THIAMINE ION

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17N4OS
Molecular Weight	265.3561
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

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

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	264.3482
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 10 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 609
carbohydrate metabolic process 10 Target ID: GO:0005975 Sources: https://www.trc-canada.com/product-detail/?CatNum=T344185	Modulator 780
Oxidative Stress 149 Target ID: WP408 Sources: https://www.bocsci.com/thiamine-cas-70-16-6-item-41803.html	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thiamine deficiency 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/008809s066lbl.pdf	Preventing		Approved 8043	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 594 OCTN2 66	OCT1 302	CYP4B1 10

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP4B1 11	inducer 1440 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000059438, https://pubmed.ncbi.nlm.nih.gov/15328374/	yes	THIAMINE 10
OCT2 595	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 10
OCTN2 71	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 10

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 302	substrate 3113 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 10

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
Thiamine for Alzheimer's disease.	2001	11405995
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].	2001	11355481
Effects of vitamins on hepatic nuclear binding of L-tryptophan.	2001	11332447
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.	2001 Apr	11398710
Severe metabolic acidosis and heart failure due to thiamine deficiency.	2001 Apr	11369178
Do breastfed infants need supplemental vitamins?	2001 Apr	11339161
[Chronic alcohol abuse. Benfotiamine in alcohol damage is a must].	2001 Apr 19	11367995
The multifaceted and widespread pathology of magnesium deficiency.	2001 Feb	11425281
Inhibitors of advanced glycation end product-associated protein cross-linking.	2001 Feb 14	11341999
Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.	2001 Feb 15	11368334
Molecular cloning of human thiamin pyrophosphokinase.	2001 Jan 26	11342117
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.	2001 Jan 26	11342111
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.	2001 Jan-Feb	11358373
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Low thiamine intake and risk of cataract.	2001 Jul	11425658
Nerve conduction changes in patients with mitochondrial diseases treated with dichloroacetate.	2001 Jul	11410919
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
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
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.	2001 Jun	11430779
Nutritional status in elderly female hip fracture patients: comparison with an age-matched home living group attending day centres.	2001 Jun	11430778
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
Slc19a2: cloning and characterization of the murine thiamin transporter cDNA and genomic sequence, the orthologue of the human TRMA gene.	2001 Jun	11386850
Simultaneous determination of thiamine and pyridoxine in pharmaceuticals by using a single flow-through biparameter sensor.	2001 Jun	11377043
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001 Jun	11368826
Chronic heart failure and micronutrients.	2001 Jun 1	11401109
Comparison of ion-pair and amide-based column reversed-phase liquid chromatography for the separation of thiamine-related compounds.	2001 Jun 15	11417875
Painful alcoholic polyneuropathy with predominant small-fiber loss and normal thiamine status.	2001 Jun 26	11425941
Catalytic acid-base groups in yeast pyruvate decarboxylase. 1. Site-directed mutagenesis and steady-state kinetic studies on the enzyme with the D28A, H114F, H115F, and E477Q substitutions.	2001 Jun 26	11412090
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
[Shoshin beriberi: myth or reality?].	2001 Mar	11338786
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
[Isolation, purification and properties of acetolactate synthase from cultured Lactococcus lactis].	2001 Mar-Apr	11357431
[Other drugs administered with TPN solution].	2001 May	11439537
[Metabolic acidosis induced by TPN].	2001 May	11439535
[Solutions for the hyperalimentation].	2001 May	11439519
The application of capillary electrophoresis to the analysis of vitamins in food and beverages.	2001 May	11386658
Pharmacotherapy of mental illness--a historical analysis.	2001 May	11383974
Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias.	2001 May	11383938
A novel mutation in the SLC19A2 gene in a Tunisian family with thiamine-responsive megaloblastic anaemia, diabetes and deafness syndrome.	2001 May	11380424
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
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.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 09:56:51 UTC 2021` Edited by `admin` on `Sat Jun 26 09:56:51 UTC 2021`
Record UNII	4ABT0J945J
Record Status	`Validated (UNII)`
Record Version