Identification

Name
Biotin
Accession Number
DB00121  (NUTR00019)
Type
Small Molecule
Groups
Approved, 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
Product Images
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 Inc.1985-12-312001-06-22Canada
Biotin Ctr Srt 1000mcgTablet, extended release1 mgOralBioenergy Inc.1979-12-311998-06-03Canada
Biotin Tab 250mcgTablet250 mcgOralVita Health Products Inc1979-12-312002-07-31Canada
Biotin Tab 300mcgTablet300 mcgOralPure Life International Prods Inc.1992-12-312001-08-07Canada
Biotin Tab 300mcgTablet300 mcgOralGahler Enterprises Ltd.1986-12-312007-08-07Canada
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/Other Brands
Appearex / Biodermatin / Biotin Forte / Meribin / Nail-ex
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adult Infuvite Multiple VitaminsBiotin (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) + Thiamine Hydrochloride (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 VitaminsBiotin (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) + Thiamine Hydrochloride (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 VitaminsBiotin (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) + Thiamine Hydrochloride (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 VitaminsBiotin (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) + Thiamine Hydrochloride (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
Am CapsBiotin (150 mcg) + Cyanocobalamin (3 mcg) + Folic Acid (0.2 mg) + Nicotinamide (10 mg) + Pyridoxine hydrochloride (1 mg) + Riboflavin (0.90 mg) + Thiamine (0.75 mg) + Vitamin A (1250 unit) + Vitamin C (30 mg) + Vitamin D (100 unit)CapsuleOralNew Vision Nutritionals Company1998-10-012002-11-20Canada
Am CapsBiotin (150 mcg) + Beta carotene (2500 unit) + Cholecalciferol (200 unit) + Cyanocobalamin (5 mcg) + Folic Acid (0.20 mg) + Nicotinamide (10 mg) + Pyridoxine hydrochloride (1 mg) + Riboflavin (0.85 mg) + Selenium (50 mcg) + Thiamine (0.75 mg) + Calcium ascorbate (30 mg) + Vitamin E (15 unit)CapsuleOralNew Vision Nutritionals CompanyNot applicableNot applicableCanada
B 50 CapsulesBiotin (50 mcg) + Choline bitartrate (50 mg) + Cyanocobalamin (50 mcg) + Folic Acid (.4 mg) + Inositol nicotinate (50 mg) + Nicotinamide (50 mg) + Calcium pantothenate (50 mg) + Pyridoxine hydrochloride (50 mg) + Riboflavin (50 mg) + Thiamine mononitrate (50 mg)CapsuleOralRheingold Food International Ltd.1987-12-312007-07-26Canada
B Complex 25mg Vitamin SupplementBiotin (25 mcg) + Choline bitartrate (25 mg) + Cyanocobalamin (25 mcg) + Folic Acid (0.4 mg) + Inositol nicotinate (25 mg) + Nicotinamide (25 mg) + Pantothenic acid (25 mg) + Pyridoxine hydrochloride (25 mg) + Riboflavin (25 mg) + Thiamine Hydrochloride (25 mg)TabletOralGarden State Nutritionals1998-08-312000-06-07Canada
B Complex 50 Vitamin CapBiotin (50 mcg) + Choline bitartrate (50 mg) + Cyanocobalamin (55 mcg) + Folic Acid (.4 mg) + Inositol nicotinate (50 mg) + Nicotinamide (50 mg) + Pantothenic acid (50 mg) + Pyridoxine (50 mg) + Riboflavin (50 mg) + Thiamine (50 mg)CapsuleOralBioforce Canada Inc.1994-12-311997-07-22Canada
B Complex 50+ CapletBiotin (50 mcg) + Choline (50 mg) + Cyanocobalamin (100 mcg) + Folic Acid (1 mg) + Inositol nicotinate (50 mg) + Nicotinamide (50 mg) + Calcium pantothenate (100 mg) + Pyridoxine hydrochloride (50 mg) + Riboflavin (50 mg) + Thiamine mononitrate (50 mg)TabletOralHealth Wise Nutrition Inc.1994-12-312002-07-18Canada
Categories
UNII
6SO6U10H04
CAS number
58-85-5
Weight
Average: 244.311
Monoisotopic: 244.088163078
Chemical Formula
C10H16N2O3S
InChI Key
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][[email protected]]12CS[[email protected]@H](CCCCC(O)=O)[[email protected]@]1([H])NC(=O)N2

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance.

Structured Indications
Not Available
Pharmacodynamics

Biotin 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 action

Biotin 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.

TargetActionsOrganism
UPropionyl-CoA carboxylase beta chain, mitochondrialNot AvailableHuman
UBiotin--protein ligaseNot AvailableHuman
USodium-dependent multivitamin transporterNot AvailableHuman
UMethylcrotonoyl-CoA carboxylase beta chain, mitochondrialNot AvailableHuman
UAcetyl-CoA carboxylase 2Not AvailableHuman
UMethylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialNot AvailableHuman
UPyruvate carboxylase, mitochondrialNot AvailableHuman
UPropionyl-CoA carboxylase alpha chain, mitochondrialNot AvailableHuman
UAcetyl-CoA carboxylase 1Not AvailableHuman
Absorption

Systemic - approximately 50%

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Prolonged skin contact may cause irritation.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
3-Methylcrotonyl Coa Carboxylase Deficiency Type IDisease
Pyruvate Carboxylase DeficiencyDisease
Primary hyperoxaluria II, PH2Disease
Fructose-1,6-diphosphatase deficiencyDisease
Multiple carboxylase deficiency, neonatal or early onset formDisease
Succinic semialdehyde dehydrogenase deficiencyDisease
The oncogenic action of FumarateDisease
Propanoate MetabolismMetabolic
Valine, Leucine and Isoleucine DegradationMetabolic
Citric Acid CycleMetabolic
2-Hydroxyglutric Aciduria (D And L Form)Disease
Beta-Ketothiolase DeficiencyDisease
Leigh SyndromeDisease
Malonic AciduriaDisease
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencyDisease
Hyperinsulinism-Hyperammonemia SyndromeDisease
Threonine and 2-Oxobutanoate DegradationMetabolic
Transfer of Acetyl Groups into MitochondriaMetabolic
Glycogenosis, Type IA. Von gierke diseaseDisease
Glutaminolysis and CancerDisease
Ammonia RecyclingMetabolic
Pyruvate MetabolismMetabolic
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyDisease
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseDisease
3-hydroxyisobutyric acid dehydrogenase deficiencyDisease
3-hydroxyisobutyric aciduriaDisease
Pyruvate dehydrogenase deficiency (E3)Disease
Pyruvate kinase deficiencyDisease
Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)Disease
Triosephosphate isomeraseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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
Human Metabolome Database
HMDB00030
KEGG Drug
D00029
KEGG Compound
C00120
PubChem Compound
171548
PubChem Substance
46508694
ChemSpider
149962
BindingDB
12
ChEBI
15956
ChEMBL
CHEMBL857
PharmGKB
PA448625
HET
BTN
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Biotin
ATC Codes
A11HA05 — Biotin
AHFS Codes
  • 88:08.00 — Vitamin B Complex
PDB Entries
1avd / 1bdo / 1bib / 1df8 / 1f27 / 1hxd / 1kqs / 1luq / 1mep / 1mk5
show 87 more
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Active Not RecruitingTreatmentBiotinidase Deficiency1
2Active Not RecruitingOtherAmyotrophic Lateral Sclerosis (ALS) / Motor Neurone Disease1
2, 3CompletedTreatmentAdrenoleukodystrophy / Adrenomyeloneuropathy / AMN1
3RecruitingTreatmentDisseminated Sclerosis1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral300 mcg
Tablet, extended releaseOral
SolutionOral
LiquidTopical.01 mL/100mL
TabletOral500 mcg
CapsuleOral500 mcg
Tablet, extended releaseOral1 mg
TabletOral250 mcg
LiquidTopical.002 mL/mL
Capsule, liquid filledOral
TabletOral5 mcg
CapsuleOral
LiquidTopical
Tablet, effervescentOral
Tablet, chewableOral
Capsule, gelatin coatedOral
ShampooTopical.06 mL/100mL
SolutionTopical.06 mL/100mL
Solution / dropsOral
LiquidIntravenous
Injection, powder, lyophilized, for solutionIntravenous
PowderTopical
SprayTopical
ShampooTopical
SolutionIntravenous
Injection, solutionIntravenous
TabletOral
Tablet, coatedOral
PowderOral
Liquid; tabletOral
LiquidTopical.01 mg/100mL
KitOral
Capsule, extended releaseOral
LiquidOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)232 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (9.84 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0f76-1960000000-b21ddd69490cac3254f8
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0f76-3960000000-a8a94e2de123f66979d8
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f76-1960000000-b21ddd69490cac3254f8
GC-MS Spectrum - GC-MSGC-MSsplash10-0f76-3960000000-a8a94e2de123f66979d8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0006-0090000000-6d956bb533d353d449c9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0006-0190000000-01f67d1bdf8c742e48c8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0fxx-3920000000-f0b9613cbd9371e4be92
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9400000000-107f2a44f521c2513578
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-1a3f65d909dc40055e87
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-004i-0090000000-c928e8d0a18f3f848262
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-066s-1920000000-5f795e0b7f1d7cf986e5
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0ar1-1920000000-c298be862857cb3bbc7f
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000t-0900000000-cdc4a4c359ff765fd32d
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-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0090000000-bcffb0dcf77e8fd727a4
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0f6x-0390000000-c209523d36e9a7681f44
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0090000000-c0f81ee86772310db415
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0190000000-016eb89528e564c74720
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0fxx-3920000000-f0b9613cbd9371e4be92
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9400000000-107f2a44f521c2513578
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-d08e1b3709844e1e91b0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0190000000-21d0f2512788276bbb89
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0690000000-dc372934024e58bdcc60
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0790000000-3dc732a115953d99a259
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9000000000-0dcf3287376f08cde6b9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9000000000-fb6f5d6679dea0ec8f1b
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-1090000000-a44a68df615196a327c9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-1090000000-2e33eb7d14f0f9ca9150
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0090000000-f48642f6233836198f74
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0090000000-76deccfabe183e0493ce
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-002b-0090000000-3cb9f7103e4e1c5acb62
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-ce581561c6acbdbbd1f5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0940000000-54c1616d9935143625fc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-060a-1900000000-11a5d4190980b5a6935f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-074j-2900000000-e841b569650afc851aa0
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-004i-0090000000-5b10fe54708d7ca5c408
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-1590000000-a16a26fc2f2cb15db60f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05bb-0090000000-4acb49d8f6dd27ef371f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-d49f9fcc9039367efbdf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-e33611580a206e3bea79
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05bb-0090000000-88e1ac3f0b5053c20229
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0090000000-e7a8a723fba0a18a4f06
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0090000000-10bd2f9f4f19b0e117b6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014l-0090700000-cd3e4fbf4459f0f16e33
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014l-0090800000-eeb273d2eaf881339ed0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05xs-1920000000-3be430b63e9c748c681a
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Biotin and derivatives
Sub Class
Not Available
Direct Parent
Biotin and derivatives
Alternative Parents
Imidazolyl carboxylic acids and derivatives / Medium-chain fatty acids / Thia fatty acids / Heterocyclic fatty acids / Thiolanes / Imidazolines / Isoureas / Azacyclic compounds / Carboximidamides / Carboxylic acids
show 7 more
Substituents
Biotin / Imidazolyl carboxylic acid derivative / Medium-chain fatty acid / Heterocyclic fatty acid / Thia fatty acid / Fatty acid / Fatty acyl / Thiolane / 2-imidazoline / Isourea
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
biotins (CHEBI:15956) / Water-soluble vitamins (C00120)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Propionyl-coa carboxylase activity
Specific Function
Not Available
Gene Name
PCCB
Uniprot ID
P05166
Uniprot Name
Propionyl-CoA carboxylase beta chain, mitochondrial
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-meth...
Gene Name
HLCS
Uniprot ID
P50747
Uniprot Name
Biotin--protein ligase
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
Uniprot Name
Sodium-dependent multivitamin transporter
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 isova...
Gene Name
MCCC2
Uniprot ID
Q9HCC0
Uniprot Name
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial
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 inhibit...
Gene Name
ACACB
Uniprot ID
O00763
Uniprot Name
Acetyl-CoA carboxylase 2
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 isovale...
Gene Name
MCCC1
Uniprot ID
Q96RQ3
Uniprot Name
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial
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...
Gene Name
PC
Uniprot ID
P11498
Uniprot Name
Pyruvate carboxylase, mitochondrial
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
Uniprot Name
Propionyl-CoA carboxylase alpha chain, mitochondrial
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
Uniprot Name
Acetyl-CoA carboxylase 1
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 un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
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]

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