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 data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB00152
Name	Thiamine
Groups	investigational vet_approved 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	Vitamin B1 thiamine(1+) Antiberiberi factor Thiamine chloride Thiaminum Thiamine hydrochloride Tiamina Thiamine mononitrate Aneurin thiamine(1+) ion thiaminium Thiamine Thiamin Vitamin B 1
Brand Names	Chewable Multiple Vitamins Plus Extra C Deriton Infuvite Adult Vitamines Pour Bebes Et Enfants Multiple Vitamins Tab Thiamine Hydrochloride TRONVite DuetDHA Complete Duet DHA 400 Multiple Vitamins With Minerals Tablets Multivitamines Et Mineraux Matervia Poly Vi Flor Chewable Tab Thiamine HCl 100mg W C 20mg Childrens Chewable Multivitamins Stress Formula NovaFerrum Multivitamin with Iron Pediatric Drops Super-pote Vitamin Supplement Virt-Tabs Vita-Pac Inatal Advance Multivitamins W Minerals Extra Strength Stress B&c Tab Vitamin B Complex 100 Vita Plex Tab Complexe B Compose 75 Card-floe II Tab B Complex 50+ Caplet Revit Plus Cap One A Day Advance Adults Vitamin B Complex + C 300mg Cap Prenatal Plus Iron Multivitamins and Minerals for Women RayaVit PNV Ferrous Fumarate Docusate Folic Acid Prenatabs FA Hi Potency Multi Tab Multiple Vitamins - Tablet Neonatal19 Meplex T 750 Nutra-clear Poly-Vitamin with Fluoride Tendera-OB Multivitamins and Minerals With Betacarotene Tablets Dynam Ampoule Et Tablet Quflora Pediatric Drops B Complex With C 300mg Cc II Vitramyn Vol-Tab Rx Premium Prenatal Palm Springs Multvit and Min Tab Dexatrim Tablets Infuvite Pediatric Triveen-Duo DHA Dayavite Ventrixyl Childrens Chewable Tab PROTECT IRON Liquid Centratex Metavite Folika-V Poly-Vi-Flor with Iron Orifer F Master Key Multi Vitamin Multi Mineral Formula 2 Supplement De Multivitamines Infusion Arome Fruits Rouges Liquid B Complex 50 Megavite Rx Children Choice Multivit Chewable Tab Multi Vitamines - Liq NovaMV Multivitamin Childrens Chewable Multiple Vitamins Tab Complete One A Day Tab Natal-V RX Multi-vitamin/Multi-mineral Kanga-kid Multi-vitamin & Mineral Novel Vita PureVita Vitamin B1 RE Nata OB Maxi 10 Tab Virt-Bal DHA Plus Vitaplex Balanced B-complex Vit + Vit C&e Tab Dexifol Cavan Alpha Materna Children's Chewable Multi-vitamin Complete With Minerals Multi Rol Stress Tab Quflora FE Milltrium Senior Vitamin and Mineral Supplement Great Day/am Formula Tab Children's Chewable Multi Vitamins With Iron Tablets Prenate Elite Acti-MN + B1 + C Caplet Mycelized Childrens Multi-vitamin Liq Supravite C 1000 Zenvita B-50 Complex Tab Neonatal Plus Vitamin Children's Chewable Multiple Vitamins With Extra Vitamin C (chewable Tablets) Children's Vitamins Chewable Vita-vim With Beta-carotene - Tab Folic-K Vinate AZ Folet DHA Floravit - Syr Geritol Liquid Complete Multivitamins and Minerals Tablets Timed Release Vitamin B1 100 mg Vitrion Extra P.N. Vitamin-mineral Drink Mix Vol-Nate B-plus - Tab Vitranol Glyco Plus Ect Super Daily No 2 Surbex-500 With Zinc Multivitamines Et Mineraux Reguliers / Regular Multivitamins and Minerals Stress B Complex With C,e, Zinc and Copper Prenatal Vi-min NataFort Enrich Core Pack - Children Vitamin and Mineral Supplement B-Combo Pnv-VP-U Dialyvite 5000 Balanced B 125 Srt PNV-Select Prenatal Multivitamins and Minerals - Complete Multi - N.T.O.x Formula - Tab B-100 Hi Potency B Vitamins Tab Kanga Sport Vitamins B & C Plus Minerals Alertonic Genicin Vita-Q Multivitamins Nutri-Tab OB plus DHA Dialyvite 3000 Thiamine Hydrochloride Injection, USP Vitazyme Stress Tab With Zinc, Copper and Vitamin E Poly-VI-flor Enviroflex - Tab Fem Time Tab Paramettes Multivits Plus Iron Tab (teens) B Complex 25mg Vitamin Supplement Multivitamines Pour Enfants (chewable Tablets) Diaplex 50 Plus Children's Multivitamins Megavites Tab Complete One-A-day - Tab Multipack II Chewable Multiple Vitamins Plus Iron Tab G.A.S. Complex Multi Pro Iron 25mg With Vit B-cmplx, Vit C, Cu & Mo VitaXyme Gtf-vitamin-minerals & Pancreatin Tab Se-Natal Vitamin B1 100mg Tablet Irospan 24/6 Vita-B-75 Cap Vitaflex Dietary Suplement Ultimate OB DHA Sopalamine/3b Tab Distilpure Msm Flintstones W Extra C Tab Vitamin B Complex Tab Chela Potassium Plus Virexa Vol-Plus Supravite 10ml Ampoule Children Choice Multivitamin W Iron Chew Tab Vitrexyl plus Iron Floradix Formula Liq Ventrixyl Fe Se-Tan PLUS Prenate Star Jenliva Maltlevol Liq SetonET Omniquin For Kids Only Chewable Multivitamins Flintstones Multiple Vitamins Mega Plex III - Pck Nephron FA Prenatal Vitamin and Mineral Supplement Virt-Pn Super Charged Energy Somarexin and C 1000 Thiamine Hydrochloride Inj 100mg/ml Vita-amine Cap 100mg Tricare Prenatal DHA One Prenatal and Post Partum Supplement Multi-Vit with Fluoride Puralor Folivane-Plus with Ascorbic Acid Precursors One-A-day Advance Men's NewVite Super Pantoplex Nephrocaps-QT RenaPlex-D Infantol Drops Fizz Multivitamins for Kids W C Loz Complete Multivitamins and Minerals for Children Children's Chewable Multi Vitamins Iron Folate Plus Select OB Croq-vit Pour Enfants WesCaps Only One - Tablet Twin Opti Pwr Multivit Et Fer Ampoules Et Comprimes Zalvit Viamon Ampoules Et Comprimes Am Caps Poly-Vi-Flor Childrens Chewable Multivitamins W Iron FloraFol Duet DHA One-A-day Advance Fem - Tablets Se-Natal One Tricare Prenatal Quick Dissolve C. 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Complex Swiss One Timed Release Tab Provida DHA Venexa Women's Change Formula NEONATAL Complete Hemarexin Liquid and Drinkable Ampoules Ziphex Floravita Mini Vol-Care Rx B-complex With Vitamin C, Biotin, Folic Acid Vitranol Fe Tender Age Multi Vitamins Viva CT Prenatal Chewable Children's Complete Multivitamins With Essential Minerals Multi B Ultra Enerforce Multi Enfants Tab Vita-Rx Diabetic Vitamin Vitamin B Compound W Vit C 250mg Tab Adeks Tablets PR Natal 400 ec healthy mamaBE WELL ROUNDED BE WELL ROUNDED Gynedyn Tab Mebolic Multra With Iron MultiVitamin with Fluoride Integra Plus Chewable Adult Multivitamins With Minerals Trexion Zavitrol One Daily Vitamin and Mineral Dietary Supplement Maintain Multiple Vitamin & Minerals NatalChew Children's Chewable Multivitamin Complete With Minerals Childrens Chewab Vitamin W Chel Minerals Usana Megavitamin Tablets - Tab Stress Formula + Iron Bev B-150 Mini-B Tab Hi Potency B Complex W Chelated Minerals RE FAC-x Strovite One Caplets Concept DHA Matronex Children's Vitamins W Iron Chewable Supravite Pour Enfants Time Release B 100 Compound - Tablet Corvita Vit-HA Multi Vitamin and Zinc Supplement Efferlife Multivitamins and Minerals Neo-vites & Minerals Tab Multivitamine Multivitamin Drops with Fluoride B Complex 500 Tab bioJET Multicaps Amladex Foltabs Prenatal Supravite Stress Avec Vit E WesTab Plus Multi-Vit-Flor Infa Drops Multivitamins Vp-heme Ob Paramettes Adults Omega-3 Rx Complete Relnate DHA B-complex Virt-PN Vita Vim With Beta Carotene-caplet Cavan Folate DHA Prenatal Mega Antioxidant Kimchi Vitamin chewable multivitamin Cedevita Sugar-free Vitamin Supplement Livita Adults HemeNatal OB plus DHA tensioSAN Multi Tabs Dialyvite with Zinc Tini-cal Ampoules Childrens Multiple Vit and Min Chew Tab PreNatal Vitamins Plus PNV Tabs 29-1 Bal-Care DHA Prenatvite Plus Multi-vitamines Enfants Comprime Total Living Concepts Formula One - Tab K.L. 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Adult Stress Tab With Iron and Vitamin E PreTAB Mvc Balanced B50 Complex Chela-chromium 200 Prenate Max Multi Nt-OX Phytoplex B Liq O-Cal Prenatal Vitamin Medi Msm (methyl Sulfonyl Methane) Omnivex Flinstones Multiple Plus Iron Vita-vim - Tab Multiple Vitamins Plus Iron for Women Vitamin and Mineral Supplement - Liq Natural Source Spectrum With Beta Carotene Everyday Multiple Vitamins Dalivit Swical-energy-2 Iron, Vit & Min Supp Florafol FE Pediatric 0.25 mg/mL Multivitamin and Fluoride Liquid Drops Embriva Prenatol-M Multiple Vitamins With Iron Tablets Timed Release B Complex 100 Srt Tonimol Cap Liq Vitara Balanced B-100 B-complex Vitamins Tab Thrivite Rx Prenara Swiss One Stress B Complex With C, E & Iron Multi-Vitamin Fluoride Drops Magnum-75 Vitamin and Mineral Supplement Avon Vitadvance Multi-kids Complete Corvite One Per Day Vitamin and Mineral Dietary Supplement Vitamin B + C Cap Vita Day Tab Sopalamine/3b Plus C NataChew Stressmates FolaMed DHA Stress Formula Tab Multi Vitamin Drops with Fluoride and Iron Vitamin B Tablets Multi II IV Vi Tab Prenatal Vitamins Plus Multivitamin with Fluoride Focalgin 90 DHA Multivitamins W Iron NephPlex Rx Multi-vitamins Virt-Nate DHA DaVITE Formula B NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Nrg Plus Liq Century Complete NESTABS DHA Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA PNV Prenatal Vitamin Plus Vitamin A Twin G.F. 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Complex Super Vita-vim With Beta-carotene - Tab Daily Multiple Vitamins Tricare Prenatal Compleat Floriva Plus Vitafol-OB Plus DHA Prenatal Supplement Plus DHA Central-vite 18 Essential VIL-Rx Vita B Complex Tab Formula F L W Vita Balance 2000 Allbee With C 550 Cap Multi-Vit with Fluoride and Iron Hill.vite Vitamin B Compound Tab B-100 Complex Tablets Supravite Bouteille 250ml Natal PNV Phytovim Cap INATAL Ultra Vp-pnv-dha Moms Choice Rx Childrens Chewable Vitamins W Iron L.G.I.T. Lexazin VitaPhil Aide Renate DHA Advanced B & T Formula THIAMINE HYDROCHLORIDE injection, solution Neo Bex Elixir Cal M Tab B Compound 50mg Tab Revitex Ampoules Et Comprimes D'pantothenic Acid-B1-B2 Tab WesNatal DHA Complete Allevia Revival 1 Tab NESTABS Prenatal Multi-vitamin/Mineral Supplement B-complex 100 Gesticare DHA Alkadrenergy Tablets Paramettes Chewable Multivits With Iron Tab Vinacal Prenatrix Nutrol-B-complex Super Kids Chewable Multivitamin Multimineral (chewable Tablets) Vitafol One Olympian Multi Vit Plus Minerals Tab Maxum Multi-vite Livita Children Multitol-M Super Vitalex Ampoule Buvable Extra Once A Day Viva Kids - Tab Strovite Forte Caplet B 6 Plus Cobalefol Neo-bex Injectable Phytofortis + Calcium A-D Se-Natal 19 Chewable Orange Flavored Crystal Chews Tab Daily Energy Brand B-complex B Complex Tablets Q.T. Vitamin and Mineral Drink Mix Insur-all Vitamin Supplement Se-Natal 19 Reaphirm Plant Source DHA Dialyvite Nutrifer Plus Tablets Vitamin B Complex W C 300mg Tab Vitaday Tab Adult Formula 50+ Thiamine HCl Tab 25mg Luna Vitamin and Mineral Bar for Women Childrens Chewable Multiple Vitamins W.iron Zeldana PureVita B-Complex Hylavite Vitrexyl Pro Hers Vanilla Folika-NC Vitamin B1 Tab 100mg USP Cavan Folate OB Bacmin Kaydia Patch Pretrate OB Complete DHA Vitamin B Complex Plus C 300mg Timed Release Zyvit Stress B Complex With C and E Tab Vigem 12 Liquid Vit B1 Ctr Srt 100mg Multi-force for Adults Tab OB Complete Petite Women's Biomultiple Vitamin and Mineral Supplement Micronex Multivitamin Adeks - Dps CitraNatal 90 DHA B-complex Tablets Terravitra Vitamin B Complex W C Tab Pnv Ob DHA PNV Prenatal Vitamin Maxine Vitamin and Mineral Supplement Phosthenine Vitamines Et Fer (ampoules Buvable) Materna - Tab Vitamine B1 Tab 100mg USP Hylazinc Thiamiject Injection - Liq Im IV 100mg/ml Florafol Pediatric 0.25 mg/mL Multivitamin and Fluoride Liquid Drops Lipotropic Ctr M-Natal Plus Abavite New Chapter's D'adamo 4 Your Type Multiple for Type O Chewable Multiple Vitamins for Children MultiVitamin, Iron and Fluoride Drops One A Day Multiple Vit W Minerals Adult Infuvite Multiple Vitamins MultiVitamin Drops with Fluoride and Iron Multivitamin Chewable with Methylfolate PR Natal 430 Vit B Complex Ctr Davimet with Iron Hemarexin Amp Vita Vim Multivitamins and Minerals Tab PNV 27-Ca/Fe/FA Vitamin B Complex Dermamed Nutrition for troubled skin DuetDHA Balanced Livron Plus Tab FolaSync DHA Gemvites Jr Tab Chewable Vitaphil DHA Hypo Vites Tab Balanced B100 Glyco-aide Tab Multivitamin with 1.0 mg Fluoride Complete Natal DHA Poly-Vite/Iron Oral Solution Multinate DHA Hemarexin Tab Vitachrom Gc Spectrum Performa Multivitamins and Minerals Tablets Natalvirt Ca Neonatal Vitamin Ultimate Tab For Kids Only Chewable Multivitamins - Tab Multivitamines Neo Vites Tab Multiple Vitamin Tab Ferra Naka Plus Vitamins Thrivite 19 Hi Potency Balanced B-100 Complex - Tab Nutri-Tab OB B Complex Plus C 300mg Tab Multisol Se-Care Conceive
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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

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