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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS
Molecular Weight 265.355
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of THIAMINE ION

SMILES

CC1=C(CCO)SC=[N+]1CC2=C(N)N=C(C)N=C2

InChI

InChIKey=JZRWCGZRTZMZEH-UHFFFAOYSA-N
InChI=1S/C12H17N4OS/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)/q+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

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
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.
2001 Apr
Severe metabolic acidosis and heart failure due to thiamine deficiency.
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
Evidence for non-enzymatic glycosylation in Escherichia coli.
2001 Feb
Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.
2001 Feb 15
Phylogenetic analyses and comparative genomics of vitamin B6 (pyridoxine) and pyridoxal phosphate biosynthesis pathways.
2001 Jan
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
2001 Jan
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.
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
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
The crystal structure of yeast thiamin pyrophosphokinase.
2001 Jun
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001 Jun
Wernicke's encephalopathy in patients with hyperemesis gravidarum.
2001 Mar
[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
[Metabolic acidosis induced by TPN].
2001 May
[Solutions for the hyperalimentation].
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 role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA.
2001 Sep 7
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 18:13:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:13:14 GMT 2025
Record UNII
4ABT0J945J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-
Preferred Name English
THIAMINE ION
Common Name English
Code System Code Type Description
DAILYMED
4ABT0J945J
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
CAS
70-16-6
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID50220251
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
CHEBI
18385
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
FDA UNII
4ABT0J945J
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
RXCUI
1546268
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY RxNorm
PUBCHEM
1130
Created by admin on Mon Mar 31 18:13:14 GMT 2025 , Edited by admin on Mon Mar 31 18:13:14 GMT 2025
PRIMARY
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