U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H17NO5
Molecular Weight 219.2353
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTOTHENIC ACID

SMILES

CC(C)(CO)[C@]([H])(C(=NCCC(=O)O)O)O

InChI

InChIKey=GHOKWGTUZJEAQD-ZETCQYMHSA-N
InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H17NO5
Molecular Weight 219.2353
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Pantothenic acid (known as Vitamin B5) is a water-soluble member of the B-vitamin family that is converted into 4’-phosphopantetheine, which is then converted to co-enzyme A (CoA) via adenosine triphosphate. Pantothenic acid regulates epidermal barrier function and keratinocytes differentiation via CoA metabolism. Pantothenic acid is incorporated into co-enzyme A and protects cells against peroxidative damage by increasing the level of glutathione. A recent feasibility study has also shown that daily oral supplementation of a nutritional agent containing pantothenic acid for 8 weeks was feasible and safe. It was discovered the different pharmacological implementation of pantothenic acid, such as treatment of acne, obesity. Existed some reports, mentioned efficacy using pantothenic acid in systemic lupus erythematosus. Significant reduction in morning stiffness, degree of disability, and severity of pain was reported for persons taking pantothenic acid in case of osteoarthritis and rheumatoid arthritis. Vitamin B5 may increase the effects of a group of drugs called cholinesterase inhibitors, which are used to treat Alzheimer's disease. That might lead to severe side effects.

CNS Activity

Curator's Comment:: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9BZ23|||Q8TCR5
Gene ID: 80025.0
Gene Symbol: PANK2
Target Organism: Homo sapiens (Human)
Target ID: Q8TE04
Gene ID: 53354.0
Gene Symbol: PANK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VITAPED

Approved Use

For treatment of pernicious anemia (due to lack of or inhibition of intrinsic factor) and for prevention and treatment of vitamin B 12 deficiency.

Launch Date

7.5703681E11
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Studies on calluses induced from various explants of Cistanche deserticola].
2001 Apr
Pantothenic acid: an organ-specific pro-oxidant vitamin. Brain and liver neuroprostane levels in rats fed a pantothenic acid-deficient diet.
2002
[Gel with provitamin B5 applied during tests with the Goldmann triple-mirror].
2003
[Clinical evaluation of provitamin B5 drops and gel for postoperative treatment of corneal and conjuctival injuries].
2003
Protection by pantothenic acid against apoptosis and cell damage by oxygen free radicals--the role of glutathione.
2003
Fermentative activity and production of volatile compounds by Saccharomyces grown in synthetic grape juice media deficient in assimilable nitrogen and/or pantothenic acid.
2003
[Advance in therapy of acute rhinitis--comparison of efficacy and safety of xylometazoline in combination xylometazoline-dexpanthenol in patients with acute rhinitis].
2003 Apr
Use of the mannitol pathway in fructose fermentation of Oenococcus oeni due to limiting redox regeneration capacity of the ethanol pathway.
2003 Apr
Efficacy of dexpanthenol in skin protection against irritation: a double-blind, placebo-controlled study.
2003 Aug
Determination of water-soluble vitamins in soft drinks and vitamin supplements using capillary electrophoresis.
2003 Aug
Structure of E. coli ketopantoate hydroxymethyl transferase complexed with ketopantoate and Mg2+, solved by locating 160 selenomethionine sites.
2003 Aug
Long-term treatment of Barth syndrome with pantothenic acid: a retrospective study.
2003 Dec
The optimization of HPLC-UV conditions for use with FTIR detection in the analysis of B vitamins.
2003 Feb
[Ogilvie's syndrome: a rare cause of the acute abdomen].
2003 Feb
Specialization of function among aldehyde dehydrogenases: the ALD2 and ALD3 genes are required for beta-alanine biosynthesis in Saccharomyces cerevisiae.
2003 Jan
Committee on food nutrition. Water-soluble vitamins.
2003 Jan-Feb
Competitive and interactions affecting a fermentative spirochete in anaerobic chemostats.
2003 Jul
Pantothenic acid quantification by a stable isotope dilution assay based on liquid chromatography-tandem mass spectrometry.
2003 Jul
The crystal structure of the first enzyme in the pantothenate biosynthetic pathway, ketopantoate hydroxymethyltransferase, from M tuberculosis.
2003 Jul
Biotin uptake by human intestinal and liver epithelial cells: role of the SMVT system.
2003 Jul
An evaluation of protein assays for quantitative determination of drugs.
2003 Jul 31
Vitamin intake in Japanese women college students.
2003 Jun
Magnetic resonance imaging and Hallervorden-Spatz syndrome.
2003 Jun
Lactation performance by dairy cows fed supplemental biotin and a B-vitamin blend.
2003 Jun
Structural insights into the evolution of the pantothenate-biosynthesis pathway.
2003 Jun
[The protective effect of dexpanthenol in nasal sprays. First results of cytotoxic and ciliary-toxic studies in vitro].
2003 Mar
Transport of biotin in human keratinocytes.
2003 Mar
[Regulation of acetate metabolism in a strain of Acinetobacter sp., growing on ethanol].
2003 Mar-Apr
Risk analysis applied to food fortification.
2003 May
[Development of nutrient medium for the cultivation of Lactobacillus plantarum 8R-A3 ].
2003 May-Jun
Pharmacotherapy for dyslipidaemia--current therapies and future agents.
2003 Nov
Environmental, life-style, and physical precursors of clinical Parkinson's disease: recent findings from the Honolulu-Asia Aging Study.
2003 Oct
Substrate specificity and kinetic isotope effect analysis of the Eschericia coli ketopantoate reductase.
2003 Sep 30
Metabolic network analysis during fed-batch cultivation of Corynebacterium glutamicum for pantothenic acid production: first quantitative data and analysis of by-product formation.
2003 Sep 4
Cofactor engineering of intracellular CoA/acetyl-CoA and its effect on metabolic flux redistribution in Escherichia coli.
2004 Apr
Mitochondrial decay, a major cause of aging, can be delayed.
2004 Apr
Cell division defects of Schizosaccharomyces pombe liz1- mutants are caused by defects in pantothenate uptake.
2004 Apr
Determination of vitamin B5 in a range of fortified food products by reversed-phase liquid chromatography-mass spectrometry with electrospray ionisation.
2004 Apr 2
Fluorimetric determination of pantothenic acid in foods by liquid chromatography with post-column derivatization.
2004 Apr 30
The structure of the pantothenate kinase.ADP.pantothenate ternary complex reveals the relationship between the binding sites for substrate, allosteric regulator, and antimetabolites.
2004 Aug 20
Vanin-1(-/-) mice show decreased NSAID- and Schistosoma-induced intestinal inflammation associated with higher glutathione stores.
2004 Feb
Clear hydro-gel, compared to ointment, provides improved eye comfort after brief surgery.
2004 Feb
Prevention of tungiasis using a biological repellent: a small case series.
2004 Jan
Organisation of the pantothenate (vitamin B5) biosynthesis pathway in higher plants.
2004 Jan
One-pot chemoenzymatic preparation of coenzyme A analogues.
2004 Jan 1
Copper-mediated synthesis of N-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801.
2004 Jan 8
Coenzyme A biosynthesis: reconstruction of the pathway in archaea and an evolutionary scenario based on comparative genomics.
2004 Jul
Are WHO/UNAIDS/UNICEF-recommended replacement milks for infants of HIV-infected mothers appropriate in the South African context?
2004 Mar
[Riboflavin-radical formation by mechanochemical solid-state reaction using stainless steel vessel].
2004 Mar
Chemo- and regioselective peptide cyclization triggered by the N-terminal fatty acid chain length: the recombinant cyclase of the calcium-dependent antibiotic from Streptomyces coelicolor.
2004 Mar 16
Patents

Sample Use Guides

The Dietary Reference Intake (DRI) established by the Institute of Medicine for pantothenic acid is as follows: 1–3 years old: 2 mg/d; 4–8 years old: 3 mg/d; 9–13 years old: 4 mg/d; 14 years old and over: 5 mg/d; Pregnancy: 6 mg/d; Lactation: 7 mg/d
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:46:56 UTC 2021
Edited
by admin
on Sat Jun 26 12:46:56 UTC 2021
Record UNII
19F5HK2737
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PANTOTHENIC ACID
HSDB   INCI   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INCI  
Official Name English
CHICK ANTIDERMATITIS FACTOR
Common Name English
PANTOTHENIC ACID [WHO-DD]
Common Name English
VITAMIN B-5
Common Name English
PANTOTHENIC ACID (D)
Common Name English
PANTOTHENIC ACID [INCI]
Common Name English
VITAMIN B5
GREEN BOOK   VANDF  
Common Name English
PANTOTHENIC ACID [MI]
Common Name English
PANTOTHENIC ACID [ORANGE BOOK]
Common Name English
.BETA.-ALANINE, N-(2,4-DIHYDROXY-3,3-DIMETHYL-1-OXOBUTYL)-, (R)-
Common Name English
VITAMIN B5 [GREEN BOOK]
Common Name English
D-PANTOTHENIC ACID
Systematic Name English
PANTOTHENATE
Systematic Name English
VITAMIN B5 [VANDF]
Common Name English
PANTOTHENIC ACID [MART.]
Common Name English
N-((2R)-2,4-DIHYDROXY-3,3-DIMETHYL-1-OXOBUTYL)-.BETA.-ALANINE
Systematic Name English
PANTOTHENIC ACID [HSDB]
Common Name English
PANTOTHENIC ACID [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 27351-6
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
LIVERTOX 738
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
LOINC 75066-1
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
DSLD 1791 (Number of products:46)
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
NCI_THESAURUS C45812
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
LOINC 2722-7
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
DSLD 2547 (Number of products:2298)
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
LOINC 75060-4
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
Code System Code Type Description
EVMPD
SUB14758MIG
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL1594
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
MERCK INDEX
M8388
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PANTOTHENIC ACID
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
PUBCHEM
6613
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-229-0
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
DRUG BANK
DB01783
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
CAS
79-83-4
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
RXCUI
62400
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
ALTERNATIVE
HSDB
1020
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
RXCUI
7891
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
MESH
D010205
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
NCI_THESAURUS
C47783
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
FDA UNII
19F5HK2737
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
EPA CompTox
79-83-4
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
EVMPD
SUB127094
Created by admin on Sat Jun 26 12:46:56 UTC 2021 , Edited by admin on Sat Jun 26 12:46:56 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Nutritional value per 100 g (3.5 oz) - 0.573 mg (11%)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY