BIOTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H16N2O3S
Molecular Weight	244.3121
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CCC(=O)O)C[C@@]1([H])[C@]2([H])[C@]([H])(CS1)N=C(N2)O

InChI

InChIKey=YBJHBAHKTGYVGT-ZKWXMUAHSA-N

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

HIDE SMILES / InChI

Description
Sources: www.ncbi.nlm.nih.gov/pubmed/18356320
Curator's Comment:: description was created based on several sources, including www.ncbi.nlm.nih.gov/pubmed/17182796, www.ncbi.nlm.nih.gov/pubmed/19056639

Biotin (also known as vitamin H and vitamin B7) is a water-soluble vitamin which is required for normal cellular functions, growth and development. Biotin is an important cofactor for many mitochondria and cytoplasm enzymes: acetyl-CoA carboxylase a (ACCa),7 ACCb, pyruvate carboxylase (PC), propionyl-CoA carboxylase (PCC), and methylcrotonyl-CoA carboxylase (MCC) and plays critical role in in the intermediate metabolism of gluconeogenesis, fatty acid synthesis, and amino acid catabolism. The vitamin cannot be synthesized by humans and must be obtained from diet. If there is a lack of biotin, an organism starts suffering from biotin deficiency, a condition which is very common among pregnant women, for example. The vitamin deficiency effects hair, nail growth and skin health. For preventing measures, biotin should be taken as a dietary supplement (in a form of vitamin complex or as a pure biotin) which are marketed worldwide under different names. Biotin is a part of many formulations which were approved by FDA.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vitamin deficiency 14 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021163s032,021559s025lbl.pdf	Preventing		Approved 7997	INFUVITE ADULT Approved Use INFUVITE ADULT is a combination of vitamins indicated for prevention of vitamin deficiency in adults and children aged 11 and older receiving parenteral nutrition. Launch Date 9.5852161E11
Biotin deficiency 1 Sources: https://cscprivatelabel.com/wp-content/uploads/2016/05/Biotin.pdf	Preventing		Approved 7997	BIOTIN Approved Use As a dietary supplement.

C_max

Value	Dose	Analyte	Population
508.5 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
84.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
494.9 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
823.8 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
214.6 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
184 ng/mL REVIEW https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
41 ng/mL EXPERIMENT https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
91 ng/mL EXPERIMENT https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1652.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
210 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
2315 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4010 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
605.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6574044/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
15 h REVIEW https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15 h EXPERIMENT https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15 h EXPERIMENT https://www.future-science.com/doi/pdf/10.4155/ipk-2017-0013	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	BIOTIN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
81% REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
81% REVIEW https://pubmed.ncbi.nlm.nih.gov/26699811/	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		BIOTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1B1 50

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1B1 64	inducer 1333 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000058855, https://pubmed.ncbi.nlm.nih.gov/15333708/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15956	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15956
ChemicalBook	CB3271542	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3271542
MolPort	MolPort-002-507-373	https://www.molport.com/shop/molecule-link/MolPort-002-507-373
Selleck Chemicals	biotin-vitamin-b7	http://www.selleckchem.com/products/biotin-vitamin-b7.html
ZINC	ZINC000035024346	http://zinc15.docking.org/substances/ZINC000035024346
eMolecules	1970569	https://www.emolecules.com/cgi-bin/more?vid=1970569
eMolecules	481810	https://www.emolecules.com/cgi-bin/more?vid=481810

PubMed

Title	Date	PubMed
[Development and identification of T. aestivum-S. cereale-H. villosa double translocation line 1RS.1BL, 6VS.6AL via chromosome C-banding and dual color FISH].	2001	11281000
Intra- and inter-areal connections between the primary visual cortex V1 and the area immediately surrounding V1 in the rat.	2001	11226668
Immunohistochemistry of MMPs and TIMPs.	2001	11217311
Amplification methods for the immunolocalization of rare molecules in cells and tissues.	2001	11194866
A new quantitative analytical method of serum biotinidase activity using biocytin as a substrate and its clinical significance in Japan.	2001 Apr	11282096
Avidin expression during chick chondrocyte and myoblast development in vitro and in vivo: regulation of cell proliferation.	2001 Apr	11282023
Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins.	2001 Apr	11279261
Optical measurement of transverse molecular diffusion in a microchannel.	2001 Apr	11259309
Progress towards single-molecule sequencing: enzymatic synthesis of nucleotide-specifically labeled DNA.	2001 Apr 13	11257538
Polymer support for exonucleolytic sequencing.	2001 Apr 13	11257537
Mu-opioid receptors are present in functionally identified sympathoexcitatory neurons in the rat rostral ventrolateral medulla.	2001 Apr 23	11283947
The Bacillus subtilis RNase P holoenzyme contains two RNase P RNA and two RNase P protein subunits.	2001 Feb	11233980
Effects of supplemental dietary biotin on performance of Holstein cows during early lactation.	2001 Feb	11233035
Reconstruction of the transected cat spinal cord following NeuroGel implantation: axonal tracing, immunohistochemical and ultrastructural studies.	2001 Feb	11226756
Axon trajectories in local circuits of the primary motor cortex in the macaque monkey (Macaca fuscata).	2001 Feb	11223469
An in situ hybridization protocol to detect rare mRNA expressed in neural tissue using biotin-labelled oligonucleotide probes.	2001 Feb	11223418
Longitudinal study of anti-Candida albicans mucosal immunity against aspartic proteinases in HIV-infected patients.	2001 Feb 1	11242180
In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B.	2001 Feb 1	11221827
Relationship between serum biotin concentration and moisture content of the sole horn in cows with clinical laminitis or sound hooves.	2001 Feb 17	11265999
Screening effect of PEG on avidin binding to liposome surface receptors.	2001 Feb 19	11282238
Combined laser tweezers and dielectric field cage for the analysis of receptor-ligand interactions on single cells.	2001 Jan	11288894
Azospirillum doebereinerae sp. nov., a nitrogen-fixing bacterium associated with the C4-grass Miscanthus.	2001 Jan	11211255
Postnatal development of biotinylated dextran amine-labeled corpus callosum axons projecting from the visual and auditory cortices to the visual cortex of the rat.	2001 Jan	11206280
Thalamocortical arbors extend beyond single cortical barrels: an in vivo intracellular tracing study in rat.	2001 Jan	11206278
Enhanced surface plasmon resonance immunosensing using a streptavidin-biotinylated protein complex.	2001 Jan	11205509
Liposomes labeled with biotin and horseradish peroxidase: a probe for the enhanced amplification of antigen--antibody or oligonucleotide--DNA sensing processes by the precipitation of an insoluble product on electrodes.	2001 Jan 1	11195517
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder.	2001 Jan 15	11208975
Expression sequence tag-specific full-length cDNA cloning: actin cDNAs.	2001 Jan 24	11223266
Avidin-biotin-immobilized liposome column for chromatographic fluorescence on-line analysis of solute-membrane interactions.	2001 Jan 5	11204223
Erbin is a protein concentrated at postsynaptic membranes that interacts with PSD-95.	2001 Jun 1	11279080
Functional signal peptides bind a soluble N-terminal fragment of SecA and inhibit its ATPase activity.	2001 Jun 1	11279006
Structural characterization of pyrrolic cross-links in collagen using a biotinylated Ehrlich's reagent.	2001 Jun 1	11278513
Abnormal thiol reactivity of tropomyosin in essential hypertension and its association with abnormal sodium-lithium countertransport kinetics.	2001 Mar	11288819
Neuroendocrine differentiation in bronchial carcinomas of classic squamous-cell type: an immunohistochemical study of 29 cases applying the tyramide signal amplification technique.	2001 Mar	11277422
In situ hybridization detection of calcitonin mRNA in routinely fixed, paraffin-embedded tissue sections: a comparison of different types of probes combined with tyramide signal amplification.	2001 Mar	11277417
Stimulation of corticospinal tract regeneration in the chronically injured spinal cord.	2001 Mar	11264681
PCR-ELISAs for the detection of Campylobacter jejuni and Campylobacter coli in poultry samples.	2001 Mar	11252796
Synthesis and application of circularizable ligation probes.	2001 Mar	11252794
Investigating the surface expression of the renal type IIa Na+/Pi-cotransporter in Xenopus laevis oocytes.	2001 Mar 1	11284206
Axonal transport of TNF-alpha in painful neuropathy: distribution of ligand tracer and TNF receptors.	2001 Mar 1	11240015
Single epitope multiple staining to detect ultralow frequency B cells.	2001 Mar 1	11226471
Propagation of synchronous epileptiform events from subiculum backward into area CA1 of rat brain slices.	2001 Mar 23	11259758
Association of membrane-bound amyloid precursor protein APP with the apolipoprotein E receptor LRP.	2001 Mar 5	11245926
Alginate, a bioresorbable material derived from brown seaweed, enhances elongation of amputated axons of spinal cord in infant rats.	2001 Mar 5	11189043
Cloning and characterization of biotin biosynthetic genes of Kurthia sp.	2001 Mar 7	11255013
Metabolic biotinylation of secreted and cell surface proteins from mammalian cells.	2001 Mar 9	11237761
Sodium ion-translocating decarboxylases.	2001 May 1	11248185
Adsorption of avidin on microfabricated surfaces for protein biochip applications.	2001 May 20	11283915
Rotation of a complex of the gamma subunit and c ring of Escherichia coli ATP synthase. The rotor and stator are interchangeable.	2001 May 4	11279047
Immobilization of sugar-non-specific nucleases by utilizing the streptavidin--biotin interaction.	2001 May 4	11278037

Patents

Sample Use Guides

In Vivo Use Guide

Recommended daily dosage is 10 ml (in a form of infuvite adult) or 1 tablet a day in a form of Biotin dietary supplement (the dosage may vary).

Route of Administration: Other

In Vitro Use Guide

Human T lymphoma Jurkat cells and monocytic myeloid U937 cells were incubated with different concentrations of biotin (nM): 0.025, 0.25 and 10, representing plasma levels in biotin-deﬁcient, biotin-sufﬁcient and biotin-supplemented adults. When taken together with folate, biotin synergizes in the repression of pro-inﬂammatory cytokines and long-terminal repeats (LTRs), mediated by interactions between HLCS and other chromatin proteins.

Name

Type

Language

BIOTIN

Official Name

English

NSC-63865

Code

English

(3AS,4S,6AR)-HEXAHYDRO-2-OXO-1H-THIENO(3,4-D)IMIDAZOLE-4-VALERIC ACID

Common Name

English

BIOTIN [MI]

Common Name

English

BIOTIN [USP]

Common Name

English

BIOTIN [ORANGE BOOK]

Common Name

English

D-(+)-BIOTIN

Common Name

English

BIOTIN [INCI]

Common Name

English

BIOTIN [WHO-DD]

Common Name

English

BIOTIN [VANDF]

Common Name

English

BIOTIN [EP MONOGRAPH]

Common Name

English

BIOTIN [HSDB]

Common Name

English

BIOTIN [USP-RS]

Common Name

English

RITATIN

Common Name

English

MD-1003

Code

English

BIOEPIDERM

Brand Name

English

BIOTIN [JAN]

Common Name

English

D-BIOTIN

Common Name

English

BIOTIN [INN]

Common Name

English

BIOTIN [FCC]

Common Name

English

BIOTIN [MART.]

Common Name

English

D-BIOTIN [VANDF]

Common Name

English

BIOTIN [EP]

Common Name

English

Classification Tree Code System Code

DSLD

2669 (Number of products:7171)