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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N4O6PS
Molecular Weight 466.448
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BENFOTIAMINE

SMILES

CC(N(CC1=C(N)N=C(C)N=C1)C=O)=C(CCOP(O)(O)=O)SC(=O)C2=CC=CC=C2

InChI

InChIKey=BTNNPSLJPBRMLZ-LGMDPLHJSA-N
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-

HIDE SMILES / InChI

Molecular Formula C19H23N4O6PS
Molecular Weight 466.448
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.medscape.com/viewarticle/583556_3 http://herbnutritionals.com/nutraceuticals/benfotiamine

Benfotiamine is a derivative of vitamin B1. It was developed in Japan specifically to treat Korsakoff's syndrome and patented in the United States in 1962, but never became popular. It has been in use as a widely used prescription drug in Europe since 1978 to treat diabetes and is available at many vitamin shops in the United States. It has been licensed for use in Germany since 1993 under the trade name Milgamma. (Combinations with pyridoxine or cyanocobalamin are also sold under this name). 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. Unfortunately apparent evidences from human studies are scarce and especially endpoint studies are missing. Benfotiamine has proven to affect glucose metabolic process through various mode of actions, and plays a part in obstructing age-associated glycation end products (AGEs). Benfotiamine reduces the extra biosynthesis and accumulation of a number of glucose metabolites, including glyceraldeyde-3-phosphate and dihydroxyacetone phosphate. Elevated levels of those glucose intermediates function as a trigger to most of the mechanisms accountable for hyperglycemia-caused cell damage. Benfotiamine increases tissue amounts of thiamine diphosphate, consequently growing transketolase activity and producing a significant decrease in glucose metabolites and precursors to AGEs. Up to now, two of the most effective AGE inhibitors in living microorganisms would be the Vitamin B1 derivative, benfotiamine and also the Vitamin B6 derivative, pyridoxamine. Additionally, benfotiamine has long been proven to lessen NF-kB activity, therefore restricting the over-production from the harmful superoxide toxin. Excess superoxide production may partly hinder a vital enzyme in glucose metabolic process, glyceraldehyde-3-phosphate dehydrogenase, directing glucose metabolites from glycolysis in to the major glucose-driven signaling paths that cause hyperglycemic damage. Theoretically, overdose with benfotiamine should cause menopausal flashes, bluish skin (because of rapid utilization of oxygen), tingling, and difficulty breathing, but used, this merely has not happened.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Benfotiamine attenuates nicotine and uric acid-induced vascular endothelial dysfunction in the rat.
2008 Nov-Dec
[Pharmacologic therapy in peripheral diabetic polyneuropathy].
2010 Apr-Jun
The defensive effect of benfotiamine in sodium arsenite-induced experimental vascular endothelial dysfunction.
2010 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Amount Per capsule: Benfotiamine 80 mg each pill
Suggested Use: One capsule a few times a week or as recommended by health care provider
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Thiamine and benfotiamine reduce aldose reductase mRNA expression, activity, sorbitol concentrations, and intracellular glucose while increasing the expression and activity of transketolase, for which it is a coenzyme, in human endothelial cells and bovine retinal pericytes cultured in high glucose. Thiamine and benfotiamine correct polyol pathway activation induced by high glucose in vascular cells.
Human umbilical vein endothelial cells and bovine retinal pericytes were cultured in normal (5.6 mmol/liter) or high (28 mmol/liter) glucose, with or without thiamine or benfotiamine 50 or 100 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:12:10 GMT 2023
Edited
by admin
on Fri Dec 15 17:12:10 GMT 2023
Record UNII
Y92OUS2H9B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENFOTIAMINE
INN   JAN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
benfotiamine [INN]
Common Name English
BENPHOTHIAMINE
Common Name English
S-BENZOYLTHIAMINE MONOPHOSPHATE
Common Name English
BENZENECARBOTHIOIC ACID, S-(2-(((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)FORMYLAMINO)-1-(2-(PHOSPHONOOXY)ETHYL)-1-PROPEN-1-YL) ESTER
Common Name English
BENFOTHIAMINE
Common Name English
BTMP
Common Name English
8088 C.B.
Code English
8088CB
Code English
BENFOTIAMINE [JAN]
Common Name English
Benfotiamine [WHO-DD]
Common Name English
BENFOTIAMINE [VANDF]
Common Name English
8088 C.B
Code English
BENFOTIAMINE [MI]
Common Name English
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-N-(4-HYDROXY-2-MERCAPTO-1-METHYL-1-BUTENYL)FORMAMIDE S-BENZOATE O-PHOSPHATE
Common Name English
8088-CB
Code English
S-BENZOYLTHIAMINE O-MONOPHOSPHATE
Common Name English
BENZOYLTHIAMINMONOPHOSPHAT
Common Name English
NSC-758241
Code English
BIOTAMIN
Brand Name English
BENFOTIAMINE [MART.]
Common Name English
BENZOYLTHIAMINE O-MONOPHOSPHATE
Common Name English
BENZOYLTHIAMINE MONOPHOSPHATE
Common Name English
Classification Tree Code System Code
WHO-ATC A11DA03
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
WHO-VATC QA11DA03
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
DSLD 2452 (Number of products:105)
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
Code System Code Type Description
DRUG CENTRAL
308
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
INN
1300
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
EVMPD
SUB05716MIG
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
DAILYMED
Y92OUS2H9B
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL1491875
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
RXCUI
18891
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C169805
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-013-4
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
CHEBI
41039
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
MERCK INDEX
m2313
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY Merck Index
PUBCHEM
2320
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID3045433
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
DRUG BANK
DB11748
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
NSC
758241
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
MESH
C013835
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
SMS_ID
100000086330
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
FDA UNII
Y92OUS2H9B
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
CAS
22457-89-2
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
WIKIPEDIA
BENFOTIAMINE
Created by admin on Fri Dec 15 17:12:10 GMT 2023 , Edited by admin on Fri Dec 15 17:12:10 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY