THIAMINE ION

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 Search

SMILES

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16550223 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/008809s066lbl.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thiamin pyrophosphokinase 1 11 Target ID: Q9H3S4 Gene ID: 27010.0 Gene Symbol: TPK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16550223	Substrate 661
carbohydrate metabolic process 11 Target ID: GO:0005975 Sources: https://www.trc-canada.com/product-detail/?CatNum=T344185	Modulator 828
Oxidative Stress 160 Target ID: WP408 Sources: https://www.bocsci.com/thiamine-cas-70-16-6-item-41803.html	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thiamine deficiency 13 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/008809s066lbl.pdf	Preventing		Approved 8429	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

C_max

Value	Dose	Analyte	Population
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
500 mg single, intravenous Highest studied dose Dose: 500 mg Route: intravenous Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31932197/	unhealthy, adult n = 19 Health Status: unhealthy Condition: various patients Age Group: adult Sex: unknown Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/31932197/	Sources: https://pubmed.ncbi.nlm.nih.gov/31932197/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 647 OCTN2 66	OCT1 327	CYP4B1 11

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP4B1 12	inducer 1573 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000059438, https://pubmed.ncbi.nlm.nih.gov/15328374/	yes	THIAMINE 11
OCT2 648	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11
OCTN2 71	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 327	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11

Sourcing

Vendor/Aggregator	ID	URL
Aurora Fine Chemicals LLC	K04.000.720	http://online.aurorafinechemicals.com/info?ID=K04.000.720
BLD Pharm	BD153807	http://www.bldpharm.com/products/70-16-6.html
ChemMol	49416419	http://www.chemmol.com/chemmol/49416419.html
ChemMol	49416566	http://www.chemmol.com/chemmol/49416566.html
Chemspace	CSSS00160641068	https://chem-space.com/CSSS00160641068
MolPort	MolPort-001-920-086	https://www.molport.com/shop/molecule-link/MolPort-001-920-086
Smolecule	S598516	https://www.smolecule.com/products/s598516
THE BioTek	bt-295268	https://www.thebiotek.com/product/others/bt-295268
eNovation Chemicals	D535901	https://www.enovationchem.com/ProductDetails.asp?ProductID=D535901
iChemical	EBD3681937	http://www.ichemical.com/products/70-16-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-2198445125	https://mcule.com/MCULE-2198445125/

PubMed

Title	Date	PubMed
Juvenile polyneuropathy due to vitamin B1 deficiency-clinical observations and pathogenetic analysis of 24 cases.	1976	1017763
Cloning of the human thiamine transporter, a member of the folate transporter family.	1999 Nov 5	10542220
Effect of thiamine hydrochloride on lead induced lipid peroxidation in rat liver and kidney.	2000 Aug	10928693
Low plasma thiamine levels in elder patients admitted through the emergency department.	2000 Oct	11015250
Thiamine for Alzheimer's disease.	2001	11405995
Effects of vitamins on hepatic nuclear binding of L-tryptophan.	2001	11332447
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.	2001	11244182
Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms.	2001	11153266
Severe metabolic acidosis and heart failure due to thiamine deficiency.	2001 Apr	11369178
Analysis of slc19a2, on 1q23.3 encoding a thiamine transporter as a candidate gene for type 2 diabetes mellitus in pima indians.	2001 Apr	11286512
Suppression of the accumulation of triosephosphates and increased formation of methylglyoxal in human red blood cells during hyperglycaemia by thiamine in vitro.	2001 Apr	11275553
The multifaceted and widespread pathology of magnesium deficiency.	2001 Feb	11425281
Wernicke's encephalopathy following gastroplasty for morbid obesity.	2001 Feb	11252304
Chorea induced by thiamine deficiency in hemodialysis patients.	2001 Feb	11157387
Consequences of a modified putative substrate-activation site on catalysis by yeast pyruvate decarboxylase.	2001 Feb 13	11327837
Glucose induced IEG expression in the thiamin-deficient rat brain.	2001 Feb 16	11172768
Probing the mechanism of inactivation of human pyruvate dehydrogenase by phosphorylation of three sites.	2001 Feb 23	11092882
Cresol red thallium acetate sucrose inulin (CTSI) agar for the selective recovery of Carnobacterium spp.	2001 Feb 28	11252499
[Unusual MR findings of Wernicke encephalopathy with cortical involvement].	2001 Jan	11211734
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.	2001 Jan	11170615
Solution structure of ThiS and implications for the evolutionary roots of ubiquitin.	2001 Jan	11135670
Sorption and desorption studies on chitin gels.	2001 Jan 10	11164225
Impact of the reduced folate carrier on the accumulation of active thiamin metabolites in murine leukemia cells.	2001 Jan 12	11038362
Molecular cloning of human thiamin pyrophosphokinase.	2001 Jan 26	11342117
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.	2001 Jan 26	11342111
Marginal vitamin and mineral intake of Costa Rican adolescents.	2001 Jan-Feb	11282184
Cardiac beriberi among illegal mainland Chinese immigrants.	2001 Jan-Feb	11277346
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).	2001 Jan-Feb	11276063
Effects of glucose, vitamins, and DO concentrations on pyruvate fermentation using Torulopsis glabrata IFO 0005 with metabolic flux analysis.	2001 Jan-Feb	11170481
Learning from biomedical time series through the integration of qualitative models and fuzzy systems.	2001 Jan-Mar	11154888
Low thiamine intake and risk of cataract.	2001 Jul	11425658
Mechanism of thiamine uptake by human colonocytes: studies with cultured colonic epithelial cell line NCM460.	2001 Jul	11408266
Sulphoacetaldehyde sulpho-lyase (EC 4.4.1.12) from Desulfonispora thiosulfatigenes: purification, properties and primary sequence.	2001 Jul 15	11439112
Sulfur compounds reduce potato toxins during extrusion cooking.	2001 Jun	11409974
Vitamin B1 and B6 retention in milk after continuous-flow microwave and conventional heating at high temperatures.	2001 Jun	11403146
Crystal structure of thiamin pyrophosphokinase.	2001 Jun 29	11419946
Relationships between dietary intake and cognitive function level in Korean elderly people.	2001 Mar	11406779
Wernicke's encephalopathy in patients with hyperemesis gravidarum.	2001 Mar	11405565
Comparison of a self-administered quantitative food amount frequency questionnaire with 4-day estimated food records.	2001 Mar	11303463
The genes for anabolic 2-oxoglutarate: ferredoxin oxidoreductase from Hydrogenobacter thermophilus TK-6.	2001 Mar 30	11401501
[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	11386051
The value of oral thiamine.	2001 Mar-Apr	11259217
[Other drugs administered with TPN solution].	2001 May	11439537
[Metabolic acidosis induced by TPN].	2001 May	11439535
[Solutions for the hyperalimentation].	2001 May	11439519
Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias.	2001 May	11383938
Stability of thiamine and vitamins E and A during storage of enteral feeding formula.	2001 May	11368595
Examination of donor substrate conversion in yeast transketolase.	2001 May 11	11278369
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.	2001 May-Jun	11417630
The role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA.	2001 Sep 7	11443125

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

THIAMINE ION

Common Name

English

THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-

Systematic Name

English

Code System Code Type Description

DAILYMED

4ABT0J945J