THIAMINE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H17N4OS.Cl.ClH
Molecular Weight	337.269
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DPJRMOMPQZCRJU-UHFFFAOYSA-M

InChI=1S/C12H17N4OS.2ClH/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);2*1H/q+1;;/p-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

Molecular Formula	ClH
Molecular Weight	36.461
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 656
carbohydrate metabolic process 11 Target ID: GO:0005975 Sources: https://www.trc-canada.com/product-detail/?CatNum=T344185	Modulator 822
Oxidative Stress 162 Target ID: WP408 Sources: https://www.bocsci.com/thiamine-cas-70-16-6-item-41803.html	Inhibitor 8228

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thiamine deficiency 13 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/008809s066lbl.pdf	Preventing		Approved 8360	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 638 OCTN2 66	OCT1 322	CYP4B1 11

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP4B1 12	inducer 1542 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000059438, https://pubmed.ncbi.nlm.nih.gov/15328374/	yes	THIAMINE 11
OCT2 639	inhibitor 3240 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11
OCTN2 71	inhibitor 3240 Sources: https://go.drugbank.com/drugs/DB00152	yes	THIAMINE 11

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 322	substrate 3326 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
[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
Rapid diagnosis of alcoholic ketoacidosis by proton NMR.	2001 Apr	11398710
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
[Chronic alcohol abuse. Benfotiamine in alcohol damage is a must].	2001 Apr 19	11367995
Lactic acidosis update for critical care clinicians.	2001 Feb	11251027
Neurotoxicity and neurocognitive impairments with alcohol and drug-use disorders: potential roles in addiction and recovery.	2001 Feb	11236849
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
Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.	2001 Feb 15	11368334
Cresol red thallium acetate sucrose inulin (CTSI) agar for the selective recovery of Carnobacterium spp.	2001 Feb 28	11252499
[Postoperative encephalopathies: thiamine deficiency, an unrecognized etiology].	2001 Jan	11234577
Longitudinal vitamin and homocysteine levels in normal pregnancy.	2001 Jan	11227033
Nutritional evaluation of some processed catering foods.	2001 Jan	11225180
[Unusual MR findings of Wernicke encephalopathy with cortical involvement].	2001 Jan	11211734
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
Marginal vitamin and mineral intake of Costa Rican adolescents.	2001 Jan-Feb	11282184
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
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.	2001 Jul-Aug	11445257
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
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
Wernicke's encephalopathy in patients with hyperemesis gravidarum.	2001 Mar	11405565
[Shoshin beriberi: myth or reality?].	2001 Mar	11338786
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
[Other drugs administered with TPN solution].	2001 May	11439537
[Metabolic acidosis induced by TPN].	2001 May	11439535
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
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
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 `Thu Jul 06 00:44:34 UTC 2023` Edited by `admin` on `Thu Jul 06 00:44:34 UTC 2023`
Record UNII	M572600E5P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIAMINE HYDROCHLORIDE

Common Name

English

FEMA NO. 3322

Code

English

BETAMIN

Brand Name

English

ESKAPHEN

Common Name

English

THIAMINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

THIAMINUM HYDROCHLORICUM [HPUS]

Common Name

English

CLOTIAMINA

Common Name

English

THIAMINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

THIAMINUM HYDROCHLORICUM

Common Name

English

THIAMINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

THIAMINE HYDROCHLORIDE [MART.]

Common Name

English

THIAMINE HYDROCHLORIDE [EP IMPURITY]

Common Name

English

THIAMINE HYDROCHLORIDE [FCC]

Common Name

English

THIAMINE HYDROCHLORIDE [USP-RS]

Common Name

English

THIAMINE CHLORIDE, HYDROCHLORIDE [WHO-IP]

Common Name

English

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

Common Name

English

THIAMINE CHLORIDE HYDROCHLORIDE

Common Name

English

Thymine hydrochloride [WHO-DD]

Common Name

English

THIAMINI HYDROCHLORIDUM [WHO-IP LATIN]

Common Name

English

VITAMIN B1 [FHFI]

Common Name

English

THIAMINE CHLORIDE HYDROCHLORIDE [JAN]

Common Name

English

THIAMINE HYDROCHLORIDE [MI]

Common Name

English

BETALIN S

Brand Name

English

THIAMINE HYDROCHLORIDE [VANDF]

Common Name

English

THIAMINE HYDROCHLORIDE [WHO-IP]

Common Name

English

NSC-36226

Code

English

Thiamine hydrochloride [WHO-DD]

Common Name

English

THIAMINE HCL [INCI]

Common Name

English

THIAMINE HCL

Official Name

English

Classification Tree Code System Code

CFR

21 CFR 310.529