pivenfrine

{{Short description|Chemical compound}}

{{Drugbox

| image = Pivenfrine.svg

| width = 225px

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 67577-23-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RB4XQ0T71U

| ATC_prefix = None

| ATC_suffix =

| PubChem = 130545

| DrugBank =

| ChemSpiderID = 115481

| ChEMBL = 2107163

| synonyms = Pivalylphenylephrine; Phenylephrine pivalate; β,3-Dihydroxy-N-methylphenethylamine 3-pivalate

| IUPAC_name = 3-[1-Hydroxy-2-(methylamino)ethyl]phenyl pivalate

| C=14 | H=21 | N=1 | O=3

| SMILES = CC(C)(C)C(=O)Oc1cccc(c1)C(CNC)O

| StdInChI = 1S/C14H21NO3/c1-14(2,3)13(17)18-11-7-5-6-10(8-11)12(16)9-15-4/h5-8,12,15-16H,9H2,1-4H3

| StdInChIKey = DQCAWJLMFJKICG-UHFFFAOYSA-N

}}

Pivenfrine ({{Abbrlink|INN|International Nonproprietary Name}}), also known as pivalylphenylephrine or phenylephrine pivalate, is a sympathomimetic and mydriatic agent which was never marketed.{{cite book | last=Elks | first=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=PA1001 | access-date=2024-09-01 | pages=61,1001}}{{cite book| vauthors = Ganellin CR, Triggle DJ |title=Dictionary of Pharmacological Agents|url=https://books.google.com/books?id=Z_mfTTIApVEC&pg=PA615|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=615–}}{{cite book|author=World Health Organization|title=International Nonproprietary Names (INN) for Pharmaceutical Substances|url=https://books.google.com/books?id=HcogPwAACAAJ|year=2000|publisher=World Health Organization|isbn=978-0-11-986227-0}}{{cite book| vauthors = Korolkovas A |title=Essentials of medicinal chemistry|url=https://books.google.com/books?id=6hxtAAAAMAAJ|year=1988|publisher=John Wiley & Sons, Incorporated|isbn=978-0-471-88356-2}} It is the 3-pivalyl ester of phenylephrine. Pivenfrine has much greater lipophilicity than phenylephrine.{{cite web | title=Pivenfrine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/130545 | access-date=1 September 2024}} Higher lipophilicity is known to greatly improve corneal permeability, as in dipivefrine (epinephrine dipivalate).{{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 = }} Another related compound is etilefrine pivalate (ethylnorphenylephrine pivalate).