Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pramocaine: Difference between pages

{{Short description|Chemical compound}}

{{Use mdy dates|date=October 2013}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464213174

| IUPAC_name = 4-[3-(4-Butoxyphenoxy)propyl]morpholine

| image = Pramoxine.svg

<!--Clinical data-->| tradename = Analpram HC, Caladryl, Caladryl Clear, Cortane-B, Epifoam, Gold Bond Maximum Relief, Itch-X, Pramosone, Prax, Proctodan-HC, Proctofoam, Tronolane, Vagisil Medicated

| Drugs.com = {{drugs.com|international|pramocaine}}

| MedlinePlus = a682429

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = C

| pregnancy_category =

| legal_status = Depends on country, some formulations OTC others Rx only

| DailyMedID = 8bfeea34-25d5-4721-a17f-d9f1d0084cc3, 81ab7fa7-d9b0-49dc-9782-02f37e588c5e

| routes_of_administration = Topical, rectal, Vaginal

<!--Pharmacokinetic data-->| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion = <!--Identifiers-->

| index2_label = hydrochloride

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 140-65-8

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 637-58-1

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

| UNII = 068X84E056

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 88AYB867L5

| ATC_prefix = D04

| ATC_suffix = AB07

| ATC_supplemental = {{ATC|C05|AD07}}

| PubChem = 4886

| KEGG = D08407

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB09345

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4717

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 8357

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1198

<!--Chemical data-->| C = 17

| H = 27

| N = 1

| O = 3

| smiles = O(c2ccc(OCCCN1CCOCC1)cc2)CCCC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DQKXQSGTHWVTAD-UHFFFAOYSA-N

'''Pramocaine''' ([[International Nonproprietary Name|INN]] and [[British Approved Name|BAN]], also known as '''pramoxine''' or '''pramoxine HCl''') is a [[topical anesthetic]] discovered at [[Abbott Laboratories]] in 1953<ref name="Schmidt_1953">{{cite journal | vauthors = Schmidt JL, Blockus LE, Richards RK | title = The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic | journal = Current Researches in Anesthesia & Analgesia | volume = 32 | issue = 6:1 | pages = 418–25 | date = 1953 | pmid = 13107298 | doi = }}</ref> and used as an [[antipruritic]]. During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.<ref name="Schmidt_1953" /> Pharmacologic study revealed it to be potent and of low acute and subacute toxicity, well tolerated by most mucous membranes and of a low sensitizing index in humans.<ref name="Schmidt_1953" /> Like other [[local anesthetics]], pramocaine decreases the permeability of neuronal membranes to sodium ions, blocking both initiation and conduction of nerve impulses. Depolarization and repolarization of excitable neural membranes is thus inhibited, leading to numbness.

== Use ==

Topical anesthetics are used to relieve pain and itching caused by conditions such as [[sunburn]] or other minor burns, insect bites or stings, [[poison ivy]], [[poison oak]], [[poison sumac]], and minor cuts and scratches.<ref>{{cite web|url=https://www.nlm.nih.gov/medlineplus/druginfo/meds/a682429.html |title=Pramoxine |work=MedlinePlus Drug Information |publisher= U.S. National Library of Medicine |date=September 25, 2013 |access-date=October 9, 2013}}</ref> The popular itch creams [[Gold Bond]] and some forms of [[calamine lotion]] use pramocaine [[hydrochloride]] to numb sensitive skin, as does the pain relief variant of [[Neosporin]] and some formulations of Sarna. The hydrochloride [[salt (chemistry)|salt]] form of pramocaine is water-soluble.

Pramocaine is a common component of [[Over-the-counter drug|over the counter]] [[hemorrhoid]] preparations.

Pramocaine is also included in some topical antibiotics like [[Neosporin|Neosporin Plus Pain Relief]] used to treat or prevent infections due to its pain relieving effects. However, there is no additional antibiotic effect compared to antibiotics without pramocaine.<ref>{{cite web |title=Neosporin Plus Pain Relief Ointment, TriBiozene Ointment (neomycin/polymyxin B/ bacitracin/pramoxine) dosing, indications, interactions, adverse effects, and more |url=https://reference.medscape.com/drug/neosporin-plus-pain-relief-ointment-tribiozene-ointment-neomycin-polymyxin-b-bacitracin-pramoxine-999349 |website=reference.medscape.com |access-date=3 July 2023}}</ref>

==Synthesis==

[[File:Pramocaine synthesis.svg|thumb|center|500px|Patent:<ref>Salva Salvatore Joseph De & Migliarese Joseph Francis, {{US patent|3172805}} (1965 to Colgate Palmolive Co).</ref> Sino:<ref>Li Yuedong, et al. {{Cite patent|CN|106045942}} (2016 to Shandong Chengchuang Blue Sea Pharmaceutical Technology Co., Ltd.).</ref>]]

The ether formation between [[hydroquinone]] ('''1''') and [[1-bromobutane]] ('''2''') gives 4-butoxyphenol [122-94-1] ('''3'''). Alkylation with 4-(3-chloropropyl)morpholine [57616-74-7] ('''4''') gives pramocaine ('''5''').

== See also ==

* [[Local anesthesia]]

== References ==

{{Reflist}}

{{Vasoprotectives}}

{{Antipruritics}}

[[Category:Local anesthetics]]

[[Category:4-Morpholinyl compounds]]

[[Category:Phenol ethers]]