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{{short description|Pair / mixture of stereoisomers}} |
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{{chembox |
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| verifiedrevid = 399900966 |
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| verifiedrevid = 458948255 |
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|ImageFile=Panthenol.png |
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| ImageFile = Dexpanthenol.svg |
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| ImageClass = skin-invert-image |
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|ImageSize= |
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| ImageCaption = <small>D</small>-panthenol |
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|IUPACName=(2''R'')-2,4-dihydroxy-''N''-(3-hydroxypropyl)-3,3-dimethylbutanamide |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|OtherNames=Dexpanthenol, Bepanthen |
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| ImageSize = 160 |
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|Section1= {{Chembox Identifiers |
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| ImageName = Stereo, skeletal formula of panthenol (R) |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = 2,4-Dihydroxy-''N''-(3-hydroxypropyl)-3,3-dimethylbutanamide<ref>{{cite web|title=Dexpanthenol – Compound summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4678&loc=ec_rcs#x291|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=29 June 2012|location=US|date=25 March 2005|at=Identification}}</ref> |
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| OtherNames = {{unbulleted list|Pantothenol|Pantothenyl alcohol|''N''-Pantoylpropanolamine|Bepanthen (trade name)|Dexpanthenol (<small>D</small> form) |
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}} |
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|Section1={{Chembox Identifiers |
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| CASNo = 16485-10-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 81-13-0 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Comment = <small>''R''</small> |
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| PubChem = 4678 |
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| PubChem1 = 131204 |
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| PubChem1_Comment = <small>''R''</small> |
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| PubChem2 = 5748487 |
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| PubChem2_Comment = <small>''S''</small> |
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| ChemSpiderID = 4516 |
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| ChemSpiderID = 4516 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 115991 |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1_Comment = <small>''R''</small> |
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| ChemSpiderID2 = 4677984 |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2_Comment = <small>''S''</small> |
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| UNII = WV9CM0O67Z |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1O6C93RI7Z |
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| UNII1 = 1O6C93RI7Z |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| UNII1_Comment = (<small>''R''</small>) |
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| ChEMBL = <!-- blanked - oldvalue: 1200979 --> |
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| EINECS = 240-540-6 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D03726 |
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| KEGG = D03726 |
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| KEGG2 = D00193 |
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| InChI = 1/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) |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChIKey = SNPLKNRPJHDVJA-UHFFFAOYAQ |
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| MeSHName = dexpanthenol |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI = 27373 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1200979 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| RTECS = ES4316500 |
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| Beilstein = 1724945, 1724947 <small>''R''</small> |
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| 3DMet = B00882 |
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| SMILES = CC(C)(CO)C(O)C(=O)NCCCO |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SNPLKNRPJHDVJA-UHFFFAOYSA-N |
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| StdInChIKey = SNPLKNRPJHDVJA-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo=81-13-0 |
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|Section2={{Chembox Properties |
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| PubChem=4678 |
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| C=9 | H=19 | N=1 | O=4 |
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| SMILES = O=C(NCCCO)C(O)C(C)(C)CO |
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| Appearance = Highly viscous, colourless liquid |
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| Density = 1.2 g mL<sup>−1</sup> (at 20 °C) |
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| BoilingPtC = 118 to 120 |
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| BoilingPt_notes = at 2.7 Pa |
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| MeltingPtC = 66 to 69 |
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| MeltingPt_notes = {{contradict-inline|reason=is a viscous liquid at room temperature|date=July 2016}} |
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| LogP = −0.989 |
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| pKa = 13.033 |
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| pKb = 0.964 |
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| RefractIndex = 1.499 |
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| SpecRotation = +29° to +30° |
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}} |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = A11 |
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| ATCCode_suffix = HA30 |
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| ATC_Supplemental = {{aTC|D03|AX03}}, {{aTC|S01|XA12}} |
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}} |
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|Section7={{Chembox Hazards |
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| LD50 = 10,100 mg kg<sup>−1</sup> (intraperitoneal, mouse); 15,000 mg kg<sup>−1</sup> (oral, mouse) |
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| NFPA-H = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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}} |
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|Section8={{Chembox Related |
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| OtherCompounds = {{unbulleted list|]|]|]|]}} |
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}} |
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}} |
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|Section2= {{Chembox Properties |
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| Formula=C<sub>9</sub>H<sub>19</sub>NO<sub>4</sub> |
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| MolarMass=205.251g/mol |
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| Appearance= |
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| Density= |
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| MeltingPt= |
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| Solubility= |
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}} |
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|Section3= {{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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'''Panthenol''' is the ] ] of ] (vitamin B<sub>5</sub>), and is thus a ] of B<sub>5</sub>. In organisms it is quickly oxidized to pantothenate. Panthenol is a highly viscous transparent liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is soluble in water, ] and ], soluble in ] and ], and slightly soluble in ]. |
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'''Panthenol''' (also called '''pantothenol''') is the ] ] of ] (vitamin B<sub>5</sub>), and is thus a ] of B<sub>5</sub>. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and children's products as a ] and to hasten wound healing. |
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Panthenol comes in two ]s, <small>D</small> and <small>L</small>. Only <small>D</small>-panthenol (''dexpanthenol'') is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in <small>D</small> form, or as a ] mixture of <small>D</small> and <small>L</small> (<small>DL</small>-panthenol). |
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==Uses== |
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Panthenol's expanded chemical formula is: HO-CH<sub>2</sub>-C(CH<sub>3</sub>)<sub>2</sub>-CH(OH)-CONH-CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>-OH. |
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In pharmaceuticals, cosmetics, and personal-care products, panthenol is a moisturizer and ], used in ]s, lotions, shampoos, nasal sprays, eye drops, ]s, and cleaning solutions for contact lenses. |
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In ointments it is used for the treatment of ]s, mild ], minor skin injuries, and skin disorders (in concentrations of up to 2–5%).<ref name="AC" /> It improves ], reduces itching and inflammation of the skin, improves skin elasticity, and accelerates ] wounds' rate of healing.<ref name=EbnerEtAl2002>{{cite journal | vauthors = Ebner F, Heller A, Rippke F, Tausch I | title = Topical use of dexpanthenol in skin disorders | journal = American Journal of Clinical Dermatology | volume = 3 | issue = 6 | pages = 427–33 | year = 2002 | pmid = 12113650 | doi = 10.2165/00128071-200203060-00005 | s2cid = 35836478 }}</ref> For this purpose, it is sometimes combined with ]. A case study of dexpanthenol application to regenerate bat's dry patagium was reporterd<ref>Marcin M. Granat (2024). Patagium regeneration after dexpanthenol administration: bat case study. Przegląd Przyrodniczy, XXXV, 3: 83–85.</ref>. |
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== Uses == |
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In ], panthenol is a ], ] and ]. It binds to the hair shaft readily and is a frequent component of ]s and ]s (in concentrations of 0.1-1%). It coats the hair and seals its surface{{Fact|date=March 2007}}, ] the hair shaft and making strands appear shiny. It is also recommended by many tattoo artists as a moisturising cream for new tattoos. |
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It binds to the hair shaft readily, due to which it is a common component of commercial ]s and ]s (in concentrations of 0.1–1%). It coats the hair and seals its surface,{{Citation needed|date=March 2007}} ] the hair shaft and giving it a shiny appearance. |
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<small>D</small>-panthenol (dexpanthenol) is sometimes used as an ingredient in tattoo aftercare products, with one study finding it can assist in wound care and tattoo preservation.<ref>{{Cite journal |last1=Schmid |first1=Daphné A. |last2=Domingues |first2=Marisa P. |last3=Nanu |first3=Alina |last4=Kluger |first4=Nicolas |last5=de Salvo |first5=Raffaella |last6=Trapp |first6=Sonja |year=2022 |title=Exploratory evaluation of tolerability, performance, and cosmetic acceptance of dexpanthenol-containing dermo-cosmetic wash and sun-care products for tattoo aftercare |journal=Health Science Reports |volume=5 |issue=4 |pages=e635 |doi=10.1002/hsr2.635 |issn=2398-8835 |pmc=9235347 |pmid=35782304 |quote=The 2.5% dexpanthenol‐containing wash demonstrated to be suitable for mild effective cleansing of fresh tattoos to complement standard tattoo aftercare with a dexpanthenol‐containing ointment. ... In the current study, 2.5% dexpanthenol‐containing sun‐care SPF50+ cream was demonstrated to maintain the esthetic appearance of existing tattoos by preserving vibrant colors and preventing fading of the tattoos, while it was easy to apply and keeping the tattooed skin smooth and hydrated. Assessment of the skin barrier function showed a decrease in TEWL, or outward diffusion of water through the skin, after 28 days of daily application, an observation which confirms the ability of the 2.5% dexpanthenol‐containing sun‐care SPF50+ cream to maintain the skin barrier and prevent the drying out of tattooed skin in addition to providing protection against UV radiation.}}</ref> |
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In ]s, panthenol has good skin penetration.<ref name=EbnerEtAl2002>Ebner F, Heller A, Rippke F, Tausch I. "Topical use of dexpanthenol in skin disorders". ''American journal of clinical dermatology''. 2002;3(6):427-33. ()</ref> It is sometimes mixed with ], in concentrations of up to 2-5%, and is used for treatment of ]s, mild ] and minor skin disorders.{{Fact|date=September 2008}} It improves hydration, reduces itching and inflammation of the skin and accelerates and improves healing of ] wounds.<ref name=EbnerEtAl2002>Ebner F, Heller A, Rippke F, Tausch I. "Topical use of dexpanthenol in skin disorders". ''American journal of clinical dermatology''. 2002;3(6):427-33.</ref> |
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==Adverse effects== |
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If ingested, panthenol is metabolized to ]. |
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Panthenol is generally well tolerated. In rare cases, skin irritation and ] have been reported.<ref name="AC" /><ref name=EbnerEtAl2002/> |
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==Synonyms== |
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==Pharmacology== |
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Panthenol readily penetrates into the skin and ]s (including the ]), where it is quickly oxidized to pantothenic acid. Pantothenic acid is extremely ].<ref>{{cite book|title=Arzneistoff-Profile| veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|date=1991|edition=8|volume=7|at=Pantothensäure|isbn=978-3-7741-9846-3|language=German}}</ref> It is also used in the biosynthesis of ], which plays a role in a wide range of ] reactions and in cell growth.<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Bepanthen Creme|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2015|language=German}}</ref><ref name=EbnerEtAl2002/> |
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] |
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==Physical and chemical properties== |
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Other names for panthenol include: |
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*Butanamide, 2,4-dihydroxy-''N''-(3-hydroxypropyl)-3,3-dimethyl-, (''R'')- |
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Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature,<ref name="Hager">{{cite book|title=Hagers Handbuch der pharmazeutischen Praxis| veditors = List PH, Hörhammer L |volume=2|page=699|publisher=Springer|language=de|year=1969}}</ref> but salts of pantothenic acid (for example sodium pantothenate) are powders that are typically white. It is easily soluble in water and ], moderately soluble in ], soluble in ] (1:100),<ref name="Hager" /> in ], and slightly soluble in ]. |
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*Butyramide, 2,4-dihydroxy-''N''-(3-hydroxypropyl)-3,3-dimethyl-, <small>D</small>-(+)- |
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*Butanamide, 2,4-dihydroxy-''N''-(3-hydroxypropyl)-3,3-dimethyl-, (2''R'')- |
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*<small>D</small>-Panthenol |
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*Dexpanthenol (]) |
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*Dexpanthenolum |
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*Propanolamine, ''N''-pantoyl- |
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*d-Pantothenyl alcohol |
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*Bepanthen |
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Panthenol's expanded chemical formula is HO–CH<sub>2</sub>–C(CH<sub>3</sub>)<sub>2</sub>–CH(OH)–CONH–CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>–OH. |
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==References== |
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===Stereochemistry=== |
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Panthenol comes in two ]s: <small>D,</small> and <small>L</small>. Only <small>D</small>-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in <small>D</small> form, or as a ] mixture of <small>D</small> and <small>L</small> (<small>DL</small>-panthenol). |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{vitamin}} |
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==External links== |
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{{preparations for treatment of wounds and ulcers}} |
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* {{HPD|788}} |
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* {{ATC|A11|HA30}} |
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{{Authority control}} |
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{{Vitamin}} |
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{{Preparations for treatment of wounds and ulcers}} |
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