NIO

NICOTINIC ACID

Created:	1999-07-08
Last modified:	2024-10-02

Find Related PDB Entry
56 entries where NIO is found as a standalone ligand16 entries where NIO is found in a polymer sequence

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	14
Chiral Atom Count	0
Bond Count	14
Aromatic Bond Count	6

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	NICOTINIC ACID
Systematic Name (OpenEye OEToolkits)	pyridine-3-carboxylic acid
Formula	C₆ H₅ N O₂
Molecular Weight	123.109
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)c1cccnc1
SMILES	CACTVS	3.341	OC(=O)c1cccnc1
SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
Canonical SMILES	CACTVS	3.341	OC(=O)c1cccnc1
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1cc(cnc1)C(=O)O
InChI	InChI	1.03	InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
InChIKey	InChI	1.03	PVNIIMVLHYAWGP-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00627
Name	Niacin
Groups	approved investigational nutraceutical
Description	Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions.[L7550,L7553,L7556,L7559,L7562,L7565]
Synonyms	Acide nicotinique Niacina Acidum Nicotinicum Nicotinic acid 3-carboxypyridine 3-Pyridylcarboxylic acid anti-pellagra vitamin ácido nicotínico β-pyridinecarboxylic acid 3-Pyridinecarboxylic acid Niacin pyridine-β-carboxylic acid m-pyridinecarboxylic acid Nikotinsäure
Brand Names	Novel Vita Tri B3 Src 300mg Niacin Ctr Srt 500mg Niacin Tab 100mg Vc II Provida OB Master Key Formula 3 Tab Iron Folate-F Iron, Vit & Min Supp Niacin 100mg Tablets USP Gtf Support Caplet Multi Vitamines - Liq Mega Vitaminerals Cavan Prenatal Orange Flavored Crystal Chews Tab Phytovim Cap Niacin-100 Tab 100mg DermaNIC Formula Cw Niacin 500 Mg and Inositol Super Daily No 2 Simcor Armax Vita Vim Multivitamins and Minerals Tab WesCap-C-DHA M-Natal Plus Complex 5 - Pwr Multi #2 Lustime Unicorn Nutra Boost Cal M Tab Niacin 100 mg Niacin 50mg Metacinamide Tab Dr. AVi MULTIVITAMIN with Zinc, Real Ginger, Lemon and Lemongrass Niacor Vitafol Fe Plus B3 MVC-Fluoride My Favorite Niacin and Inositol Tab One Daily VITES Red Bull Revit Multi-vitamins and Minerals Revitalize Multi-vitamin and Mineral Complex Flush Free Niacin With Inositol Formula Cw-caplet Niacin Tablets 500mg USP Abavite NESTABS ABC Prenatal Multi-vitamin/Mineral Supplement with DHA/EPA Vege Swiss One Multivitamin W Chel Mins Tab Vita-Rx Diabetic Vitamin Irospan 24/6 Reno Caps Timed Release Vita-vim Srt Usana Megavitamin Tablets - Tab Vitamin B + C Cap Spectrum 2 Cap Extra Once A Day JEUNCELL Hair restorer and Hair Growth Solution Vasodyn Tab Vp-pnv-dha Vitamin B Compound Tab Shen Min Vitamin Supplement Master Key Multi Vitamin Multi Mineral Formula 2 PROTECT IRON Liquid Mycelized Childrens Multi-vitamin Liq Hi Potency B Complex W Chelated Minerals Formula F L W Maxum Multi-vite Bev 29 Tab Formula Lf Niacin 500mg ahoSAN Niacin Tab 500mg Men's 50+ NovaMV Multivitamin Envirocomplex Strovite Forte Caplet Prenatal Formula Tab Swiss One Timed Release Tab Vitalife - Capsule Multivitamins and Minerals for Young Men One A Day Advance Adults 50+ Folika-T Niacin Tab 100mg Yeast Free Chromemate Niacin Card-floe II Tab Maximum Once A Day Red American Eagle Vitamin Supplement Drink Hyporyl - Tab Escavite Lq Mega 13 Multivitamin Formula NovaFerrum Multivitamin with Iron Pediatric Drops Niacin 100mg Tab Multicaps Taron-C DHA Antivert Tab Poly-Vi-Sol Luna Vitamin and Mineral Bar for Women Complete One A Day Tab Vita-vim With Beta-carotene - Tab Iron Folate Plus Vitafol One OB Complete 400 Niacin 250mg 50 Plus O-Cal Prenatal Vitamin Vita Vim With Beta Carotene-caplet O-Cal FA multivitamin Poly-Vi-Flor Gummies Vitamin & Mineral Formula 1 Dietary Supplement Integra Plus Nephrocaps Lip - Fac Formula Cool B Harvest Of Values All B Complex Tab Vtb Vitamin and Mineral Supplement Pro Enz Tab Se-Natal Folivane-F Vita Balance 2000 Vita-vim - Tab Kindervites Niacin Cap 250mg Folivane-Plus with Ascorbic Acid Precursors Provida DHA Rogenic Sustained Release Niacin 500mg Sveets Multitabs Iron 25mg With Vit B-cmplx, Vit C, Cu & Mo Concept DHA Cc II Niaspan Multi-Vitamin With Fluoride Niacin Tab 50mg Vitafol OB Caplet Vitamin B3 Tab 10mg USP Chewable Ifb Prenatal Mega Antioxidant Ni-C-E-LE Plus Select OB Integra F Vyo Cylate - Pwr Children's Chewable Tab Animal Shapes Remedium - Liq Orl Nephrocaps-QT Nicaprin Lipall Plus Tab TriStart ONE Multi Vitamin-mineral Formula Vitafol-OB Plus DHA Prenatal Supplement Plus DHA Nicazyme Davimet-M Concept OB Doctor's Choice Brand for Men Niacin Tab 250mg One A Day Advance Adults healthy mamaBE WELL ROUNDED BE WELL ROUNDED Niaspan Fct Niacin Caps 100mg Integra Folivane-OB Natural Source Spectrum With Beta Carotene Gtf-vitamin-minerals & Pancreatin Tab Niacin-niacinamide Tab TL-Fluorivite B6 Plus Tab Cda-21 Vitamins With Non-medicinal Probiotic Complex Lustime Angel Multi-actin Vitamin B Complex Suppl Prenatal Vitamins Plus Low Iron Dothelle DHA Daily-Vite B 6 Plus Tendera-OB Stress Formula Multi-B Comp + 500mg Vit C Cap VITAFOL Gummies Formula Cp Cap Formula # 7 Tab 50mg Vita Day Tab B-3 500mg Continuous Released Fusion Activator Formula Tab TriStart FREE Acti-niacin Caplet 500mg Virt-C DHA Multi-phyto Capsules Niacin 100mg Escavite D Niacin Src 400mg Puralor WestGel DHA Gesticare DHA Vp-heme Ob DHA Ultimate Tab Myhephron Dialysis and Stress Supplement Multi Tabs PreNatal Vitamins Plus Vitafol Caplet Mega Capsules American Eagle Energizer Plus Vitamin Supplement Drink Multivitamins and Minerals With Betacarotene Tablets Nitro Vites - Tab Multivitamin with fluoride Niacin Inj 100mg/ml Men's Cavan Heme OB 24 Multivitamins + Minerals Davimet with Fluoride Hemocyte Plus Lipovitan Vita B Complex Tab C-B Complex Formula Hh Prenatal American Plus Energy & Vitamin Drink Niacin 100 Mg Tablets B-complex Tab Super Stress Mega B Plus 1000mg Vit C Tab Lipo-B-C Tab Lutime Multi-Vitamin Fluoride and Iron Drops Innersource Tab Niodan 500 Mg Time Release Tablets Multi Flow Tablets Lipotropic Ctr Protect Cardio AF Multivitamin with Fluoride Davimet One-A-day Advance Men's Multivit with Fluoride Multivitamins and Minerals for Young Women Niachrom Capsule Mhb Pro Hers Vanilla bioJET Only One - Tablet Reaphirm Plant Source DHA Niacin Tab 475mg Adeks Tablets Hsn Formula Advicor Multi-Vitamin Fluoride Drops Vitafol Plus Vitamin B Complex Tab Niacin Tab 100mg USP Prenatal, DHA Phytopure Fusion Plus Nata Komplete Time Released Niacin 500 mg Formula O.C. Niaspan ER Fortistress Tab Niacin Pwr 800mg/1.25ml Protect Plus SO 60 Wellness Formula Genicin Vita-S TriStart DHA Multi-force for Women Tab Multi-Vitamin Grand Master Formula Tab Body Rox
Indication	Niacin is indicated to prevent vitamin deficiencies in pediatric and adult patients receiving parenteral nutrition as part of multivitamin intravenous injections.[L7550,L7553,L7556,L7559] Niacin oral tablets are indicated as a monotherapy or in combination with simvastatin or lovastatin to treat primary hyperlipidemia and mixed dyslipidemia.[L7562,L7565] It can also be used to reduce the risk of nonfatal myocardial infarctions in patients with a history of myocardial infarction and hyperlipidemia.[L7562,L7565] Niacin is also indicated with bile acid binding resins to treat atherosclerosis in patients with coronary artery disease and hyperlipidemia or to treat primary hyperlipidemia.[L7562,L7565] Finally niacin is indicated to treat severe hypertriglyceridemia.[L7562,L7565]
Categories	Agents Causing Muscle Toxicity Cardiovascular Agents Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Diet, Food, and Nutrition Food Growth Substances Hyperglycemia-Associated Agents Hypolipidemic Agents Hypolipidemic Agents Indicated for Hyperlipidemia Lipid Modifying Agents Lipid Modifying Agents, Plain Lipid Regulating Agents Micronutrients Miscellaneous Antilipemic Agents Nicotinic Acid and Derivatives Nicotinic Acids Non-statin Hypolipidemic Agents Indicated for Hyperlipidemia Noxae Organic Anion Transporting Polypeptide 2B1 Inhibitors Peripheral Vasodilators Physiological Phenomena Pyridines Thyroxine-binding globulin inhibitors Toxic Actions Vasodilating Agents Vitamin B Complex Vitamins
ATC-Code	C10AD02 C10AD52 C10BA01 C04AC01
CAS number	59-67-6

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Hydroxycarboxylic acid receptor 3	MNRHHLQDHFLEIDKKNCCVFRDDFIAKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Hydroxycarboxylic acid receptor 2	MNRHHLQDHFLEIDKKNCCVFRDDFIVKVLPPVLGLEFIFGLLGNGLALW...	unknown	agonist
Nicotinate-nucleotide pyrophosphorylase [carboxylating]	MDAEGLALLLPPVTLAALVDSWLREDCPGLNYAALVSGAGPSQAALWAKS...	unknown	binder
Nicotinamide N-methyltransferase	MESGFTSKDTYLSHFNPRDYLEKYYKFGSRHSAESQILKHLLKNLFKIFC...	unknown	binder
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	inhibitor
Thyroxine-binding globulin	MSPFLYLVLLVLGLHATIHCASPEGKVTACHSSQPNATLYKMSSINADFA...	unknown	inhibitor
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
Monocarboxylate transporter 1	MPPAVGGPVGYTPPDGGWGWAVVIGAFISIGFSYAFPKSITVFFKEIEGI...	unknown	substrate
Sodium-coupled monocarboxylate transporter 1	MDTPRGIGTFVVWDYVVFAGMLVISAAIGIYYAFAGGGQQTSKDFLMGGR...	unknown
Monocarboxylate transporter 4	MGGAVVDEGPTGVKAPDGGWGWAVLFGCFVITGFSYAFPKAVSVFFKELI...	unknown
View More

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