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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H19NO4
Molecular Weight 205.2515
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXPANTHENOL

SMILES

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

InChI

InChIKey=SNPLKNRPJHDVJA-ZETCQYMHSA-N
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

HIDE SMILES / InChI

Molecular Formula C9H19NO4
Molecular Weight 205.2515
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: http://www.ncbi.nlm.nih.gov/pubmed/?term=PMID%3A+21982351; https://www.aako.nl/product-groups/personal-hair-care/products/active-ingredient/dl-panthenol-100; www.fda.gov/downloads/cosmetics/guidanceregulation/guidancedocuments/ucm208412.pdf; http://www.fda.gov/downloads/drugs/developmentapprovalprocess/developmentresources/over-the-counterotcdrugs/statusofotcrulemakings/ucm078437.pdf; http://www.ncbi.nlm.nih.gov/pubmed/20061726; http://crystalderma.rs/panthenol-care-and-regeneration/; http://tri-k.com/dl-panthenol

Panthenol (pantothenol) is an alcohol form of the B5 vitamin pantothenic acid. It easily penetrates the skin retaining water and is a humectant, emollient and moisturizer. Panthenol mitigates signs of inflammation and stimulates epithelization. Panthenol comes in two enantiomers, D and L. Only D-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. Because of the ability to attract and hold moisture panthenol is used in skincare products as a humectant. It also has a role as provitamin (called pro-vitamin B5) and is used as a vitamin supplement in complex ( M.V.I. ADULT injection, Hospira Worldwide, Inc.) and alone, and as a cholinergic drug. Panthenol is a highly viscous transparent liquid at room temperature, but salts of pantothenic acid (sodium pantothenate) are powders (typically white). It is soluble in water, alcohol, propylene glycol, ether and chloroform, and slightly soluble in glycerin. Panthenol mixes readily with many different types of ingredients, making it a versatile ingredient to be used in formulas because it improves skin’s barrier function and maintains the proliferation of fibroblasts. In organisms it is quickly oxidized to pantothenate (pantothenic acid). Defficiency of Vitamin B5 results in many dermatological disorder. Due to the fact that only D-Panthenol is converted to Vitamin B5 and not L-Panthenol, the racemic mixture of D- and L- panthenol (DL-panthenol) has only half of the physiological activity of the D-Panthenol. These include stimulation of epithelisation, wound healing effect and anti-infl ammatory effect. Panthenol is FDA approved for cosmetic use and comes either in D form, or as a racemic mixture. It is also in the FDA list of over-the-counter drug products that are not generally recognized as safe and effective or are misbranded: as "Insect Bite and Sting Drug Products" and "Poison Ivy, Poison Oak, and Poison Sumac Drug Products".

Originator

Curator's Comment: The product line was first introduced in Europe in 1946 by Hoffmann-La Roche of Switzerland. The brand name was bought by Procter&Gamble in 1985 to compete in the 'beauty product' market (Dyer, Davis (2004). Rising Tide: lessons from 165 years of brand building at Procter & Gamble. Harvard Business Press. p. 277) # Hoffmann-La Roche, Switzerland

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
REVERSE IT KIT

Approved Use

USE HELPS PROTECT AGAINST SUNBURN

Launch Date

2014
Preventing
BABOR BABORGANIC AGE PREVENTING BODY CREAM

Approved Use

Unknown

Launch Date

1954
Doses

Doses

DosePopulationAdverse events​
5 % 2 times / day multiple, topical
Recommended
Dose: 5 %, 2 times / day
Route: topical
Route: multiple
Dose: 5 %, 2 times / day
Sources:
healthy, 18–45
n = 21
Health Status: healthy
Condition: skin irritation
Age Group: 18–45
Sex: M+F
Population Size: 21
Sources:
5 % multiple, topical
Recommended
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: radiotherapy effects
Population Size: 1
Sources:
Disc. AE: Allergic contact dermatitis...
AEs leading to
discontinuation/dose reduction:
Allergic contact dermatitis
Sources:
5 % multiple, topical
Recommended
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: stasis dermatitis
Population Size: 1
Sources:
Disc. AE: Allergic contact dermatitis...
AEs leading to
discontinuation/dose reduction:
Allergic contact dermatitis
Sources:
AEs

AEs

AESignificanceDosePopulation
Allergic contact dermatitis Disc. AE
5 % multiple, topical
Recommended
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: radiotherapy effects
Population Size: 1
Sources:
Allergic contact dermatitis Disc. AE
5 % multiple, topical
Recommended
Dose: 5 %
Route: topical
Route: multiple
Dose: 5 %
Sources:
unhealthy
n = 1
Health Status: unhealthy
Condition: stasis dermatitis
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Dexpanthenol enhances skin barrier repair and reduces inflammation after sodium lauryl sulphate-induced irritation.
2002 Dec
Conservative procedures in skin reconstitution.
2005
Allergic contact dermatitis to panthenol and cocamidopropyl PG dimonium chloride phosphate in a facial hydrating lotion.
2006 Dec
Development of a w/o/w emulsion for chemical peeling applications containing glycolic acid.
2006 Nov-Dec
Comparison of dexpanthenol and zinc oxide ointment with ointment base in the treatment of irritant diaper dermatitis from diarrhea: a multicenter study.
2006 Oct
Efficacy of Tonimer gel spray on postoperative nasal care after endonasal surgery.
2007
[Can dexpanthenol prevent peritoneal adhesion formation? An experimental study].
2007 Apr
Wound-healing activity of St. John's Wort (Hypericum perforatum L.) on chicken embryonic fibroblasts.
2007 Apr 20
Feedback inhibition of pantothenate kinase regulates pantothenol uptake by the malaria parasite.
2007 Aug 31
Natural advances in eczema care.
2007 Dec
Therapy of acute wounds with water-filtered infrared-A (wIRA).
2007 Dec 28
[Clinical evaluation of the efficacy and tolerability of the ''NoAll Bimbi Pasta Trattante'' barrier cream in napkin dermatitis].
2007 Feb
The protective effect of dexpanthenol on testicular atrophy at 60th day following experimental testicular torsion.
2007 Mar
[Can dexpanthenol prevent peritoneal adhesion formation? An experimental study].
2007 Oct
Lactobacillus supplementation for diarrhoea related to chemotherapy of colorectal cancer: a randomised study.
2007 Oct 22
How pantothenol intervenes in Coenzyme-A biosynthesis of Mycobacterium tuberculosis.
2007 Oct 5
Hamamelis in children with skin disorders and skin injuries: results of an observational study.
2007 Sep
Simultaneous determination of some water-soluble vitamins and preservatives in multivitamin syrup by validated stability-indicating high-performance liquid chromatography method.
2008 Aug 22
Oxymetazoline plus dexpanthenol in nasal congestion.
2008 Dec
targetTB: a target identification pipeline for Mycobacterium tuberculosis through an interactome, reactome and genome-scale structural analysis.
2008 Dec 19
Skin protection creams in medical settings: successful or evil?
2008 Jul 25
Safety and efficacy of a new honey ointment on diabetic foot ulcers: a prospective pilot study.
2008 Mar
Miscellaneous.
2008 Oct
Comparison on the efficacy of dexpanthenol in sea water and saline in postoperative endoscopic sinus surgery.
2008 Oct
Topical fentanyl in a randomized, double-blind study in patients with corneal damage.
2008 Oct
Ointments as a source of meticillin-resistant Staphylococcus aureus spread.
2008 Oct
Antioxidant systems and oxidative stress in the testes.
2008 Oct-Dec
Tracheostomy cannulas and voice prosthesis.
2009
Vitiligo treatment with vitamins, minerals and polyphenol supplementation.
2009
[Evidence-based cosmetics: concepts and applications in photoaging of the skin and xerosis].
2009
Corneal re-epithelialization following phototherapeutic keratectomy for recurrent corneal erosion as in vivo model of epithelial wound healing.
2009
Comparison of primary human fibroblasts and keratinocytes with immortalized cell lines regarding their sensitivity to sodium dodecyl sulfate in a neutral red uptake cytotoxicity assay.
2009
Water-filtered infrared-A (wIRA) in acute and chronic wounds.
2009 Dec 16
Hippophae rhamnoides L. and dexpanthenol-bepanthene on blood flow after experimental skin burns in rats using 133Xe clearance technique.
2009 Jan-Apr
[Study of skin care in premature and newborn infants].
2009 Mar
[Effects of panthenol and carnitine on aldehyde metabolic enzymes in rats with tetrachloromethane-induced liver injury].
2009 Mar-Apr
[Efficacy and patient benefit of treatment of irritated skin with ointments containing dexpanthenol: health services research (observational study) on self-medication in a pharmaceutical network].
2009 May
Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts.
2009 Nov
[Survey of sensory perception and patients' subjective assessment of the application of nasal sprays - the nasal-spray-sensoric-scale].
2009 Sep
Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses.
2010
A management dilemma: infectious keratitis associated with soft contact lens use and dubious treatment compliance.
2010
Conservative treatment of a patient with epidermolysis bullosa presenting as bart syndrome: a case report.
2010
The nitric acid burn trauma of the skin.
2010 Apr
Enhancement of L-3-hydroxybutyryl-CoA dehydrogenase activity and circulating ketone body levels by pantethine. Relevance to dopaminergic injury.
2010 Apr 23
[Glued eyelids by cyanoacrylate glue (superglue)].
2010 Feb
[Simulation of corneal epithelial injuries by mechanical and corrosive damage : Influence of fetal bovine serum and dexpanthenol on epithelial regeneration in a cell culture model].
2010 Jun
Tissue extract from Eisenia foetida as a wound-healing agent.
2010 Mar
Identifying essential genes in bacterial metabolic networks with machine learning methods.
2010 May 3
[Simultaneous determination of pantothenic acid and D-panthenol in cosmetics by high performance liquid chromatography].
2010 Nov
[Severe inflammation of the muzzle caused by a nose ring in a breeding bull].
2010 Sep
Patents

Sample Use Guides

Anti-aging body cream (1.8 ml panthenol/200 ml) for dry skin used to treat the skin and leave it soft and supple. Repairs the skin's protective barrier, strengthening it against external influences.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:24 GMT 2023
Record UNII
1O6C93RI7Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXPANTHENOL
EP   FCC   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
CORNERGEL
Common Name English
D-PANTOTHENYL ALCOHOL
Systematic Name English
DEXPANTHENOL [ORANGE BOOK]
Common Name English
PROVITAMIN B5
Common Name English
D-PANTHENOL 50
Common Name English
DEXPANTHENOL [USAN]
Common Name English
PROPANOLAMINE, N-PANTOYL-
Common Name English
DOLOBENE
Common Name English
DEXPANTHENOL [USP MONOGRAPH]
Common Name English
D-PANTOTHENOL
Systematic Name English
dexpanthenol [INN]
Common Name English
BUTYRAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-, D-(+)-
Common Name English
DEXPANTHENOL [HSDB]
Common Name English
DEXPANTHENOL [USP-RS]
Common Name English
(+)-PANTHENOL
Systematic Name English
BUTANAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-, (2R)-
Systematic Name English
MOTILYN
Common Name English
DEXPANTHENOL [EP MONOGRAPH]
Common Name English
PANTHENOL 50W
Common Name English
BEPANTHENE
Common Name English
BEPANTOL
Common Name English
DEXPANTHENOL [MI]
Common Name English
BUTANAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-, (R)-
Systematic Name English
D(+)-PANTHENOL
Common Name English
D-PANTHENOL
VANDF  
Systematic Name English
COZYME
Common Name English
PANTHENOL, (+)-
Systematic Name English
PANTOL
Common Name English
PANTHENOL [JAN]
Common Name English
URUPAN
Common Name English
DEXPANTHENOL [MART.]
Common Name English
D-P-A INJECTION
Common Name English
PANADON
Common Name English
D-PANTHENOL [VANDF]
Common Name English
DEXPANTHENOL [VANDF]
Common Name English
DEXPANTENOL
Common Name English
Dexpanthenol [WHO-DD]
Common Name English
INTRAPAN
Common Name English
ILOPAN
Brand Name English
PANTHENOL, (R)-
Systematic Name English
PROVITAMIN B
Common Name English
ZENTINIC
Common Name English
ALCOPAN 250
Common Name English
D(+)-.ALPHA.,.GAMMA.-DIHYDROXY-N-(3-HYDROXYPROPYL)-.BETA.,.BETA.-DIMETHYLBUTYRAMIDE
Common Name English
NSC-302962
Code English
PANTOTHENYL ALCOHOL
Systematic Name English
THENALTON
Common Name English
PANTHODERM
Common Name English
BEPANTHEN
Common Name English
SYNAPAN
Common Name English
DEXPANTHENOL [FCC]
Common Name English
D(+)-2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYLBUTYRAMIDE
Common Name English
(2R)-2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYLBUTANAMIDE
Systematic Name English
PANTENYL
Common Name English
D(+)-PANTOTHENYL ALCOHOL
Common Name English
Classification Tree Code System Code
WHO-VATC QS01XA12
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
WHO-VATC QD03AX03
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
WHO-ATC A11HA30
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
CFR 21 CFR 310.527
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
LIVERTOX 292
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
WHO-ATC S01XA12
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
WHO-VATC QA11HA30
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
WHO-ATC D03AX03
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
NCI_THESAURUS C26017
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
Code System Code Type Description
CAS
50584-68-4
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
SUPERSEDED
CAS
81-13-0
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
CAS
1113-70-8
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
SUPERSEDED
RS_ITEM_NUM
1179504
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-327-3
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
DRUG CENTRAL
838
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
PUBCHEM
131204
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
HSDB
296
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
SMS_ID
100000092075
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200979
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
NSC
302962
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
CHEBI
27373
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
RXCUI
22701
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY RxNorm
EVMPD
SUB07042MIG
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
INN
1023
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
CAS
17307-32-3
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID3022906
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
DRUG BANK
DB09357
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
FDA UNII
1O6C93RI7Z
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
MESH
C007288
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
NCI_THESAURUS
C47481
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
DAILYMED
1O6C93RI7Z
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY
MERCK INDEX
m4219
Created by admin on Fri Dec 15 15:07:24 GMT 2023 , Edited by admin on Fri Dec 15 15:07:24 GMT 2023
PRIMARY Merck Index
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