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a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/01/14 12:39:34」(JST)

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Dipivefrine (INN) or dipivefrin (USAN), trade name Propine among others, is a prodrug of epinephrine, and is used to treat open-angle glaucoma.^[1]^[2] It is available^{[citation needed]} as a 0.1% ophthalmic solution. It is no longer available in the United States.^[3]

Contraindications

Use in narrow-angle glaucoma may be dangerous because it could make the eye susceptible to an attack of angle closure,^[2] causing an increase in pressure and pain, and possibly loss of vision.

Side effects

The most common side effects of dipivefrine are burning, stinging and other irritations of the eye. Possible, but uncommon, side effects are those of epinephrine: tachycardia (fast heartbeat), hypertension (high blood pressure) and arrhythmias (irregular heartbeat).^[2]

Pharmacology

Dipivefrine penetrates the cornea and is then hydrolysed to epinephrine by esterase enzymes. It increases outflow of the aqueous humour and also reduces its formation (mediated by its action on α₁ and α₂ receptors), thus reducing pressure inside the eye. It also increases the conductivity of trabecular filtering cells (a β₂ receptor mediated action). It is preferred to epinephrine because it is longer acting, more consistent in its action and better tolerated.^[1]

References

^ ^a ^b KD Tripari. Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN 81-8061-187-6.
^ ^a ^b ^c Dipivefrin FDA Professional Drug Information.
^ Zhang L, Weizer JS, Musch DC (2017). "Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty". Cochrane Database Syst Rev (2): CD010746. doi:10.1002/14651858.CD010746.pub2. PMID 28231380.

UpToDate Contents

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1. 原発性乳児緑内障 primary infantile glaucoma

English Journal

Effects of topical adrenergic agents on prostaglandin E2-induced aqueous flare and intraocular pressure elevation in pigmented rabbits.

Nakamura-Shibasaki M1, Latief MA2, Ko JA1, Funaishi K1, Kiuchi Y3.
Japanese journal of ophthalmology.Jpn J Ophthalmol.2016 Mar;60(2):95-102. doi: 10.1007/s10384-016-0428-2. Epub 2016 Feb 2.
PURPOSE: To evaluate the effects of signals through adrenergic receptors on the changes in the aqueous flare and intraocular pressure (IOP) induced by topical prostaglandin E2 (PGE2) in pigmented rabbits.METHODS: Adrenergic agents were applied topically to pigmented Dutch rabbits, and PGE2 was then
PMID 26832333

Bidirectional Modulation of Alcohol-Associated Memory Reconsolidation through Manipulation of Adrenergic Signaling.

Schramm MJ1, Everitt BJ1, Milton AL1.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.Neuropsychopharmacology.2016 Mar;41(4):1103-11. doi: 10.1038/npp.2015.248. Epub 2015 Aug 17.
Alcohol addiction is a problem of great societal concern, for which there is scope to improve current treatments. One potential new treatment for alcohol addiction is based on disrupting the reconsolidation of the maladaptive Pavlovian memories that can precipitate relapse to drug-seeking behavior.
PMID 26279079

Update on the role of alpha-agonists in glaucoma management.

Arthur S1, Cantor LB.
Experimental eye research.Exp Eye Res.2011 Sep;93(3):271-83. doi: 10.1016/j.exer.2011.04.002. Epub 2011 Apr 20.
Glaucoma is the second most common cause of world blindness (following cataract) with estimated cases reaching 79.6 million by 2020. Although the etiology of glaucoma is multi-factorial, intraocular pressure (IOP) is the only modifiable factor in glaucoma management proven to alter the natural cours
PMID 21524649

Japanese Journal

原発開放隅角緑内障および高眼圧症に対する塩酸ブナゾシン点眼液とマレイン酸チモロール点眼液の併用効果の検討 : 塩酸ジピベフリン点眼液との比較

東郁郎,北澤克明,塚原重雄,高瀬正彌,米虫節夫
あたらしい眼科 = Journal of the eye 19(2), 261-266, 2002-02-28
NAID 10017003508

「ジピベフリン」

Dipivefrine
Clinical data
Trade names	Propine, Pivalephrine
Synonyms	Dipivefrin
AHFS/Drugs.com	International Drug Names
MedlinePlus	a686005
Pregnancy; category	US: B (No risk in non-human studies); ;
Routes of; administration	Eye drops
ATC code	S01EA02 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name [2-(2,2-Dimethylpropanoyloxy)-4-(1-hydroxy-2-methylamino-ethyl)-phenyl] 2,2-dimethylpropanoate;
CAS Number	52365-63-6 ;
PubChem CID	3105;
IUPHAR/BPS	7166;
DrugBank	DB00449 ;
ChemSpider	2994 ;
UNII	8Q1PVL543G;
KEGG	D02349 ;
ChEBI	CHEBI:4646 ;
ChEMBL	CHEMBL1201262 ;
Chemical and physical data
Formula	C19H29NO5
Molar mass	351.437 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(Oc1cc(ccc1OC(=O)C(C)(C)C)C(O)CNC)C(C)(C)C ;
	InChI InChI=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 ; Key:OCUJLLGVOUDECM-UHFFFAOYSA-N ;
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