Pramocaine: Difference between revisions

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{{drugbox |
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 464213174
| IUPAC_name = 4-[3-(4-butoxyphenoxy)propyl]morpholine
| IUPAC_name = 4-[3-(4-butoxyphenoxy)propyl]morpholine
| image = Pramoxine.svg
| image = Pramoxine.svg
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|pramocaine}}
| MedlinePlus = a682429
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_UK = POM
| legal_US =
| legal_CA = OTC
| legal_status =  OTC/POM
| routes_of_administration = Topical, rectal, Vaginal
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 140-65-8
| CAS_number = 140-65-8
| CAS_supplemental = {{CAS|637-58-1}} ([[hydrochloride]])
| CAS_supplemental = {{CAS|637-58-1}}
| ATC_prefix = D04
| ATC_prefix = D04
| ATC_suffix = AB07
| ATC_suffix = AB07
| ATC_supplemental = {{ATC|C05|AD07}}
| ATC_supplemental =   {{ATC|C05|AD07}}
| PubChem = 4886
| PubChem = 4886
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 17 | H = 27 | N = 1 | O = 3
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4717
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 068X84E056
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8357
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1198
 
<!--Chemical data-->
| C=17 | H=27 | N=1 | O=3  
| molecular_weight = 293.401 g/mol
| molecular_weight = 293.401 g/mol
| bioavailability =  
| smiles = O(c2ccc(OCCCN1CCOCC1)cc2)CCCC
| protein_bound =  
| 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
| metabolism =  
| InChIKey = DQKXQSGTHWVTAD-UHFFFAOYAU
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| 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
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US =  <!-- A / B            / C / D / X -->
| StdInChIKey = DQKXQSGTHWVTAD-UHFFFAOYSA-N
| pregnancy_category =
| legal_UK = POM
| legal_US = Rx-only
| legal_status = <small>(with [[hydrocortisone]])</small>
| routes_of_administration = Topical, rectal
}}
}}
'''Pramocaine''' ([[International Nonproprietary Name|INN]] and [[British Approved Name|BAN]], also known as '''pramoxine''') is a [[topical anesthetic]] used as an [[antipruritic]].
'''Pramocaine''' ([[International Nonproprietary Name|INN]] and [[British Approved Name|BAN]], also known as '''pramoxine''' or '''pramoxine HCI''') is a [[topical anesthetic]] discovered at Abbott Laboratories in 1953<ref name=":2">Schmidt JL, Blockus LE, Richards RK. The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic. Curr Res Anesth Analg. 1953 Nov-Dec;32(6:1):418-25.</ref> and used as an [[antipruritic]]. Chemically, it is ''p''-n butoxyphenyl gammamorpholinopropyl ether hydrochloride. During research and development, pramoxine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.<ref name=":2" /> 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 man.<ref name=":2" /> Like other [[local anesthetics]], paramoxine 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.


Popular itch cream [[Gold Bond]] uses pramocaine [[hydrochloride]] (hydrochloride used to ease absorption in the skin) to numb sensitive skin.
The popular itch creams [[Gold Bond]] and [[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]] form of pramocaine is water-soluble.


== Usage ==
== Usage ==


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>http://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202042.html</ref>
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=http://www.nlm.nih.gov/medlineplus/druginfo/meds/a682429.html |title=Pramoxine |work=MedlinePlus Drug Information |publisher=National Library of Medicine |date=September 25, 2013 |accessdate=October 9, 2013}}</ref> Pramocaine and [[dibucaine]] are also common ingredients in [[Over-the-counter drug|over the counter]] [[hemorrhoid]] preparations.


== Notes ==
==Synthesis==
{{Reflist}}
[[File:Pramoxine synthesis.png|thumb|center|700px|Pramoxine synthesis:<ref>{{cite doi|10.1021/jo01145a021}}</ref>]]


== See also ==
== See also ==
* [[Local anesthesia]]
* [[Local anesthesia]]
== Notes ==
{{Reflist|2}}
{{Vasoprotectives}}
{{Vasoprotectives}}
{{Antipruritics}}
{{Antipruritics}}
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[[Category:Local anesthetics]]
[[Category:Local anesthetics]]
[[Category:Morpholines]]
[[Category:Morpholines]]
[[Category:Phenol ethers]]
[[Category:Drug]]

Revision as of 15:00, 10 April 2015

Pramocaine
File:Pramoxine.svg
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682429
Routes of
administration		Topical, rectal, Vaginal
ATC code
Legal status
Legal status
  • CA: OTC
  • UK: POM (Prescription only)
  • OTC/POM
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC17H27NO3
Molar mass293.401 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCI) is a topical anesthetic discovered at Abbott Laboratories in 1953[1] and used as an antipruritic. Chemically, it is p-n butoxyphenyl gammamorpholinopropyl ether hydrochloride. During research and development, pramoxine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.[1] 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 man.[1] Like other local anesthetics, paramoxine 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.

The popular itch creams Gold Bond and 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 form of pramocaine is water-soluble.

Usage

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.[2] Pramocaine and dibucaine are also common ingredients in over the counter hemorrhoid preparations.

Synthesis

Pramoxine synthesis:[3]

See also

Notes

  1. ↑ 1.0 1.1 1.2 Schmidt JL, Blockus LE, Richards RK. The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic. Curr Res Anesth Analg. 1953 Nov-Dec;32(6:1):418-25.
  2. ↑ "Pramoxine". MedlinePlus Drug Information. National Library of Medicine. September 25, 2013. Retrieved October 9, 2013.
  3. ↑ Template:Cite doi


Template:Vasoprotectives Template:Antipruritics

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