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Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS.Br
Molecular Weight 345.2597
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMINE BROMIDE

SMILES

Cc1c(CCO)sc[n+]1Cc2cnc(C)[nH]c2=N.[Br-]

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 264.3482
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula BrH
Molecular Weight 80.9115
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
Juvenile polyneuropathy due to vitamin B1 deficiency-clinical observations and pathogenetic analysis of 24 cases.
1976
Low plasma thiamine levels in elder patients admitted through the emergency department.
2000 Oct
Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms.
2001
Thiamine-responsive acute neurological disorders in nonalcoholic patients.
2001
Do breastfed infants need supplemental vitamins?
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
Lactic acidosis update for critical care clinicians.
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
Glucose induced IEG expression in the thiamin-deficient rat brain.
2001 Feb 16
[Unusual MR findings of Wernicke encephalopathy with cortical involvement].
2001 Jan
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
2001 Jan
In vivo microdialysis in an animal model of neurological disease: thiamine deficiency (Wernicke) encephalopathy.
2001 Jan
Solution structure of ThiS and implications for the evolutionary roots of ubiquitin.
2001 Jan
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.
2001 Jan 26
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).
2001 Jan-Feb
Effects of glucose, vitamins, and DO concentrations on pyruvate fermentation using Torulopsis glabrata IFO 0005 with metabolic flux analysis.
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
Mechanism of thiamine uptake by human colonocytes: studies with cultured colonic epithelial cell line NCM460.
2001 Jul
Sulphoacetaldehyde sulpho-lyase (EC 4.4.1.12) from Desulfonispora thiosulfatigenes: purification, properties and primary sequence.
2001 Jul 15
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.
2001 Jul-Aug
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
Crystal structure of thiamin pyrophosphokinase.
2001 Jun 29
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
Wernicke's encephalopathy in patients with hyperemesis gravidarum.
2001 Mar
[Metabolic acidosis induced by TPN].
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
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
Examination of donor substrate conversion in yeast transketolase.
2001 May 11
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 Sat Jun 26 02:13:26 UTC 2021
Edited
by admin
on Sat Jun 26 02:13:26 UTC 2021
Record UNII
JIJ7B8T57F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
THIAMINE BROMIDE [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
JIJ7B8T57F
Created by admin on Sat Jun 26 02:13:26 UTC 2021 , Edited by admin on Sat Jun 26 02:13:26 UTC 2021
PRIMARY
CAS
7019-71-8
Created by admin on Sat Jun 26 02:13:26 UTC 2021 , Edited by admin on Sat Jun 26 02:13:26 UTC 2021
PRIMARY
PUBCHEM
71284
Created by admin on Sat Jun 26 02:13:26 UTC 2021 , Edited by admin on Sat Jun 26 02:13:26 UTC 2021
PRIMARY
MESH
C003434
Created by admin on Sat Jun 26 02:13:26 UTC 2021 , Edited by admin on Sat Jun 26 02:13:26 UTC 2021
PRIMARY
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ACTIVE MOIETY