Pramocaine

Pramocaine
Names
Trade namesAnalpram, Fleet Pain-Relief, Itch-X, Preparation H, others
Other namesPramoxine, pramoxine HCI
IUPAC name
  • 4-[3-(4-Butoxyphenoxy)propyl]morpholine
Clinical data
Main usesPain, itching[1][2]
Side effectsBurning at the site of application[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Topical, rectal, Vaginal
External links
AHFS/Drugs.comMonograph
MedlinePlusa682429
Legal
Legal status
  • Depends on country, some formulations OTC others Rx only
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 checkY
  • Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N checkY

Pramocaine, also known as pramoxine, is a medication used to improve pain and itching such as occurs in hemorrhoids or insect bites.[1][2] It is applied to the skin.[1] There are versions that come mixed with corticosteroids.[1]

Common side effects include burning at the site of application.[1] Other side effects may include allergic reactions, though it is generally safe even if someone has reactions to other local anesthetics.[1] It works by stabilizing the cell membrane of neurons.[1]

Pramocaine was described in 1953.[3] It is available over the counter.[1] In the United States a bottle costs about 5 USD as of 2021.[4]

Medical 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.[5] 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.

History

During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.[3]

Notes

  1. 1 2 3 4 5 6 7 8 9 "Pramoxine Monograph for Professionals". Drugs.com. Archived from the original on March 4, 2021. Retrieved October 29, 2021.
  2. 1 2 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 103. ISBN 978-0857114105.
  3. 1 2 SCHMIDT, JL; BLOCKUS, LE; RICHARDS, RK (November 1953). "The pharmacology of pramoxine hydrochloride: a new topical local anesthetic". Current researches in anesthesia & analgesia. 32 (6:1): 418–25. PMID 13107298.
  4. ↑ "Compare Pramoxine Hcl Prices - GoodRx". GoodRx. Retrieved October 29, 2021.
  5. ↑ "Pramoxine". MedlinePlus Drug Information. National Library of Medicine. September 25, 2013. Archived from the original on April 20, 2015. Retrieved October 9, 2013.
Identifiers:
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