You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameThiamine
Accession NumberDB00152  (APRD00552, EXPT03222, NUTR00009)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. Thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.

Structure
Thumb
Synonyms
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium
Aneurin
Antiberiberi factor
Thiamin
Thiamine
thiamine(1+)
thiamine(1+) ion
thiaminium
Vitamin B1
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
B1 400mg Ctr Tabtablet (extended-release)400 mgBioenergy Inc.1979-12-311998-06-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Betaxinsolution100 mgintramuscular; intravenousHospira Healthcare Corporation2002-06-01Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Betaxin Liq 100mg/mlliquid100 mgintramuscular; intravenousSanofi Canada, Inc.1936-12-312001-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamiject Injection - Liq Im IV 100mg/mlliquid100 mgintramuscular; intravenousOmega Laboratories Ltd1998-07-16Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine HCl Inj 100mg/mlliquid100 mgintramuscular; intravenousKripps Pharmacy Ltd.1979-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine HCl Injection - Liq 100mg/mlliquid100 mgintramuscular; intravenousFaulding (Canada) Inc.1998-04-302001-07-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine Hydrochloride Inj 100mg/mlliquid100 mgintramuscularSaanich Pharmacy1988-12-311997-02-20Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine Hydrochloride Injection USP, 100mg/mlliquid100 mgintramuscular; intravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine Hydrochloride Injection, USPliquid100 mgintramuscular; intravenousSterimax Inc2001-05-01Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vit B1 Ctr Srt 100mgtablet (extended-release)100 mgBioenergy Inc.1981-12-311998-06-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1solution100 mgintramuscular; intravenousSandoz Canada Incorporated1989-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1solution100 mgintramuscular; intravenousMylan Pharmaceuticals Ulc1994-12-312015-11-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Thiamineinjection, solution100 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamineinjection, solution100 mg/mLintramuscular; intravenousCardinal Health2000-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-09-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousMylan Institutional LLC2013-06-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousPhysicians Total Care, Inc.2001-04-18Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-08-21Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acti-thiamine Caplet 100mgtablet100 mgoralActi Form Ltd.1991-12-312005-03-21Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
B-1 Caps 500mgcapsule500 mgoralTwin Laboratories Inc.1995-12-311999-11-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
B1 Tab 100mgtablet100 mgoralVita Health Products Inc1979-12-312002-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Bewon Elixirliquid.05 mgoralLaboratoires Charton Laboratories1995-12-311999-01-16Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Bewon Elixir 0.05mg/mlelixir.05 mgoralWyeth Ayerst Canada Inc.1994-12-311998-01-28Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine HCl Tab 100mgtablet100 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine HCl Tab 25mgtablet25 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312000-08-17Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine HCl Tab 50mgtablet50 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Thiamine Hydrochloride Inj 100mg/ml USPliquid100 mgintramuscular; intravenousDavid Bull Laboratories (Pty) Ltd.1991-12-311998-08-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vita-amine Cap 100mgcapsule100 mgoralLes Laboratoires Vachon Inc.1991-12-311997-08-08Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B-1 100 Mg Tabletstablet100 mgoralGeneral Nutrition Canada Inc.1997-05-062007-08-01Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B-1 Thiamine HCl 100mgcapsule100 mgoralAlbi Naturals1999-04-302009-07-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 100 mgcapsule100 mgoralFlora Manufacturing And Distributing Ltd.2002-03-152004-08-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 100mgtablet100 mgoralGreat Earth Companies, Inc.1998-08-252002-10-02Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 100mg Tablettablet100 mgoralNutricorp International2000-01-242009-08-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tab 100mgtablet100 mgoralWampole Brands, A Division Of Pangeo Pharma (Canada) Inc.1978-12-312002-07-29Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tab 100mgtablet100 mgoralShoppers Drug Mart Inc.1980-12-311997-08-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tab 100mg USPtablet100 mgoralPharmavite Llc1987-12-311998-09-08Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tab 100mg USPtablet100 mgoralQuest Vitamins A Div Of Purity Life Health Products1987-12-312001-07-06Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tab 2mg USPtablet2 mgoralLab Gernetic Int Ltee1985-12-311997-02-21Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B1 Tablets 100mgtablet100 mgoralNu Life Nutrition Ltd.1987-12-312005-03-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamine B1 100 Mg - Tablettablet100 mgoralNobel Pharm Enr.1995-12-312001-10-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamine B1 Tab 100mg USPtablet100 mgoralLaboratoire Lalco Inc.1986-12-312002-09-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International Brands
NameCompany
Betalin SEli Lilly
BiamineNot Available
Brand mixtures
NameLabellerIngredients
AntlervironClassical Remedia Ltd
Avon Nutrivance Stress FormulaAvon Canada Ulc
B 6 PlusAnabolic Laboratories Inc.
B Complex TabletsGolden Neo Life Diamite International, Limited
B Complex W Vit C W Non-med Yeast&liver TabPharmavite Llc
B Complex With C 300mg TabPharmavite Llc
B Plus C 300mg Timed ReleaseVita Health Products Inc
B Stress C + Iron & ViteStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
B With C 500 CapPharmetics (2011) Inc
B-50 Complex TabVita Health Products Inc
B-complex TabletsShaklee Canada Inc
B-plexLand Art Inc.
B-plex 100Merit Pharmaceutical
B50 B Complex TabNutristar Health Products (1987) Inc.
B6 Plus TabVita Health Products Inc
Balanced B-100 B-complex Vitamins TabPharmavite Llc
Balanced B-100 Timed ReleasePharmavite Llc
Balanced B-50 ComplexLeiner Health Products Inc.
Balanced B-complex Vit + Vit C&e TabPharmavite Llc
Beminal 500 TabsWyeth Canada
Beminal With C Fortis PwsWyeth Ayerst Canada Inc.
BiovitaIldong Pharmaceutical Co., Ltd.
C-B ComplexAvacare, Division Of Jeunique International Inc.
C-forcePrairie Naturals
C.R.T. X Multivitamin & Mineral Powder MixMetaform Ltd.
Carbassist TabletsWyeth Consumer Healthcare Inc.
Cc IIAdded Dimensions
Cda-21 Vitamins With Non-medicinal Probiotic ComplexRx Vitamins Inc.
Cedevita Plus Vitamin SupplementPliva, Pharmaceutical, Chemical, Food And Cosmetic Industry, Inc.
Cedevita Sugar-free Vitamin SupplementPliva, Pharmaceutical, Chemical, Food And Cosmetic Industry, Inc.
Centrum Junior (chewable)Whitehall Robins Inc.
Centrum Junior Regular (chewable Tablets)Whitehall Robins Inc.
Chela Potassium PlusNu Life Nutrition Ltd.
Chewable Children's Complete Multivitamins With Essential MineralsWn Pharmaceuticals Ltd.
Chewable MultivitaminsWn Pharmaceuticals Ltd.
Chewable Multivitamins Plus IronWn Pharmaceuticals Ltd.
Chewable Multivitamins With Extra CWn Pharmaceuticals Ltd.
Children Choice Multivit Chewable TabSwiss Herbal Remedies Ltd.
Children's Chewable Multi-vitaminWn Pharmaceuticals Ltd.
Children's Chewable Multi-vitamin Complete With MineralsWn Pharmaceuticals Ltd.
Children's Chewable Multiple VitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Children's Chewable Multivitamins With MineralsWn Pharmaceuticals Ltd.
Children's Vitamins ChewableVita Health Products Inc
Childrens Chewable Multiple Vitamins TabPharmavite Llc
Citranatal DHAMission Pharmacal Company
Citranatal RxMission Pharmacal Company
Complex 5 - PwrAst Research
Complex-75Frega Inc.
Complexe B-75Frega Inc.
Concept DHAUs Pharmaceutical Corporation
Concept ObUs Pharmaceutical Corporation
D'pantothenic Acid-B1-B2 TabHealth Thru Herbs Inc.
Daily Energy Brand B-complexEnzymatic Therapy (Canada) Inc.
Dia-viteR & D Laboratories Inc.
DiaplexNephro Tech, Inc.
Feminique W Iron and Calcium TabStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Ferra Naka Plus VitaminsNaka Sales Ltd.
Floradix Formula LiqFlora Manufacturing And Distributing Ltd.
Floravit - SyrFlora Manufacturing And Distributing Ltd.
For Kids Only Chewable MultivitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Formula D.S.Golden Pride International
Formula Fm Vitamins & Minerals TabMetagenics, Inc.
Geritol LiquidGlaxosmithkline Consumer Healthcare Inc.
Hemarexin AmpLab Bio Chimique Inc.,Division Of Technilab Pharma Inc.
Hemenatal ObWh Nutritionals, Llc
Hi Potency Balanced B-100 Complex - TabLeiner Health Products Inc.
Hill.viteHillestad Pharmaceuticals Usa
Hormodausse Plus Calc Et D TabLaboratoires Charton Laboratories
Integra PlusUs Pharmaceutical Corporation
Junior Multi Vitamins - RegularVita Health Products Inc
Kanga Sport Vitamins B & C Plus MineralsLacombe Drugs (1992) Ltd
Kanga-B Vitamin B Group + CLacombe Drugs (1992) Ltd
Kanga-kid Multi-vitamin & MineralLacombe Drugs (1992) Ltd
Kanga-kid Vitamins & IronLacombe Drugs (1992) Ltd
Kid's Choice Children's Chewable Vitamins - TabVita Health Products Inc
Kids Stuff TabletsVita Health Products Inc
Kids Stuff With Iron TabletsVita Health Products Inc
Kimchi Vitamin Chewable MultivitaminTobico
Leritone JuniorInstitut De Recherche Biologique Yves Ponroy Canada Inc.
Livron Plus AmpouleMedic Laboratory LtÉe
Maxi 6 LiqDesbergers LtÉe, Division Of Technilab Inc.
Megavites TabIcn Canada Ltd.
Multi #2W 7 Clay Inc.
Multi Vitamin & MineralsWn Pharmaceuticals Ltd.
Multi Vitamin and FluorideLibertas Pharma, Inc.
Multi Vitamin Drops With FluorideSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride and IronSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride With IronStratus Pharmaceuticals
Multi Vitamin Plus IronWn Pharmaceuticals Ltd.
Multi Vitamin, Iron and FluorideLibertas Pharma, Inc.
Multi-vitaminLLC Federal Solutions
Multi-vitamin FluorideStratus Pharmaceuticals
Multi-vitamin Fluoride and Iron DropsBoca Pharmacal, LLC
Multi-vitamin Fluoride DropsH.J. Harkins Company, Inc.
Multi-vitamin With FluorideGolden State Medical Supply, Inc.
Multi-vitaminsWn Pharmaceuticals Ltd.
Multi-vitamins for Infusion LiqDavid Bull Laboratories (Pty) Ltd.
Multiple VitaminsGfr Pharma Ltd.
Multivit-liqPharmalab Inc.
MultivitaminLaboratoires Confab Inc
Multivitamines Plus C Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Plus Fer Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamins for ChildrenQuest Vitamins A Div Of Purity Life Health Products
MvcSancilio & Company Inc
Mvc-fluorideSancilio & Company Inc.
Mynephrocaps Dialysis/stress Vitamin SupplementMartin Ekwealor Pharmaceuticals, Inc.
Nata KompleteWh Nutritionals, Llc
Neo Bex ElixirNeolab Inc
Neo-bexNeolab Inc
Neo-vites & Minerals TabNeolab Inc
NephrocapsCardinal Health
Nutrol-B-complexRolmex International Inc.
O-cal Prenatal VitaminPharmics, Inc.
Penta-thion PwrSabex Inc
Phosthenine Vitamines Et Fer (ampoules Buvable)Laboratoires Cortunon Inc.
Polymine Avec Zinc Et CuivreLes Laboratoires Vachon Inc.
Prefera Ob Plus DHAAlaven Pharmaceutical LLC
PreferaobMEDA Pharmaceuticals
Preferaob Plus DHAAlaven Pharmaceutical LLC
Prenatal Mega AntioxidantUsana Health Services, Inc.
Prenatal Vitamins Plusbryant ranch prepack
Prenate StarAvion Pharmaceuticals, Llc
Prevital TabBio Vita
Purevit Dualfe PlusPure Tek Corporation
Reaphirm Plant Source DHAEverett Laboratories, Inc.
Reno CapsNnodum Pharmaceuticals
ReplaviteStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Se-tan PlusSeton Pharmaceuticals
Somarexin and C 1000Laboratoire Lalco Inc.
Sopalamine/3b TabTechnilab Pharma Inc.
Stress B Complex With C, E & IronPharmavite Llc
Stress Complex 600 Avec Vit E Cuivre ZincFrega Inc.
Stress FormulaVita Health Products Inc
Stress Formula + IronVita Health Products Inc
Stress Formula Multivitamin Tablets USPLeiner Health Products Inc.
Stress Formula TabNature's Sunshine Products Of Canada Ltd.
Stress Tab With Iron and Vitamin EVita Health Products Inc
Stress Tab With Zinc, Copper and Vitamin EVita Health Products Inc
Stressease Plus Vitamins and MineralsJamieson Laboratories Ltd
Strovite Forte CapletEverett Laboratories, Inc.
Strovite One CapletsEverett Laboratories, Inc.
Super PantoplexNu Life Nutrition Ltd.
Super Vitalex Ampoule BuvableCarmaran LtÉe
Supravite 10ml AmpouleNobel Pharm Enr.
Supravite Bouteille 250mlNobel Pharm Enr.
Supravite C 1000Nobel Pharm Enr.
Supravite Stress Avec Vit EPharmalab Inc.
Supravite Stress Avec Vit E Cuivre Et ZincPharmalab Inc.
Supravite Stress Avec Vit E Et FerPharmalab Inc.
Swical-energy-2Les Laboratoires Swisse Inc.
T.R.I. B-plex SrcAnabolic Laboratories Inc.
Tandem ObUs Pharmaceutical Corporation
Tandem PlusUs Pharmaceutical Corporation
Tender Age Multi VitaminsJamieson Laboratories Ltd
Thiamine HCl 100mg W C 20mgGahler Enterprises Ltd.
Toni Com LiqVitalab
Ultra EnerforceNutribon (1986) Inc.
V-natalVirtus Pharmaceuticals
Vigem 12 LiquidPharmavite Laboratories (1987) Inc.
Vigo Multivitamins Drops/lozengeAshbury Research Corporation
Virt-bal DHA PlusVirtus Pharmaceuticals
Virt-capsVirtus Pharmaceuticals LLC
Virt-PNVirtus Pharmaceuticals
Virt-vite PlusVirtus Pharmaceuticals LLC
Vita-B-75 CapLes Laboratoires Vachon Inc.
Vitabanks Vitamin TabVitabank Inc.
Vitafer - LiqFrega Inc.
Vitafol CapletEverett Laboratories, Inc.
Vitafol Ob CapletEverett Laboratories, Inc.
Vitafol OneEverett Laboratories, Inc.
Vitafol PlusEverett Laboratories, Inc.
Vitamin B ComplexMylan Institutional LLC
Vitamin B Complex Plus C 300mg Timed ReleaseVita Health Products Inc
Vitamin B Complex TabNutristar Health Products (1987) Inc.
Vitamin B Compound TabNutrilite, A Division Of Access Business Group, Llc
Vitamine Du Groupe B Plus Fer - LiqPharmalab Inc.
Vitamines Pour Bebes Et EnfantsHerbes Universelles Inc.
Vitogen B Compound W C Fortis CapsulesStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Vitogen B Stress C Vit E Zinc & CopStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Vp-heme ObVirtus Pharmaceuticals LLC
Salts
Name/CASStructureProperties
Thiamine Hydrochloride
67-03-8
Thumb
  • InChI Key: DPJRMOMPQZCRJU-UHFFFAOYSA-M
  • Monoisotopic Mass: 336.057837322
  • Average Mass: 337.269
DBSALT000205
Thiamine mononitrate
ThumbNot applicableDBSALT001495
Categories
CAS number59-43-8
WeightAverage: 265.355
Monoisotopic: 265.112306876
Chemical FormulaC12H17N4OS
InChI KeyInChIKey=JZRWCGZRTZMZEH-UHFFFAOYSA-N
InChI
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
IUPAC Name
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
SMILES
CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiamines. These are compounds containing a thiamine moiety, which is structurally chracterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamines
Alternative Parents
Substituents
  • Thiamine
  • Aminopyrimidine
  • 4,5-disubstituted 1,3-thiazole
  • Imidolactam
  • Primary aromatic amine
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis.
PharmacodynamicsThiamine is a vitamin with antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. Thiamine has been found to protect against lead-induced lipid peroxidation in rat liver and kidney. Thiamine deficiency results in selective neuronal death in animal models. The neuronal death is associated with increased free radical production, suggesting that oxidative stress may play an important early role in brain damage associated with thiamine deficiency. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. Inhibition of endothelial cell proliferation may also promote atherosclerosis. Endothelial cells in culture have been found to have a decreased proliferative rate and delayed migration in response to hyperglycemic conditions. Thiamine has been shown to inhibit this effect of glucose on endothelial cells.
Mechanism of actionIt is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. There are five known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and the recently discovered adenosine thiamine triphosphate (AThTP), and adenosine thiamine diphosphate. Each derivative has unique functions, however, most are involved as coenzymes.
AbsorptionAbsorbed mainly from duodenum, by both active and passive processes
Volume of distributionNot Available
Protein binding90-94%
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThiamine toxicity is uncommon; as excesses are readily excreted, although long-term supplementation of amounts larger than 3 gram have been known to cause toxicity. Oral mouse LD50 = 8224 mg/kg, oral rat LD50 = 3710 mg/kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7976
Blood Brain Barrier+0.933
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5593
P-glycoprotein inhibitor INon-inhibitor0.9814
P-glycoprotein inhibitor IINon-inhibitor0.8504
Renal organic cation transporterNon-inhibitor0.7559
CYP450 2C9 substrateNon-substrate0.842
CYP450 2D6 substrateNon-substrate0.7591
CYP450 3A4 substrateNon-substrate0.7256
CYP450 1A2 substrateNon-inhibitor0.58
CYP450 2C9 inhibitorNon-inhibitor0.7521
CYP450 2D6 inhibitorNon-inhibitor0.7523
CYP450 2C19 inhibitorNon-inhibitor0.7397
CYP450 3A4 inhibitorNon-inhibitor0.8019
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7795
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8999
BiodegradationNot ready biodegradable0.86
Rat acute toxicity2.4577 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9415
hERG inhibition (predictor II)Non-inhibitor0.6221
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Abraxis pharmaceutical products
  • Akorn inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Bel mar laboratories inc
  • Dell laboratories inc
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Parke davis div warner lambert co
  • Watson laboratories inc
  • Wyeth ayerst laboratories
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tablet (extended-release)oral
Capsuleoral500 mg
Injection, solutionintramuscular; intravenous
Tablet (extended-release)400 mg
Powder for solutionintravenous
Liquidoral.05 mg
Elixiroral.05 mg
Granuleoral
Tabletoral
Syruporal
Tablet (effervescent)oral
Solution/ dropsoral
Liquidoral
Solutionoral
Liquidintravenous
Tablet, chewableoral
Elixiroral
Powderoral
Tablet, coatedoral
Liquid; tabletoral
Capsule (sustained-release)oral
Liquidintramuscular; intravenous100 mg
Tabletoral25 mg
Tabletoral50 mg
Injection, solutionintramuscular; intravenous100 mg/mL
Liquidintramuscular100 mg
Lozengeoral
Kit
Tablet (extended-release)100 mg
Capsuleoral100 mg
Tablet
Capsuleoral
Capsule, gelatin coatedoral
Capsule, liquid filledoral
Injectionintravenous
Solutionintramuscular; intravenous100 mg
Tabletoral2 mg
Tablet, film coatedoral
Prices
Unit descriptionCostUnit
Thiamine 100 mg/ml vial8.61USD ml
Infuvite pediatric vial2.58USD ml
Vitamin B-1 100 mg/ml1.64USD ml
Thiamiject 100 mg/ml1.24USD ml
Thiamine Hcl 100 mg/ml1.24USD ml
Thiamine hcl powder0.73USD g
Thiamine 100 mg tablet0.21USD tablet
Thiamine 500 mg tablet0.18USD tablet
Vitamin b-1 250 mg tablet0.06USD tablet
Vitamin b-1 100 mg tablet0.05USD tablet
Thiamine 250 mg tablet0.03USD tablet
CVS Pharmacy vitamin b-1 100 mg tablet0.02USD tablet
Vitamin b-1 50 mg tablet0.02USD tablet
Thiamine hcl 50 mg tablet0.01USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point248 dec °CPhysProp
water solubility5E+005 mg/LMERCK INDEX (1996); approx.
Predicted Properties
PropertyValueSource
Water Solubility0.0153 mg/mLALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)15.5ChemAxon
pKa (Strongest Basic)5.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.91 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.4 m3·mol-1ChemAxon
Polarizability28.14 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-231z000000-48864f31ba475645654bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-za00000000-2ec0f3e9e364cffde16eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-z100000000-0184506492d9f5b68b97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01z0000000-872150be83cbd75d8ecfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ze0000000-ecf71c75bdea859139d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0z00000000-4d9113fdc633fb1ccbb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-1z00000000-4a8016299623af0c3027View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-5z00000000-773912c9f325c419c77dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0dz0000000-95f3ca57c95542bdc7e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0z00000000-e079d1fc1e06396dc524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-2z00000000-ebb16d4f204f291b9a3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-gz00000000-ad4d4779d76b9edb7ec5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-zo00000000-b631eed5be831527fc17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0z10000000-50f2f613f576814eb627View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-2z00000000-2f184bbfec6bc0ef00c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-z200000000-35bc744495a2570a565fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-4z10000000-d8a7ac327273c32b4524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0z70000000-ca80ef6513c61be5b5e9View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Nobuyuki Kitamori, Masaya Maeno, Seiji Izuhara, “Granules of thiamine salt and the production thereof.” U.S. Patent US4702919, issued July, 1974.

US4702919
General References
  1. Slater PV: Multi-level preparation for nursing impact on nursing practice. Aust Nurses J. 1978 Jun;7(11):40-3. Pubmed
  2. Kopriva V, Bilkovic R, Licko T: [Tumours of the small intestine (author’s transl)] Cesk Gastroenterol Vyz. 1977 Dec;31(8):549-53. Pubmed
  3. Beissel J: [The role of right catheterization in valvular prosthesis surveillance (author’s transl)] Ann Cardiol Angeiol (Paris). 1977 Dec;26(6):587-9. Pubmed
  4. Lonsdale D, Shamberger RJ, Audhya T: Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study. Neuro Endocrinol Lett. 2002 Aug;23(4):303-8. Pubmed
  5. Lonsdale D: A review of the biochemistry, metabolism and clinical benefits of thiamin(e) and its derivatives. Evid Based Complement Alternat Med. 2006 Mar;3(1):49-59. Pubmed
External Links
ATC CodesNot Available
AHFS Codes
  • 88:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.2 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

1. Thiamin pyrophosphokinase 1

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: ligand

Components

Name UniProt ID Details
Thiamin pyrophosphokinase 1 Q9H3S4 Details

References:

  1. Pylypchuk SIu, Parkhomenko IuM, Protasova ZS, Vovk AI, Donchenko HV: [Interaction of rat brain thiamine kinase with thiamine and its derivatives] Ukr Biokhim Zh. 2001 Mar-Apr;73(2):51-6. Pubmed
  2. Melnick J, Lis E, Park JH, Kinsland C, Mori H, Baba T, Perkins J, Schyns G, Vassieva O, Osterman A, Begley TP: Identification of the two missing bacterial genes involved in thiamine salvage: thiamine pyrophosphokinase and thiamine kinase. J Bacteriol. 2004 Jun;186(11):3660-2. Pubmed
  3. Bellyei S, Szigeti A, Boronkai A, Szabo Z, Bene J, Janaky T, Barna L, Sipos K, Minik O, Kravjak A, Ohmacht R, Melegh B, Zavodszky P, Than GN, Sumegi B, Bohn H, Than NG: Cloning, sequencing, structural and molecular biological characterization of placental protein 20 (PP20)/human thiamin pyrophosphokinase (hTPK). Placenta. 2005 Jan;26(1):34-46. Pubmed
  4. de Jong L, Meng Y, Dent J, Hekimi S: Thiamine pyrophosphate biosynthesis and transport in the nematode Caenorhabditis elegans. Genetics. 2004 Oct;168(2):845-54. Pubmed

2. Thiamine transporter 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Thiamine transporter 1 O60779 Details

References:

  1. Liberman MC, Tartaglini E, Fleming JC, Neufeld EJ: Deletion of SLC19A2, the high affinity thiamine transporter, causes selective inner hair cell loss and an auditory neuropathy phenotype. J Assoc Res Otolaryngol. 2006 Sep;7(3):211-7. Epub 2006 Apr 27. Pubmed
  2. Diaz GA, Banikazemi M, Oishi K, Desnick RJ, Gelb BD: Mutations in a new gene encoding a thiamine transporter cause thiamine-responsive megaloblastic anaemia syndrome. Nat Genet. 1999 Jul;22(3):309-12. Pubmed
  3. Fleming JC, Tartaglini E, Steinkamp MP, Schorderet DF, Cohen N, Neufeld EJ: The gene mutated in thiamine-responsive anaemia with diabetes and deafness (TRMA) encodes a functional thiamine transporter. Nat Genet. 1999 Jul;22(3):305-8. Pubmed
  4. Labay V, Raz T, Baron D, Mandel H, Williams H, Barrett T, Szargel R, McDonald L, Shalata A, Nosaka K, Gregory S, Cohen N: Mutations in SLC19A2 cause thiamine-responsive megaloblastic anaemia associated with diabetes mellitus and deafness. Nat Genet. 1999 Jul;22(3):300-4. Pubmed

Enzymes

1. Cytochrome P450 4B1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 4B1 P13584 Details

References:

  1. Liu S, Stromberg A, Tai HH, Moscow JA: Thiamine transporter gene expression and exogenous thiamine modulate the expression of genes involved in drug and prostaglandin metabolism in breast cancer cells. Mol Cancer Res. 2004 Aug;2(8):477-87. Pubmed

Transporters

1. Solute carrier family 22 member 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

References:

  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. Pubmed
  2. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. Pubmed

2. Solute carrier family 22 member 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. Pubmed
  2. Sinclair CJ, Chi KD, Subramanian V, Ward KL, Green RM: Functional expression of a high affinity mammalian hepatic choline/organic cation transporter. J Lipid Res. 2000 Nov;41(11):1841-8. Pubmed
  3. Green RM, Lo K, Sterritt C, Beier DR: Cloning and functional expression of a mouse liver organic cation transporter. Hepatology. 1999 May;29(5):1556-62. Pubmed
  4. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. Pubmed

3. Solute carrier family 22 member 5

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

References:

  1. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. Pubmed
  2. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on December 03, 2015 09:51