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=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

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 846
Oxidative Stress 162 Target ID: WP408 Sources: https://www.bocsci.com/thiamine-cas-70-16-6-item-41803.html	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thiamine deficiency 13 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/008809s066lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	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	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

T_1/2

Value	Dose	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

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 Health Status: unhealthy Age Group: adult Sex: unknown 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 779 OCTN2 71	OCT1 393	CYP4B1 11

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP4B1 12	inducer 1966 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000059438, https://pubmed.ncbi.nlm.nih.gov/15328374/	yes	THIAMINE 11
OCT2 782	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11
OCTN2 71	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 393	substrate 4014 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
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/
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

PubMed

Title	Date	PubMed
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].	2001	11355481
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.	2001 Apr	11398710
Severe metabolic acidosis and heart failure due to thiamine deficiency.	2001 Apr	11369178
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
[Chronic alcohol abuse. Benfotiamine in alcohol damage is a must].	2001 Apr 19	11367995
Aroma extract dilution analysis of a beeflike process flavor from extruded enzyme-hydrolyzed soybean protein.	2001 Feb	11262030
Evidence for non-enzymatic glycosylation in Escherichia coli.	2001 Feb	11251824
Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.	2001 Feb 15	11368334
Phylogenetic analyses and comparative genomics of vitamin B6 (pyridoxine) and pyridoxal phosphate biosynthesis pathways.	2001 Jan	11200221
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.	2001 Jan	11168365
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.	2001 Jan-Feb	11358373
Effects of glucose, vitamins, and DO concentrations on pyruvate fermentation using Torulopsis glabrata IFO 0005 with metabolic flux analysis.	2001 Jan-Feb	11170481
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Sulphoacetaldehyde sulpho-lyase (EC 4.4.1.12) from Desulfonispora thiosulfatigenes: purification, properties and primary sequence.	2001 Jul 15	11439112
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.	2001 Jul-Aug	11445257
The crystal structure of yeast thiamin pyrophosphokinase.	2001 Jun	11435118
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001 Jun	11368826
Wernicke's encephalopathy in patients with hyperemesis gravidarum.	2001 Mar	11405565
[Isolation, purification and properties of acetolactate synthase from cultured Lactococcus lactis].	2001 Mar-Apr	11357431
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
Early recognition of acute cardiovascular beriberi by interpretation of hemodynamics.	2001 May	11377164
Wernicke's encephalopathy in a non-alcoholic man: case report and brief review.	2001 May	11373696
Stability of thiamine and vitamins E and A during storage of enteral feeding formula.	2001 May	11368595
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.

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