Dexpanthenol

Identification

Summary

Dexpanthenol is an alcoholic analogue of D-pantothenic acid that is used as a supplement or application to support a healthy epithelium and is also used to prevent vitamin deficiency in patients receiving total parenteral nutrition (TPN).

Brand Names
Fortaplex, Infuvite, Infuvite Pediatric, Mvi Pediatric, Neo-bex
Generic Name
Dexpanthenol
DrugBank Accession Number
DB09357
Background

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 epithelium2.

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 205.2515
Monoisotopic: 205.131408101
Chemical Formula
C9H19NO4
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
  • Dexpanthenol
  • Dexpanthenolum
  • Pantol
  • Pantothenyl alcohol
  • Provitamin B
External IDs
  • 201-327-3
  • BAY 81-2996
  • NSC-302962

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).

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofAllergic rhinitis (ar)Combination Product in combination with: Xylometazoline (DB06694)••••••••••••••••••••••••••• •••••••
Used in combination for symptomatic treatment ofBursitisCombination Product in combination with: Heparin (DB01109), Dimethyl sulfoxide (DB01093)••• ••••••
Treatment ofCanker sore•••••••••••••••••••
Used in combination for symptomatic treatment ofContusionsCombination Product in combination with: Dimethyl sulfoxide (DB01093), Heparin (DB01109)••• ••••••
Treatment ofDermabrasion••• ••••••••
Associated Therapies
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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 epithelium2.

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.

Hover over products below to view reaction partners

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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir 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.
AcetazolamideAcetazolamide may increase the excretion rate of Dexpanthenol which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Active Moieties
NameKindUNIICASInChI Key
Pantothenic acidunknown19F5HK273779-83-4GHOKWGTUZJEAQD-ZETCQYMHSA-N
International/Other Brands
Cozyme / Ilopan / Motilyn / Panadon / Panthoderm / Synapan / Thenalton / Zentinic
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DexpanthenolInjection, solution250 mg/1mLIntramuscular; IntravenousAmerican Regent1993-08-202016-11-09US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BabysonsOintment50 mg/1gTopicalLaboratorios Quimica Son's, S.A. de C.V2020-06-15Not applicableUS flag
BEPANTHEN OINTMENTOintmentTopicalBAYER CO. (MALAYSIA) SDN. BHD.2020-09-08Not applicableMalaysia flag
Eros Aqua Sensations and Care WomanGel0.5 g/100mLTopicalMEGASOL COSMETIC GMBH2012-10-012018-01-17US flag
MAR PLUS 5% NASAL SPRAYSolution; Spray50 mg/1mLNasalบริษัท สตาดา (ประเทศไทย) จำกัด2014-08-21Not applicableThailand flag
Perfect Pore Clean ILiquid0.001 g/1mLTopicalAmi Cosmetic Co.,Ltd.2014-04-142019-01-15US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 salt dihydrate (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, solutionIntravenousSandoz Inc2003-06-16Not applicableUS flag
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 salt dihydrate (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, solutionIntravenousSandoz Inc2003-06-16Not applicableUS flag
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 salt dihydrate (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, solutionIntravenousSandoz Inc2005-05-18Not applicableUS flag
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 salt dihydrate (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, solutionIntravenousSandoz Inc2005-05-18Not applicableUS flag
Alsimine W Vitamins A DDexpanthenol (5 mg / amp) + Dexpanthenol (400 unit / amp) + Calcium glycerophosphate (13 mg / amp) + Cyanocobalamin (10 mcg / amp) + Ferrous gluconate (16 mg / amp) + Riboflavin-5'-phosphate sodium salt dihydrate (2 mg / amp) + Nicotinamide (40 mg / amp) + Pyridoxine hydrochloride (3 mg / amp) + Thiamine hydrochloride (4.5 mg / amp) + Vitamin A (10000 unit / amp)Capsule; LiquidOralAlsi Cie Ltee1978-12-312003-05-21Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Atomy Herbal Hair TonicDexpanthenol (0.4 mL/200mL) + Levomenthol (0.6 mL/200mL) + Salicylic acid (0.5 mL/200mL)LiquidTopicalAtomy Co., Ltd.2010-04-29Not applicableUS flag
B-ComboDexpanthenol (1 mg/1mL) + Mecobalamin (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 flag
B-plex 100Dexpanthenol (2 mg/1mL) + Riboflavin-5'-phosphate sodium salt dihydrate (2 mg/1mL) + Nicotinamide (100 mg/1mL) + Pyridoxine hydrochloride (2 mg/1mL) + Thiamine hydrochloride (100 mg/1mL)Injection, solutionIntramuscular; IntravenousMerit Pharmaceutical2012-01-01Not applicableUS flag
Black Repair Hair Boosting TonicDexpanthenol (0.2 g/100mL) + Menthol (0.3 g/100mL) + Salicylic acid (0.25 g/100mL)LiquidTopicalDERMA CENTRIC INC2021-03-28Not applicableUS flag
Ch6 Greenol Herb Aloforthya Deep ForestDexpanthenol (0.2 g/100mL) + Nicotinamide (0.1 g/100mL) + Salicylic acid (0.2 g/100mL)ShampooTopicalRea Company2022-10-01Not applicableUS flag

Categories

ATC Codes
D03AX03 — DexpanthenolS01XA12 — DexpanthenolA11HA30 — Dexpanthenol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkanolamine / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Organic 1,3-dipolar compound / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Primary alcohol
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
monocarboxylic acid amide, amino alcohol (CHEBI:27373)
Affected organisms
Not Available

Chemical Identifiers

UNII
1O6C93RI7Z
CAS number
81-13-0
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

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. [Article]
  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. [Article]
  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. [Article]
  4. DRUGS.COM [Link]
  5. Webmd [Link]
  6. Pubchem [Link]
  7. ChemIDplus [Link]
  8. BASG Product Information: Dolobene (DMSO/heparin sodium/dexpanthenol) topical gel [Link]
KEGG Drug
D00193
KEGG Compound
C05944
PubChem Compound
131204
PubChem Substance
347827835
ChemSpider
115991
RxNav
22701
ChEMBL
CHEMBL1200979
ZINC
ZINC000001530303
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Panthenol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceCell Proliferation / Gene Expression / Promotion of wound healing1
4CompletedTreatmentErythemas / Skin Recovery1
4CompletedTreatmentPromotion of wound healing1
4CompletedTreatmentSkin Recovery2
4RecruitingTreatmentAcute Kidney Injury (AKI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule; liquidOral
SyrupOral
LiquidTopical
SolutionIntravenous1.914 mg
OintmentTopical50 mg/1g
Tablet, coated
Solution
Solution500 mg
ElixirOral
Powder, for solutionIntramuscular; Intravenous
Powder, for solutionIntravenous
Injection, solution500 MG/2ML
Tablet100 MG
Ointment
OintmentCutaneous5 mg
CreamTopical
OintmentTopical
Lozenge100 mg
OintmentNasal; Ophthalmic
SolutionIntramuscular; Intravenous; Subcutaneous500 mg/2ml
OintmentNasal; Ophthalmic50 mg/g
SolutionOral50 mg/g
SprayTopical
Ointment50 mg/g
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, powder, for solutionIntravenous
GelOphthalmic
GelOphthalmic50 mg/g
GelOphthalmic120 mg/0.6mL
GelOphthalmic30 mg/0.6mL
GelOphthalmic60 mg/0.6mL
Solution / drops; suspension / dropsOphthalmic50 mg/mL
Solution / drops; suspension / dropsOphthalmic30 mg/0.6mL
Solution / drops; suspension / dropsOphthalmic60 mg/0.6mL
GelTopical
LozengeOral
OintmentTopical5 %
Injection, solutionIntramuscular; Intravenous250 mg/1mL
CreamCutaneous
CreamTopical50 mg/g
Solution / drops; suspension / dropsOphthalmic
LiquidOral
GelTopical0.5 g/100mL
LiquidIntramuscular; Intravenous
SolutionNasal
InjectionIntramuscular
Injection, solution, concentrate; kitIntravenous
Injection, powder, lyophilized, for solutionIntravenous
KitIntravenous
Solution; sprayNasal50 mg/1mL
SprayNasal10 mg/1ml
SolutionIntravenous
LiquidIntravenous
SolutionParenteral
Solution / dropsOral
SprayNasal50 mg/ml
ShampooTopical
Powder, for solutionOral
SolutionIntramuscular; Intravenous
SolutionBuccal; Oropharyngeal
GelBuccal; Oral
Solution / drops; suspension / dropsOphthalmic50 mg
Injection, solutionIntramuscular; Intravenous500 mg
Ointment5 %
SolutionOral5 %
OintmentOphthalmic5 g
CreamTopical100 g
CreamTopical20 g
CreamTopical50 g
CreamNasal50 mg/g
CreamTopical5 G/100G
CreamTopical5 %
Injection, solutionIntramuscular; Intravenous; Subcutaneous500 mg
Cream
Injection, solution; kitIntravenous
Injection, solutionIntravenous
SolutionOral
PatchTopical
LiquidTopical0.001 g/1mL
Syrup
Solution / dropsOphthalmic
Solution / dropsOphthalmic
Cream5 %
Liquid; tabletOral
Injection, powder, for solutionIntravenous100 mg
OintmentTopical
LiquidTopical0.0005 g/1mL
InjectionIntramuscular; Intravenous
InjectionIntravenous
Injection, solutionIntramuscular; Intravenous
SprayNasal
Spray, meteredNasal
LiquidTopical0.2 g/100g
Solution; sprayNasal
CreamTopical
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-MSsplash10-0ul0-6900000000-954514bfa59a23c86e49
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-3690000000-f795a326de750e1ce69d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-8790000000-6ed7330b7a5f4cd7ffbb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9500000000-ef0609f53481a1cdbfdd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-9100000000-d350b93723479d042415
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-1c3304c420d96001b861
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-9d3b189b80a6c90c2950
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.2441028
predicted
DarkChem Lite v0.1.0
[M-H]-146.73924
predicted
DeepCCS 1.0 (2019)
[M+H]+149.1636028
predicted
DarkChem Lite v0.1.0
[M+H]+149.13481
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.2653028
predicted
DarkChem Lite v0.1.0
[M+Na]+155.24326
predicted
DeepCCS 1.0 (2019)

Drug created at November 30, 2015 19:10 / Updated at May 29, 2021 18:14