Pramocaine

Pramocaine
Clinical data

AHFS/Drugs.com	International Drug Names
MedlinePlus	a682429
Routes of administration	Topical, rectal, Vaginal
ATC code	D04AB07 (WHO) C05AD07 (WHO)
Legal status
Legal status	CA: OTC UK: POM (Prescription only) OTC/POM
Identifiers
IUPAC name 4-[3-(4-Butoxyphenoxy)propyl]morpholine
CAS Number	140-65-8^N 637-58-1 (HCl)
PubChem (CID)	4886
ChemSpider	4717^Y
UNII	068X84E056^Y
ChEBI	CHEBI:8357^Y
ChEMBL	CHEMBL1198^Y
ECHA InfoCard	100.004.933
Chemical and physical data
Formula	C₁₇H₂₇NO₃
Molar mass	293.401 g/mol
3D model (Jmol)	Interactive image
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)

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.

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 and dibucaine are also common ingredients in over the counter hemorrhoid preparations.

Notes

1 2 3 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.
↑ "Pramoxine". MedlinePlus Drug Information. National Library of Medicine. September 25, 2013. Retrieved October 9, 2013.

Vasoprotectives (C05)

Antihemorrhoidals for topical use

corticosteroids	Hydrocortisone Prednisolone Betamethasone Fluorometholone Fluocortolone Dexamethasone Fluocinolone acetonide Fluocinonide

local anesthetics	Lidocaine Tetracaine Benzocaine Dibucaine Procaine Oxetacaine Pramocaine

other	Tribenoside

Antivaricose therapy

heparins or heparinoids for topical use	Organo-heparinoid Sodium apolate Heparin Pentosan polysulfate

sclerosing agents for local injection	Monoethanolamine oleate Polidocanol Inverted sugar syrup Sodium tetradecyl sulfate Phenol

other	Calcium dobesilate

Capillary stabilising agents

bioflavonoids	Rutoside Monoxerutin Diosmin Troxerutin Hidrosmin

other	Tribenoside Etamsylate

Antipruritics (D04)

Antihistamines for topical use	Thonzylamine Mepyramine Thenalidine Tripelennamine Chloropyramine Promethazine Tolpropamine Dimetindene Clemastine Bamipine Isothipendyl Diphenhydramine Chlorphenoxamine

Anesthetics for topical use	Lidocaine Dibucaine Oxybuprocaine Benzocaine Quinisocaine Tetracaine Pramocaine

Others	Corticosteroids (e.g., hydrocortisone) Counterirritants (e.g., mint oil, menthol, camphor) Nalfurafine

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Pramocaine

Use

See also

Notes