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
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
| 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 |
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 |
|---|---|---|---|---|
| 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 |
|
5 % multiple, topical Recommended |
unhealthy |
Disc. AE: Allergic contact dermatitis... AEs leading to discontinuation/dose reduction: Allergic contact dermatitis Sources: |
5 % multiple, topical Recommended |
unhealthy |
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 |
| Allergic contact dermatitis | Disc. AE | 5 % multiple, topical Recommended |
unhealthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Simultaneous determination of pantothenic acid and D-panthenol in cosmetics by high performance liquid chromatography]. | 2010-11 |
|
| Impact of repeated four-monthly anthelmintic treatment on Plasmodium infection in preschool children: a double-blind placebo-controlled randomized trial. | 2010-09-21 |
|
| [Severe inflammation of the muzzle caused by a nose ring in a breeding bull]. | 2010-09 |
|
| A search for mosquito larvicidal compounds by blocking the sterol carrying protein, AeSCP-2, through computational screening and docking strategies. | 2010-07 |
|
| [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]. | 2010-06 |
|
| Identifying essential genes in bacterial metabolic networks with machine learning methods. | 2010-05-03 |
|
| Final report of the safety assessment of allantoin and its related complexes. | 2010-05 |
|
| Enhancement of L-3-hydroxybutyryl-CoA dehydrogenase activity and circulating ketone body levels by pantethine. Relevance to dopaminergic injury. | 2010-04-23 |
|
| The nitric acid burn trauma of the skin. | 2010-04 |
|
| Tissue extract from Eisenia foetida as a wound-healing agent. | 2010-03 |
|
| [Glued eyelids by cyanoacrylate glue (superglue)]. | 2010-02 |
|
| The effects of a daily facial lotion containing vitamins B3 and E and provitamin B5 on the facial skin of Indian women: a randomized, double-blind trial. | 2010-01-12 |
|
| Photoprotective potential of emulsions formulated with Buriti oil (Mauritia flexuosa) against UV irradiation on keratinocytes and fibroblasts cell lines. | 2010-01 |
|
| 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 |
|
| Water-filtered infrared-A (wIRA) in acute and chronic wounds. | 2009-12-16 |
|
| Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts. | 2009-11 |
|
| Antioxidant systems and oxidative stress in the testes. | 2009-10-02 |
|
| Common cosmeceuticals. | 2009-08-22 |
|
| [Effects of panthenol and carnitine on aldehyde metabolic enzymes in rats with tetrachloromethane-induced liver injury]. | 2009-05-16 |
|
| Patterns of soil-transmitted helminth infection and impact of four-monthly albendazole treatments in preschool children from semi-urban communities in Nigeria: a double-blind placebo-controlled randomised trial. | 2009-02-19 |
|
| Tracheostomy cannulas and voice prosthesis. | 2009 |
|
| Vitiligo treatment with vitamins, minerals and polyphenol supplementation. | 2009 |
|
| Oxymetazoline plus dexpanthenol in nasal congestion. | 2008-12 |
|
| Miscellaneous. | 2008-10 |
|
| Skin protection creams in medical settings: successful or evil? | 2008-07-25 |
|
| Safety and efficacy of a new honey ointment on diabetic foot ulcers: a prospective pilot study. | 2008-03 |
|
| Therapy of acute wounds with water-filtered infrared-A (wIRA). | 2007-12-28 |
|
| A phase III trial comparing an anionic phospholipid-based cream and aloe vera-based gel in the prevention of radiation dermatitis in pediatric patients. | 2007-12-19 |
|
| In vitro human nail penetration and kinetics of panthenol. | 2007-08 |
|
| Development and validation of reversed phase high performance liquid chromatography method for determination of dexpanthenol in pharmaceutical formulations. | 2007-02-19 |
|
| [Clinical evaluation of the efficacy and tolerability of the ''NoAll Bimbi Pasta Trattante'' barrier cream in napkin dermatitis]. | 2007-02 |
|
| Allergic contact dermatitis to panthenol and cocamidopropyl PG dimonium chloride phosphate in a facial hydrating lotion. | 2006-12 |
|
| Facilitating facial retinization through barrier improvement. | 2006-10 |
|
| Pharmacologic interventions in aging hair. | 2006 |
|
| Xenobiotics in vitro: the influence of L-cystine, pantothenat, and miliacin on metabolic and proliferative capacity of keratinocytes. | 2006 |
|
| Evaluation of the ultrasound influence in the cutaneous penetration of d-panthenol: test in vitro. | 2005-01 |
|
| Conservative procedures in skin reconstitution. | 2005 |
|
| [The influence of panthotenic acid mitochondrial oxidation and oxidative phosphorylation in liver of rats with alimentary obesity]. | 2004 |
|
| [Gel with provitamin B5 applied during tests with the Goldmann triple-mirror]. | 2003 |
|
| [Clinical evaluation of provitamin B5 drops and gel for postoperative treatment of corneal and conjuctival injuries]. | 2003 |
|
| Dexpanthenol enhances skin barrier repair and reduces inflammation after sodium lauryl sulphate-induced irritation. | 2002-12 |
|
| Colorimetric and fluorimetric methods for determination of panthenol in cosmetic and pharmaceutical formulation. | 2002-02-01 |
|
| Abuse of silver-nitrate solution for planing periorbital folds. | 2002-02 |
|
| Topical use of dexpanthenol in skin disorders. | 2002 |
|
| Hypolipidemic effect of pantothenic acid derivatives in mice with hypothalamic obesity induced by aurothioglucose. | 2001-10 |
|
| Effect of topically applied dexpanthenol on epidermal barrier function and stratum corneum hydration. Results of a human in vivo study. | 2000-07 |
|
| [Clinical study of the effectiveness of a dexpanthenol containing artificial tears solution (Siccaprotect) in treatment of dry eyes]. | 1996-08-01 |
|
| [The metabolism of panthenol in patients with postoperative intestinal atony]. | 1990-12 |
| Substance Class |
Chemical
Created
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| Record UNII |
1O6C93RI7Z
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WHO-VATC |
QS01XA12
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QD03AX03
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WHO-ATC |
A11HA30
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CFR |
21 CFR 310.527
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LIVERTOX |
292
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WHO-ATC |
S01XA12
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QA11HA30
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WHO-ATC |
D03AX03
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NCI_THESAURUS |
C26017
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50584-68-4
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81-13-0
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1113-70-8
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1179504
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201-327-3
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838
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296
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100000092075
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CHEMBL1200979
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302962
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27373
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22701
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SUB07042MIG
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1023
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17307-32-3
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DTXSID3022906
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DB09357
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1O6C93RI7Z
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C007288
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C47481
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1O6C93RI7Z
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m4219
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ACTIVE MOIETY |