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Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS.Br.BrH
Molecular Weight 426.171
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMINE HYDROBROMIDE ANHYDROUS

SMILES

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

InChI

InChIKey=BICSXHHXUZPOLW-UHFFFAOYSA-M
InChI=1S/C12H17N4OS.2BrH/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);2*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

1953
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Doses

Doses

DosePopulationAdverse events​
500 mg single, intravenous
Highest studied dose
Dose: 500 mg
Route: intravenous
Route: single
Dose: 500 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].
2001
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.
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
Nutritional evaluation of ethanol-extracted lentil flours.
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
[Chronic alcohol abuse. Benfotiamine in alcohol damage is a must].
2001 Apr 19
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
Lactic acidosis update for critical care clinicians.
2001 Feb
In vivo and in vitro proton NMR spectroscopic studies of thiamine-deficient rat brains.
2001 Feb
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
Nutritional evaluation of some processed catering foods.
2001 Jan
[Unusual MR findings of Wernicke encephalopathy with cortical involvement].
2001 Jan
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.
2001 Jan
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
2001 Jan
Molecular cloning of human thiamin pyrophosphokinase.
2001 Jan 26
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.
2001 Jan 26
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.
2001 Jan-Feb
Cardiac beriberi among illegal mainland Chinese immigrants.
2001 Jan-Feb
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).
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
Nerve conduction changes in patients with mitochondrial diseases treated with dichloroacetate.
2001 Jul
Mechanism of thiamine uptake by human colonocytes: studies with cultured colonic epithelial cell line NCM460.
2001 Jul
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.
2001 Jul-Aug
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 a self-administered quantitative food amount frequency questionnaire with 4-day estimated food records.
2001 Mar
Aging potentiates the acute and chronic neurological symptoms of pyrithiamine-induced thiamine deficiency in the rodent.
2001 Mar 15
The genes for anabolic 2-oxoglutarate: ferredoxin oxidoreductase from Hydrogenobacter thermophilus TK-6.
2001 Mar 30
[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
The value of oral thiamine.
2001 Mar-Apr
[Other drugs administered with TPN solution].
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
Wernicke's encephalopathy in a non-alcoholic man: case report and brief review.
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
The use of thiamine and thiamine antagonists to investigate the etiology of early mortality syndrome in lake trout (Salvelinus namaycush).
2001 May
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 Mon Mar 31 23:06:04 GMT 2025
Edited
by admin
on Mon Mar 31 23:06:04 GMT 2025
Record UNII
K971V37HSF
Record Status Validated (UNII)
Record Version
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Name Type Language
THIAMINE BROMIDE HYDROBROMIDE
Preferred Name English
THIAMINE HYDROBROMIDE ANHYDROUS
WHO-IP  
Common Name English
3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4- METHYLTHIAZOLIUM BROMIDE, MONOHYDROBROMIDE
Systematic Name English
THIAMINE HYDROBROMIDE [WHO-IP]
Common Name English
THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-, BROMIDE, HYDROBROMIDE (1:1:1)
Systematic Name English
THIAMINE BROMIDE-HYDROBROMIDE
Common Name English
THIAMINE HYDROBROMIDE, ANHYDROUS [WHO-IP]
Common Name English
THIAMINI HYDROBROMIDUM [WHO-IP LATIN]
Common Name English
THIAMINE BROMIDE, MONOHYDROBROMIDE
Common Name English
THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-, BROMIDE, MONOHYDROBROMIDE
Systematic Name English
Code System Code Type Description
CAS
4234-86-0
Created by admin on Mon Mar 31 23:06:04 GMT 2025 , Edited by admin on Mon Mar 31 23:06:04 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
THIAMINE HYDROBROMIDE, ANHYDROUS
Created by admin on Mon Mar 31 23:06:04 GMT 2025 , Edited by admin on Mon Mar 31 23:06:04 GMT 2025
PRIMARY Description: A white to yellowish white, crystalline powder; odour, slight and characteristic. Solubility: Freely soluble in water and in methanol R; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Component of vitamin B. Storage: Thiamine hydrobromide should be kept in a tightly closed, non-metallic container, protected from light. Definition: Thiamine hydrobromide contains not less than 98.0% and not more than 101.0% of C12H17BrN4OS, HBr, calculated with reference to the dried substance.
PUBCHEM
14216038
Created by admin on Mon Mar 31 23:06:04 GMT 2025 , Edited by admin on Mon Mar 31 23:06:04 GMT 2025
PRIMARY
FDA UNII
K971V37HSF
Created by admin on Mon Mar 31 23:06:04 GMT 2025 , Edited by admin on Mon Mar 31 23:06:04 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY