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| 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 |
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| Routes of administration | Topical, rectal, Vaginal |
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| ECHA InfoCard | 100.004.933 |
| Chemical and physical data | |
| Formula | C17H27NO3 |
| Molar mass | 293.407 g·mol−1 |
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Pramocaine (INN andBAN, also known aspramoxine orpramoxine HCl) is atopical anesthetic discovered atAbbott Laboratories in 1953[1] and used as anantipruritic. 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 otherlocal 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.
Topical anesthetics are used to relieve pain and itching caused by conditions such assunburn or other minor burns, insect bites or stings,poison ivy,poison oak,poison sumac, and minor cuts and scratches.[2] The hydrochloridesalt form of pramocaine is water-soluble.
Pramocaine is a common component ofover the counterhemorrhoid preparations.
Pramocaine is also included in some topical antibiotics likeNeosporin Plus Pain Relief used to treat or prevent infections due to its pain relieving effects. However, there is no additional antibiotic effect compared to antibiotics without pramocaine.[3]
The ether formation betweenhydroquinone (1) and1-bromobutane (2) gives 4-butoxyphenol [122-94-1] (3). Alkylation with 4-(3-chloropropyl)morpholine [57616-74-7] (4) gives pramocaine (5).