Pramocaine

Pramocaine
Clinical data
Trade names	Analpram HC, Caladryl, Caladryl Clear, Cortane-B, Epifoam, Gold Bond Maximum Relief, Itch-X, Pramosone, Prax, Proctodan-HC, Proctofoam, Tronolane, Vagisil Medicated
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682429
License data	US DailyMed: 8bfeea34-25d5-4721-a17f-d9f1d0084cc3, 81ab7fa7-d9b0-49dc-9782-02f37e588c5e;
Routes of; administration	Topical, rectal, Vaginal
ATC code	D04AB07 (WHO) C05AD07 (WHO);
Legal status
Legal status	Depends on country, some formulations OTC others Rx only;
Identifiers
	IUPAC name 4-[3-(4-Butoxyphenoxy)propyl]morpholine;
CAS Number	140-65-8 ; hydrochloride: 637-58-1 ;
PubChem CID	4886;
DrugBank	DB09345 ;
ChemSpider	4717 ;
UNII	068X84E056; hydrochloride: 88AYB867L5 ;
KEGG	D08407;
ChEBI	CHEBI:8357 ;
ChEMBL	ChEMBL1198 ;
CompTox Dashboard (EPA)	DTXSID8040692 ;
ECHA InfoCard	100.004.933
Chemical and physical data
Formula	C17H27NO3
Molar mass	293.407 g·mol−1
3D model (JSmol)	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 ; Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N ;
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Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCl) 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.

^ ^a ^b ^c 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.

[Schmidt_1953-1] 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.

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