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Revision as of 16:03, 15 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit		Latest revision as of 04:03, 9 December 2024 edit undoCitation bot (talk | contribs)Bots5,459,931 edits Added series. Removed parameters. | Use this bot. Report bugs. | Suggested by Abductive | Category:Prodrugs | #UCB_Category 29/338
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			{{Short description|Chemical compound}}
			{{cs1 config|name-list-style=vanc|display-authors=6}}
			{{Redir|Propine|the hydrocarbon compound|propyne}}
	{{Drugbox		{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = verified
			| Watchedfields = verified
	| verifiedrevid = 402003721		| verifiedrevid = 460793250
⚫	| IUPAC_name = 2,2-dimethylpropanoate
	| image = Dipivefrine.svg		| image = Dipivefrine.svg
			| width = 200px
	<!--Clinical data-->		<!-- Clinical data -->
			| tradename = AKPro, D Epifrin, Diopine, Glaucothil, Pro-Epinephrine, Propine, Pivalephrine, Thilodrin, Vistapine, others
	| tradename =
	| Drugs.com = {{drugs.com|international|dipivefrine}}		| Drugs.com = {{drugs.com|international|dipivefrine}}
	| MedlinePlus = a686005		| MedlinePlus = a686005
	| pregnancy_US = B		| pregnancy_US = B
	| legal_status =		| legal_status = Rx-only
			| class = ]; ]
	| routes_of_administration =		| routes_of_administration = ]s<ref name="DrugBank" />
	<!--Pharmacokinetic data-->		<!-- Pharmacokinetic data -->
	| bioavailability =		| bioavailability =
	| metabolism =		| protein_bound =
			| metabolism =
⚫	| elimination_half-life =
			| metabolites =
		⚫	| elimination_half-life =
			| excretion =
	<!--Identifiers-->		<!-- Identifiers -->
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|correct|CAS}}
	| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 52365-63-6		| CAS_number = 52365-63-6
	| ATC_prefix = S01		| ATC_prefix = S01
	| ATC_suffix = EA02		| ATC_suffix = EA02
	| ATC_supplemental =		| ATC_supplemental =
	| PubChem = 3105		| PubChem = 3105
			| IUPHAR_ligand = 7166
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB00449		| DrugBank = DB00449
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	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 8Q1PVL543G		| UNII = 8Q1PVL543G
	| KEGG_Ref = {{keggcite|changed|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D02349		| KEGG = D02349
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 4646		| ChEBI = 4646
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = <!-- blanked - oldvalue: 1201262 -->		| ChEMBL = 1201262
			| synonyms = Dipivefrin; Dipivephrine; Dipivephrin; Dipivalyl epinephrine; Dipivalylepinephrine; DPE; Epinephrine dipivalate; Epinephrine dipivalate ester; Adrenaline dipivalate; K-30081; 3,4-Dipivalyloxy-β-hydroxy-''N''-methylphenethylamine; 3,4-Dipivalyloxy-β-hydroxy-''N''-methyl-β-phenylethylamine
⚫	| C=19 | H=29 | N=1 | O=5
	| molecular_weight = 351.437 g/mol
			<!-- Chemical data -->
⚫	| smiles = O=C(Oc1cc(ccc1OC(=O)C(C)(C)C)C(O)CNC)C(C)(C)C
		⚫	| IUPAC_name = 2,2-dimethylpropanoate
	| InChI = 1/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
		⚫	| C=19 | H=29 | N=1 | O=5
	| InChIKey = OCUJLLGVOUDECM-UHFFFAOYAQ
		⚫	| SMILES = O=C(Oc1cc(ccc1OC(=O)C(C)(C)C)C(O)CNC)C(C)(C)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3		| StdInChI = 1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
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	}}		}}
			'''Dipivefrine''', or '''dipivefrin''', also known as '''epinephrine pivalate''' and sold under the brand name '''Propine''' among others, is a ] ] which is used in the treatment of ].<ref name="Tripari2004">{{cite book|title=Essentials of Medical Pharmacology|publisher=Jaypee Brothers Medical Publishers(P) Ltd.|isbn=81-8061-187-6|page=88|author=KD Tripari|date=2004 |edition=5}}</ref><ref name="Drugs.com">Dipivefrin {{Drugs.com|pro|dipivefrin}}.</ref> It is available as a 0.1% ] ] (]).<ref name="DrugBank">{{cite web | title=Dipivefrin: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 December 1995 | url=https://go.drugbank.com/drugs/DB00449 | access-date=31 August 2024}}</ref><ref name="BaranowskiKarolewiczGajda2014">{{cite journal | vauthors = Baranowski P, Karolewicz B, Gajda M, Pluta J | title = Ophthalmic drug dosage forms: characterisation and research methods | journal = ScientificWorldJournal | volume = 2014 | issue = | pages = 861904 | date = 2014 | pmid = 24772038 | pmc = 3977496 | doi = 10.1155/2014/861904 | doi-access = free | url = }}</ref>
	'''Dipivefrine''' is a ] of ] used to treat ]. It is available as ophthalmic solution. It causes vasoconstriction, decreased aqueous humor production, and decreases intraoccular pressure. It is converted to epinephrine upon penetration of the cornea.
			<!-- Side effects, mechanism of action, and chemistry -->
⚫	== References ==
			]s of dipivefrine include local eye reactions among others. Dipivefrine is a ] of ] (adrenaline) and hence acts as a ] ] ].<ref name="ArthurCantor2011">{{cite journal | vauthors = Arthur S, Cantor LB | title = Update on the role of alpha-agonists in glaucoma management | journal = Exp Eye Res | volume = 93 | issue = 3 | pages = 271–283 | date = September 2011 | pmid = 21524649 | doi = 10.1016/j.exer.2011.04.002 | url = }}</ref> It is a ] and ] and is an ] of epinephrine with much greater ].<ref name="PubChem" /><ref name="GoldbergKolkerKass1980" /><ref name="StellaBorchardtHageman2007" />
⚫	{{Reflist}}
	{{Unreferenced|date=March 2010}}
			<!-- History, society, and culture -->
			Dipivefrine was first described by 1975.<ref name="McClure1975">{{cite book | vauthors=McClure DA | chapter=The Effect of a Pro-drug of Epinephrine (Dipivalyl Epinephrine) in Glaucoma—General Pharmacology, Toxicology, and Clinical Experience | pages=225–235| title=Pro-drugs as Novel Drug Delivery Systems | series=ACS Symposium Series | publisher=American Chemical Society | publication-place=Washington, D. C. | volume=14 | date=1 June 1975 | isbn=978-0-8412-0291-7 | doi=10.1021/bk-1975-0014.ch006 }}</ref> It is widely marketed throughout the world.<ref name="IndexNominum2004" /> However, it is no longer available in the ].<ref name="Zhang2017">{{cite journal |vauthors=Zhang L, Weizer JS, Musch DC| title= Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty | journal= Cochrane Database Syst Rev | volume= 2017 | pages= CD010746 | date= 2017 | issue= 2 | pmid= 28231380 | doi= 10.1002/14651858.CD010746.pub2 | pmc=5477062}}</ref>
			==Medical uses==
	{{Opthalmologicals}}
			Dipivefrine is used in the treatment of ].<ref name="Tripari2004" />
	{{Adrenergics}}
			==Contraindications==
⚫	]
			Use in ] may be dangerous because it could make the eye susceptible to an attack of angle closure,<ref name="Drugs.com"/> causing an increase in pressure and pain and possibly loss of vision.
⚫	]
⚫	]
⚫	]
⚫	]
			==Side effects==
	{{pharmacology-stub}}
			The most common ]s of dipivefrine are burning, stinging, and other irritations of the eye. Possible but uncommon side effects are the same as those of epinephrine and include ] (fast heartbeat), ] (high blood pressure) and ]s (irregular heartbeat).<ref name="Drugs.com"/>
			==Pharmacology==
	]
			Dipivefrine penetrates the ] and is then ] to epinephrine by ] ]s.<ref name="StellaBorchardtHageman2007" /> It increases outflow of the ] and also reduces its formation (mediated by its action on ] and ]s), thus reducing ]. It also increases the conductivity of ] filtering cells (a ]-mediated action). It is preferred to epinephrine because it is longer-acting, more consistent in its action, and better-tolerated.<ref name="Tripari2004" />
	]
	]
			==Chemistry==
	]
			Dipivefrine, also known as epinephrine dipivalate or as 3,4-dipivalyloxy-β-hydroxy-''N''-methylphenethylamine, is a ] and ].<ref name="PubChem">{{cite web | title=Dipivefrin | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/3105 | access-date=31 August 2024}}</ref> It is the 3,4-] ] of ] (adrenaline).<ref name="PubChem" />
			The experimental ] of dipivefrine is 1.7 and its predicted log P ranges from 1.49 to 3.71.<ref name="PubChem" /><ref name="DrugBank">{{cite web | title=Dipivefrin: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 December 1995 | url=https://go.drugbank.com/drugs/DB00449 | access-date=31 August 2024}}</ref><ref name="ChemSpider">{{cite web | title=C19H29NO5 | website=Dipivefrin | date=31 August 2024 | url=https://www.chemspider.com/Chemical-Structure.2994.html | language=la | access-date=31 August 2024}}</ref> It is dramatically more ] (600-fold) than epinephrine,<ref name="GoldbergKolkerKass1980">{{cite journal | vauthors = Goldberg I, Kolker AE, Kass MA, Becker B | title = Dipivefrin: current concepts | journal = Aust J Ophthalmol | volume = 8 | issue = 2 | pages = 147–150 | date = May 1980 | pmid = 7004425 | doi = 10.1111/j.1442-9071.1980.tb01673.x | url = }}</ref><ref name="StellaBorchardtHageman2007">{{cite book | vauthors = Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J | title=Prodrugs: Challenges and Rewards | publisher=Springer New York | series=Biotechnology: Pharmaceutical Aspects | year=2007 | isbn=978-0-387-49782-2 | url=https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA130 | access-date=2024-08-31 | page=130}}</ref><ref name="BaranowskiKarolewiczGajda2014" /> which is highly ] and has a log P of -1.37.<ref name="PubChem-Epinephrine">{{cite web | title=Epinephrine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/5816 | access-date=31 August 2024}}</ref> The lipophilicity of dipivefrine allows it to penetrate the ] much more readily (17-fold) than epinephrine.<ref name="GoldbergKolkerKass1980" /><ref name="StellaBorchardtHageman2007" /><ref name="BaranowskiKarolewiczGajda2014" /> Eye drops containing 0.1% dipivefrine have similar effectiveness to conventional eye drops containing 2% epinephrine in lowering ].<ref name="BaranowskiKarolewiczGajda2014" />
			Dipivefrine is used ] mainly as the ] ].<ref name="Elks2014" /><ref name="IndexNominum2004" />
			A similar ] that was never marketed is ], which is the 3-pivalate ester of ].<ref name="Elks2014" />
			==History==
			Dipivefrine was first described in the ] by 1975.<ref name="McClure1975" />
			==Society and culture==
			===Names===
			''Dipivefrine'' is the ] of the drug and its {{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|BAN|British Approved Name}}, and {{Abbrlink|DCF|Dénomination Commune Française}}, while ''dipivefrin'' is its {{Abbrlink|USAN|United States Adopted Name}} and ''dipivefrina'' is its {{Abbrlink|DCIT|Denominazione Comune Italiana}}.<ref name="Elks2014">{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA455 | access-date=2024-08-31 | pages=455,1001}}</ref><ref name="IndexNominum2004">{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2004 | isbn=978-3-88763-101-7 | url=https://books.google.com/books?id=EgeuA47Ocm4C&pg=PA411 | access-date=2024-08-31 | page=411}}</ref><ref name="MortonHall2012">{{cite book | vauthors = Morton IK, Hall JM | title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms | publisher=Springer Netherlands | year=2012 | isbn=978-94-011-4439-1 | url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA101 | access-date=31 August 2024 | page=101}}</ref> In the case of the ] ], ''dipivefrine hydrochloride'' is its {{Abbrlink|BANM|British Approved Name}} while ''dipivefrin hydrochloride'' is its {{Abbrlink|USAN|United States Adopted Name}} and {{Abbrlink|JAN|Japanese Accepted Name}}.<ref name="Elks2014" /><ref name="IndexNominum2004" /><ref name="MortonHall2012" />
			Synonyms of dipivefrine include ''epinephrine pivalate'', ''adrenaline pivalate'', and ''dipivalyl epinephrine'', among others.<ref name="Elks2014" /><ref name="IndexNominum2004" />
			Dipivefrine has been sold under brand names including ''Diopine'', ''Glaucothil'', ''Pro-Epinephrine'', ''Propine'', ''Thilodrin'', and ''Vistapine'', among many others.<ref name="Elks2014" /><ref name="IndexNominum2004" />
			==See also==
			* ]
		⚫	==References==
		⚫	{{Reflist}}
			{{Antiglaucoma preparations and miotics}}
			{{Adrenergic receptor modulators}}
			]
			]
			]
		⚫	]
		⚫	]
			]
		⚫	]
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		⚫	]
		⚫	]