Pramocaine

Last updated

Pramocaine
Pramoxine.svg
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a682429
Routes of
administration
Topical, rectal, Vaginal
ATC code
Legal status
Legal status
  • Depends on country, some formulations OTC others Rx only
Identifiers
  • 4-[3-(4-Butoxyphenoxy)propyl]morpholine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.933 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H27NO3
Molar mass 293.407 g·mol−1
3D model (JSmol)
  • O(c2ccc(OCCCN1CCOCC1)cc2)CCCC
  • 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 Yes check.svgY
  • Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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.

Contents

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.

Pramocaine is also included in some topical antibiotics like Neosporin Plus Pain Relief used to treat or prevent infections due to its pain releving effects. However there is no additional antibiotic effect compared to antibiotics without pramocaine [3]

Synthesis

Patent: Sino: Pramocaine synthesis.svg
Patent: Sino:

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

See also

Related Research Articles

<span class="mw-page-title-main">Anesthesia</span> State of medically-controlled temporary loss of sensation or awareness

Anesthesia or anaesthesia is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia, paralysis, amnesia, and unconsciousness. An individual under the effects of anesthetic drugs is referred to as being anesthetized.

Local anesthesia is any technique to induce the absence of sensation in a specific part of the body, generally for the aim of inducing local analgesia, i.e. local insensitivity to pain, although other local senses may be affected as well. It allows patients to undergo surgical and dental procedures with reduced pain and distress. In many situations, such as cesarean section, it is safer and therefore superior to general anesthesia.

<span class="mw-page-title-main">Local anesthetic</span> Medications to reversibly block pain

A local anesthetic (LA) is a medication that causes absence of all sensation in a specific body part without loss of consciousness, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes unconsciousness. Local anesthetics are most commonly used to eliminate pain during or after surgery. When it is used on specific nerve pathways, paralysis also can be induced.

<span class="mw-page-title-main">Procaine</span> Local anesthetic drug

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.

<span class="mw-page-title-main">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

<span class="mw-page-title-main">Benzocaine</span> Anesthetic

Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old. In the European Union, the contraindication applies to children under 12 years of age.

<span class="mw-page-title-main">Nystatin</span> Pharmaceutical drug

Nystatin, sold under the brandname Mycostatin among others, is an antifungal medication. It is used to treat Candida infections of the skin including diaper rash, thrush, esophageal candidiasis, and vaginal yeast infections. It may also be used to prevent candidiasis in those who are at high risk. Nystatin may be used by mouth, in the vagina, or applied to the skin.

<span class="mw-page-title-main">Topical medication</span> Medication applied to body surfaces

A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes including creams, foams, gels, lotions, and ointments. Many topical medications are epicutaneous, meaning that they are applied directly to the skin. Topical medications may also be inhalational, such as asthma medications, or applied to the surface of tissues other than the skin, such as eye drops applied to the conjunctiva, or ear drops placed in the ear, or medications applied to the surface of a tooth. The word topical derives from Greek τοπικόςtopikos, "of a place".

Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit the itching often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those from mosquitoes, fleas, and mites, and contact dermatitis and urticaria caused by plants such as poison ivy or stinging nettle. It can also be caused by chronic kidney disease and related conditions.

<span class="mw-page-title-main">Inhalational anesthetic</span> Volatile or gaseous anesthetic compound delivered by inhalation

An inhalational anesthetic is a chemical compound possessing general anesthetic properties that can be delivered via inhalation. They are administered through a face mask, laryngeal mask airway or tracheal tube connected to an anesthetic vaporiser and an anesthetic delivery system. Agents of significant contemporary clinical interest include volatile anesthetic agents such as isoflurane, sevoflurane and desflurane, as well as certain anesthetic gases such as nitrous oxide and xenon.

<span class="mw-page-title-main">Eye drop</span> Liquid applied directly to the eye

Eye drops or eyedrops are liquid drops applied directly to the surface of the eye usually in small amounts such as a single drop or a few drops. Eye drops usually contain saline to match the salinity of the eye. Drops containing only saline and sometimes a lubricant are often used as artificial tears to treat dry eyes or simple eye irritation such as itching or redness. Eye drops may also contain one or more medications to treat a wide variety of eye diseases. Depending on the condition being treated, they may contain steroids, antihistamines, sympathomimetics, beta receptor blockers, parasympathomimetics, parasympatholytics, prostaglandins, nonsteroidal anti-inflammatory drugs (NSAIDs), antibiotics, antifungals, or topical anesthetics.

Neomycin/polymyxin B/bacitracin, also known as triple antibiotic ointment, is an antibiotic medication used to reduce the risk of infections following minor skin injuries. It contains the three antibiotics neomycin, polymyxin B, and bacitracin. It is for topical use.

<span class="mw-page-title-main">Bupivacaine</span> Pair of enantiomers

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease feeling in a specific area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

<span class="mw-page-title-main">Proxymetacaine</span> Chemical compound

Proxymetacaine (INN) or proparacaine (USAN) is a topical anesthetic drug of the aminoester group.

A topical anesthetic is a local anesthetic that is used to numb the surface of a body part. They can be used to numb any area of the skin as well as the front of the eyeball, the inside of the nose, ear or throat, the anus and the genital area. Topical anesthetics are available in creams, ointments, aerosols, sprays, lotions, and jellies. Examples include benzocaine, butamben, dibucaine, lidocaine, oxybuprocaine, pramoxine, proxymetacaine (proparacaine), and tetracaine.

<span class="mw-page-title-main">Ear drop</span> Form of medication placed in ears

Ear drops are a form of topical medication for the ears used to treat infection, inflammation, impacted ear wax and local anesthesia. They are commonly used for short-term treatment and can be purchased with or without a prescription. Before using ear drops, refer to the package insert or consult a health professional for the amount of drops to use and the duration of treatment.

<span class="mw-page-title-main">Cinchocaine</span> Chemical compound

Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.

Cetacaine is a topical anesthetic that contains the active ingredients benzocaine (14%), butamben (2%), and tetracaine hydrochloride (2%). Cetacaine also contains small amounts of benzalkonium chloride at 0.5% and 0.005% of cetyl dimethyl ethyl ammonium bromide all in a bland water-soluble base. Although Cetacaine has been widely used in the medical and dental fields, it has yet to be officially approved by the FDA. Cetacaine is produced by the company Cetylite Industries, Inc. and they provide Cetacaine in three forms: liquid, gel, and spray.

<span class="mw-page-title-main">Ketocaine</span> Chemical compound

Ketocaine (INN) is an amino ether local anesthetic of the butyrophenone family used topically for pain relief. It is marketed in Italy.

Obstetric anesthesia or obstetric anesthesiology, also known as ob-gyn anesthesia or ob-gyn anesthesiology, is a sub-specialty of anesthesiology that provides peripartum pain relief (analgesia) for labor and anesthesia for cesarean deliveries ('C-sections').

References

  1. 1 2 3 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. "Neosporin Plus Pain Relief Ointment, TriBiozene Ointment (neomycin/polymyxin B/ bacitracin/pramoxine) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved July 3, 2023.
  4. Salva Salvatore Joseph De & Migliarese Joseph Francis, U.S. Patent 3,172,805 (1965 to Colgate Palmolive Co).
  5. Li Yuedong, et al. CN 106045942 (2016 to Shandong Chengchuang Blue Sea Pharmaceutical Technology Co., Ltd.).