| Revision as of 14:06, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 456918017 of page Pramocaine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 07:42, 21 December 2024 edit 38.49.72.163 (talk) →Use: rmv unsupported segment that primarily promotes brands and includes information better presented elsewhere with refsTags: Mobile edit Mobile web edit |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use mdy dates|date=October 2013}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 416734986 |
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| verifiedrevid = 464213174 |
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| IUPAC_name = 4-morpholine |
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| IUPAC_name = 4-morpholine |
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| image = Pramoxine.svg |
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| image = Pramoxine.svg |
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<!--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 |
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<!--Clinical data--> |
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| Drugs.com = {{drugs.com|international|pramocaine}} |
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| tradename = |
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| MedlinePlus = a682429 |
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| Drugs.com = {{drugs.com|international|pramocaine}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| MedlinePlus = a682429 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = C |
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| pregnancy_category = |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_status = Depends on country, some formulations OTC others Rx only |
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| pregnancy_category = |
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| DailyMedID = 8bfeea34-25d5-4721-a17f-d9f1d0084cc3, 81ab7fa7-d9b0-49dc-9782-02f37e588c5e |
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| legal_UK = POM |
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| routes_of_administration = Topical, rectal, Vaginal |
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| legal_US = Rx-only |
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| legal_status = <small>(with ])</small> |
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| routes_of_administration = Topical, rectal |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| bioavailability = |
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| protein_bound = |
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| bioavailability = |
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| metabolism = |
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| protein_bound = |
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| elimination_half-life = |
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| metabolism = |
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| excretion = <!--Identifiers--> |
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| elimination_half-life = |
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| index2_label = hydrochloride |
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| excretion = |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 140-65-8 |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| CAS_number2 = 637-58-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 068X84E056 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 88AYB867L5 |
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| ATC_prefix = D04 |
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| ATC_suffix = AB07 |
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| ATC_supplemental = {{ATC|C05|AD07}} |
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| PubChem = 4886 |
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| KEGG = D08407 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB09345 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4717 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 8357 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1198 |
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<!--Chemical data-->| C = 17 |
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<!--Identifiers--> |
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| H = 27 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| N = 1 |
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| CAS_number = <!-- blanked - oldvalue: 140-65-8 --> |
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| O = 3 |
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| CAS_supplemental = {{CAS|637-58-1}} |
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| smiles = O(c2ccc(OCCCN1CCOCC1)cc2)CCCC |
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| ATC_prefix = D04 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ATC_suffix = AB07 |
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| 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 |
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| ATC_supplemental = {{ATC|C05|AD07}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem = 4886 |
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| StdInChIKey = DQKXQSGTHWVTAD-UHFFFAOYSA-N |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4717 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 068X84E056 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 8357 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1198 |
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<!--Chemical data--> |
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| C=17 | H=27 | N=1 | O=3 |
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| molecular_weight = 293.401 g/mol |
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| smiles = O(c2ccc(OCCCN1CCOCC1)cc2)CCCC |
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| InChI = 1/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 |
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| InChIKey = DQKXQSGTHWVTAD-UHFFFAOYAU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DQKXQSGTHWVTAD-UHFFFAOYSA-N |
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}} |
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}} |
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'''Pramocaine''' (] and ], also known as '''pramoxine''' or '''pramoxine HCl''') is a ] discovered at ] 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 ]. 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 ], 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. |
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== Use == |
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Topical anesthetics are used to relieve pain and itching caused by conditions such as ] or other minor burns, insect bites or stings, ], ], ], 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 hydrochloride ] form of pramocaine is water-soluble. |
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Pramocaine is a common component of ] ] preparations. |
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Pramocaine is also included in some topical antibiotics like ] 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> |
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==Synthesis== |
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] |
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The ether formation between ] ('''1''') and ] ('''2''') gives 4-butoxyphenol ('''3'''). Alkylation with 4-(3-chloropropyl)morpholine ('''4''') gives pramocaine ('''5'''). |
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== See also == |
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* ] |
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== References == |
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{{Reflist}} |
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{{Vasoprotectives}} |
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{{Antipruritics}} |
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] |
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] |
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] |