# DDAIP

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/DDAIP
> Markdown URL: https://mediated.wiki/source/DDAIP.md
> Source: https://en.wikipedia.org/wiki/DDAIP
> Source revision: 1330140708
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
<code></code>{{Drugbox
| verifiedrevid = 451606534
| IUPAC_name = 2-Dimethylaminopropionic acid dodecyl ester (Decyl (C10) ester shown)
| image = DDAIP.svg
| image_class = skin-invert-image
| width = 200

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

<!--Pharmacokinetic data-->
| bioavailability = <1% (topical)
| protein_bound = >99%
| metabolism = Esterase mediated
| elimination_half-life = 5 hours
| excretion = Urinary

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

<!--Chemical data-->
| C=17 | H=36 | Cl=1 | N=1 | O=2 
| 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 [topical](/source/topical) products to increase penetration through the skin.  Chemically, DDAIP is an [ester](/source/ester) of [''N'',''N''-dimethylalanine](/source/N%2CN-Dimethylalanine) and [dodecanol](/source/dodecanol), although as of now the structural formula shows an ester with [decanol](/source/decanol) (C10) instead.  DDAIP is typically formulated as its [hydrochloride](/source/hydrochloride) [salt](/source/salt_(chemistry)) (DDAIP.HCl).  This salt is a white crystalline solid with a melting range of 88-93&nbsp;°C and is an [amphiphilic](/source/Amphiphile) 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 [Apricus Biosciences](/source/Apricus_Biosciences).<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 ==
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 [solubility](/source/solubility) 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 ==
DDAIP hydrochloride is a functional inactive [excipient](/source/excipient) currently used in the topical drug Vitaros, an [alprostadil](/source/alprostadil) [vasodilator](/source/vasodilator) 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 [terbinafine](/source/terbinafine) [antifungal](/source/Antifungal_medication) nail lacquer for [onychomycosis](/source/onychomycosis) currently in phase-III clinical trials.

== Safety ==
Overall, about 5,000 patients have been exposed to this compound with no serious adverse events recorded.  DDAIP is primarily metabolized by [esterase](/source/esterase)s on cell surfaces and plasma to ''N'',''N''-dimethylalanine, which is further demethylated to [alanine](/source/alanine); and [dodecanol](/source/dodecanol) which is oxidized to [lauric acid](/source/lauric_acid), both naturally occurring compounds already present in the body.

== References ==
{{reflist}}

Category:Excipients
Category:Amino acid derivatives
Category:Carboxylate esters
Category:Decyl esters

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Adapted from the Wikipedia article [DDAIP](https://en.wikipedia.org/wiki/DDAIP) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/DDAIP?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.