BIOTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H16N2O3S
Molecular Weight	244.311
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2

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

Molecular Formula	C10H16N2O3S
Molecular Weight	244.311
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021163s032,021559s025lbl.pdf	Preventing		Approved 8429	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 2000
Biotin deficiency 2 Sources: https://cscprivatelabel.com/wp-content/uploads/2016/05/Biotin.pdf	Preventing		Approved 8429	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 51

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1B1 67	inducer 1573 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
Prenatal diagnosis and treatment of holocarboxylase synthetase deficiency.	1999 Feb	10215065
Biotin status: which are valid indicators and how do we know?	1999 Feb	10064317
Human placental Na+-dependent multivitamin transporter. Cloning, functional expression, gene structure, and chromosomal localization.	1999 May 21	10329687
Immunohistochemistry of MMPs and TIMPs.	2001	11217311
Biosynthesis of biotin and lipoic acid.	2001	11153271
Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins.	2001 Apr	11279261
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
An in situ hybridization protocol to detect rare mRNA expressed in neural tissue using biotin-labelled oligonucleotide probes.	2001 Feb	11223418
Two-site ELISA for the quantitative determination of fatty acid synthase.	2001 Feb	11165205
Development and evaluation of an IgM-capture ELISA for detection of recent infection with bluetongue viruses in cattle.	2001 Feb	11164499
Metabotropic glutamate receptor type 1alpha and tubulin assemble into dynamic interacting complexes.	2001 Feb	11158246
In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B.	2001 Feb 1	11221827
Stimulation of intercellular communication of poor-communicating cells by gap-junction-competent cells enhances the HSV-TK/GCV bystander effect in vitro.	2001 Feb 15	11251978
Relationship between serum biotin concentration and moisture content of the sole horn in cows with clinical laminitis or sound hooves.	2001 Feb 17	11265999
Agonist-stimulated internalisation of the ligand-gated ion channel P2X(1) in rat vas deferens.	2001 Feb 2	11165241
Mutational analysis of protein substrate presentation in the post-translational attachment of biotin to biotin domains.	2001 Feb 2	11042165
Azospirillum doebereinerae sp. nov., a nitrogen-fixing bacterium associated with the C4-grass Miscanthus.	2001 Jan	11211255
Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea.	2001 Jan	11152648
Trigemino-reticulo-facial and trigemino-reticulo-hypoglossal pathways in the rat.	2001 Jan 1	11086291
Expression sequence tag-specific full-length cDNA cloning: actin cDNAs.	2001 Jan 24	11223266
Efferent projections of infralimbic and prelimbic areas of the medial prefrontal cortex in the Japanese monkey, Macaca fuscata.	2001 Jan 5	11146055
Effects of glucose, vitamins, and DO concentrations on pyruvate fermentation using Torulopsis glabrata IFO 0005 with metabolic flux analysis.	2001 Jan-Feb	11170481
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
PCR-ELISAs for the detection of Campylobacter jejuni and Campylobacter coli in poultry samples.	2001 Mar	11252796
Molecular characterization of the 5' regulatory region of rat sodium-dependent multivitamin transporter gene.	2001 Mar	11171574
Biotin induces tetramerization of a recombinant monomeric avidin. A model for protein-protein interactions.	2001 Mar 16	11076945
Metabolic biotinylation of secreted and cell surface proteins from mammalian cells.	2001 Mar 9	11237761
Sodium ion-translocating decarboxylases.	2001 May 1	11248185
Coupling mechanism of the oxaloacetate decarboxylase Na(+) pump.	2001 May 1	11248184
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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:20:10 GMT 2023` Edited by `admin` on `Fri Dec 15 15:20:10 GMT 2023`
Record UNII	6SO6U10H04
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIOTIN

Official Name

English

NSC-63865

Code

English

Vitamin B7

Common Name

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 [ORANGE BOOK]

Common Name

English

D-(+)-BIOTIN

Common Name

English

BIOTIN [INCI]

Common Name

English

BIOTIN [VANDF]

Common Name

English

BIOTIN [EP MONOGRAPH]

Common Name

English

Biotin [WHO-DD]

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

BIOTIN [EP IMPURITY]

Common Name

English

D-BIOTIN

Common Name

English

biotin [INN]

Common Name

English

BIOTIN [USP MONOGRAPH]

Common Name

English

BIOTIN [FCC]

Common Name

English

BIOTIN [MART.]

Common Name

English

D-BIOTIN [VANDF]

Common Name

English

Classification Tree Code System Code

DSLD

2669 (Number of products:7171)