THIAMINE HYDROBROMIDE HEMIHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C12H17N4OS.2Br.2BrH.H2O
Molecular Weight	870.356
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of THIAMINE HYDROBROMIDE HEMIHYDRATE

Structure Search

SMILES

O.Br.Br.[Br-].[Br-].CC1=C(CCO)SC=[N+]1CC2=CN=C(C)N=C2N.CC3=C(CCO)SC=[N+]3CC4=CN=C(C)N=C4N

InChI

InChIKey=FRXIQIQFJIRBSL-UHFFFAOYSA-L

InChI=1S/2C12H17N4OS.4BrH.H2O/c2*1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13;;;;;/h2*5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15);4*1H;1H2/q2*+1;;;;;/p-2

HIDE SMILES / InChI

Molecular Formula	C12H17N4OS
Molecular Weight	265.355
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Br
Molecular Weight	79.904
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
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 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 1953

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
Thiamine for Alzheimer's disease.	2001	11405995
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
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.	2001 Apr	11398710
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
Aroma extract dilution analysis of a beeflike process flavor from extruded enzyme-hydrolyzed soybean protein.	2001 Feb	11262030
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
Inhibitors of advanced glycation end product-associated protein cross-linking.	2001 Feb 14	11341999
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
Nutritional evaluation of some processed catering foods.	2001 Jan	11225180
Phylogenetic analyses and comparative genomics of vitamin B6 (pyridoxine) and pyridoxal phosphate biosynthesis pathways.	2001 Jan	11200221
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.	2001 Jan	11170615
In vivo microdialysis in an animal model of neurological disease: thiamine deficiency (Wernicke) encephalopathy.	2001 Jan	11162149
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
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.	2001 Jan 26	11342111
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).	2001 Jan-Feb	11276063
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Low thiamine intake and risk of cataract.	2001 Jul	11425658
The crystal structure of yeast thiamin pyrophosphokinase.	2001 Jun	11435118
Sulfur compounds reduce potato toxins during extrusion cooking.	2001 Jun	11409974
Chronic heart failure and micronutrients.	2001 Jun 1	11401109
Crystal structure of thiamin pyrophosphokinase.	2001 Jun 29	11419946
Wernicke's encephalopathy in patients with hyperemesis gravidarum.	2001 Mar	11405565
Wernicke's encephalopathy in a child: case report and MR findings.	2001 Mar	11297079
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
The value of oral thiamine.	2001 Mar-Apr	11259217
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
The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.	2001 May	11320134

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 Dec 16 10:11:57 GMT 2023` Edited by `admin` on `Sat Dec 16 10:11:57 GMT 2023`
Record UNII	WV7TS40872
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

THIAMINE HYDROBROMIDE HEMIHYDRATE

Common Name

English

THIAMINE HYDROBROMIDE HEMIHYDRATE [WHO-IP]

Common Name

English

THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-, BROMIDE, MONOHYDROBROMIDE, HYDRATE (2:1)

Systematic Name

English

THIAMINE BROMIDE, MONOHYDROBROMIDE, HEMIHYDRATE

Common Name

English

3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4- METHYLTHIAZOLIUM BROMIDE, MONO-HYDROBROMIDE, HEMIHYDRATE

Systematic Name

English

THIAMINE BROMIDE, MONOHYDROBROMIDE, HEMIHYDRATE [WHO-IP]

Common Name

English

THIAMINI HYDROBROMIDUM HEMIHYDRATE [WHO-IP LATIN]

Common Name

English

THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-, BROMIDE, HYDROBROMIDE, HYDRATE (2:2:2:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

WV7TS40872

Created by admin on Sat Dec 16 10:11:57 GMT 2023 , Edited by admin on Sat Dec 16 10:11:57 GMT 2023

PRIMARY

PUBCHEM

92135631

Created by admin on Sat Dec 16 10:11:57 GMT 2023 , Edited by admin on Sat Dec 16 10:11:57 GMT 2023

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

THIAMINE HYDROBROMIDE HEMIHYDRATE

Created by admin on Sat Dec 16 10:11:57 GMT 2023 , Edited by admin on Sat Dec 16 10:11:57 GMT 2023

PRIMARY

Description: A white to yellowish white, crystalline powder; odour, slight and characteristic. Solubility: Freely soluble in water and in methanol R; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Component of vitamin B. Storage: Thiamine hydrobromide should be kept in a tightly closed, non-metallic container, protected from light. Definition: Thiamine hydrobromide contains not less than 98.0% and not more than 101.0% of C12H17BrN4OS,HBr, calculated with reference to the dried substance.

CAS

62084-87-1

Created by admin on Sat Dec 16 10:11:57 GMT 2023 , Edited by admin on Sat Dec 16 10:11:57 GMT 2023

PRIMARY

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Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

Drug as perpetrator