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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[Closure of the wound defect by transferred flap of skin]. | 2002 Nov-Dec |
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[Ogilvie's syndrome: a rare cause of the acute abdomen]. | 2003 Feb |
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[Febrile respiratory infection and erythema in a 25-year-old man]. | 2003 Feb 7 |
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[The protective effect of dexpanthenol in nasal sprays. First results of cytotoxic and ciliary-toxic studies in vitro]. | 2003 Mar |
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Clear hydro-gel, compared to ointment, provides improved eye comfort after brief surgery. | 2004 Feb |
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[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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Investigation of some topical formulations containing dexpanthenol. | 2004 Nov-Dec |
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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 |
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Conservative procedures in skin reconstitution. | 2005 |
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[Conservative and surgical treatment of neurotrophic keratopathy]. | 2005 Jan |
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Prevention of and therapies for nipple pain: a systematic review. | 2005 Jul-Aug |
|
Effects of dexpanthenol with or without Aloe vera extract on radiation-induced oral mucositis: preclinical studies. | 2005 Mar |
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[Guidelines for treatment and prevention of diaper rash]. | 2005 Nov |
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Anaphylaxis after dexpanthenol exposure by multivitamin tablets. | 2005 Nov |
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Allergic contact dermatitis to panthenol and cocamidopropyl PG dimonium chloride phosphate in a facial hydrating lotion. | 2006 Dec |
|
Effects of gentiopicroside, sweroside and swertiamarine, secoiridoids from gentian (Gentiana lutea ssp. symphyandra), on cultured chicken embryonic fibroblasts. | 2006 Mar |
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Development of a w/o/w emulsion for chemical peeling applications containing glycolic acid. | 2006 Nov-Dec |
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Comparison of dexpanthenol and zinc oxide ointment with ointment base in the treatment of irritant diaper dermatitis from diarrhea: a multicenter study. | 2006 Oct |
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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 pastille and benzydamine hydrochloride spray for the prevention of post-operative sore throat. | 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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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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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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Antioxidant systems and oxidative stress in the testes. | 2008 Oct-Dec |
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Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts. | 2009 Nov |
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Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses. | 2010 |
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The nitric acid burn trauma of the skin. | 2010 Apr |
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[Glued eyelids by cyanoacrylate glue (superglue)]. | 2010 Feb |
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[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 |
|
Identifying essential genes in bacterial metabolic networks with machine learning methods. | 2010 May 3 |
|
[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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SUB124270
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PANTHENOL
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1494501
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
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