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
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)
DescriptionCurator'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
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
Sources: http://www.google.com/patents/US2413077
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL245 Sources: https://www.genome.jp/dbget-bin/www_bget?dr:D00193 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Inactive ingredient | REVERSE IT KIT Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2014 |
|||
Preventing | BABOR BABORGANIC AGE PREVENTING BODY CREAM Approved UseUnknown Launch Date1954 |
Doses
Dose | Population | Adverse 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 |
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 |
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
AE | Significance | Dose | Population |
---|---|---|---|
Allergic contact dermatitis | Disc. AE | 5 % multiple, topical Recommended |
unhealthy n = 1 Health Status: unhealthy Condition: radiotherapy effects Population Size: 1 Sources: |
Allergic contact dermatitis | Disc. AE | 5 % multiple, topical Recommended |
unhealthy n = 1 Health Status: unhealthy Condition: stasis dermatitis Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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Topical corticosteroid therapy for acute radiation dermatitis: a prospective, randomized, double-blind study. | 2002 Jun |
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[Gel with provitamin B5 applied during tests with the Goldmann triple-mirror]. | 2003 |
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[Clinical evaluation of provitamin B5 drops and gel for postoperative treatment of corneal and conjuctival injuries]. | 2003 |
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Efficacy of dexpanthenol in skin protection against irritation: a double-blind, placebo-controlled study. | 2003 Aug |
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[Ogilvie's syndrome: a rare cause of the acute abdomen]. | 2003 Feb |
|
Clear hydro-gel, compared to ointment, provides improved eye comfort after brief surgery. | 2004 Feb |
|
[Dexpanthenol nasal spray in comparison to dexpanthenol nasal ointment. A prospective, randomised, open, cross-over study to compare nasal mucociliary clearance]. | 2004 Jul |
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Allergic and non-allergic periorbital dermatitis: patch test results of the Information Network of the Departments of Dermatology during a 5-year period. | 2004 Jul |
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Pantothenic acid and pantothenol increase biosynthesis of glutathione by boosting cell energetics. | 2004 Jul 2 |
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[Siccaprotect eye drop--results of treatment in clinical practice]. | 2004 Nov |
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[Bilateral keratitis in lagophthalmos and lower lid ectropion]. | 2004 Sep |
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Evaluation of protective and therapeutic effects of dexpanthenol on nasal decongestants and preservatives: results of cytotoxic studies in vitro. | 2004 Sep-Oct |
|
Conservative procedures in skin reconstitution. | 2005 |
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[Conservative and surgical treatment of neurotrophic keratopathy]. | 2005 Jan |
|
Effects of gentiopicroside, sweroside and swertiamarine, secoiridoids from gentian (Gentiana lutea ssp. symphyandra), on cultured chicken embryonic fibroblasts. | 2006 Mar |
|
Development of a w/o/w emulsion for chemical peeling applications containing glycolic acid. | 2006 Nov-Dec |
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Efficacy of Tonimer gel spray on postoperative nasal care after endonasal surgery. | 2007 |
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[Can dexpanthenol prevent peritoneal adhesion formation? An experimental study]. | 2007 Apr |
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Wound-healing activity of St. John's Wort (Hypericum perforatum L.) on chicken embryonic fibroblasts. | 2007 Apr 20 |
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Feedback inhibition of pantothenate kinase regulates pantothenol uptake by the malaria parasite. | 2007 Aug 31 |
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Natural advances in eczema care. | 2007 Dec |
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[Clinical evaluation of the efficacy and tolerability of the ''NoAll Bimbi Pasta Trattante'' barrier cream in napkin dermatitis]. | 2007 Feb |
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Dexpanthenol attenuates lipid peroxidation and testicular damage at experimental ischemia and reperfusion injury. | 2007 Feb |
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Development and validation of reversed phase high performance liquid chromatography method for determination of dexpanthenol in pharmaceutical formulations. | 2007 Feb 19 |
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The protective effect of dexpanthenol on testicular atrophy at 60th day following experimental testicular torsion. | 2007 Mar |
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[Can dexpanthenol prevent peritoneal adhesion formation? An experimental study]. | 2007 Oct |
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Lactobacillus supplementation for diarrhoea related to chemotherapy of colorectal cancer: a randomised study. | 2007 Oct 22 |
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How pantothenol intervenes in Coenzyme-A biosynthesis of Mycobacterium tuberculosis. | 2007 Oct 5 |
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Hamamelis in children with skin disorders and skin injuries: results of an observational study. | 2007 Sep |
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Simultaneous determination of some water-soluble vitamins and preservatives in multivitamin syrup by validated stability-indicating high-performance liquid chromatography method. | 2008 Aug 22 |
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targetTB: a target identification pipeline for Mycobacterium tuberculosis through an interactome, reactome and genome-scale structural analysis. | 2008 Dec 19 |
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Skin protection creams in medical settings: successful or evil? | 2008 Jul 25 |
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Safety and efficacy of a new honey ointment on diabetic foot ulcers: a prospective pilot study. | 2008 Mar |
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Miscellaneous. | 2008 Oct |
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Comparison on the efficacy of dexpanthenol in sea water and saline in postoperative endoscopic sinus surgery. | 2008 Oct |
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Topical fentanyl in a randomized, double-blind study in patients with corneal damage. | 2008 Oct |
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Ointments as a source of meticillin-resistant Staphylococcus aureus spread. | 2008 Oct |
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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 |
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Water-filtered infrared-A (wIRA) in acute and chronic wounds. | 2009 Dec 16 |
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Hippophae rhamnoides L. and dexpanthenol-bepanthene on blood flow after experimental skin burns in rats using 133Xe clearance technique. | 2009 Jan-Apr |
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[Study of skin care in premature and newborn infants]. | 2009 Mar |
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Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts. | 2009 Nov |
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[Survey of sensory perception and patients' subjective assessment of the application of nasal sprays - the nasal-spray-sensoric-scale]. | 2009 Sep |
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A management dilemma: infectious keratitis associated with soft contact lens use and dubious treatment compliance. | 2010 |
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Conservative treatment of a patient with epidermolysis bullosa presenting as bart syndrome: a case report. | 2010 |
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The nitric acid burn trauma of the skin. | 2010 Apr |
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Tissue extract from Eisenia foetida as a wound-healing agent. | 2010 Mar |
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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 |
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C45678
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16485-10-2
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WV9CM0O67Z
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CHEMBL1371937
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62507-76-0
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100000079739
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27373
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C82290
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SUB124270
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PANTHENOL
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1494501
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
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