Identification

Name
Dexpanthenol
Accession Number
DB09357
Type
Small Molecule
Groups
Approved
Description

Dexpanthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium[2].

Due to its good penetration and high local concentrations, dexpanthanol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties [3].

Dexpanthenol is also available as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol) as Panthenol. While pantothenic acid is optically active, only the dextrorotatory form (dexpanthenol) is biologically active.

Structure
Thumb
Synonyms
  • (+)-Panthenol
  • (2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
  • Bepanthen
  • Bepanthene
  • Bepantol
  • D-panthenol
  • D-panthenol 50
  • D-Pantothenol
  • D-Pantothenyl alcohol
  • D(+)-Panthenol
  • Dexpantenol
  • Pantol
  • Pantothenyl alcohol
  • Provitamin B
External IDs
201-327-3 / NSC-302962
Active Moieties
NameKindUNIICASInChI Key
Pantothenic acidunknown19F5HK273779-83-4GHOKWGTUZJEAQD-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eros Aqua Sensations and Care WomanGel0.5 g/100mLTopicalMEGASOL COSMETIC GMBH2012-10-012018-01-17Us
Perfect Pore Clean ILiquid0.001 g/1mLTopicalAmi Cosmetic Co.,Ltd.2014-04-14Not applicableUs
Vitalizer WhiteLiquid0.0005 g/1mLTopicalAmi Cosmetic Co.,Ltd.2014-04-14Not applicableUs
Yozum Well Being Hair ColorLiquid0.2 g/100gTopicalYozum Korea2014-12-08Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adult Infuvite Multiple VitaminsDexpanthenol (15 mg/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsDexpanthenol (15 mg/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsDexpanthenol (15 mg/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsDexpanthenol (15 mg/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Alsimine W Vitamins A DDexpanthenol (5 mg) + Dexpanthenol (400 unit) + Calcium (13 mg) + Cyanocobalamin (10 mcg) + Ferrous gluconate (16 mg) + Riboflavin 5'-phosphate sodium (2 mg) + Nicotinamide (40 mg) + Pyridoxine hydrochloride (3 mg) + Thiamine hydrochloride (4.5 mg) + Vitamin A (10000 unit)Capsule; LiquidOralAlsi Cie Ltee1978-12-312003-05-21Canada
Alsimine W Vitamins A DDexpanthenol (5 mg) + Dexpanthenol (400 unit) + Calcium (13 mg) + Cyanocobalamin (10 mcg) + Ferrous gluconate (16 mg) + Riboflavin 5'-phosphate sodium (2 mg) + Nicotinamide (40 mg) + Pyridoxine hydrochloride (3 mg) + Thiamine hydrochloride (4.5 mg) + Vitamin A (10000 unit)Capsule; LiquidOralAlsi Cie Ltee1978-12-312003-05-21Canada
Aquasol A CreamDexpanthenol (21.4 mg) + Vitamin A palmitate (7055 unit)CreamTopicalRhone Poulenc Rorer1993-12-311998-08-12Canada
Atomy Herbal Hair TonicDexpanthenol (0.4 mL/200mL) + Menthol (0.6 mL/200mL) + Salicylic acid (0.5 mL/200mL)LiquidTopicalAtomy Co., Ltd.2010-04-29Not applicableUs
B Complex W C and B12 InjDexpanthenol (60 mg) + Ascorbic acid (500 mg) + Cyanocobalamin (10 mg) + Riboflavin 5'-phosphate sodium (50 mg) + Nicotinamide (1.25 g) + Pyridoxine hydrochloride (50 mg) + Thiamine hydrochloride (500 mg)LiquidIntramuscular; IntravenousE L Stickley And Co Ltd.1963-12-311996-09-09Canada
B Vitamin Compound With B12 ThunasDexpanthenol (.5 mg) + Cyanocobalamin (.11 mcg) + Nicotinamide (.8 mg) + Riboflavin (.15 mg) + Thiamine mononitrate (.15 mg)LiquidOralThuna Herbal Remedies Ltd.1984-05-312002-10-16Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
B-ComboDexpanthenol (1 mg/1mL) + Methylcobalamin (1 mg/1mL) + Nicotinamide (1 mg/1mL) + Pyridoxine (1 mg/1mL) + Riboflavin (1 mg/1mL) + Thiamine chloride (1 mg/1mL)InjectionIntramuscularPerdido Key Health And Wellness Inc2015-11-23Not applicableUs
B-plex 100Dexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)Injection, solutionIntramuscular; IntravenousMerit Pharmaceuticals2012-01-01Not applicableUs
DexpanthenolDexpanthenol (250 mg/1mL)Injection, solutionIntramuscular; IntravenousAmerican Regent1993-08-202016-11-09Us
LipoviteDexpanthenol (1 mg/1mL) + Choline (1 mg/1mL) + Chromium (1 mg/1mL) + Inositol (1 mg/1mL) + L-Carnitine (1 mg/1mL) + L-Citrulline (1 mg/1mL) + Lidocaine (1 mg/1mL) + Methionine sulfoximine (1 mg/1mL) + Methylcobalamin (1 mg/1mL) + Nicotinamide (1 mg/1mL) + Pyridoxine (1 mg/1mL) + Riboflavin (1 mg/1mL) + Thiamine chloride (1 mg/1mL)InjectionIntramuscularPerdido Key Health And Wellness Inc2015-11-23Not applicableUs
Vitamin B ComplexDexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)InjectionIntramuscular; IntravenousFlon Laboratories Llc2017-04-01Not applicableUs
Vitamin B ComplexDexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)InjectionIntravenousMylan Institutional2013-05-10Not applicableUs
Vitamin B ComplexDexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)Injection, solutionIntramuscular; IntravenousRaw Materials International Overseas Llc2015-07-06Not applicableUs
Vitamin B Complex 100Dexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)InjectionIntramuscular; IntravenousFisiopharma Srl2017-12-28Not applicableUs
Vitamin B-ComplexDexpanthenol (2 mg/1mL) + Riboflavin 5'-phosphate sodium (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)Injection, solutionIntramuscular; IntravenousMcGuff Pharmaceuticals Inc.2010-01-252010-12-30Us
International/Other Brands
Cozyme / Ilopan / Motilyn / Panadon / Panthoderm / Synapan / Thenalton / Zentinic
Categories
UNII
1O6C93RI7Z
CAS number
81-13-0
Weight
Average: 205.2515
Monoisotopic: 205.131408101
Chemical Formula
C9H19NO4
InChI Key
SNPLKNRPJHDVJA-ZETCQYMHSA-N
InChI
InChI=1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14)/t7-/m0/s1
IUPAC Name
(2R)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
SMILES
CC(C)(CO)[C@@H](O)C(=O)NCCCO

Pharmacology

Indication

Injection: Prophylactic use immediately after major abdominal surgery to minimize the possibility of paralytic ileus. Intestinal atony causing abdominal distention; postoperative or postpartum retention of flatus, or postoperative delay in resumption of intestinal motility; paralytic ileus.

Topical: This medication is used as a moisturizer to treat or prevent dry, rough, scaly, itchy skin and minor skin irritations (e.g., diaper rash, skin burns from radiation therapy).

Associated Therapies
Pharmacodynamics

Pantothenic acid is a precursor of coenzyme A, which serves as a cofactor for a variety of enzyme-catalyzed reactions involving transfer of acetyl groups. The final step in the synthesis of acetylcholine consists of the choline acetylase transfer of acetyl group from acetylcoenzyme A to choline. Acetylcholine is the neurohumoral transmitter in the parasympathetic system and as such maintains the normal functions of the intestine. Decrease in acetylcholine content would result in decreased peristalsis and in extreme cases adynamic ileus.

Mechanism of action

Dexpanthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium[2].

Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties [3].

Absorption

Dexpanthenol is soluble in water and alcohol, although insoluble in fats and oil based substances. With the appropriate vehicle, Dexpanthenol is easily penetrated into the skin. Rate of penetration and absorption is reduced when Dexpanthenol is administered as an oil/water formula.

Volume of distribution

Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A. Highest concentrations are found in the liver, adrenal glands, heart, and kidneys.

Protein binding

Plasma protein binding have not been reported.

Metabolism

Dexpanthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A.

Route of elimination

Milk of nursing mothers receiving a normal diet contains about 2 ug of pantothenic acid per mL. About 70% of an oral dose of pantothenic acid is excreted unchanged in urine and about 30% in feces.

Half life

Half life have not been reported

Clearance
Not Available
Toxicity

Mouse LD50 : 9gm/kg (Intraperitoneal) Mouse: LD50 7gm/kg (Intravenous) Mouse: LD50 15gm/kg (Oral) Rabbit LD50 4gm/kg (Oral)

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AcrivastineDexpanthenol may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Dexpanthenol which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Slyshenkov VS, Dymkowska D, Wojtczak L: Pantothenic acid and pantothenol increase biosynthesis of glutathione by boosting cell energetics. FEBS Lett. 2004 Jul 2;569(1-3):169-72. [PubMed:15225628]
  2. Proksch E, de Bony R, Trapp S, Boudon S: Topical use of dexpanthenol: a 70th anniversary article. J Dermatolog Treat. 2017 Dec;28(8):766-773. doi: 10.1080/09546634.2017.1325310. Epub 2017 May 14. [PubMed:28503966]
  3. Biro K, Thaci D, Ochsendorf FR, Kaufmann R, Boehncke WH: Efficacy of dexpanthenol in skin protection against irritation: a double-blind, placebo-controlled study. Contact Dermatitis. 2003 Aug;49(2):80-4. [PubMed:14641355]
  4. DRUGS.COM [Link]
  5. Webmd [Link]
  6. Pubchem [Link]
  7. ChemIDplus [Link]
External Links
KEGG Drug
D00193
KEGG Compound
C05944
PubChem Compound
131204
PubChem Substance
347827835
ChemSpider
115991
ChEMBL
CHEMBL1200979
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dexpanthenol
ATC Codes
A11HA30 — DexpanthenolD03AX03 — DexpanthenolS01XA12 — Dexpanthenol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentDry Eye Syndrome of Unspecified Lacrimal Gland / Eye Dryness1
2CompletedTreatmentTemporomandibular Joint Disorders1
2Unknown StatusTreatmentOral Mucositis (Ulcerative) Due to Radiation1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentDiabetic Foot Ulcers (DFU)1
3CompletedTreatmentHbA1c Level / Plasma Homocysteine1
3CompletedTreatmentHydatidiform Mole1
3RecruitingTreatmentNasal Stuffiness / Rhinitis1
3TerminatedTreatmentDiabetic Foot Ulcers (DFU)1
4CompletedBasic ScienceCell Proliferation / Gene Expression / Wound Healing1
4CompletedTreatmentWound Healing1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Capsule; liquidOral
CreamTopical
LiquidTopical
Liquid; tabletOral
ElixirOral
Powder, for solutionIntramuscular; Intravenous
Powder, for solutionIntravenous
Injection, solutionIntramuscular; Intravenous250 mg/1mL
GelTopical0.5 g/100mL
LiquidIntramuscular; Intravenous
InjectionIntramuscular
Injection, powder, lyophilized, for solutionIntravenous
LiquidIntravenous
ShampooTopical
SolutionIntramuscular; Intravenous
Kit
Injection, solutionIntravenous
LiquidTopical0.001 g/1mL
LiquidOral
LiquidTopical0.0005 g/1mL
InjectionIntramuscular; Intravenous
InjectionIntravenous
Injection, solutionIntramuscular; Intravenous
LiquidTopical0.2 g/100g
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility121.0 mg/mLALOGPS
logP-1ALOGPS
logP-1.7ChemAxon
logS-0.23ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.88 m3·mol-1ChemAxon
Polarizability21.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0f8a-1921000000-f1d6cd175435f0634e26
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0ar9-0940000000-60184a3322815ca33b8c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Secondary alcohols
Alternative Parents
Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Alkanolamines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Secondary alcohol / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidic acid derivative / Carboximidic acid / Alkanolamine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
monocarboxylic acid amide, amino alcohol (CHEBI:27373)

Drug created on November 30, 2015 12:10 / Updated on November 05, 2018 09:20