DrugBank: Pantothenic acid (DB01783)

targets (1)

Identification

Name

Pantothenic acid

Accession Number

DB01783 (EXPT02501)

Type

small molecule

Groups

nutraceutical

Description

Pantothenic acid, also called pantothenate or vitamin B5 (a B vitamin), is a water-soluble vitamin discovered by Roger J. Williams in 1919. For many animals, pantothenic acid is an essential nutrient. Animals require pantothenic acid to synthesize coenzyme-A (CoA), as well as to synthesize and metabolize proteins, carbohydrates, and fats.
Pantothenic acid is the amide between pantoic acid and β-alanine. Small quantities of pantothenic acid are found in nearly every food, with high amounts in whole-grain cereals, legumes, eggs, meat, royal jelly, avocado, and yogurt. It is commonly found as its alcohol analog, the provitamin panthenol, and as calcium pantothenate. Pantothenic acid is an ingredient in some hair and skin care products. Only the dextrorotatory (D) isomer of pantothenic acid possesses biologic activity. The levorotatory (L) form may antagonize the effects of the dextrorotatory isomer. [Wikipedia]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

(+)-Pantothenic acid
D-pantothenic acid
N-(2,4-dihydroxy-3,3-dimethylbutanoyl)-β-alanine
Pantothenate
Vitamin B5

Salts

D-Calcium Pantothenate

Brand names

Not Available

Brand mixtures

Not Available

Categories

Vitamin B Complex

CAS number

79-83-4

Weight

Average: 219.235
Monoisotopic: 219.110672659

Chemical Formula

C₉H₁₇NO₅

InChI Key

InChIKey=GHOKWGTUZJEAQD-UHFFFAOYSA-N

InChI

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)

Plain Text

IUPAC Name

3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid

SMILES

CC(C)(CO)C(O)C(=O)NCCC(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Studied for the treatment of many uses such as treatment of testicular torsion, diabetic ulceration, wound healing, acne, obesity, diabetic peripheral polyneuropathy. It has also been investigated for its hypolipidemic effects and as cholesterol lowering agent.

Pharmacodynamics

Pantothenic acid is used in the synthesis of coenzyme A (CoA). Coenzyme A may act as an acyl group carrier to form acetyl-CoA and other related compounds; this is a way to transport carbon atoms within the cell. CoA is important in energy metabolism for pyruvate to enter the tricarboxylic acid cycle (TCA cycle) as acetyl-CoA, and for α-ketoglutarate to be transformed to succinyl-CoA in the cycle. CoA is also important in the biosynthesis of many important compounds such as fatty acids, cholesterol, and acetylcholine. CoA is incidentally also required in the formation of ACP, which is also required for fatty acid synthesis in addition to CoA. Pantothenic acid in the form of CoA is also required for acylation and acetylation, which, for example, are involved in signal transduction and enzyme activation and deactivation, respectively. Since pantothenic acid participates in a wide array of key biological roles, it is essential to all forms of life. As such, deficiencies in pantothenic acid may have numerous wide-ranging effects, as discussed below.

Mechanism of action

Pantothenic acid is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.

Absorption

When found in foods, most pantothenic acid is in the form of CoA or acyl carrier protein (ACP). For the intestinal cells to absorb this vitamin, it must be converted into free pantothenic acid. Within the lumen of the intestine, CoA and ACP are hydrolyzed into 4'-phosphopantetheine. The 4'-phosphopantetheine is then dephosphorylated into pantetheine. Pantetheinase, an intestinal enzyme, then hydrolyzes pantetheine into free pantothenic acid. Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system. At high levels of intake, when this mechanism is saturated, some pantothenic acid may also be absorbed via passive diffusion. As intake increases 10-fold, however, absorption rate decreases to 10%. [Wikipedia]

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

No Tolerable Upper Level Intake (UL) has been established for the vitamin.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	195ºC (D-Calcium Pantothenate salt)	MSDS
water solubility	Soluble	MSDS

Predicted Properties

Property	Value	Source
water solubility	6.05e+01 g/l	ALOGPS
logP	-1.1	ALOGPS
logP	-1.4	ChemAxon
logS	-0.56	ALOGPS
pKa (strongest acidic)	4.35	ChemAxon
pKa (strongest basic)	-2.8	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	5	ChemAxon
hydrogen donor count	4	ChemAxon
polar surface area	106.86	ChemAxon
rotatable bond count	6	ChemAxon
refractivity	51.51	ChemAxon
polarizability	21.92	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Trumbo, P. R. (2006). “Pantothenic Acid”. In Shils, M. E.; Shike, M.; Ross, A. C. et al.. Modern Nutrition in Health and Disease (10th ed.). Philadelphia, PA: Lippincott Williams & Wilkins. pp. 462–467. ISBN 0-7817-4133-5.

External Links

Resource	Link
KEGG Drug	D07413
KEGG Compound	C00864
ChEBI	7916
ChEMBL	7916
HET	PAU
Wikipedia	http://en.wikipedia.org/wiki/Pantothenic_acid

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1SQ5

FDA label

Not Available

MSDS

show (47.9 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Pantothenate kinase Pharmacological action: unknown ATP + (R)-pantothenate = ADP + (R)-4'- phosphopantothenate Organism class: bacterial UniProt ID: P0A6I3 Gene: coaA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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

Targets

1. Pantothenate kinase

Pharmacological action: unknown

ATP + (R)-pantothenate = ADP + (R)-4'- phosphopantothenate

Organism class: bacterial
UniProt ID: P0A6I3 Link_out

Gene: coaA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

Comments

Drug created on June 13, 2005 07:24 / Updated on March 09, 2013 13:12