Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H34O4S.C16H33O4S.C12H17N4OS |
Molecular Weight | 909.354 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CCO)SC=[N+]1CC2=CN=C(C)N=C2N.CCCCCCCCCCCCCCCCOS(O)(=O)=O.CCCCCCCCCCCCCCCCOS([O-])(=O)=O
InChI
InChIKey=HVIVKYLMXRWCDK-UHFFFAOYSA-M
InChI=1S/2C16H34O4S.C12H17N4OS/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-21(17,18)19;1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h2*2-16H2,1H3,(H,17,18,19);5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q;;+1/p-1
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 | C16H34O4S |
Molecular Weight | 322.504 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7120152
Curator's Comment: The transport of thiamine across the blood brain barrier was shown in rats.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q9H3S4 Gene ID: 27010.0 Gene Symbol: TPK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16550223 |
|||
Target ID: GO:0005975 |
|||
Target ID: WP408 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | M.V.I.-12 Approved UseM.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 Date1953 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
214 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.92 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22305197/ |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://go.drugbank.com/drugs/DB00152 |
yes | |||
Sources: https://go.drugbank.com/drugs/DB00152 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://go.drugbank.com/drugs/DB00152 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Thiamine for Alzheimer's disease. | 2001 |
|
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 |
|
Evidence for non-enzymatic glycosylation in Escherichia coli. | 2001 Feb |
|
In vivo and in vitro proton NMR spectroscopic studies of thiamine-deficient rat brains. | 2001 Feb |
|
Glucose induced IEG expression in the thiamin-deficient rat brain. | 2001 Feb 16 |
|
Cresol red thallium acetate sucrose inulin (CTSI) agar for the selective recovery of Carnobacterium spp. | 2001 Feb 28 |
|
[Postoperative encephalopathies: thiamine deficiency, an unrecognized etiology]. | 2001 Jan |
|
Longitudinal vitamin and homocysteine levels in normal pregnancy. | 2001 Jan |
|
Thiamin treatment and working memory function of alcohol-dependent people: preliminary findings. | 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 |
|
Marginal vitamin and mineral intake of Costa Rican adolescents. | 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 |
|
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic. | 2001 Jun |
|
Nutritional status in elderly female hip fracture patients: comparison with an age-matched home living group attending day centres. | 2001 Jun |
|
Wernicke's encephalopathy in patients with hyperemesis gravidarum. | 2001 Mar |
|
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 |
|
[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 |
|
Examination of donor substrate conversion in yeast transketolase. | 2001 May 11 |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10516094
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
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Record UNII |
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Record Status |
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Record Version |
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