Pramocaine

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. During research and development, pramocaine 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 humans.[1] 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.

Pramocaine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682429
Routes of
administration		Topical, rectal, Vaginal
ATC code
Legal status
Legal status
  • Depends on country, some formulations OTC others Rx only
Identifiers
IUPAC name
  • 4-[3-(4-Butoxyphenoxy)propyl]morpholine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.933
Chemical and physical data
FormulaC17H27NO3
Molar mass293.407 g·mol−1
3D model (JSmol)
SMILES
  • O(c2ccc(OCCCN1CCOCC1)cc2)CCCC
InChI
  • InChI=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 Y
  • Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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.[2] 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 form of pramocaine is water-soluble.

Pramocaine is a common component of over the counter hemorrhoid preparations.

Synthesis
Patent:[3] Sino:[4]

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

See also

References
  1. Schmidt JL, Blockus LE, Richards RK (1953). "The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic". Current Researches in Anesthesia & Analgesia. 32 (6:1): 418–25. PMID 13107298.
  2. "Pramoxine". MedlinePlus Drug Information. U.S. National Library of Medicine. September 25, 2013. Retrieved October 9, 2013.
  3. Salva Salvatore Joseph De & Migliarese Joseph Francis, U.S. Patent 3,172,805 (1965 to Colgate Palmolive Co).
  4. Li Yuedong, et al. CN 106045942 (2016 to Shandong Chengchuang Blue Sea Pharmaceutical Technology Co., Ltd.).
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