U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS.Br
Molecular Weight 345.259
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMINE BROMIDE

SMILES

[Br-].CC1=C(CCO)SC=[N+]1CC2=CN=C(C)N=C2N

InChI

InChIKey=URCYCZPVXXIFSR-UHFFFAOYSA-M
InChI=1S/C12H17N4OS.BrH/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula C12H16N4OS
Molecular Weight 264.347
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Thiamine, also known as vitamin B1, plays a key role in the human metabolism. It is present in many dietary sources such as meats, eggs, fish, beans and peas, nuts, and whole grains. Upon administration thiamine is converted by thiamine pyrophosphokinase-1 (TPK1) to the active form, thiamine pyrophosphate, which serves as a cofactor for enzymes involved in the TCA cycle and the non-oxidative part of the pentose phosphate pathway. The lack of thiamine may cause the thiamine deficiency. The classical syndrome caused primarily by thiamine deficiency in humans is beriberi, however, symptoms of thiamine deficiency also include congestive heart failure, metabolic acidosis, confusion, ataxia and seizures. Thiamine is a component of many vitamin complexes, which are approved for the treatmen and prevention of general vitamin deficiency, including the thiamine deficiency.

CNS Activity

Curator's Comment: The transport of thiamine across the blood brain barrier was shown in rats.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H3S4
Gene ID: 27010.0
Gene Symbol: TPK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
M.V.I.-12

Approved Use

M.V.I.-12 Unit Vial, is indicated for the prevention of vitamin deficiency in adults and children aged 11 years and above who are on warfarin anticoagulant therapy receiving home parenteral nutrition.

Launch Date

-5.32137607E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
386 nM
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
40 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
95 nM
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
39 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
397 nM
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
113 nM
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2046 nM × h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
214 nM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
623 nM × h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
177 nM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2059 nM × h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
612 nM × h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.78 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2.97 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
3.92 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
500 mg single, intravenous
Highest studied dose
Dose: 500 mg
Route: intravenous
Route: single
Dose: 500 mg
Sources:
unhealthy, adult
n = 19
Health Status: unhealthy
Condition: various patients
Age Group: adult
Sex: unknown
Population Size: 19
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Effects of vitamins on hepatic nuclear binding of L-tryptophan.
2001
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.
2001 Apr
Severe metabolic acidosis and heart failure due to thiamine deficiency.
2001 Apr
Do breastfed infants need supplemental vitamins?
2001 Apr
Conditioned nutritional deficiencies in the cardiomyopathic hamster heart.
2001 Apr
Analysis of slc19a2, on 1q23.3 encoding a thiamine transporter as a candidate gene for type 2 diabetes mellitus in pima indians.
2001 Apr
Suppression of the accumulation of triosephosphates and increased formation of methylglyoxal in human red blood cells during hyperglycaemia by thiamine in vitro.
2001 Apr
The multifaceted and widespread pathology of magnesium deficiency.
2001 Feb
Aroma extract dilution analysis of a beeflike process flavor from extruded enzyme-hydrolyzed soybean protein.
2001 Feb
Wernicke's encephalopathy following gastroplasty for morbid obesity.
2001 Feb
Evidence for non-enzymatic glycosylation in Escherichia coli.
2001 Feb
Lactic acidosis update for critical care clinicians.
2001 Feb
Consequences of a modified putative substrate-activation site on catalysis by yeast pyruvate decarboxylase.
2001 Feb 13
Inhibitors of advanced glycation end product-associated protein cross-linking.
2001 Feb 14
Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.
2001 Feb 15
Cresol red thallium acetate sucrose inulin (CTSI) agar for the selective recovery of Carnobacterium spp.
2001 Feb 28
Certification of B-group vitamins (B1, B2, B6, and B12) in four food reference materials.
2001 Jan
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.
2001 Jan-Feb
Marginal vitamin and mineral intake of Costa Rican adolescents.
2001 Jan-Feb
Cardiac beriberi among illegal mainland Chinese immigrants.
2001 Jan-Feb
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.
2001 Jul
Low thiamine intake and risk of cataract.
2001 Jul
Sulphoacetaldehyde sulpho-lyase (EC 4.4.1.12) from Desulfonispora thiosulfatigenes: purification, properties and primary sequence.
2001 Jul 15
The crystal structure of yeast thiamin pyrophosphokinase.
2001 Jun
Nutritional status in elderly female hip fracture patients: comparison with an age-matched home living group attending day centres.
2001 Jun
Sulfur compounds reduce potato toxins during extrusion cooking.
2001 Jun
Slc19a2: cloning and characterization of the murine thiamin transporter cDNA and genomic sequence, the orthologue of the human TRMA gene.
2001 Jun
Simultaneous determination of thiamine and pyridoxine in pharmaceuticals by using a single flow-through biparameter sensor.
2001 Jun
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001 Jun
Chronic heart failure and micronutrients.
2001 Jun 1
Comparison of ion-pair and amide-based column reversed-phase liquid chromatography for the separation of thiamine-related compounds.
2001 Jun 15
Painful alcoholic polyneuropathy with predominant small-fiber loss and normal thiamine status.
2001 Jun 26
Catalytic acid-base groups in yeast pyruvate decarboxylase. 1. Site-directed mutagenesis and steady-state kinetic studies on the enzyme with the D28A, H114F, H115F, and E477Q substitutions.
2001 Jun 26
Crystal structure of thiamin pyrophosphokinase.
2001 Jun 29
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
[Shoshin beriberi: myth or reality?].
2001 Mar
Comparison of a self-administered quantitative food amount frequency questionnaire with 4-day estimated food records.
2001 Mar
[Metabolic characteristics of the Yarrowia lipolytica strain producing alpha-ketoglutaric and citric acids from ethanol and the effect of [NH4+] and [O2] on yeast respiration and biosynthesis].
2001 Mar-Apr
[Isolation, purification and properties of acetolactate synthase from cultured Lactococcus lactis].
2001 Mar-Apr
[Other drugs administered with TPN solution].
2001 May
[Metabolic acidosis induced by TPN].
2001 May
[Solutions for the hyperalimentation].
2001 May
The application of capillary electrophoresis to the analysis of vitamins in food and beverages.
2001 May
Pharmacotherapy of mental illness--a historical analysis.
2001 May
Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias.
2001 May
A novel mutation in the SLC19A2 gene in a Tunisian family with thiamine-responsive megaloblastic anaemia, diabetes and deafness syndrome.
2001 May
Early recognition of acute cardiovascular beriberi by interpretation of hemodynamics.
2001 May
Stability of thiamine and vitamins E and A during storage of enteral feeding formula.
2001 May
The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.
2001 May
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.
2001 May-Jun
Patents

Sample Use Guides

The starting dose (as a component of M.V.I.–12) is one 10 mL daily dose added directly to an intravenous fluid.
Route of Administration: Intravenous
Human Caco-2 cells were incubated (37 Celsius) in Krebs-Ringer buffer (pH 7.4) for different periods of time in the presence of 0.1 uM and 10 uM thiamine. The uptake study demonstrated that thiamine is transported across the cell membrane with Michaelis-Menten constant of 3.18 uM.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:44:10 UTC 2023
Edited
by admin
on Thu Jul 06 02:44:10 UTC 2023
Record UNII
JIJ7B8T57F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIAMINE BROMIDE
WHO-DD  
Common Name English
Thiamine bromide [WHO-DD]
Common Name English
3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYLTHIAZOLIUM BROMIDE
Systematic Name English
THIAMINIUM BROMIDE
Common Name English
Code System Code Type Description
FDA UNII
JIJ7B8T57F
Created by admin on Thu Jul 06 02:44:10 UTC 2023 , Edited by admin on Thu Jul 06 02:44:10 UTC 2023
PRIMARY
CAS
7019-71-8
Created by admin on Thu Jul 06 02:44:10 UTC 2023 , Edited by admin on Thu Jul 06 02:44:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID40990431
Created by admin on Thu Jul 06 02:44:10 UTC 2023 , Edited by admin on Thu Jul 06 02:44:10 UTC 2023
PRIMARY
PUBCHEM
71284
Created by admin on Thu Jul 06 02:44:10 UTC 2023 , Edited by admin on Thu Jul 06 02:44:10 UTC 2023
PRIMARY
MESH
C003434
Created by admin on Thu Jul 06 02:44:10 UTC 2023 , Edited by admin on Thu Jul 06 02:44:10 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY