Dipivefrine

Dipivefrine
Clinical data
Trade namesAKPro, D Epifrin, Diopine, Glaucothil, Pro-Epinephrine, Propine, Pivalephrine, Thilodrin, Vistapine, others
Other namesDipivefrin; Dipivephrine; Dipivephrin; Dipivalyl epinephrine; Dipivalylepinephrine; DPE; Epinephrine dipivalate; Epinephrine dipivalate ester; Adrenaline dipivalate; Dipivalyl adrenaline; Dipivalyladrenaline; K-30081; 3,4-Dipivalyloxy-β-hydroxy-N-methylphenethylamine; 3,4-Dipivalyloxy-β-hydroxy-N-methyl-β-phenylethylamine
AHFS/Drugs.comInternational Drug Names
MedlinePlusa686005
Routes of
administration		Eye drops[1]
Drug classAdrenergic receptor agonist; Sympathomimetic
ATC code
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H29NO5
Molar mass351.443 g·mol−1
3D model (JSmol)
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 Y
  • Key:OCUJLLGVOUDECM-UHFFFAOYSA-N Y
  (verify)

Dipivefrine, or dipivefrin, also known as epinephrine pivalate and sold under the brand name Propine among others, is a sympathomimetic medication which is used in the treatment of open-angle glaucoma.[2][3] It is available as a 0.1% ophthalmic solution (eye drop).[1][4]

Side effects of dipivefrine include local eye reactions among others. Dipivefrine is a prodrug of epinephrine (adrenaline) and hence acts as a non-selective adrenergic receptor agonist.[5] It is a substituted phenethylamine and catecholamine and is an ester of epinephrine with much greater fat solubility.[6][7][8]

Dipivefrine was first described by 1975.[9] It is widely marketed throughout the world.[10] However, it is no longer available in the United States.[11]

  1. ^ a b "Dipivefrin: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1995. Retrieved 31 August 2024.
  2. ^ KD Tripari (2004). Essentials of Medical Pharmacology (5 ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN 81-8061-187-6.
  3. ^ Dipivefrin FDA Professional Drug Information.
  4. ^ Baranowski P, Karolewicz B, Gajda M, Pluta J (2014). "Ophthalmic drug dosage forms: characterisation and research methods". ScientificWorldJournal. 2014: 861904. doi:10.1155/2014/861904. PMC 3977496. PMID 24772038.
  5. ^ Arthur S, Cantor LB (September 2011). "Update on the role of alpha-agonists in glaucoma management". Exp Eye Res. 93 (3): 271–283. doi:10.1016/j.exer.2011.04.002. PMID 21524649.
  6. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference GoldbergKolkerKass1980 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference StellaBorchardtHageman2007 was invoked but never defined (see the help page).
  9. ^ McClure DA (1 June 1975). "The Effect of a Pro-drug of Epinephrine (Dipivalyl Epinephrine) in Glaucoma—General Pharmacology, Toxicology, and Clinical Experience". Pro-drugs as Novel Drug Delivery Systems. ACS Symposium Series. Vol. 14. Washington, D. C.: American Chemical Society. pp. 225–235. doi:10.1021/bk-1975-0014.ch006. ISBN 978-0-8412-0291-7.
  10. ^ Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
  11. ^ Zhang L, Weizer JS, Musch DC (2017). "Perioperative medications for preventing temporarily increased intraocular pressure after laser trabeculoplasty". Cochrane Database Syst Rev. 2017 (2): CD010746. doi:10.1002/14651858.CD010746.pub2. PMC 5477062. PMID 28231380.
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