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Details

Stereochemistry RACEMIC
Molecular Formula C9H19NO4
Molecular Weight 205.2515
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PANTHENOL

SMILES

CC(C)(CO)C(O)C(=O)NCCCO

InChI

InChIKey=SNPLKNRPJHDVJA-UHFFFAOYSA-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)

HIDE SMILES / InChI

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

1.40400001E12
Preventing
BABOR BABORGANIC AGE PREVENTING BODY CREAM

Approved Use

Unknown

Launch Date

-4.86345605E11
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
Name Type Language
PANTHENOL
INCI   INN   JAN   MART.   USAN   USP   VANDF   WHO-DD  
USAN   INN   INCI  
Official Name English
PANTHENOL [USAN]
Common Name English
PANTHENOL, DL-
Systematic Name English
BUTYRAMIDE, .ALPHA.,.GAMMA.-DIHYDROXY-N-(3-HYDROXYPROPYL)-.BETA.,.BETA.-DIMETHYL-
Systematic Name English
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
Systematic Name English
DL-PANTHENOL [VANDF]
Common Name English
DL-PANTHENOL [FCC]
Common Name English
PANTHENOL, RACEMIC [USP-RS]
Common Name English
(±)-PANTOTHENYL ALCOHOL
Systematic Name English
BUTANAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-, (±)-
Systematic Name English
BUTANAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-
Systematic Name English
panthenol [INN]
Common Name English
PANTHENOL [INCI]
Common Name English
DL-PANTHENOL
FCC   VANDF  
Systematic Name English
PANTHENOL [MART.]
Common Name English
Panthenol [WHO-DD]
Common Name English
PANTHENOL [USP MONOGRAPH]
Common Name English
PANTHENOL [VANDF]
Common Name English
NSC-759899
Code English
(±)-2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYLBUTYRAMIDE
Systematic Name English
PANTOTHENOL
Systematic Name English
BUTYRAMIDE, 2,4-DIHYDROXY-N-(3-HYDROXYPROPYL)-3,3-DIMETHYL-, (±)-
Systematic Name English
PANTHENOL, RACEMIC
USP-RS  
Common Name English
DL-PANTOTHENYL ALCOHOL
Systematic Name English
DL-PANTOTHENOL
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C45678
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
CONCEPT Industrial Aid
PUBCHEM
4678
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
CAS
16485-10-2
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
EPA CompTox
DTXSID3044598
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
DAILYMED
WV9CM0O67Z
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
ChEMBL
CHEMBL1371937
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
CAS
62507-76-0
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
ALTERNATIVE
SMS_ID
100000079739
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
CHEBI
27373
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
NCI_THESAURUS
C82290
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
NSC
759899
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
EVMPD
SUB124270
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
WIKIPEDIA
PANTHENOL
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
240-540-6
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
FDA UNII
WV9CM0O67Z
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
RXCUI
1044977
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB11204
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
EVMPD
SUB14756MIG
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
INN
1744
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY
RS_ITEM_NUM
1494501
Created by admin on Sat Dec 16 16:52:36 UTC 2023 , Edited by admin on Sat Dec 16 16:52:36 UTC 2023
PRIMARY