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
SynonymLanguageCode
3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-iumNot AvailableNot Available
AneurinNot AvailableNot Available
Antiberiberi factorNot AvailableNot Available
ThiaminNot AvailableNot Available
ThiamineNot AvailableNot Available
thiamine(1+)Not AvailableNot Available
thiamine(1+) ionNot AvailableNot Available
thiaminiumNot AvailableNot Available
Vitamin B1Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2013-08-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousPhysicians Total Care, Inc.2001-04-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamineinjection, solution100 mg/mLintramuscular; intravenousCardinal Health2000-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamineinjection, solution100 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamineinjection, solution100 mg/mLintramuscular; intravenousFresenius Kabi USA, LLC2000-09-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Thiamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousMylan Institutional LLC2013-06-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
Betalin SEli Lilly
BetaxinNot Available
BiamineNot Available
Brand mixtures
Brand NameIngredients
Centrum ForteBeta-Carotene + Biotin + Calcium (Calcium Phosphate, Calcium Carbonate) + Chlorine (Potassium Chloride) + Chromium (Chromic Chloride) + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide) + Iron (Ferrous Fumarate) + Magnesium (Magnesium Oxide) + Manganese (Manganese Sulfate) + Molybdenum (Sodium Molybdate) + Nickel (Nickel Sulfate) + Nicotinamide + Phosphorus (Calcium Phosphate) + Potassium (Potassium Chloride) + Selenium (Sodium Selenate) + Silicon (Sodium Metasilicate) + Tin (Stannous Chloride) + Vanadium (Sodium Metavanadate) + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 (Cyanocobalamin) + Vitamin B2 (Riboflavin) + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C (Ascorbic Acid) + Vitamin D (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc (Zinc Oxide)
Centrum ProtegraBeta-Carotene + Biotin + Calcium (Calcium Phosphate (Dibasic), Calcium Carbonate) + Chlorine (Potassium Chloride) + Chromium (Chromic Chloride) + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide) + Iron (Ferrous Fumarate) + Magnesium (Magnesium Oxide) + Manganese (Manganese Sulfate) + Molybdenum (Sodium Molybdate) + Nickel (Nickel Sulfate) + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Potassium (Potassium Chloride) + Selenium (Sodium Selenate) + Silicon (Sodium Metasilicate) + Tin (Stannous Chloride) + Vanadium (Sodium Metavanadate) + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 + Vitamin B2 + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc (Zinc Oxide)
Centrum SelectBeta-Carotene + Biotin + Calcium (Calcium Phosphate (Dibasic), Calcium Carbonate) + Chlorine (Potassium Chloride) + Chromium (Chromic Chloride) + Copper (Cupric Oxide) + D-Pantothenic Acid (Calcium D-Pantothenate) + Folic Acid + Iodine (Potassium Iodide) + Iron (Ferrous Fumarate) + Magnesium (Magnesium Oxide) + Manganese (Manganese Sulfate) + Molybdenum (Sodium Molybdate) + Nickel (Nickel Sulfate) + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Potassium (Potassium Chloride) + Selenium (Sodium Selenate) + Silicon (Sodium Metasilicate) + Tin (Stannous Chloride) + Vanadium (Sodium Metavanadate) + Vitamin a (Vitamin a Acetate) + Vitamin B1 (Thiamine Mononitrate) + Vitamin B12 + Vitamin B2 + Vitamin B6 (Pyridoxine Hydrochloride) + Vitamin C + Vitamin D (Cholecalciferol) + Vitamin E (Dl-Alpha Tocopheryl Acetate) + Zinc (Zinc Oxide)
Salts
Name/CASStructureProperties
Thiamine Hydrochloride
67-03-8
Thumb
  • InChI Key: DPJRMOMPQZCRJU-UHFFFAOYSA-M
  • Monoisotopic Mass: 336.057837322
  • Average Mass: 337.269
DBSALT000205
Categories
CAS number59-43-8
WeightAverage: 265.355
Monoisotopic: 265.112306876
Chemical FormulaC12H17N4OS
InChI KeyJZRWCGZRTZMZEH-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
Pathways
PathwayCategorySMPDB ID
Thiamine MetabolismMetabolicSMP00076
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 substrateNon-inhibitor0.7521
CYP450 2D6 substrateNon-inhibitor0.7523
CYP450 2C19 substrateNon-inhibitor0.7397
CYP450 3A4 substrateNon-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
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
Injection, solutionintramuscular; intravenous100 mg/mL
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
SpectraMS/MSLC-MS1D NMR2D NMR
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 Reference
  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 September 16, 2013 17:08