Identification

Name
Thiamine
Accession Number
DB00152  (NUTR00009, APRD00552, EXPT03222)
Type
Small Molecule
Groups
Approved, Nutraceutical, Vet Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Thiamine HydrochlorideM572600E5P67-03-8DPJRMOMPQZCRJU-UHFFFAOYSA-M
Thiamine mononitrate8K0I04919X532-43-4UIERGBJEBXXIGO-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BetaxinSolution100 mgIntramuscular; IntravenousHospira, Inc.2002-06-01Not applicableCanada
Betaxin Liq 100mg/mlLiquid100 mgIntramuscular; IntravenousSanofi1936-12-312001-08-10Canada
Thiamiject Injection - Liq Im IV 100mg/mlLiquid100 mgIntramuscular; IntravenousOmega Laboratories Ltd1998-07-16Not applicableCanada
Thiamine HCl Inj 100mg/mlLiquid100 mgIntramuscular; IntravenousKripps Pharmacy Ltd.1979-12-31Not applicableCanada
Thiamine HCl Injection - Liq 100mg/mlLiquid100 mgIntramuscular; IntravenousFaulding Consumer, Inc.1998-04-302001-07-30Canada
Thiamine Hydrochloride Inj 100mg/mlLiquid100 mgIntramuscularSaanich Pharmacy1988-12-311997-02-20Canada
Thiamine Hydrochloride Injection USP, 100mg/mlLiquid100 mgIntramuscular; IntravenousAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Thiamine Hydrochloride Injection, USPLiquid100 mgIntramuscular; IntravenousSterimax Inc2001-05-01Not applicableCanada
Vitamin B1Solution100 mgIntramuscular; IntravenousSandoz Canada Incorporated1989-12-31Not applicableCanada
Vitamin B1Solution100 mgIntramuscular; IntravenousMylan Pharmaceuticals1994-12-312015-11-03Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ThiamineInjection, solution100 mg/mLIntramuscular; IntravenousFresenius Kabi2000-09-01Not applicableUs
ThiamineInjection, solution100 mg/mLIntramuscular; IntravenousCardinal Health2000-09-01Not applicableUs
Thiamine HydrochlorideInjection, solution100 mg/mLIntramuscular; IntravenousPhysicians Total Care, Inc.2001-04-18Not applicableUs
Thiamine HydrochlorideInjection, solution100 mg/mLIntramuscular; IntravenousGeneral Injectables & Vaccines2010-09-012017-01-20Us
Thiamine HydrochlorideInjection, solution100 mg/mLIntramuscular; IntravenousMylan Institutional2013-06-04Not applicableUs
Thiamine HydrochlorideInjection, solution100 mg/mLIntramuscular; IntravenousGeneral Injectables & Vaccines2013-08-21Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acti-thiamine Caplet 100mgTablet100 mgOralActi Form Ltd.1991-12-312005-03-21Canada
B-1 Caps 500mgCapsule500 mgOralTwin Laboratories Inc.1995-12-311999-11-10Canada
B1 400mg Ctr TabTablet, extended release400 mgOralBioenergy Inc.1979-12-311998-06-03Canada
B1 Tab 100mgTablet100 mgOralVita Health Products Inc1979-12-312002-07-31Canada
Bewon ElixirLiquid.05 mgOralLaboratoires Charton Laboratories1995-12-311999-01-16Canada
Bewon Elixir 0.05mg/mlElixir.05 mgOralWyeth Ayerst Canada Inc.1994-12-311998-01-28Canada
Thiamine HCl Tab 100mgTablet100 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada
Thiamine HCl Tab 25mgTablet25 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312000-08-17Canada
Thiamine HCl Tab 50mgTablet50 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada
Thiamine Hydrochloride Inj 100mg/ml USPLiquid100 mgIntramuscular; IntravenousDavid Bull Laboratories (Pty) Ltd.1991-12-311998-08-13Canada
International/Other Brands
Betalin S (Eli Lilly) / Biamine
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acti-MN + B1 + C CapletThiamine Hydrochloride (20 mg) + Manganese (30.0 mg) + Calcium ascorbate (100 mg)TabletOralActi Form Ltd.1991-12-312005-03-21Canada
Active FEThiamine Hydrochloride (4 mg/1) + Beta carotene (2100 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (30 ug/1) + Folic Acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Vitamin C (160 mg/1) + Vitamin E (40 [iU]/1) + Zinc oxide (20 mg/1)TabletOralGm Pharmaceuticals2013-11-11Not applicableUs
Adult Infuvite Multiple VitaminsThiamine Hydrochloride (6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsThiamine Hydrochloride (6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsThiamine Hydrochloride (6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsThiamine Hydrochloride (6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
AlertonicThiamine Hydrochloride (0.222 mg) + Choline (2.222 mg) + Inositol nicotinate (2.222 mg) + Nicotinamide (1.111 mg) + Pipradrol hydrochloride (0.044 mg) + Pyridoxine hydrochloride (0.042 mg) + Riboflavin (0.111 mg)ElixirOralOdan Laboratories Ltd1995-12-31Not applicableCanada
AlertonicThiamine Hydrochloride (.222 mg) + Choline (2.222 mg) + Inositol nicotinate (2.222 mg) + Nicotinamide (1.111 mg) + Pipradrol hydrochloride (.044 mg) + Pyridoxine hydrochloride (.042 mg) + Riboflavin (.111 mg)LiquidOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1967-12-311996-09-09Canada
Allbee With C 550 CapThiamine mononitrate (15 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Riboflavin (10 mg) + Vitamin C (550 mg)CapsuleOralWhitehall Robins Inc.1994-12-312003-08-01Canada
Allbee With Vitamin C CapThiamine mononitrate (15 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Riboflavin (10 mg) + Vitamin C (300 mg)CapsuleOralWhitehall Robins Inc.1994-12-312000-07-26Canada
Categories
UNII
4ABT0J945J
CAS number
59-43-8
Weight
Average: 265.355
Monoisotopic: 265.112306876
Chemical Formula
C12H17N4OS
InChI Key
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

Pharmacology

Indication

For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis.

Structured Indications
Not Available
Pharmacodynamics

Thiamine 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 action

It 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.

TargetActionsOrganism
AThiamin pyrophosphokinase 1
ligand
Human
UThiamine transporter 1
binder
Human
Absorption

Absorbed mainly from duodenum, by both active and passive processes

Volume of distribution
Not Available
Protein binding

90-94%

Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Thiamine 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
PathwayCategory
Thiamine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not 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:249270]
  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:603941]
  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:606152]
  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:12195231]
  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:16550223]
External Links
Human Metabolome Database
HMDB00235
KEGG Compound
C00378
PubChem Compound
1130
PubChem Substance
46507321
ChemSpider
1098
BindingDB
50373877
ChEBI
18385
ChEMBL
CHEMBL1547
Therapeutic Targets Database
DAP000870
PharmGKB
PA451652
HET
VIB
Drugs.com
Drugs.com Drug Page
Wikipedia
Thiamine
ATC Codes
A11DA01 — Thiamine (vit b1)
AHFS Codes
  • 88:28.00 — Multivitamin Preparations
  • 88:08.00 — Vitamin B Complex
PDB Entries
1ig0 / 1ig3 / 1sbr / 2hh9 / 2lh8 / 3lm8 / 3myu / 3rlb / 4kys / 4nmy
show 2 more
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I / Mycobacterium avium complex infection1
1CompletedBasic ScienceBeriberi1
1CompletedDiagnosticHealthy Volunteers1
1CompletedPreventionHIV / AIDS1
1CompletedTreatmentCancers / Metastases1
1Not Yet RecruitingBasic ScienceAging / Mineral deficiency / Vitamin Deficiency1
1RecruitingTreatmentAcidosis, Respiratory / Shock, Septic / Thiamine Deficiency1
1, 2CompletedTreatmentShock, Septic1
1, 2SuspendedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentCardiac Surgical Procedures / Coronary Artery Bypass Graft1
2CompletedTreatmentCritically Ill / Respiratory Failure1
2CompletedTreatmentDiabetes / Heart Failure, Unspecified1
2Enrolling by InvitationPreventionDelirium / Hematopoietic Stem Cell Transplantation (HSCT) / Thiamine Deficiency1
2Not Yet RecruitingTreatmentCritically Ill / Shock, Septic / Vasoplegic Syndrome1
2RecruitingTreatmentAcidosis, Respiratory / Cardiac Arrest / Shock / Thiamin Deficiency1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kidney Diseases1
2, 3CompletedTreatmentAcidosis, Respiratory1
2, 3CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Mortality1
3CompletedPreventionComplications, Pregnancy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAnemias1
3CompletedTreatmentChronic Heart Failure (CHF)1
3CompletedTreatmentDiarrheal Illnesses / Growth Faltering / Respiratory Illness1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis, Pulmonary1
3CompletedTreatmentHydatidiform Mole1
3TerminatedTreatmentHyperemesis Gravidarum1
3Unknown StatusNot AvailableAnemias / Low Birth Weight / Neonatal Mortality1
3Unknown StatusTreatmentAlzheimer's Disease (AD) / Down Syndrome (DS)1
4CompletedHealth Services ResearchAcidosis, Respiratory / Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentPregnancy1
4RecruitingTreatmentCritical Illness / Fluid Overload / Sepsis / Shock, Septic1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentWernicke-Korsakoff syndrome1
4WithdrawnTreatmentNephritis / Proteinuria / Systemic Lupus Erythematosus (SLE)1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionNeural Tube Defects (NTDs)1
Not AvailableCompletedTreatmentAcute Respiratory Failure1
Not AvailableCompletedTreatmentHeart Failure, Unspecified1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentThyrotoxicosis1
Not AvailableEnrolling by InvitationTreatmentSepsis1
Not AvailableRecruitingTreatmentTemporomandibular Joint Disorders1
Not AvailableUnknown StatusTreatmentSciatica Due to Intervertebral Disc Disorder1
Not AvailableWithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentDiabetes Complications / Diabetes Mellitus (DM) / Peripheral Neuropathy1

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
ElixirOral
CapsuleOral500 mg
Tablet, extended releaseOral
InjectionIntramuscular
Injection, solutionIntramuscular; Intravenous
Tablet, extended releaseOral400 mg
Powder, for solutionIntramuscular; Intravenous
Powder, for solutionIntravenous
LiquidOral.05 mg
ElixirOral.05 mg
GranuleOral
Capsule, liquid filledOral
CapsuleOral
SyrupOral
LiquidIntramuscular; Intravenous
Tablet, effervescentOral
Tablet, chewableOral
LiquidIntravenous
Injection, powder, lyophilized, for solutionIntravenous
PowderTopical
Liquid; tabletOral
Solution / dropsOral
SolutionIntravenous
LiquidOral
SolutionOral
SolutionIntramuscular; Intravenous
Injection, solutionIntravenous
PowderOral
TabletOral
Kit
Tablet, coatedOral
KitOral
Capsule, extended releaseOral
LiquidIntramuscular; Intravenous100 mg
TabletOral25 mg
TabletOral50 mg
Injection, solutionIntramuscular; Intravenous100 mg/mL
LiquidIntramuscular100 mg
Capsule; liquidOral
LozengeOral
Capsule, gelatin coatedOral
Tablet, extended releaseOral100 mg
CapsuleOral100 mg
InjectionIntramuscular; Intravenous
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)248 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-000i-0109000000-48864f31ba475645654b
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-05o1-9200000000-2ec0f3e9e364cffde16e
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-0aou-9000000000-0184506492d9f5b68b97
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0090000000-872150be83cbd75d8ecf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-0930000000-ecf71c75bdea859139d5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0002-0900000000-4d9113fdc633fb1ccbb5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0002-0900000000-4a8016299623af0c3027
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0002-1900000000-773912c9f325c419c77d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0390000000-95f3ca57c95542bdc7e7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-0900000000-e079d1fc1e06396dc524
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00di-0900000000-ebb16d4f204f291b9a3a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00e9-4900000000-ad4d4779d76b9edb7ec5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001i-9600000000-b631eed5be831527fc17
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-0900000000-50f2f613f576814eb627
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-002b-0900000000-2f184bbfec6bc0ef00c6
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-001i-9000000000-35bc744495a2570a565f
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-00di-1900000000-d8a7ac327273c32b4524
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0002-0920000000-ca80ef6513c61be5b5e9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0090000000-872150be83cbd75d8ecf
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0930000000-ecf71c75bdea859139d5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-4d9113fdc633fb1ccbb5
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-4a8016299623af0c3027
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-1900000000-773912c9f325c419c77d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0920000000-ca80ef6513c61be5b5e9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0390000000-95f3ca57c95542bdc7e7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-e079d1fc1e06396dc524
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-ebb16d4f204f291b9a3a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00e9-4900000000-ad4d4779d76b9edb7ec5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9600000000-c2e5c7c9870f8f37862a
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0900000000-c22d0fe35bf57449634f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-d8a7ac327273c32b4524
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0900000000-94915e2f982d965cb1c6
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as thiamines. These are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Thiamines
Alternative Parents
Aminopyrimidines and derivatives / 4,5-disubstituted thiazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives / Organic cations
Substituents
Thiamine / 4,5-disubstituted 1,3-thiazole / Aminopyrimidine / Imidolactam / Azole / Thiazole / Heteroaromatic compound / Azacycle / Alcohol / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiamine (CHEBI:18385) / Water-soluble vitamins (C00378) / a vitamin (THIAMINE)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Ligand
General Function
Thiamine diphosphokinase activity
Specific Function
Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate.
Gene Name
TPK1
Uniprot ID
Q9H3S4
Uniprot Name
Thiamin pyrophosphokinase 1
Molecular Weight
27265.05 Da
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 (1999). 2001 Mar-Apr;73(2):51-6. [PubMed:11642045]
  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:15150256]
  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:15664409]
  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:15514058]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Thiamine uptake transmembrane transporter activity
Specific Function
High-affinity transporter for the intake of thiamine.
Gene Name
SLC19A2
Uniprot ID
O60779
Uniprot Name
Thiamine transporter 1
Molecular Weight
55399.49 Da
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:16642288]
  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:10391223]
  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:10391222]
  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:10391221]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP4B1
Uniprot ID
P13584
Uniprot Name
Cytochrome P450 4B1
Molecular Weight
58990.64 Da
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:15328374]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
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:12089365]
  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:11758759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
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:12606755]
  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:11060354]
  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:10216142]
  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:11758759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
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:11160873]
  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:10454528]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34