THIAMINE HYDROBROMIDE HEMIHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C12H17N4OS.2Br.2BrH.H2O
Molecular Weight	870.3575
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of THIAMINE HYDROBROMIDE HEMIHYDRATE

Structure Search

SMILES

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

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	H2O
Molecular Weight	18.0153
Charge	0
Count

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

Molecular Formula	C12H17N4OS
Molecular Weight	265.3561
Charge	1
Count

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

Molecular Formula	Br
Molecular Weight	79.9035
Charge	-1
Count

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

Molecular Formula	BrH
Molecular Weight	80.9115
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
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.	2001	11244182
Severe metabolic acidosis and heart failure due to thiamine deficiency.	2001 Apr	11369178
Conditioned nutritional deficiencies in the cardiomyopathic hamster heart.	2001 Apr	11329545
Nutritional evaluation of ethanol-extracted lentil flours.	2001 Apr	11308336
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
[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
Aroma extract dilution analysis of a beeflike process flavor from extruded enzyme-hydrolyzed soybean protein.	2001 Feb	11262030
Wernicke's encephalopathy following gastroplasty for morbid obesity.	2001 Feb	11252304
Evidence for non-enzymatic glycosylation in Escherichia coli.	2001 Feb	11251824
Lactic acidosis update for critical care clinicians.	2001 Feb	11251027
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
Certification of B-group vitamins (B1, B2, B6, and B12) in four food reference materials.	2001 Jan	11305253
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
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
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
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
Nutritional status in elderly female hip fracture patients: comparison with an age-matched home living group attending day centres.	2001 Jun	11430778
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
Painful alcoholic polyneuropathy with predominant small-fiber loss and normal thiamine status.	2001 Jun 26	11425941
Relationships between dietary intake and cognitive function level in Korean elderly people.	2001 Mar	11406779
Comparison of a self-administered quantitative food amount frequency questionnaire with 4-day estimated food records.	2001 Mar	11303463
Wernicke's encephalopathy in a child: case report and MR findings.	2001 Mar	11297079
[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
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
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
Stability of thiamine and vitamins E and A during storage of enteral feeding formula.	2001 May	11368595
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
Examination of donor substrate conversion in yeast transketolase.	2001 May 11	11278369
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 13:15:25 UTC 2021` Edited by `admin` on `Sat Jun 26 13:15:25 UTC 2021`
Record UNII	WV7TS40872
Record Status	`Validated (UNII)`
Record Version

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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 Jun 26 13:15:25 UTC 2021 , Edited by admin on Sat Jun 26 13:15:25 UTC 2021

PRIMARY

PUBCHEM

92135631

Created by admin on Sat Jun 26 13:15:25 UTC 2021 , Edited by admin on Sat Jun 26 13:15:25 UTC 2021

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

THIAMINE HYDROBROMIDE HEMIHYDRATE

Created by admin on Sat Jun 26 13:15:25 UTC 2021 , Edited by admin on Sat Jun 26 13:15:25 UTC 2021

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 Jun 26 13:15:25 UTC 2021 , Edited by admin on Sat Jun 26 13:15:25 UTC 2021

PRIMARY

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ACTIVE MOIETY

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