Butamirate

Last updated
Butamirate
Butamirate.png
Clinical data
Trade names Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix
AHFS/Drugs.com International Drug Names
ATC code
Pharmacokinetic data
Protein binding 98%
Elimination half-life 6 hours
Excretion 90% renal
Identifiers
  • 2-(2-diethylaminoethoxy)ethyl 2-phenylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.038.172 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H29NO3
Molar mass 307.434 g·mol−1
3D model (JSmol)
  • O=C(OCCOCCN(CC)CC)C(c1ccccc1)CC
  • InChI=1S/C18H29NO3/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3/h7-11,17H,4-6,12-15H2,1-3H3 Yes check.svgY
  • Key:DDVUMDPCZWBYRA-UHFFFAOYSA-N Yes check.svgY
   (verify)

Butamirate (or brospamin, trade names Acodeen, Codesin, Pertix, Sinecod, Sinecoden, Sinecodix) is a cough suppressant. [1] It has been marketed in Europe and Mexico, but not in the United States. [2]

Contents

As the citrate salt, it is sold in the form of lozenges, syrup, tablets, dragées, or pastilles. Adverse effects can include nausea, diarrhea, vertigo, and exanthema. [2]

Pharmacology

A study found it to bind to the cough center in the medulla oblongata, more specifically the dextromethorphan-binding site in guinea pig brain with high affinity. [3]

As a 2-(2-diethylaminoethoxy)ethyl ester, it is chemically related to oxeladin and pentoxyverine, which are in the same class. (Oxeladin has an additional ethyl group in its carboxylic acid, pentoxyverine has both ethyl groups of oxeladin replaced by one cyclopentyl in the same place.)

See also

Related Research Articles

<span class="mw-page-title-main">Recreational use of dextromethorphan</span>

Dextromethorphan, or DXM, a common active ingredient found in many over-the-counter cough suppressant cold medicines, is used as a recreational drug and entheogen for its dissociative effects. It has almost no psychoactive effects at medically recommended doses. However, dextromethorphan has powerful dissociative properties when administered in doses well above those considered therapeutic for cough suppression. Recreational use of DXM is sometimes referred to in slang form as "robo-tripping", whose prefix derives from the Robitussin brand name, or "Triple Cs", which derives from the Coricidin brand whose tablets are printed with "CC+C" for "Coricidin Cough and Cold". However, this brand presents additional danger when used at recreational doses due to the presence of chlorpheniramine.

<span class="mw-page-title-main">Cold medicine</span> Medication taken to relieve cold symptoms

Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including analgesics, antihistamines and decongestants, among many others. It also includes drugs which are marketed as cough suppressants or antitussives, but their effectiveness in reducing cough symptoms is unclear or minimal.

ATC code R05Cough and cold preparations is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup R05 is part of the anatomical group R Respiratory system.

<span class="mw-page-title-main">Promethazine</span> First-generation antihistamine and antiemetic

Promethazine is a first-generation antihistamine and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use. Promethazine is available by mouth in syrup or tablet dosage forms, as a rectal suppository, or by injection into a muscle.

<span class="mw-page-title-main">Dextrorphan</span> Psychoactive cough suppressant medication

Dextrorphan (DXO) is a psychoactive drug of the morphinan class which acts as an antitussive or cough suppressant and dissociative hallucinogen. It is the dextrorotatory enantiomer of racemorphan; the levorotatory enantiomer is levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan.

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

Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

<span class="mw-page-title-main">Dextromethorphan</span> Antitussive medication of the dissociative class

Dextromethorphan is a medication most often used as a cough suppressant in over-the-counter cold and cough medicines. It is sold in syrup, tablet, spray, and lozenge forms. In 2022, the FDA approved a certain formulation of it to serve as a rapid acting antidepressant in patients with major depressive disorder.

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

Pholcodine is a drug which is an opioid cough suppressant (antitussive). It helps suppress unproductive coughs and also has a mild sedative effect, but has little or no analgesic effects. It is also known as morpholinylethylmorphine and homocodeine.

<span class="mw-page-title-main">Pentoxyverine</span> Antitussive / cough suppressant

Pentoxyverine (rINN) or carbetapentane is an antitussive commonly used for cough associated with illnesses like common cold. It is sold over-the-counter in the United States as Solotuss, or in combination with other medications, especially decongestants. One such product is Certuss, a combination of guaifenesin and pentoxyverine.

<span class="mw-page-title-main">Codeine</span> Opiate and prodrug of morphine used to treat pain

Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications.

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

Clofedanol (INN) or chlophedianol (BAN) is a centrally acting cough suppressant used in the treatment of dry cough. Clofedanol has local anesthetic, antispasmodic, and antihistamine properties, and may have anticholinergic effects at high doses.

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

Tipepidine (INN), also known as tipepidine hibenzate (JAN), is a synthetic, non-opioid antitussive and expectorant of the thiambutene class. It acts as an inhibitor of G protein-coupled inwardly-rectifying potassium channels (GIRKs). The drug was discovered in the 1950s, and was developed in Japan in 1959. It is used as the hibenzate and citrate salts.

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

Cloperastine (INN) or cloperastin, in the forms of cloperastine hydrochloride (JAN) and cloperastine fendizoate, is an antitussive and antihistamine that is marketed as a cough suppressant in Japan, Hong Kong, and in some European countries. It was first introduced in 1972 in Japan, and then in Italy in 1981.

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

Oxeladin is a cough suppressant. It is a highly potent and effective drug used to treat all types of cough of various etiologies. It is not related to opium or its derivatives, so treatment with oxeladin is free of risk of dependence or addiction. Oxeladin has none of the side effects which are present when common antitussives, such as codeine and its derivatives, are used. It may be used at every age, as well as in patients with heart disease, since it has a high level of safety and a great selectivity to act on the bulbar centre of cough.

<span class="mw-page-title-main">Dimemorfan</span> Cough suppressant

Dimemorfan (INN), or dimemorfan phosphate (JAN), also known as 3,17-dimethylmorphinan, is an antitussive of the morphinan family that is widely used in Japan and is also marketed in Spain and Italy. It was developed by Yamanouchi Pharmaceutical and introduced in Japan in 1975. It was later introduced in Spain in 1981 and Japan in 1985.

<span class="mw-page-title-main">Alazocine</span> Synthetic opioid analgesic

Alazocine, also known more commonly as N-allylnormetazocine (NANM), is a synthetic opioid analgesic of the benzomorphan family related to metazocine, which was never marketed. In addition to its opioid activity, the drug is a sigma receptor agonist, and has been used widely in scientific research in studies of this receptor. Alazocine is described as a potent analgesic, psychotomimetic or hallucinogen, and opioid antagonist. Moreover, one of its enantiomers was the first compound that was found to selectively label the σ1 receptor, and led to the discovery and characterization of the receptor.

<span class="mw-page-title-main">Racemorphan</span> Racemic mixture

Racemorphan, or morphanol, is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:

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

Dextrallorphan (DXA) is an chemical of the morphinan class that is used in scientific research. It acts as a σ1 receptor agonist and NMDA receptor antagonist. It has no significant affinity for the σ2, μ-opioid, or δ-opioid receptor, or for the serotonin or norepinephrine transporter. As an NMDA receptor antagonist, in vivo, it is approximately twice as potent as dextromethorphan, and five-fold less potent than dextrorphan.

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

Caramiphen is an anticholinergic drug used in the treatment of Parkinson's disease. In combination with phenylpropanolamine it is used as a cough suppressant and nasal decongestant to treat symptoms associated with respiratory illnesses such as cold, allergies, hay fever, and sinusitis. It was added to the British National Formulary in 1963, with a dosage of 10 to 20 mg. Side effects include nausea, dizziness, and drowsiness.

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

Moguisteine is a non-narcotic, peripherally acting antitussive. In a small double-blind, randomized controlled trial, 200 mg of moguisteine suspension taken 3 times daily significantly reduced the frequency of coughing in patients with COPD, compared to placebo. It has also been studied in small trials in comparison to codeine and dextromethorphan, and has similar efficacy to both. It has not been approved for use in the United States.

References

  1. Germouty J, Weibel MA (November 1990). "[Clinical comparison of butamirate citrate with a codeine-based antitussive agent]". Revue Médicale de la Suisse Romande. 110 (11): 983–6. PMID   1980027.
  2. 1 2 Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. pp. 29–30. ISBN   0-8103-7177-4.
  3. Klein M, Musacchio JM (October 1989). "High affinity dextromethorphan binding sites in guinea pig brain. Effect of sigma ligands and other agents". The Journal of Pharmacology and Experimental Therapeutics. 251 (1): 207–15. PMID   2477524.