-596. Epub 2016 Oct 1. PubMed PMID: 27696179; PubMed Central PMCID: PMC5567484.