U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS.Cl.ClH
Molecular Weight 337.2699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMINE HYDROCHLORIDE

SMILES

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

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 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 ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Cl
Molecular Weight 35.4529
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: The transport of thiamine across the blood brain barrier was shown in rats.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H3S4
Gene ID: 27010.0
Gene Symbol: TPK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
386 nM
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2046 nM × h
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
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.78 h
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
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
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

Doses

DosePopulationAdverse events​
500 mg single, intravenous
Highest studied dose
Dose: 500 mg
Route: intravenous
Route: single
Dose: 500 mg
Sources:
unhealthy, adult
n = 19
Health Status: unhealthy
Condition: various patients
Age Group: adult
Sex: unknown
Population Size: 19
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Thiamine for Alzheimer's disease.
2001
Effects of vitamins on hepatic nuclear binding of L-tryptophan.
2001
Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms.
2001
Thiamine-responsive acute neurological disorders in nonalcoholic patients.
2001
[Chronic alcohol abuse. Benfotiamine in alcohol damage is a must].
2001 Apr 19
Inhibitors of advanced glycation end product-associated protein cross-linking.
2001 Feb 14
Glucose induced IEG expression in the thiamin-deficient rat brain.
2001 Feb 16
Certification of B-group vitamins (B1, B2, B6, and B12) in four food reference materials.
2001 Jan
[Postoperative encephalopathies: thiamine deficiency, an unrecognized etiology].
2001 Jan
Nutritional evaluation of some processed catering foods.
2001 Jan
Phylogenetic analyses and comparative genomics of vitamin B6 (pyridoxine) and pyridoxal phosphate biosynthesis pathways.
2001 Jan
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.
2001 Jan
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
2001 Jan
Sorption and desorption studies on chitin gels.
2001 Jan 10
Sulphoacetaldehyde sulpho-lyase (EC 4.4.1.12) from Desulfonispora thiosulfatigenes: purification, properties and primary sequence.
2001 Jul 15
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.
2001 Jul-Aug
The crystal structure of yeast thiamin pyrophosphokinase.
2001 Jun
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.
2001 Jun
Comparison of ion-pair and amide-based column reversed-phase liquid chromatography for the separation of thiamine-related compounds.
2001 Jun 15
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
Wernicke's encephalopathy in patients with hyperemesis gravidarum.
2001 Mar
[Shoshin beriberi: myth or reality?].
2001 Mar
Simultaneous determination of thiamin and riboflavin in mushrooms by liquid chromatography.
2001 Mar
Wernicke's encephalopathy in a child: case report and MR findings.
2001 Mar
The genes for anabolic 2-oxoglutarate: ferredoxin oxidoreductase from Hydrogenobacter thermophilus TK-6.
2001 Mar 30
[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
[Other drugs administered with TPN solution].
2001 May
[Metabolic acidosis induced by TPN].
2001 May
[Solutions for the hyperalimentation].
2001 May
The bio operon on the acquired symbiosis island of Mesorhizobium sp. strain R7A includes a novel gene involved in pimeloyl-CoA synthesis.
2001 May
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.
2001 May-Jun
The role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA.
2001 Sep 7
Patents

Sample Use Guides

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
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 Fri Jun 25 21:10:56 UTC 2021
Edited
by admin
on Fri Jun 25 21:10:56 UTC 2021
Record UNII
M572600E5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIAMINE HYDROCHLORIDE
EP   FCC   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
FEMA NO. 3322
Code English
BETAMIN
Brand Name English
THYMINE HYDROCHLORIDE [WHO-DD]
Common Name English
ESKAPHEN
Common Name English
THIAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
THIAMINUM HYDROCHLORICUM [HPUS]
Common Name English
CLOTIAMINA
Common Name English
THIAMINUM HYDROCHLORICUM
HPUS  
Common Name English
THIAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
THIAMINE HYDROCHLORIDE [MART.]
Common Name English
THIAMINE HYDROCHLORIDE [FCC]
Common Name English
THIAMINE HYDROCHLORIDE [USP]
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
JAN  
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 [EP]
Common Name English
THIAMINE HYDROCHLORIDE [WHO-IP]
Common Name English
NSC-36226
Code English
THIAMINE HCL [INCI]
Common Name English
THIAMINE HCL
INCI  
INCI  
Official Name English
Classification Tree Code System Code
CFR 21 CFR 310.529
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
NCI_THESAURUS C26017
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
CFR 21 CFR 184.1875
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
JECFA EVALUATION THIAMINE HYDROCHLORIDE
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
DSLD 2667 (Number of products:2178)
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
Code System Code Type Description
PUBCHEM
6202
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
EPA CompTox
67-03-8
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
FDA UNII
M572600E5P
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
USP_CATALOG
1656002
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M10717
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY Merck Index
EVMPD
SUB04798MIG
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-641-8
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
RXCUI
235355
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT000205
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
THIAMINE HYDROCHLORIDE
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY Description: Colourless crystals or a white or yellowish white, crystalline powder; odour, slight and characteristic. Solubility: Soluble in 1 part of water and in 100 parts of ethanol (~750 g/l) TS; practically insoluble in acetone R and ether R. Category: Component of vitamin B. Storage: Thiamine hydrochloride should be kept in a tightly closed, non-metallic container, protected from light. Additional information: Even in the absence of light, Thiamine hydrochloride is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. When exposed to air, the anhydrous product rapidly absorbsabout 4 g of water per 100 g. Melting temperature, about 248 ?C with some decomposition. In solution at pH 4.0 or less, it loses its activity only very slowly. Neutral and alkaline solutions deteriorate rapidly, especially in contact with air. Definition: Thiamine hydrochloride contains not less than 98.0% and not more than 101.0% of C12H17ClN4OS,HCl, calculated with reference to the dried substance.
NCI_THESAURUS
C48025
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
CAS
67-03-8
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL1547
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
EVMPD
SUB179894
Created by admin on Fri Jun 25 21:10:56 UTC 2021 , Edited by admin on Fri Jun 25 21:10:56 UTC 2021
PRIMARY
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