VIB

3-(4-AMINO-2-METHYL-PYRIMIDIN-5-YLMETHYL)-5-(2-HYDROXY-ETHYL)-4-METHYL-THIAZOL-3-IUM

Created:	2001-04-17
Last modified:	2020-01-26

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Chemical Details
Formal Charge	1
Atom Count	35
Chiral Atom Count	0
Bond Count	36
Aromatic Bond Count	11

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Chemical Component Summary
Name	3-(4-AMINO-2-METHYL-PYRIMIDIN-5-YLMETHYL)-5-(2-HYDROXY-ETHYL)-4-METHYL-THIAZOL-3-IUM
Synonyms	THIAMIN; VITAMIN B1
Systematic Name (OpenEye OEToolkits)	2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
Formula	C₁₂ H₁₇ N₄ O S
Molecular Weight	265.355
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	n1c(c(cnc1C)C[n+]2c(c(sc2)CCO)C)N
SMILES	CACTVS	3.341	Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1
SMILES	OpenEye OEToolkits	1.5.0	Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCO
Canonical SMILES	CACTVS	3.341	Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1
Canonical SMILES	OpenEye OEToolkits	1.5.0	Cc1c(sc[n+]1Cc2cnc(nc2N)C)CCO
InChI	InChI	1.03	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
InChIKey	InChI	1.03	JZRWCGZRTZMZEH-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00152
Name	Thiamine
Groups	investigational approved vet_approved 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.
Synonyms	thiamine(1+) ion Thiamine mononitrate Thiamin Vitamin B1 thiaminium Tiamina Antiberiberi factor Thiamine Aneurin Thiaminum thiamine(1+) Thiamine chloride Thiamine hydrochloride
Brand Names	Dayavite Natalvirt 90dha Stress Formula Tab Thiamine HCl Injection - Liq 100mg/ml Children's Chewable Vit and Min Tab Fortamines-10 Comprimes Multivitamin with 1.0 mg Fluoride Meplex T 750 Prenatal and Post Partum Supplement Hi Potency Multi Tab Prenatal Plus Iron Poly-Vite/Iron Oral Solution B Complex With C 550mg Complete Natal DHA OB Complete Prenatal Ventrixyl Fe Glyco-aide Tab WesNate DHA PureVit DualFe Plus B Complex With C 300mg Tab Vege Swiss One Multivitamin W Chel Mins Tab B Complex W C and B12 Inj WestGel DHA Multi Vite Liq Adult B-complex Tab B6 Plus Tab Children's Chewable Multivitamin and Multimineral Virt-Pn Children Choice Multivitamin W Iron Chew Tab DuetDHA Complete Kenwood Liquid Supplement Multiple Vitamins and Minerals Foliflex Flintstones W Extra C Tab Multivitamins for Children Materna - Tab Multi-vitamins With Minerals Prenara Multivitamins and Minerals Tablets Pregnancy Multivitamin Neo Bex Elixir Methaver Livita Children Timed Release Vita-vim Srt Vitazyme C-force Floriva Plus Kanga-V Multivitamins & Minerals Vit-HA Multi Vitamin and Zinc Supplement E.S.T. Complex WesCaps Super Kids Chewable Multivitamin Multimineral (chewable Tablets) Vinate AZ B Complex Tablets Prenatal Vitamin and Mineral Supplement Select OB Twin Ultra Liquid Fruit Punch Flavor Hormodausse Plus Calc Et D Tab Deriton Thiamine B Complex W C Forte Cap Phytopure Vitranol Permathene-12 - Caplet Prenatvite B Compound 50mg Tab Super-pote Vitamin Supplement Thiamine Hydrochloride Adult Infuvite Multiple Vitamins Paramettes Multivits Plus Iron Tab (teens) TriStart DHA Children's Vitamins Chewable Multi Vitamin and Fluoride Virt Nate Toni Com Liq New Chapter's D'adamo 4 Your Type Multiple for Type O Thrivite Rx Enviroflex - Tab Multi-actin B Complex 50+ Caplet Complex-75 Fusion Plus NESTABS DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Cc II Stress Forte Plus Lipotropic Factors B-50 Complex Tab Timed Release B-complex 100 Prenatal Vita Plex Tab Vitamin B Complex 100 RayaVit M.V.I. Paediatric Vitamin B Complex 50 Senior Multi One M.V.I. 12 Vitamine B1 100 Mg - Tablet B Totum 500 Chromease Tab Swiss One Multivitamin and Mineral Caplet Duet DHA 400 vitaMedMD One Rx Everyday Multiple Vitamins Orti B Virt-Caps B-complex-50 Tab Thiamine Hydrochloride Inj 100mg/ml USP Children's Chewable Multiple Vitamins - Tab Sun-rype Vitaburst Formula B Complete One A Day Tab Megavites Tab Flintstones Multiple Vitamins PreQue 10 Zeldana Cavan Folate OB Prenatal Supplement - Tab VitaXyme Xyzbac G Trinatal Rx 1 Bev B-150 NeuroBion Nutra-clear Bugs Bunny and Friends Multiple Vitamins PNV Ferrous Fumarate Docusate Folic Acid Iron, Vit & Min Supp Pre-Tabs DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Folic-K Viamon Ampoules Et Comprimes Vitamines Et Mineraux Comprimes PNV-Select Isotonix Multitech Vitamin Mineral Supplemen Viva Kids - Tab Chewable Multiple Vitamins Plus Extra C MI-Vite RX Vitaday Tab B-complex 100 Prevital Tab Vitrexyl plus Iron Distilpure Msm Multivit with Fluoride Grand Master Formula Tab PreferaOB PreTAB Virt-Nate DHA PR Natal 430 ec Vitamin B Complex + C 600mg Tab Somavit Brand Vitamins and Minerals Complex Dexifol Mangadyn P.R.O. Complex Chela-chromium 200 Manganese 50mg Plus B1 & E Tab TL-Care DHA B-complex With Vitamin C, Biotin, Folic Acid TRONVite PreNatal Vitamins Plus Vita B + C 500 Tab MultiVitamin with Fluoride Chewable Potassium Plus Vit B Complex Animal Shapes Multivitamines Et Mineraux B-plus - Tab Daily Balance Tab Dialyvite 5000 Hi Potency B52 B Complex Tab Materna Multi Vitamin & Minerals PNV-First Revit Plus Cap PM Caps Nitro Vites - Tab Relnate DHA Original Bioscal Forte Multi-vitamin Supplement Capsules Beminal Fortis Elx Dexivite Nata Komplete Se-Natal 19 V-Natal Vitamin B Complex Plus C 300mg Timed Release Multivitamine Dynam Ampoule Et Tablet Vita-vim With Beta-carotene - Tab Zyvit Stress Tablets Kids Stuff With Iron Tablets Multiple Vitamins Plus Iron for Women Multivitamins W Iron Lexazin PureFe OB Plus Super Stress Capsules Cavan Prenatal Childrens Multiple Vit and Min Chew Tab Viva CT Prenatal Multi-11 Multiple Vitamins & Minerals Tablets Escavite Vit B Complex Ctr Cavan-EC SOD DHA Multi-Vitamin Fluoride Drops Omniquin Classic Swiss One 10 Multivitamin and Mineral Tab Vc II Bacmin Biovita Pro His Mint Dermamed Nutrition for troubled skin Men's Vita-B Maltlevol 12 Liq Acti-MN + B1 + C Caplet Multi-Vitamin Bal-Care DHA Folet DHA SetonET-EC Se-Tan PLUS Stress Ctr Srt Super B Compound W 500mg Vit C Multi Vitamin, Iron and Fluoride Chewable Multiple Vitamins Tab Acti-thiamine Caplet 100mg Multi-Vitamin Drops with Fluoride and Iron Multi Pro NataChew Re Ob 90 DHA RE Prenatal Multivitamin with Iron Foltabs Prenatal Plus DHA Multiple Vitamin Tab Quflora Pediatric AzesChew Se-Plete DHA Bewon Elixir 0.05mg/ml Phytofortis + Calcium A-D Stress B Complex With C and E Tab Adeks Tablets Davimet-M Tricare Prenatal Gtf-vitamin-minerals & Pancreatin Tab Nutrol-B-complex Novel Vita Multi Vitamins & Minerals Spectrum Performa Multivitamins and Minerals Tablets SetonET Chewable Multiple Vitamins Plus Iron Tab Supravite Stress Avec Vit E Et Fer Twin Ultra Liquid Lemon-lime Flavor Kanga-kid Vitamins & Iron INATAL Ultra Low Potency B Complex Tab Multi Flow Tablets Multiple Vit Plus Iron Tab Active OB NESTABS Prenatal Multi-vitamin/Mineral Supplement Prenatal Plus Vitamins Duet DHA Vitamin B-1 Thiamine HCl 100mg Formula F L W Tandem OB For Kids Only Chewable Multivitamins - Tab Prefera OB plus DHA Vitrexyl Folivane-Plus with Ascorbic Acid Precursors Lorid Prena1 Plus Floradix Formula Liq Multivitamines Et Mineraux Reguliers / Regular Multivitamins and Minerals Virt-PN Vitamin B Complex Suppl Beminal W C Fortis Inj Multi Plex I - Tab Prenatvite Plus B With C 500 Cap Lipotropic Ctr Multi-force for Women Tab Complex 5 - Pwr HemeNatal OB Complexe B 75mg Multi-vitamines Enfants Comprime Q.T. #4 Vitamin and Mineral Dietary Supplement Multivitamins Surbex 500 Filmtab Swiss One Multi Vit & Chel Min Tab PNV Prenatal Vitamin B Complex With C 300mg hormaSAN forte Infant Multivitamin Drops Mega 13 Multivitamin Formula Folika-V Complexe B Compose 75 Davimet with Fluoride Paramettes Syrup Complexe B-75 Formula Gly Poly-Vi-Flor Diaplex Thiamine Hydrochloride Inj 100mg/ml Vitasure Zatean-Pn Chewable Multivitamins Plus Iron C-B Complex Concept OB Children's Chewable Tab Balanced B-100 B-complex Vitamins Tab Childrens Chewable Vitamin Tab OB Complete Petite Prenatrix One Tablet Daily Mens Formula Vitogen B Stress C600 Children's Chewable Multi Vitamins Kaydia Patch Medi Msm (methyl Sulfonyl Methane) Natural Source Spectrum With Beta Carotene Tonimol Cap Liq Vital-D Rx Trinatal Ultra Childrens Chewable Multiple Vitamins W.iron Zoo Chews Plus Iron Prenatabs FA Multivit-liq Prenatvite Complete Multi - N.T.O.x Formula - Tab Gtf Support Caplet B1 400mg Ctr Tab Opti-manganese + B1 + C Caplet PureFe Plus Sopalamine/3b Tab Davimet with Iron Stress B Capsules With Vitamin C Chewable Multiple Vit Plus Iron for Children Duet DHA 400 ec Multiple Vitamins W Minerals Tab Neo-vites & Minerals Tab Paramettes Chewable Multivitamins Plus Iron B-complex M.V.I. 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Dalivit Multi 12 Injection Twin Ultra Liquid Orange Flavor Beminal With C Fortis Pws Chew.multiple Vits.with Extra C for Children Edge OB Multi-vitamins Children's Multivitamins Stress Formula Vita Day Tab Vyqua Hemocyte Plus Zintrexyl-C Men's 50+ Carbassist Tablets B-plex One Per Day Vitamin and Mineral Dietary Supplement Vitamine Du Groupe B Plus Fer - Liq Stressmates Surbex-500 With Iron Revit Tab Iberet 500 B Complex 25mg Vitamin Supplement Glyco Lite Ect Multi Vitamin Plus Iron Oncovite B50 Complex Everyday Multiple Vitamins With Iron Nephrocaps-QT Multi Vitamin and Mineral vitamin Vitamines Pour Bebes Et Enfants Innersource Tab Integra Plus Vitamin B1 100 mg Cda-21 Vitamins With Non-medicinal Probiotic Complex Formula Hh Se-Care Conceive Essential Vitamins and Minerals Bev 29 Tab Alsimine W Vitamins A D Thiamine HCl Tab 25mg Renal Caps Dialysis/Stress Vitamin Supplement Mega Plex III - Pck One A Day Advance Fem Maxi 10 Tab B Complex 50 Vitamin Cap Vitamines Et Mineraux Enfants 970 Azesco Only One - Tablet Vitamin B Complex Plus 300mg Vitamin C Children's Chewable Multivitamins With Minerals Chewable Adult Multivitamins With Minerals Duet DHA Balanced Adeks - Dps Myhephron Dialysis and Stress Supplement B Complex W Vitamin C Fortis Cap Vitamin B1 Mega Capsules Children Choice Multivit Chewable Tab Marnatal F Tricare Prenatal Quick Dissolve RenaPlex-D Multra Plex Fibrik Multiple Vitamins and Minerals Capsules PR Natal 430 Protect Plus SO 60 Vtb Vitamin and Mineral Supplement Magnum-75 Vitamin and Mineral Supplement Nutri-Tab OB Formula Gm Multivitamin & Multimineral Tender Age Multi Vitamins Infantol Drops Multi Spectrum - Tablet Davimet Multivitamins and Minerals for Men Vit B Complex Plus Vit C 550mg Vitafol Plus Escavite D Maltlevol Liq Multiple Vitamins and Minerals Tab Mvc Mvc 9+4 Inj Neonatal DHA Stress Formula B-comp + 500mg Vit C Tab Prenatal Vitamins Plus Vitamin B Complex Taron-C DHA Multi Plex II - Tab Hi Potency Stress B Tension With C Phytovim Cap Poly-VI-flor Niva-Plus B Complex 500 Tab Vitamin B1 100mg Women's Biomultiple Vitamin and Mineral Supplement MYNEPHROCAPS DIALYSIS/STRESS Vitamin Supplement Kindervites C.R.T. X Multivitamin & Mineral Powder Mix Iron Polysaccharides Folic Acid DHA Multi-Vit with Fluoride and Iron Maxine Vitamin and Mineral Supplement Multiple Vitamins With Iron Tablets Amladex Children's Chewable Multi Vit W Iron Super Daily No 2 Iron Folate Plus Multiple Vitamins Plus Iron Tab Poly-Vi-Flor with Iron L-Methyl PNV DHA Neomultivite Pregvit Centratex CompleteNate Chewable Lipovite Livron Plus Tab TM-Vite RX Vita-worth B-complex Tablets Vyo Cylate - Pwr Stress Formula + Iron Mega Balance Multiple Vitamins W Iron Tab Adult Formula 50+ B 6 Plus Mebolic Choice OB DHA Quflora Pediatric Drops Kid's Choice Children's Chewable Vitamins - Tab Balanced B 125 Srt Ellis Tonic Multi B MultiVitamin with Fluoride Neo-bex Injectable Osteo-force Soluvit N Cedevita Plus Vitamin Supplement Maintain Multiple Vitamin & Minerals Multivitamin Fem Time Tab WesTab Plus Vita Vim Multivitamins and Minerals Tab Paramettes Adults One-A-day Advance Fem - Tablets Vol-Tab Rx Beminal With C Fortis Cap B50 B Complex Tab Poly-Vitamin with Fluoride Allbee With Vitamin C Cap B Plus C 300 mg Childrens Chewable Vitamins W Iron Advanced B & T Formula Elite OB Prenatal Multivitamin Daily Energy Brand B-complex Nutrilite Double X Multitol-M Orange Flavored Crystal Chews Tab Master Key Multi Vitamin Multi Mineral Formula 2 Provida DHA Vitamin & Mineral Formula 1 Dietary Supplement Complete One-A-day - Tab Vigo Multivitamins Drops/lozenge OB Complete 400 Glyco Plus Ect Vita-Rx Diabetic Vitamin Supravite Bouteille 250ml Vita-amine Cap 100mg L.C. Supplement Total Living Concepts Formula One - Tab Vita-Pac Hyporyl - Tab Vitamin B Compound W Vit C 250mg Tab M.V.I.-12 Multi Rol Dexatrim Tablets MVC-Fluoride Sopalamine 3b Plus Virt-Advance One A Day Advance Adults Nutra Boost Poly-VI-sol Drops Animal Shapes w/Iron Chewtabs Multi-kid Sopalamine/3b Plus C Zoo Chews Folika-NC Vitaphil 90 DHA Stress Tab Children's Chewable Multi-vitamin Genicin Vita-Q Poly-Vi-Sol Supravite 10ml Ampoule Childrens Chewable Tab Stress Complex 600 Avec Vit E Cuivre Zinc Vege 1 Daily Tab Vitamin B1 Tab 100mg USP Thiamine Hydrochloride Injection USP, 100mg/ml Nutri-Tab OB plus DHA Thiamine HCl Tab 50mg Multiple Vitamins - Tablet Mega-vim 75 With Beta-carotene - Tablets Liqui B Complex Prenatol-M Chewable Children's Complete Multivitamins With Essential Minerals Swiss One Timed Release Tab Vitrexate Dialyvite with Zinc Children's Vitamins W Iron Chewable Children's Chewable Multi-vitamin Complete With Minerals Mvc 9 Plus 3 Inj Q.T. Vitamin and Mineral Drink Mix B-plex 100 Chela Iron Plus C,b Complex Vitachrom Gc Earthpals Children's Chewables Multi-vitamin & Mineral Tablets Synergistic Manganese Capsules Virt-Bal DHA Plus B-100 Complex Tablets B-50 Hi Potency B Vitamins Tab Multi-12 Pediatric Pediatric Infuvite Multiple Vitamins Poly-Vite Pediatric Oral Solution B-100 Caps Numark Multivitamins Children's Chewable Multivitamins and Minerals Stress Tab With Iron and Vitamin E Totalvit Plus Orifer F Multi Vitamin Drops with Fluoride Junior Multi Vitamins - Regular THIAMINE HCl Hi Potency Balanced B-100 Complex - Tab Vp-pnv-dha MultiVitamin, Iron and Fluoride Drops Twin G.F. Powder Vanilla Flavor Swiss Total One Vitafol One Mini-B Tab Balanced B-50 B-complex Vitamins Tab Thiamiject Injection - Liq Im IV 100mg/ml Balanced B-100 Timed Release Multi Nt-OX Stress Vitamin B With C Complex Tablets CitraNatal Rx Vitamin B Complex 100 Tab Prenatal Mega Antioxidant Envirocomplex Multi Vitamin with Fluoride One-A-day Advance Men's Prenatal Vitamin and Mineral Supplement Tab Floravit - Syr V & M Vitamin and Mineral Supplement Thiamine HCl Inj 100mg/ml Childrens Chewable Multiple Vitamins Cavan Alpha Corvite CitraNatal Essence Vita Balance 2000 FolaGent DHA Multi-Vit-Flor Biovim Tab DuetDHA Balanced Alertonic 50 Plus Jenliva Dialyvite 3000 Multivitamines Plus Fer Pour Enfants (chewable Tablets) High Potency Multivitamins & Minerals Caplets CitraNatal DHA D'pantothenic Acid-B1-B2 Tab Prenatal Vitamins Plus Low Iron Liqui Vita Multi-Vitamin With Fluoride NovaMV Multivitamin Focalgin CA Maximum Once A Day Vit B1 Ctr Srt 100mg Megavite Rx Children's Chewable With Iron Cavan Heme OB Multicaps Vita B Complex Tab Vitamin B Compound With Vitamin C Fortis Capsule Dtc Active FE Maxi 6 Liq Kids Stuff Tablets Neonatal19 Vitaplex Z Bec Tab Childrens Chewable Multivitamins Vita-vim - Tab FolaMed DHA Vitamin B Compound Tab OB Complete DHA TL-Fluorivite Multi #2 Great Day/am Formula Tab
Indication	For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis.
Categories	Alimentary Tract and Metabolism Diet, Food, and Nutrition Food Growth Substances Micronutrients OCT1 substrates OCT2 Inhibitors Physiological Phenomena Pyrimidines Sulfur Compounds Thiazoles Vitamin B Complex Vitamins
ATC-Code	A11DA01
CAS number	70-16-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Thiamine pyrophosphokinase 1	MEHAFTPLEPLLSTGNLKYCLVILNQPLDNYFRHLWNKALLRACADGGAN...	unknown	substrate
Pyruvate dehydrogenase E1 component	MSERFPNDVDPIETRDWLQAIESVIREEGVERAQYLIDQLLAEARKGGVN...	unknown	cofactor
Cytochrome P450 4B1	MVPSFLSLSFSSLGLWASGLILVLGFLKLIHLLLRRQTLAKAMDKFPGPP...	unknown	inducer
Thiamine pyrophosphokinase 1	MEHAFTPLEPLLSTGNLKYCLVILNQPLDNYFRHLWNKALLRACADGGAN...	unknown	substrate
Nucleoside diphosphate phosphatase ENTPD5	MATSWGTVFFMLVVSCVCSAVSHRNQQTWFEGIFLSSMCPINVSASTLYG...	unknown	substrate
Thiamine-triphosphatase	MAQGLIEVERKFLPGPGTEERLQELGGTLEYRVTFRDTYYDTPELSLMQA...	unknown	substrate
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	substrate
Organic cation/carnitine transporter 2	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Thiamine transporter 1	MDVPGPVSRRAAAAAATVLLRTARVRRECWFLPTALLCAYGFFASLRPSE...	unknown	substrate
Thiamine transporter 2	MDCYRTSLSSSWIYPTVILCLFGFFSMMRPSEPFLIPYLSGPDKNLTSAE...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682