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Revision as of 02:25, 21 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbo← Previous edit Latest revision as of 15:58, 18 March 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits added Category:Decyl esters using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox <code></code>{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443682113 | verifiedrevid = 451606534
| IUPAC_name = 2-Dimethylaminopropionic acid dodecyl ester | IUPAC_name = 2-Dimethylaminopropionic acid dodecyl ester (Decyl (C10) ester shown)
| image = DDAIP.svg | image = DDAIP.svg
| width = 200 | width = 200


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 224297-43-2 | CAS_number = 149196-89-4
| CAS_supplemental = <br>259685-49-9 (])
| CAS_supplemental =
| ATC_prefix = | ATC_prefix =
| ATC_suffix = | ATC_suffix =
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6679UF28DO | UNII = 6679UF28DO
| PubChem = 3025823
| ChemSpiderID = 2291478
| synonyms = Dodecyl 2-N,N-dimethylaminopropionate; Dodecyl-2-(dimethylamino)propionate; N,N-Dimethylalanine dodecyl ester | synonyms = Dodecyl 2-N,N-dimethylaminopropionate; Dodecyl-2-(dimethylamino)propionate; N,N-Dimethylalanine dodecyl ester


<!--Chemical data--> <!--Chemical data-->
| C=17 | H=36 | Cl=1 | N=1 | O=2 | C=17 | H=36 | Cl=1 | N=1 | O=2
| molecular_weight = 321.93 ]/]
| smiles = CCCCCCCCCCCCOC(=O)C(C)N(C)C | smiles = CCCCCCCCCCCCOC(=O)C(C)N(C)C
| StdInChI = 1S/C17H35NO2/c1-5-6-7-8-9-10-11-12-13-14-15-20-17(19)16(2)18(3)4/h16H,5-15H2,1-4H3
| StdInChIKey = HSMMSDWNEJLVRY-UHFFFAOYSA-N
}} }}


'''DDAIP''' is a pharmaceutical ingredient added to ] products to increase penetration through the skin. Chemically, DDAIP is an ] of ] and ]. DDAIP is typically formulated as its ] ] (DDAIP.HCl). This salt is a white crystalline solid with a melting range of 88-93 °C and is an ] molecule with a pKa of 4.87 that is soluble in water up to about 40% w/v. DDAIP is proprietary to NexMed USA, a subsidiary of ].<ref name=Patent>{{cite web|url=http://www.patentstorm.us/patents/6118020/description.html|title=Patent|work=Crystalline salts of dodecyl 2-(N,N-dimethylamino)-propionate patent|accessdate=11 March 2011}}</ref> '''DDAIP''' is a pharmaceutical ingredient added to ] products to increase penetration through the skin. Chemically, DDAIP is an ] of ] and ], although as of now the structural formula shows an ester with ] (C10) instead. DDAIP is typically formulated as its ] ] (DDAIP.HCl). This salt is a white crystalline solid with a melting range of 88-93&nbsp;°C and is an ] molecule with a pKa of 4.87 that is soluble in water up to about 40% w/v. DDAIP is proprietary to NexMed USA, a subsidiary of ].<ref name=Patent>{{cite patent | country = US | number = 6118020 |title = Crystalline salts of dodecyl 2-(N,N-dimethylamino)-propionate | inventor = Buyuktimkin S, Buyuktimkin N | assign1 = Nexmed Holdings Inc | gdate = 12 September 2000 }}</ref>


== Mechanism of action == == Mechanism of action ==
DDAIP is a permeation enhancer<ref>{{cite journal|last=Das|first=Debanjan|coauthors=John Augustine, andMarcel Langenauer|title=Overcoming the Skin Barrier by Chemical Enhancements: A Formulator’s Perspective|journal=SP Formulations, LLC|accessdate=23 March 2011}}</ref> that temporarily changes the permeation dynamics of the lipid bi-layer and opens up the tight junctions between skin cells so that active drug molecules can be rapidly absorbed through the skin into systemic circulation.<ref>{{cite journal|last=Hadgraft|first=J|journal= Skin Pharmacol Appl Skin Physio|year=2001|volume=14 | issue=Suppl 1|pages=72–81|accessdate=16 March 2011 | doi=10.1159/000056393 | title=Modulation of the Barrier Function of the Skin | pmid=11509910}}</ref> It can also improve the ] of compounds resulting in enhanced drug permeation.<ref>{{cite journal|last=Michniak-Kohn|first=Bozena|coauthors=Kishore R Shah|title=Patchless Transdermal Drug Delivery (TDD)|journal=TransDermal|year=2011|month=March|pages=5–11|accessdate=23 March 2011}}</ref> DDAIP is a permeation enhancer<ref>{{cite journal| vauthors = Das D, Augustine J, Langenauer M |title=Overcoming the Skin Barrier by Chemical Enhancements: A Formulator's Perspective|journal=SP Formulations, LLC}}</ref> that temporarily changes the permeation dynamics of the lipid bilayer and opens up the tight junctions between skin cells so active drug molecules can be rapidly absorbed through the skin into systemic circulation.<ref>{{cite journal | vauthors = Hadgraft J | title = Modulation of the barrier function of the skin | journal = Skin Pharmacology and Applied Skin Physiology | volume = 14 | issue = Suppl 1 | pages = 72–81 | year = 2001 | pmid = 11509910 | doi = 10.1159/000056393 | s2cid = 33920480 }}<!--|access-date=16 March 2011 --></ref> It can also improve the ] of compounds resulting in enhanced drug permeation.<ref>{{cite journal| vauthors = Michniak-Kohn B, Shah KR |title=Patchless Transdermal Drug Delivery (TDD)|journal=TransDermal|date=March 2011|pages=5–11}}</ref>


== Clinical use == == Clinical use ==
DDAIP.HCl is a functional non-active ] currently used in the topical drug Vitaros, an ] ] cream used to treat erectile dysfunction. It is also used in MycoVa,<ref name="The Street">{{cite web|title=Apricus Biosciences Reports Additional Analysis Showing That MycoVa Is As Effective For The Treatment Of Nail Fungus As The Current European Standard Of Care For Topical Therapy, Loceryl|url=http://www.thestreet.com/story/10978767/1/apricus-biosciences-reports-additional-analysis-showing-that-mycovatm-is-as-effective-for-the-treatment-of-nail-fungus-as-the-current-european-standard-of-care-for-topical-therapy-locerylr.html|publisher=The Street|accessdate=16 March 2011}}</ref> a ] ] nail lacquer for ] currently in Phase III clinical trials. DDAIP hydrochloride is a functional inactive ] currently used in the topical drug Vitaros, an ] ] cream used to treat erectile dysfunction. It is also used in MycoVa,<ref name="The Street">{{cite web | work = GlobeNewswire |title=Apricus Biosciences Reports Additional Analysis Showing That MycoVa Is As Effective For The Treatment Of Nail Fungus As The Current European Standard Of Care For Topical Therapy, Loceryl|url=http://www.thestreet.com/story/10978767/1/apricus-biosciences-reports-additional-analysis-showing-that-mycovatm-is-as-effective-for-the-treatment-of-nail-fungus-as-the-current-european-standard-of-care-for-topical-therapy-locerylr.html | archive-url = https://web.archive.org/web/20160304231532/https://www.thestreet.com/story/10978767/1/apricus-biosciences-reports-additional-analysis-showing-that-mycovatm-is-as-effective-for-the-treatment-of-nail-fungus-as-the-current-european-standard-of-care-for-topical-therapy-locerylr.html | archive-date = 4 March 2016 |publisher=The Street|access-date=16 March 2011}}</ref> a ] ] nail lacquer for ] currently in phase-III clinical trials.


== Safety == == Safety ==
Overall, about 5000 patients have been exposed to this compound with no serious adverse events recorded. DDAIP.HCl is primarily metabolized by ]s on cell surfaces and plasma to ''N'',''N''-dimethylalanine, which is further demethylated to ]; and ] which is oxidized to ], both naturally occurring compounds already present in the body. Overall, about 5,000 patients have been exposed to this compound with no serious adverse events recorded. DDAIP is primarily metabolized by ]s on cell surfaces and plasma to ''N'',''N''-dimethylalanine, which is further demethylated to ]; and ] which is oxidized to ], both naturally occurring compounds already present in the body.


== References == == References ==
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