Pantothenic acid

Identification

Name
Pantothenic acid
Accession Number
DB01783  (EXPT02501)
Type
Small Molecule
Groups
Nutraceutical, Vet Approved
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
Thumb
Synonyms
  • (+)-Pantothenic acid
  • D-pantothenic acid
  • Pantothenate
  • Vitamin B5
Product Ingredients
IngredientUNIICASInChI Key
Calcium pantothenate568ET80C3D137-08-6FAPWYRCQGJNNSJ-UBKPKTQASA-L
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acti Pantothenic Acid 1000 Timed CapletTablet1 gOralActi Form Ltd.1991-12-312005-03-21Canada
Acti-pantothenic Acid 300 Caplet 300mgTablet300 mgOralActi Form Ltd.1991-12-312005-03-21Canada
Calcium Pantothenate Tab 250mgTablet250 mgOralTrophic Canada Ltd.1991-12-311996-09-17Canada
Calpan Tab 100mgTablet100 mgOralIcn Pharmaceuticals1973-12-311998-08-13Canada
Calpan Tab 250mgTablet250 mgOralIcn Pharmaceuticals1973-12-311998-08-13Canada
D Pantothenic Acid Tab 100mgTablet100 mgOralGahler Enterprises Ltd.1984-12-312000-08-01Canada
D-pantothenic Acid 250mgCapsule250 mgOralWn Pharmaceuticals Ltd.2001-10-072007-08-07Canada
D-pantothenic Acid 250mg CapCapsule250 mgOralGahler Enterprises Ltd.1993-12-312008-07-17Canada
D'pantothenic Acid Srt 1000mgTablet, extended release1 gOralGahler Enterprises Ltd.1981-12-312001-07-26Canada
Pantacid Tab 250mgTablet250 mgOralLes Produits Naturels Suisse Inc.1985-12-311996-09-09Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adrenergy TabletsPantothenic acid (60 mg) + Manganese (1 mg) + Nicotinamide (80 mg) + Vitamin C (150 mg) + Zinc (5 mg)TabletOralMorter HealthsystemNot applicableNot applicableCanada
Adrenogist TabPantothenic acid (100 mg) + Potassium Chloride (99 mg) + Pyridoxine hydrochloride (5 mg)TabletOralPure Life International Prods Inc.1992-12-312000-07-27Canada
Advanced 2000 CapsulesPantothenic acid (15 mg) + Choline (15 mg) + Chromium (50 mcg) + Inositol nicotinate (15 mg) + Manganese (1 mg) + Pyridoxine hydrochloride (4 mg)CapsuleOralBody Gold, A Division Of Pep Products, Inc.2000-01-012002-08-22Canada
Allbee With C 550 CapCalcium pantothenate (10 mg) + Nicotinamide (50 mg) + Pyridoxine hydrochloride (5 mg) + Riboflavin (10 mg) + Thiamine mononitrate (15 mg) + Vitamin C (550 mg)CapsuleOralWhitehall Robins Inc.1994-12-312003-08-01Canada
Allbee With Vitamin C CapCalcium pantothenate (10 mg) + Nicotinamide (50 mg) + Pyridoxine hydrochloride (5 mg) + Riboflavin (10 mg) + Thiamine mononitrate (15 mg) + Vitamin C (300 mg)CapsuleOralWhitehall Robins Inc.1994-12-312000-07-26Canada
American Eagle Energizer Plus Vitamin Supplement DrinkPantothenic acid (5 mg) + Choline (50 mg) + Cyanocobalamin (5 mg) + Inositol nicotinate (50 mg) + Niacin (20 mg) + Pyridoxine (3 mg)LiquidOralP.S.W.C. Co., Inc.Not applicableNot applicableCanada
American Plus Energy & Vitamin DrinkPantothenic acid (5 mg) + Choline (50 mg) + Cyanocobalamin (5 mcg) + Inositol nicotinate (50 mg) + Niacin (20 mg) + Pyridoxine (3 mg)LiquidOralP.S.W.C. Co., Inc.Not applicableNot applicableCanada
ArmaxCalcium pantothenate (50 mg) + Magnesium (50 mg) + Manganese (1.5 mg) + Niacin (15 mg) + Nicotinamide (150 mg) + Vitamin C (15 mg) + Zinc (1.5 mg)TabletOralEnzymatic Therapy, Inc.1997-03-202001-08-02Canada
B 50 CapsulesCalcium pantothenate (50 mg) + Biotin (50 mcg) + Choline bitartrate (50 mg) + Cyanocobalamin (50 mcg) + Folic Acid (.4 mg) + Inositol nicotinate (50 mg) + Nicotinamide (50 mg) + Pyridoxine hydrochloride (50 mg) + Riboflavin (50 mg) + Thiamine mononitrate (50 mg)CapsuleOralRheingold Food International Ltd.1987-12-312007-07-26Canada
B C Antistress CapCalcium pantothenate (20 mg) + Cyanocobalamin (10 mcg) + Nicotinamide (50 mg) + Pyridoxine hydrochloride (5 mg) + Riboflavin (15 mg) + Thiamine mononitrate (35 mg) + Vitamin C (300 mg)CapsuleOralLes Laboratoires Bio SantÉ Inc.1992-12-311996-09-10Canada
Categories
UNII
19F5HK2737
CAS number
79-83-4
Weight
Average: 219.235
Monoisotopic: 219.110672659
Chemical Formula
C9H17NO5
InChI Key
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)
IUPAC Name
3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid
SMILES
CC(C)(CO)C(O)C(=O)NCCC(O)=O

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.

Structured Indications
Not Available
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.

TargetActionsOrganism
UPantothenate kinaseNot AvailableEscherichia coli (strain K12)
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
PathwayCategory
Carnosinuria, carnosinemiaDisease
Beta-Alanine MetabolismMetabolic
Pantothenate and CoA BiosynthesisMetabolic
GABA-Transaminase DeficiencyDisease
Ureidopropionase deficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

John F. Verbeeck, "Process for the production of the calcium salt of pantothenic acid." U.S. Patent US3935256, issued February, 1971.

US3935256
General References
  1. Trumbo, P. R. (2005). Pantothenic Acid. In Modern Nutrition in Health and Disease (10th ed., pp. 462–467). Lippincott Williams & Wilkins. [ISBN:0-7817-4133-5]
External Links
Human Metabolome Database
HMDB00210
KEGG Drug
D07413
KEGG Compound
C00864
PubChem Compound
988
PubChem Substance
46505022
ChemSpider
963
ChEBI
7916
ChEMBL
CHEMBL2110806
HET
PAU
Wikipedia
Pantothenic_acid
ATC Codes
D03AX04 — Calcium pantothenateA11HA31 — Calcium pantothenate
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (47.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentPregnancy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral1 g
ElixirOral
Tablet, extended releaseOral
SolutionOral
PowderOral
Capsule, liquid filledOral
CapsuleOral
CapsuleOral250 mg
Tablet, extended releaseOral1 g
Tablet, effervescentOral
Solution / dropsOral
LiquidIntravenous
Tablet, chewableOral
TabletOral250 mg
TabletOral500 mg
CapsuleOral500 mg
CapsuleOral100 mg
TabletOral100 mg
TabletOral200 mg
Tablet, extended releaseOral500 mg
TabletOral300 mg
Tablet, coatedOral
Capsule, gelatin coatedOral
TabletOral
KitOral
Capsule, extended releaseOral
LiquidOral
CapsuleOral300 mg
TabletOral50 mg
Tablet, film coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195ºC (D-Calcium Pantothenate salt)MSDS
water solubilitySolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility60.5 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.51 m3·mol-1ChemAxon
Polarizability21.92 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6189
Blood Brain Barrier+0.6889
Caco-2 permeable-0.7055
P-glycoprotein substrateSubstrate0.5464
P-glycoprotein inhibitor INon-inhibitor0.836
P-glycoprotein inhibitor IINon-inhibitor0.9184
Renal organic cation transporterNon-inhibitor0.95
CYP450 2C9 substrateNon-substrate0.8235
CYP450 2D6 substrateNon-substrate0.8051
CYP450 3A4 substrateNon-substrate0.5411
CYP450 1A2 substrateNon-inhibitor0.9133
CYP450 2C9 inhibitorNon-inhibitor0.9137
CYP450 2D6 inhibitorNon-inhibitor0.9417
CYP450 2C19 inhibitorNon-inhibitor0.8929
CYP450 3A4 inhibitorNon-inhibitor0.9587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9305
Ames testNon AMES toxic0.9278
CarcinogenicityNon-carcinogens0.9062
BiodegradationReady biodegradable0.662
Rat acute toxicity1.7394 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.944
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-014i-3190000000-7a9e1fb7ca94ff4714e8
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00dl-9100000000-ada04a866c6d38235607
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0596-9000000000-aea14dc63426efd5a60d
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
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
N-acyl amines / Monosaccharides / Secondary carboxylic acid amides / Secondary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Beta amino acid or derivatives / Fatty amide / Monosaccharide / N-acyl-amine / Fatty acyl / Carboxamide group / Secondary carboxylic acid amide / Secondary alcohol / Carboxylic acid / Monocarboxylic acid or derivatives
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
pantothenic acids (CHEBI:7916)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pantothenate kinase activity
Specific Function
Not Available
Gene Name
coaA
Uniprot ID
P0A6I3
Uniprot Name
Pantothenate kinase
Molecular Weight
36359.435 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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:03