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Identification
NameBiotin
Accession NumberDB00121  (NUTR00019)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. [PubChem]

Structure
Thumb
Synonyms
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid
Biotin
Biotina
Biotine
Biotinum
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acid
Coenzyme R
D-(+)-Biotin
D-Biotin
D(+)-Biotin
Vitamin B7
Vitamin H
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Biotin Ctr Srt 1000mcgtablet (extended-release)1 mgBioenergy Inc.1979-12-311998-06-03Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acti-biotin 300 Caplet 300mcgtablet300 mcgoralActi Form Ltd.1991-12-312005-03-21Canada
Biotin 300mcgtablet300 mcgoralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Biotin 300 Mcg - Tablettablet300 mcgoralHealth Wise Nutrition Inc.1996-10-222002-07-18Canada
Biotin 300 Mcg Tablettablet300 mcgoralGeneral Nutrition Canada Inc.1997-04-182005-08-05Canada
Biotin 500mcgtablet500 mcgoralGeneral Nutrition Canada Inc.2001-10-202006-08-03Canada
Biotin Cap 500mcgcapsule500 mcgoralThorne Research Canada Ltd.1985-12-312001-06-22Canada
Biotin Tab 250mcgtablet250 mcgoralVita Health Products Inc1979-12-312002-07-31Canada
Biotin Tab 300mcgtablet300 mcgoralNu Life Nutrition Ltd.1987-12-312005-03-15Canada
Biotin Tab 300mcgtablet300 mcgoralGahler Enterprises Ltd.1986-12-312007-08-07Canada
Biotin Tab 300mcgtablet300 mcgoralPure Life International Prods Inc.1992-12-312001-08-07Canada
D-biotin Tab 5mcg A Croquertablet5 mcgoralLab Gernetic Int Ltee1985-12-311997-02-21Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Biona-vit Controls and Prevents Hair Lossliquid.01 mL/100mLtopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUs
Bonogen Activator Hair Loss Treatmentliquid.002 mL/mLtopicalBonogen Co., Ltd2010-04-25Not applicableUs
Hairq-plusshampoo.06 mL/100mLtopicalCresson2012-05-23Not applicableUs
Hairq-plussolution.06 mL/100mLtopicalCresson2012-05-25Not applicableUs
Spai-sons Procapellliquid.01 mL/100mLtopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUs
Spai-sons Prolac-vitliquid.01 mg/100mLtopicalSpai Sons Pharmaceutical International Cosmetics2012-08-06Not applicableUs
Tk-naxliquid.01 mL/100mLtopicalSpai Sons Pharmaceutical International Cosmetics2012-06-30Not applicableUs
International Brands
NameCompany
AppearexNot Available
BiodermatinNot Available
Biotin ForteNot Available
MeribinNot Available
Nail-exNot Available
Brand mixtures
NameLabellerIngredients
Am CapsNew Vision Nutritionals Company
B 50 CapsulesRheingold Food International Ltd.
B Complex 25mg Vitamin SupplementGarden State Nutritionals
B Complex 50 Vitamin CapBioforce Canada Inc.
B Complex 50+ CapletHealth Wise Nutrition Inc.
B Complex W Vit C W Non-med Yeast&liver TabPharmavite Llc
B Compound 50mg TabGahler Enterprises Ltd.
B-100 CapsNow Foods
B-100 Complex TabletsViva Pharmaceutical Inc.
B-100 Hi Potency B Vitamins TabNatrol, Inc.
B-100 Vitamin SupplementGarden State Nutritionals
B-50 ComplexVita Health Products Inc
B-50 Complex TabVita Health Products Inc
B-50 Hi Potency B Vitamins TabNatrol, Inc.
B-complexEnrich International
B-complex 100Great Earth Companies, Inc.
B-complex 50Great Earth Companies, Inc.
B-complex TabNature's Sunshine Products Of Canada Ltd.
B-complex TabletsShaklee Canada Inc
B-complex With Vitamin C, Biotin, Folic AcidWn Pharmaceuticals Ltd.
B-complex-50 TabJr Carlson Labs Inc
B-plexWn Pharmaceuticals Ltd.
B-plus - TabChampion's Choice Advanced Nutrition Inc.
B50 B Complex TabNutristar Health Products (1987) Inc.
B50 ComplexPreferred Nutrition Inc.
BacminMarnel Pharmaceuticals, Inc.
Balanced B 125 SrtAnabolic Laboratories Inc.
Balanced B-100 Timed ReleasePharmavite Llc
Balanced B-50 B-complex Vitamins TabPharmavite Llc
Balanced B-50 B-complex Vitamins, Timed RelePharmavite Llc
Balanced B-50 ComplexLeiner Health Products Inc.
Balanced B100Hall Laboratories, Ltd.
Balanced B50 ComplexHall Laboratories, Ltd.
Bev 29 TabBeverly International Nutrition
Bev B-150Beverly International Nutrition
Bonnoir Hair MediCellinbio Co Ltd
C-B ComplexAvacare, Division Of Jeunique International Inc.
Cda-21 Vitamins With Non-medicinal Probiotic ComplexRx Vitamins Inc.
Chela-chromium 200Nu Life Nutrition Ltd.
Children's Chewable Multi-vitamin Complete With MineralsWn Pharmaceuticals Ltd.
Complete Mega BGahler Enterprises Ltd.
Complex-75Frega Inc.
Complexe B 75mgPharmalab Inc.
Complexe B Compose 75Les Laboratoires Bio SantÉ Inc.
Complexe B-75Frega Inc.
Concept DHAUs Pharmaceutical Corporation
Concept ObUs Pharmaceutical Corporation
Dia-viteR & D Laboratories Inc.
DiaplexNephro Tech, Inc.
DivistaUs Pharmaceutical Corporation
Doll LashHanbit Korea
Efferlife Multivitamins and MineralsNaturale Science Inc.
Enviroflex - TabEnviro Tech International Canada
EscaviteGm Pharmaceuticals, Inc.
Essential B TabletsGeneral Nutrition Canada Inc.
Extra-virt Plus DHAVirtus Pharmaceuticals LLC
FerivaAvion Pharmaceuticals, Llc
Feriva FaAvion Pharmaceuticals, Llc
FerivafaAvion Pharmaceuticals, Llc
FlorivaBon Geo Pharmaceuticals, Inc.
Floriva PlusBon Geo Pharmaceuticals, Inc.
Folcaps Care OneMidlothian Laboratories
Formula O-care Vitamin and Mineral SupplementFor Mor International Inc.
Formula Pro-BBalance Plus, Inc.
Forty Plus Vitamin SupplementGarden State Nutritionals
Harvest Of Values All B Complex TabHillestad Pharmaceuticals Usa
Hemenatal ObWh Nutritionals, Llc
Hi Potency B Complex W Chelated MineralsKlaire Labs Inc.
Hi Potency B52 B Complex TabCountry Health Laboratories Ltd.
Hi Potency Balanced B-100 Complex - TabLeiner Health Products Inc.
Hi Potency Stress B Tension With CLee Adams Laboratories
Hill.viteHillestad Pharmaceuticals Usa
Hypo Vites TabPharmetics (2011) Inc
Insur-all Vitamin SupplementGarden State Nutritionals
Integra PlusUs Pharmaceutical Corporation
Iron 25mg With Vit B-cmplx, Vit C, Cu & MoQuest Vitamins A Div Of Purity Life Health Products
Kanga Sport Vitamins B & C Plus MineralsLacombe Drugs (1992) Ltd
Kanga-B Vitamin B Group + CLacombe Drugs (1992) Ltd
Kanga-kid Multi-vitamin & MineralLacombe Drugs (1992) Ltd
Kanga-V Multivitamins & MineralsLacombe Drugs (1992) Ltd
KindervitesHerbalife International Of America, Inc.
Lancell Hair Loss Prevention Hair Grower Clean FormulaMicell Bio Co., Ltd
Lipo-B-C TabMetagenics, Inc.
Liqui B ComplexTwin Laboratories Inc.
Liqui B Complex PlusTwin Laboratories Inc.
Liqui VitaTwin Laboratories Inc.
Liquid B Complex 50Jamieson Laboratories Ltd
Low Potency B Complex TabFlora Manufacturing And Distributing Ltd.
M.V.I. 12Aventis Pharma Inc
M.V.I. PaediatricAventis Pharma Inc
M.V.I. PediatricHospira Worldwide, Inc.
MaxfePronova Corporation
Mega 13 Multivitamin FormulaVita Health Products Inc
Mini-B TabTwin Laboratories Inc.
Moreturn HairMoreand Co., Ltd.
Moreturn Hair TonicMoreand Co., Ltd.
Morreturn Hair CareMoreand Co., Ltd.
Multi 12 InjectionSandoz Canada Incorporated
Multi BSeroyal International Inc.
Multi Vitamins & MineralsWn Pharmaceuticals Ltd.
Multi-11Sandoz Canada Incorporated
Multi-12 PediatricSabex Inc
Multi-12/k1 PediatricSandoz Canada Incorporated
Multi-vitamins With MineralsWn Pharmaceuticals Ltd.
Mynephrocaps Dialysis/stress Vitamin SupplementMartin Ekwealor Pharmaceuticals, Inc.
Nata KompleteWh Nutritionals, Llc
Ndm ScalpDamomedical Ltd.
NephrocapsCardinal Health
Nexa PlusUpsher Smith Laboratories, Inc.
Nioxin Recharging ComplexNioxin Research Laboratories, Inc.
Nutrol-B-complexRolmex International Inc.
One A Day Advance AdultsBayer Inc Consumer Care
One A Day Advance Adults 50+Bayer Inc Consumer Care
One A Day TabCountry Health Laboratories Ltd.
Orti BSeroyal International Inc.
Phytopecia Hair TonicPhytos Co., Ltd.
Pnv-selectAcella Pharmaceuticals, LLC
Polymine Avec Zinc Et CuivreLes Laboratoires Vachon Inc.
Prefera Ob Plus DHAAlaven Pharmaceutical LLC
PreferaobMEDA Pharmaceuticals
Preferaob OneMEDA Pharmaceuticals
Preferaob Plus DHAAlaven Pharmaceutical LLC
Prenatal Mega AntioxidantUsana Health Services, Inc.
Prenate EliteAvion Pharmaceuticals, Llc
Prenate EnhanceAvion Pharmaceuticals, Llc
Prenate EssentialAvion Pharmaceuticals, Llc
Prenate PixieAvion Pharmaceuticals, Llc
Prenate RestoreAvion Pharmaceuticals, Llc
Prenate StarAvion Pharmaceuticals, Llc
Q.T. Vitamin and Mineral Drink MixGarden State Nutritionals
Reno CapsNnodum Pharmaceuticals
ReplaviteStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Revitex Ampoules Et ComprimesLes Produits Gerbex Inc.
Se-natal OneSeton Pharmaceuticals
Shen Min Vitamin SupplementBiotech Corporation
Silica-calcium With Biotin CapsulesNaka Sales Ltd.
Spectrum 2 CapNf Formulas Inc.
Stress B & C CapletHealth Wise Nutrition Inc.
Stress B Capsules With Vitamin CRheingold Food International Ltd.
Stress B Complex With C, E & IronPharmavite Llc
Stress B With 1000 Mg Vitamin CHolista Health (Canada) Inc.
Stress B&c TabBioforce Canada Inc.
Stress Complex 600 Avec Vit E Cuivre ZincFrega Inc.
Stress Ctr SrtBioenergy Inc.
Stress FormulaVita Health Products Inc
Stress Formula + IronVita Health Products Inc
Stress Formula B-comp + 500mg Vit C TabQuest Vitamins A Div Of Purity Life Health Products
Stress Formula Multi-B Comp + 500mg Vit C CapQuest Vitamins A Div Of Purity Life Health Products
Stress Formula Multivitamin Tablets USPLeiner Health Products Inc.
Stress Formula TabNature's Sunshine Products Of Canada Ltd.
Stress Formula Vit B With C ComplexWatkins Incorporated
Stress Forte Plus Lipotropic FactorsDouglas Laboratories
Stress Vitamin B With C Complex TabletsPurity Life Health Products A Division Of Sunopta Inc.
StressmatesTwin Laboratories Inc.
Strovite Forte CapletEverett Laboratories, Inc.
Strovite One CapletsEverett Laboratories, Inc.
Super B Compound W 500mg Vit CGahler Enterprises Ltd.
Super Daily No 2W.R. Enterprises Inc.
Super PantoplexNu Life Nutrition Ltd.
Super Stress CapsulesRheingold Food International Ltd.
Super Stress Mega B Plus 1000mg Vit C TabQuest Vitamins A Div Of Purity Life Health Products
Super-pote Vitamin SupplementGarden State Nutritionals
Supravite Stress Avec Vit EPharmalab Inc.
Supravite Stress Avec Vit E Cuivre Et ZincPharmalab Inc.
Supravite Stress Avec Vit E Et FerPharmalab Inc.
T.R.I. B-plex SrcAnabolic Laboratories Inc.
Therapytion Nokmosu Neutral and Oily HairTherapytion Co., Ltd.
Therapytion Nokmosu Sensitive and Dry HairTherapytion Co., Ltd.
Time Release B 100 Compound - TabletHealth Wise Nutrition Inc.
Timed Release B Complex 100 SrtJamieson Laboratories Ltd
Timed Release B-complex 100Great Earth Companies, Inc.
Timed Release B-complex 50Great Earth Companies, Inc.
Tl-hem 150Trigen Laboratories, Inc.
Trinatal GtTrigen Laboratories, Inc.
Twin Ultra Liquid Fruit Punch FlavorTwin Laboratories Inc.
Twin Ultra Liquid Grape FlavorTwin Laboratories Inc.
Twin Ultra Liquid Lemon-lime FlavorTwin Laboratories Inc.
Twin Ultra Liquid Orange FlavorTwin Laboratories Inc.
Ultimatecare One NfTrigen Laboratories, Inc.
Ultra HrNatural Organics Inc.
Vimeral TabIcn Canada Ltd.
Virt-capsVirtus Pharmaceuticals LLC
Virt-PNVirtus Pharmaceuticals
Virt-PN PlusVirtus Pharmaceuticals LLC
Virt-vite PlusVirtus Pharmaceuticals LLC
Vit B Complex CtrBioenergy Inc.
Vit-HA Multi Vitamin and Zinc SupplementRheingold Food International Ltd.
Vita B Complex TabNutrimetics International (Canada) Inc.
Vita-BNutri Dyn Products Ltd.
Vita-B-75 CapLes Laboratoires Vachon Inc.
Vita-worth B-complex TabletsGeneral Nutrition Canada Inc.
Vitaflex Dietary SuplementHome Shopping Network Direct
Vitamin B + C CapFinlandia Consultants
Vitamin B Complex 100 TabBioforce Canada Inc.
Vitamin B Complex 50Gfr Pharma Ltd.
Vitamin B Complex SupplAvacare, Division Of Jeunique International Inc.
Vitamin B Complex TabNutristar Health Products (1987) Inc.
Vitamin B Complex W C TabAlbi Imports Ltd.
Vitamin B Compound W C Tab 500mgAdams Labs Ltd.
Vitamin B Compound W Vit C 250mg TabSwiss Herbal Remedies Ltd.
Vitamin B TabletsWeider Health Products
Vp-heme ObVirtus Pharmaceuticals LLC
Vp-heme OneVirtus Pharmaceuticals LLC
SaltsNot Available
Categories
UNII6SO6U10H04
CAS number58-85-5
WeightAverage: 244.311
Monoisotopic: 244.088163078
Chemical FormulaC10H16N2O3S
InChI KeyInChIKey=YBJHBAHKTGYVGT-ZKWXMUAHSA-N
InChI
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
IUPAC Name
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
SMILES
[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBiotin and derivatives
Sub ClassNot Available
Direct ParentBiotin and derivatives
Alternative Parents
Substituents
  • Biotin
  • Medium-chain fatty acid
  • Imidazolyl carboxylic acid derivative
  • Thia fatty acid
  • Heterocyclic fatty acid
  • Fatty acyl
  • Fatty acid
  • 2-imidazoline
  • Isourea
  • Azacycle
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor nutritional supplementation, also for treating dietary shortage or imbalance.
PharmacodynamicsBiotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.
Mechanism of actionBiotin is necessary for the proper functioning of enzymes that transport carboxyl units and fix carbon dioxide, and is required for various metabolic functions, including gluconeogenesis, lipogenesis, fatty acid biosynthesis, propionate metabolism, and catabolism of branched-chain amino acids.
Related Articles
AbsorptionSystemic - approximately 50%
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityProlonged skin contact may cause irritation.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDiseaseSMP00237
Pyruvate Carboxylase DeficiencyDiseaseSMP00350
Primary hyperoxaluria II, PH2DiseaseSMP00558
Fructose-1,6-diphosphatase deficiencyDiseaseSMP00562
Multiple carboxylase deficiency, neonatal or early onset formDiseaseSMP00564
Succinic semialdehyde dehydrogenase deficiencyDiseaseSMP00567
The oncogenic action of FumarateDiseaseSMP02295
Ammonia RecyclingMetabolicSMP00009
Pyruvate MetabolismMetabolicSMP00060
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDiseaseSMP00138
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDiseaseSMP00374
3-hydroxyisobutyric acid dehydrogenase deficiencyDiseaseSMP00521
3-hydroxyisobutyric aciduriaDiseaseSMP00522
Pyruvate dehydrogenase deficiency (E3)DiseaseSMP00550
Pyruvate kinase deficiencyDiseaseSMP00559
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)DiseaseSMP00560
Triosephosphate isomeraseDiseaseSMP00563
The oncogenic action of 2-hydroxyglutarateDiseaseSMP02291
The oncogenic action of SuccinateDiseaseSMP02292
The oncogenic action of L-2-hydroxyglutarate in HydroxygluaricaciduriaDiseaseSMP02358
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria DiseaseSMP02359
GluconeogenesisMetabolicSMP00128
3-Methylglutaconic Aciduria Type IIIDiseaseSMP00140
Methylmalonic AciduriaDiseaseSMP00200
Pyruvate Dehydrogenase Complex DeficiencyDiseaseSMP00212
Isovaleric AciduriaDiseaseSMP00238
Primary Hyperoxaluria Type IDiseaseSMP00352
Methylmalonate Semialdehyde Dehydrogenase DeficiencyDiseaseSMP00384
Fatty Acid BiosynthesisMetabolicSMP00456
Malonyl-coa decarboxylase deficiencyDiseaseSMP00502
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7395
Blood Brain Barrier+0.9383
Caco-2 permeable-0.7206
P-glycoprotein substrateSubstrate0.6413
P-glycoprotein inhibitor INon-inhibitor0.9561
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.8803
CYP450 2C9 substrateNon-substrate0.7602
CYP450 2D6 substrateNon-substrate0.7872
CYP450 3A4 substrateNon-substrate0.6911
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9252
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9762
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9598
BiodegradationNot ready biodegradable0.8923
Rat acute toxicity2.0581 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9596
hERG inhibition (predictor II)Non-inhibitor0.9145
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral300 mcg
Tablet (extended-release)oral
Solutionoral
Tablet
Liquidtopical.01 mL/100mL
Tabletoral500 mcg
Capsuleoral500 mcg
Tablet (extended-release)1 mg
Tabletoral250 mcg
Liquidtopical.002 mL/mL
Capsule, liquid filledoral
Tabletoral5 mcg
Liquidtopical
Tablet (effervescent)oral
Tablet, chewableoral
Solution/ dropsoral
Capsule, gelatin coatedoral
Shampootopical.06 mL/100mL
Solutiontopical.06 mL/100mL
Dropsoral
Liquidintravenous
Injection, powder, lyophilized, for solutionintravenous
Spraytopical
Shampootopical
Solutionintravenous
Capsuleoral
Tablet, coatedoral
Powderoral
Liquid; tabletoral
Liquidtopical.01 mg/100mL
Tabletoral
Capsule (sustained-release)oral
Liquidoral
Tablet (extended-release)
Tablet, film coatedoral
Prices
Unit descriptionCostUnit
Biotin powder14.69USD g
D-biotin powder12.0USD g
Diachrome capsule0.29USD capsule
Appearex 2.5 mg tablet0.26USD tablet
Stress b tablet0.1USD tablet
Stress 600 tablet0.08USD tablet
Biotin 800 mcg tablet0.06USD tablet
Biotin 300 mcg tablet0.03USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point232 dec °CPhysProp
water solubility220 mg/L (at 25 °C)MERCK INDEX (1996)
logP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP0.17ALOGPS
logP0.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m3·mol-1ChemAxon
Polarizability24.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.84 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0f76-1960000000-b21ddd69490cac3254f8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f76-3960000000-a8a94e2de123f66979d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0090000000-6d956bb533d353d449c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0190000000-01f67d1bdf8c742e48c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-107f2a44f521c2513578View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a3f65d909dc40055e87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0090000000-c928e8d0a18f3f848262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-066s-1920000000-5f795e0b7f1d7cf986e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0ar1-1920000000-c298be862857cb3bbc7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000t-0900000000-cdc4a4c359ff765fd32dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
References
Synthesis Reference

Takayoshi Mitsunaga, Kiyoto Chinushi, Tadashi Umezu, “Water-soluble biotin-containing preparation.” U.S. Patent US4277488, issued May, 1940.

US4277488
General References
  1. Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. [PubMed:15690449 ]
External Links
ATC CodesA11HA05
AHFS Codes
  • 88:08.00
PDB Entries
FDA labelNot Available
MSDSDownload (71.9 KB)
Interactions
Drug Interactions
Drug
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Biotin resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmdinocillinThe therapeutic efficacy of Amdinocillin can be decreased when used in combination with Biotin.
AmoxicillinThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Biotin.
AmpicillinThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Biotin.
AzidocillinThe therapeutic efficacy of Azidocillin can be decreased when used in combination with Biotin.
AzlocillinThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Biotin.
BacampicillinThe therapeutic efficacy of Bacampicillin can be decreased when used in combination with Biotin.
BenzylpenicillinThe therapeutic efficacy of Benzylpenicillin can be decreased when used in combination with Biotin.
BexaroteneThe serum concentration of Biotin can be decreased when it is combined with Bexarotene.
Bismuth SubcitrateThe serum concentration of Biotin can be decreased when it is combined with Bismuth Subcitrate.
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Biotin resulting in a reduced serum concentration and potentially a decrease in efficacy.
CarbenicillinThe therapeutic efficacy of Carbenicillin can be decreased when used in combination with Biotin.
CloxacillinThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Biotin.
ColesevelamColesevelam can cause a decrease in the absorption of Biotin resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclacillinThe therapeutic efficacy of Cyclacillin can be decreased when used in combination with Biotin.
DicloxacillinThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Biotin.
DicoumarolBiotin may increase the anticoagulant activities of Dicoumarol.
FlucloxacillinThe therapeutic efficacy of Flucloxacillin can be decreased when used in combination with Biotin.
HetacillinThe therapeutic efficacy of Hetacillin can be decreased when used in combination with Biotin.
Iron DextranBiotin can cause a decrease in the absorption of Iron Dextran resulting in a reduced serum concentration and potentially a decrease in efficacy.
LanthanumThe serum concentration of Biotin can be decreased when it is combined with Lanthanum.
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Biotin resulting in a reduced serum concentration and potentially a decrease in efficacy.
Magnesium SulfateMagnesium Sulfate can cause a decrease in the absorption of Biotin resulting in a reduced serum concentration and potentially a decrease in efficacy.
MeticillinThe therapeutic efficacy of Meticillin can be decreased when used in combination with Biotin.
MezlocillinThe therapeutic efficacy of Mezlocillin can be decreased when used in combination with Biotin.
NafcillinThe therapeutic efficacy of Nafcillin can be decreased when used in combination with Biotin.
OxacillinThe therapeutic efficacy of Oxacillin can be decreased when used in combination with Biotin.
PhenoxymethylpenicillinThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Biotin.
PhenytoinThe metabolism of Biotin can be increased when combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Biotin.
PiperacillinThe therapeutic efficacy of Piperacillin can be decreased when used in combination with Biotin.
PivampicillinThe therapeutic efficacy of Pivampicillin can be decreased when used in combination with Biotin.
PivmecillinamThe therapeutic efficacy of Pivmecillinam can be decreased when used in combination with Biotin.
St. John's WortThe serum concentration of Biotin can be decreased when it is combined with St. John's Wort.
Strontium ranelateThe serum concentration of Biotin can be decreased when it is combined with Strontium ranelate.
TicarcillinThe therapeutic efficacy of Ticarcillin can be decreased when used in combination with Biotin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Propionyl-coa carboxylase activity
Specific Function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular Weight:
58215.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [PubMed:15623830 ]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [PubMed:9311592 ]
  5. Ishii M, Chuakrut S, Arai H, Igarashi Y: Occurrence, biochemistry and possible biotechnological application of the 3-hydroxypropionate cycle. Appl Microbiol Biotechnol. 2004 Jun;64(5):605-10. Epub 2004 Feb 28. [PubMed:14997352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Enzyme binding
Specific Function:
Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl-CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase.
Gene Name:
HLCS
Uniprot ID:
P50747
Molecular Weight:
80759.345 Da
References
  1. Velazquez-Arellano A: From an inborn error patient to a search for regulatory meaning: a biotin conducted voyage. Mol Genet Metab. 2006 Mar;87(3):194-7. Epub 2005 Dec 15. [PubMed:16359899 ]
  2. Hassan YI, Zempleni J: Epigenetic regulation of chromatin structure and gene function by biotin. J Nutr. 2006 Jul;136(7):1763-5. [PubMed:16772434 ]
  3. Camporeale G, Giordano E, Rendina R, Zempleni J, Eissenberg JC: Drosophila melanogaster holocarboxylase synthetase is a chromosomal protein required for normal histone biotinylation, gene transcription patterns, lifespan, and heat tolerance. J Nutr. 2006 Nov;136(11):2735-42. [PubMed:17056793 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-dependent multivitamin transmembrane transporter activity
Specific Function:
Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name:
SLC5A6
Uniprot ID:
Q9Y289
Molecular Weight:
68641.27 Da
References
  1. Luo S, Kansara VS, Zhu X, Mandava NK, Pal D, Mitra AK: Functional characterization of sodium-dependent multivitamin transporter in MDCK-MDR1 cells and its utilization as a target for drug delivery. Mol Pharm. 2006 May-Jun;3(3):329-39. [PubMed:16749865 ]
  2. Janoria KG, Hariharan S, Paturi D, Pal D, Mitra AK: Biotin uptake by rabbit corneal epithelial cells: role of sodium-dependent multivitamin transporter (SMVT). Curr Eye Res. 2006 Oct;31(10):797-809. [PubMed:17038304 ]
  3. Reidling JC, Said HM: Regulation of the human biotin transporter hSMVT promoter by KLF-4 and AP-2: confirmation of promoter activity in vivo. Am J Physiol Cell Physiol. 2007 Apr;292(4):C1305-12. Epub 2006 Nov 29. [PubMed:17135299 ]
  4. Camporeale G, Zempleni J, Eissenberg JC: Susceptibility to heat stress and aberrant gene expression patterns in holocarboxylase synthetase-deficient Drosophila melanogaster are caused by decreased biotinylation of histones, not of carboxylases. J Nutr. 2007 Apr;137(4):885-9. [PubMed:17374649 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Methylcrotonoyl-coa carboxylase activity
Specific Function:
Carboxyltransferase subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isovaleric acid catabolism.
Gene Name:
MCCC2
Uniprot ID:
Q9HCC0
Molecular Weight:
61332.65 Da
References
  1. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [PubMed:16707089 ]
  2. de Queiroz MS, Waldrop GL: Modeling and numerical simulation of biotin carboxylase kinetics: implications for half-sites reactivity. J Theor Biol. 2007 May 7;246(1):167-75. Epub 2006 Dec 28. [PubMed:17266990 ]
  3. Ludke A, Kramer R, Burkovski A, Schluesener D, Poetsch A: A proteomic study of Corynebacterium glutamicum AAA+ protease FtsH. BMC Microbiol. 2007 Jan 25;7:6. [PubMed:17254330 ]
  4. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [PubMed:17659996 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Catalyzes the ATP-dependent carboxylation of acetyl-CoA to malonyl-CoA. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase. Involved in inhibition of fatty acid and glucose oxidation and enhancement of fat storage (By similarity). May play a role in regulation of mitochondrial fatty acid oxidation through malonyl-CoA-dependent inhibition of ...
Gene Name:
ACACB
Uniprot ID:
O00763
Molecular Weight:
276538.575 Da
References
  1. Liu Y, Zalameda L, Kim KW, Wang M, McCarter JD: Discovery of acetyl-coenzyme A carboxylase 2 inhibitors: comparison of a fluorescence intensity-based phosphate assay and a fluorescence polarization-based ADP Assay for high-throughput screening. Assay Drug Dev Technol. 2007 Apr;5(2):225-35. [PubMed:17477831 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Methylcrotonoyl-coa carboxylase activity
Specific Function:
Biotin-attachment subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isovaleric acid catabolism.
Gene Name:
MCCC1
Uniprot ID:
Q96RQ3
Molecular Weight:
80472.45 Da
References
  1. Friebel D, von der Hagen M, Baumgartner ER, Fowler B, Hahn G, Feyh P, Heubner G, Baumgartner MR, Hoffmann GF: The first case of 3-methylcrotonyl-CoA carboxylase (MCC) deficiency responsive to biotin. Neuropediatrics. 2006 Apr;37(2):72-8. [PubMed:16773504 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyruvate carboxylase activity
Specific Function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular Weight:
129632.565 Da
References
  1. Liu L, Li Y, Zhu Y, Du G, Chen J: Redistribution of carbon flux in Torulopsis glabrata by altering vitamin and calcium level. Metab Eng. 2007 Jan;9(1):21-9. Epub 2006 Aug 12. [PubMed:17008113 ]
  2. Ferreira G, Weiss WP: Effect of biotin on activity and gene expression of biotin-dependent carboxylases in the liver of dairy cows. J Dairy Sci. 2007 Mar;90(3):1460-6. [PubMed:17297119 ]
  3. Jitrapakdee S, Surinya KH, Adina-Zada A, Polyak SW, Stojkoski C, Smyth R, Booker GW, Cleland WW, Attwood PV, Wallace JC: Conserved Glu40 and Glu433 of the biotin carboxylase domain of yeast pyruvate carboxylase I isoenzyme are essential for the association of tetramers. Int J Biochem Cell Biol. 2007;39(11):2120-34. Epub 2007 Jun 27. [PubMed:17659996 ]
  4. Jitrapakdee S, Adina-Zada A, Besant PG, Surinya KH, Cleland WW, Wallace JC, Attwood PV: Differential regulation of the yeast isozymes of pyruvate carboxylase and the locus of action of acetyl CoA. Int J Biochem Cell Biol. 2007;39(6):1211-23. Epub 2007 Mar 30. [PubMed:17478118 ]
  5. Ozimek PZ, Klompmaker SH, Visser N, Veenhuis M, van der Klei IJ: The transcarboxylase domain of pyruvate carboxylase is essential for assembly of the peroxisomal flavoenzyme alcohol oxidase. FEMS Yeast Res. 2007 Oct;7(7):1082-92. Epub 2007 Feb 20. [PubMed:17316367 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Propionyl-coa carboxylase activity
Specific Function:
Not Available
Gene Name:
PCCA
Uniprot ID:
P05165
Molecular Weight:
80058.295 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Clavero S, Martinez MA, Perez B, Perez-Cerda C, Ugarte M, Desviat LR: Functional characterization of PCCA mutations causing propionic acidemia. Biochim Biophys Acta. 2002 Nov 20;1588(2):119-25. [PubMed:12385775 ]
  4. Cherbonnel-Lasserre CL, Linares-Cruz G, Rigaut JP, Sabatier L, Dutrillaux B: Strong decrease in biotin content may correlate with metabolic alterations in colorectal adenocarcinoma. Int J Cancer. 1997 Sep 4;72(5):768-75. [PubMed:9311592 ]
  5. Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [PubMed:15623830 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Catalyzes the rate-limiting reaction in the biogenesis of long-chain fatty acids. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:
ACACA
Uniprot ID:
Q13085
Molecular Weight:
265551.725 Da
References
  1. Bilder P, Lightle S, Bainbridge G, Ohren J, Finzel B, Sun F, Holley S, Al-Kassim L, Spessard C, Melnick M, Newcomer M, Waldrop GL: The structure of the carboxyltransferase component of acetyl-coA carboxylase reveals a zinc-binding motif unique to the bacterial enzyme. Biochemistry. 2006 Feb 14;45(6):1712-22. [PubMed:16460018 ]
  2. Brownsey RW, Boone AN, Elliott JE, Kulpa JE, Lee WM: Regulation of acetyl-CoA carboxylase. Biochem Soc Trans. 2006 Apr;34(Pt 2):223-7. [PubMed:16545081 ]
  3. Aoki H, Kimura K, Igarashi K, Takenaka A: Soy protein suppresses gene expression of acetyl-coA carboxylase alpha from promoter PI in rat liver. Biosci Biotechnol Biochem. 2006 Apr;70(4):843-9. [PubMed:16636450 ]
  4. Santoro N, Brtva T, Roest SV, Siegel K, Waldrop GL: A high-throughput screening assay for the carboxyltransferase subunit of acetyl-CoA carboxylase. Anal Biochem. 2006 Jul 1;354(1):70-7. Epub 2006 May 3. [PubMed:16707089 ]
  5. Leonard E, Lim KH, Saw PN, Koffas MA: Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol. 2007 Jun;73(12):3877-86. Epub 2007 Apr 27. [PubMed:17468269 ]

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 unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on October 14, 2015 12:26