Carbocisteine

Last updated
Carbocisteine
Carboxymethylcystein Formulae.png
Carbocisteine 3D.png
Names
IUPAC name
(R)-2-Amino-3-(carboxymethylsulfanyl)propanoic acid
Other names
S-Carboxymethyl-L-cysteine; Actithiol, Lisomucil, Muciclar, Mucodyne, Mucolex, Rhinathiol, Transbronchin [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.010.298 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1 Yes check.svgY
    Key: GBFLZEXEOZUWRN-VKHMYHEASA-N Yes check.svgY
  • InChI=1/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)
    Key: GBFLZEXEOZUWRN-UHFFFAOYAN
  • InChI=1/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
    Key: GBFLZEXEOZUWRN-VKHMYHEABX
  • O=C(O)C(N)CSCC(=O)O
  • O=C(O)[C@@H](N)CSCC(=O)O
Properties
C5H9NO4S
Molar mass 179.19 g·mol−1
AppearanceColorless solid
Melting point 204 to 207 °C (399 to 405 °F; 477 to 480 K)
Pharmacology
R05CB03 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Carbocisteine, also called carbocysteine, is a mucolytic that reduces the viscosity of sputum and so can be used to help relieve the symptoms of chronic obstructive pulmonary disorder (COPD) and bronchiectasis by allowing the sufferer to bring up sputum more easily. [2] [3] Carbocisteine should not be used with antitussives (cough suppressants) or medicines that dry up bronchial secretions.

It was first described in 1951 and came into medical use in 1960. [4] Carbocisteine is produced by alkylation of cysteine with chloroacetic acid. [5]

Related Research Articles

A bronchodilator or broncholytic is a substance that dilates the bronchi and bronchioles, decreasing resistance in the respiratory airway and increasing airflow to the lungs. Bronchodilators may be originating naturally within the body, or they may be medications administered for the treatment of breathing difficulties, usually in the form of inhalers. They are most useful in obstructive lung diseases, of which asthma and chronic obstructive pulmonary disease are the most common conditions. Although this remains somewhat controversial, they might be useful in bronchiolitis and bronchiectasis. They are often prescribed but of unproven significance in restrictive lung diseases.

<span class="mw-page-title-main">Cough</span> Sudden expulsion of air from the lungs as a reflex to clear irritants

A cough is a sudden expulsion of air through the large breathing passages which can help clear them of fluids, irritants, foreign particles and microbes. As a protective reflex, coughing can be repetitive with the cough reflex following three phases: an inhalation, a forced exhalation against a closed glottis, and a violent release of air from the lungs following opening of the glottis, usually accompanied by a distinctive sound.

<span class="mw-page-title-main">Sputum</span> Mucus that is coughed up from the lower airways

Sputum is mucus that is coughed up from the lower airways. In medicine, sputum samples are usually used for a naked eye examination, microbiological investigation of respiratory infections and cytological investigations of respiratory systems. It is crucial that the specimen does not include any mucoid material from the nose or oral cavity.

<span class="mw-page-title-main">Bronchiectasis</span> Disease of the lungs

Bronchiectasis is a disease in which there is permanent enlargement of parts of the airways of the lung. Symptoms typically include a chronic cough with mucus production. Other symptoms include shortness of breath, coughing up blood, and chest pain. Wheezing and nail clubbing may also occur. Those with the disease often get lung infections.

<span class="mw-page-title-main">Acetylcysteine</span> Medication used to treat overdose of paracetamol

Acetylcysteine, also known as N-acetylcysteine (NAC), is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders like pneumonia and bronchitis. It has been used to treat lactobezoar in infants. It can be taken intravenously, by mouth, or inhaled as a mist. Some people use it as a dietary supplement.

<span class="mw-page-title-main">Non-invasive ventilation</span> Breathing support administered through a face mask

Non-invasive ventilation (NIV) is the use of breathing support administered through a face mask, nasal mask, or a helmet. Air, usually with added oxygen, is given through the mask under positive pressure; generally the amount of pressure is alternated depending on whether someone is breathing in or out. It is termed "non-invasive" because it is delivered with a mask that is tightly fitted to the face or around the head, but without a need for tracheal intubation. While there are similarities with regard to the interface, NIV is not the same as continuous positive airway pressure (CPAP), which applies a single level of positive airway pressure throughout the whole respiratory cycle; CPAP does not deliver ventilation but is occasionally used in conditions also treated with NIV.

Tracheobronchitis is inflammation of the trachea and bronchi. It is characterised by a cough, fever, and purulent sputum and is therefore suggestive of pneumonia. It is classified as a respiratory tract infection.

Immunostimulants, also known as immunostimulators, are substances that stimulate the immune system usually in a non-specific manner by inducing activation or increasing activity of any of its components. One notable example is the granulocyte macrophage colony-stimulating factor. The goal of this stimulated immune response is usually to help the body have a stronger immune system response in order to improve outcomes in the case of an infection or cancer malignancy. There is also some evidence that immunostimulants may be useful to help decrease severe acute illness related to chronic obstructive pulmonary disease or acute infections in the lungs.

<span class="mw-page-title-main">Erdosteine</span> Chemical to treat chronic bronchitis

Erdosteine is a molecule with mucolytic activity. Structurally it is a thiol derivative characterized by the presence of two thiol groups. These two functional sulfhydryl groups contained in the molecule are released following first-pass metabolism with the conversion of erdosteine into its pharmacologically active metabolite Met-I.

<span class="mw-page-title-main">Bronchitis</span> Inflammation of the large airways in the lungs

Bronchitis is inflammation of the bronchi in the lungs that causes coughing. Bronchitis usually begins as an infection in the nose, ears, throat, or sinuses. The infection then makes its way down to the bronchi. Symptoms include coughing up sputum, wheezing, shortness of breath, and chest pain. Bronchitis can be acute or chronic.

<span class="mw-page-title-main">Diffuse panbronchiolitis</span> Inflammatory lung disease

Diffuse panbronchiolitis (DPB) is an inflammatory lung disease of unknown cause. It is a severe, progressive form of bronchiolitis, an inflammatory condition of the bronchioles. The term diffuse signifies that lesions appear throughout both lungs, while panbronchiolitis refers to inflammation found in all layers of the respiratory bronchioles. DPB causes severe inflammation and nodule-like lesions of terminal bronchioles, chronic sinusitis, and intense coughing with large amounts of sputum production.

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

Roflumilast, sold under the trade name Daxas among others, is a drug that acts as a selective, long-acting inhibitor of the enzyme phosphodiesterase-4 (PDE-4). It has anti-inflammatory effects and is used as an orally administered drug for the treatment of inflammatory conditions of the lungs such as chronic obstructive pulmonary disease (COPD).

Pulmonary rehabilitation, also known as respiratory rehabilitation, is an important part of the management and health maintenance of people with chronic respiratory disease who remain symptomatic or continue to have decreased function despite standard medical treatment. It is a broad therapeutic concept. It is defined by the American Thoracic Society and the European Respiratory Society as an evidence-based, multidisciplinary, and comprehensive intervention for patients with chronic respiratory diseases who are symptomatic and often have decreased daily life activities. In general, pulmonary rehabilitation refers to a series of services that are administered to patients of respiratory disease and their families, typically to attempt to improve the quality of life for the patient. Pulmonary rehabilitation may be carried out in a variety of settings, depending on the patient's needs, and may or may not include pharmacologic intervention.

<span class="mw-page-title-main">Acute exacerbation of chronic obstructive pulmonary disease</span> Medical condition

An acute exacerbation of chronic obstructive pulmonary disease, or acute exacerbations of chronic bronchitis (AECB), is a sudden worsening of chronic obstructive pulmonary disease (COPD) symptoms including shortness of breath, quantity and color of phlegm that typically lasts for several days.

In some individuals, the effect of oxygen on chronic obstructive pulmonary disease is to cause increased carbon dioxide retention,

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

Piclamilast, is a selective PDE4 inhibitor. It is comparable to other PDE4 inhibitors for its anti-inflammatory effects. It has been investigated for its applications to the treatment of conditions such as chronic obstructive pulmonary disease, bronchopulmonary dysplasia and asthma. It is a second generation compound that exhibits structural functionalities of the PDE4 inhibitors cilomilast and roflumilast. The structure for piclamilast was first elucidated in a 1995 European patent application. The earliest mention of the name "piclamilast" was used in a 1997 publication.

ELOM-080 is the active ingredient of the herbal medicine named GeloMyrtol forte. The acronym ELOM stands for the oils from Eucalyptus, Lemon, (Sweet) Orange and Myrtle that it contains.

<span class="mw-page-title-main">Chronic obstructive pulmonary disease</span> Lung disease involving long-term poor airflow

Chronic obstructive pulmonary disease (COPD) is a type of progressive lung disease characterized by long-term respiratory symptoms and airflow limitation. The main symptoms of COPD include shortness of breath and a cough, which may or may not produce mucus. COPD progressively worsens, with everyday activities such as walking or dressing becoming difficult. While COPD is incurable, it is preventable and treatable. The two most common types of COPD are emphysema and chronic bronchitis and have been the two classic COPD phenotypes. Emphysema is defined as enlarged airspaces (alveoli) whose walls have broken down resulting in permanent damage to the lung tissue. Chronic bronchitis is defined as a productive cough that is present for at least three months each year for two years. Both of these conditions can exist without airflow limitation when they are not classed as COPD. Emphysema is just one of the structural abnormalities that can limit airflow and can exist without airflow limitation in a significant number of people. Chronic bronchitis does not always result in airflow limitation but in young adults who smoke the risk of developing COPD is high. Many definitions of COPD in the past included emphysema and chronic bronchitis, but these have never been included in GOLD report definitions. Emphysema and chronic bronchitis remain the predominant phenotypes of COPD but there is often overlap between them and a number of other phenotypes have also been described. COPD and asthma may coexist and converge in some individuals. COPD is associated with low-grade systemic inflammation.

<span class="mw-page-title-main">Chronic pulmonary aspergillosis</span> Fungal infection

Chronic pulmonary aspergillosis is a long-term fungal infection caused by members of the genus Aspergillus—most commonly Aspergillusfumigatus. The term describes several disease presentations with considerable overlap, ranging from an aspergilloma—a clump of Aspergillus mold in the lungs—through to a subacute, invasive form known as chronic necrotizing pulmonary aspergillosis which affects people whose immune system is weakened. Many people affected by chronic pulmonary aspergillosis have an underlying lung disease, most commonly tuberculosis, allergic bronchopulmonary aspergillosis, asthma, or lung cancer.

<span class="mw-page-title-main">Emphysema</span> Medical condition

Emphysema is any air-filled enlargement in the body's tissues. Most commonly emphysema refers to the enlargement of air spaces (alveoli) in the lungs, and is also known as pulmonary emphysema.

References

  1. Carbocisteine. drugbank.ca
  2. Zheng JP, Kang J, Huang SG, Chen P, Yao WZ, Yang L, Bai CX, Wang CZ, Wang C, Chen BY, Shi Y, Liu CT, Chen P, Li Q, Wang ZS, Huang YJ, Luo ZY, Chen FP, Yuan JZ, Yuan BT, Qian HP, Zhi RC, Zhong NS (2008). "Effect of carbocisteine on acute exacerbation of chronic obstructive pulmonary disease (PEACE Study): A randomised placebo-controlled study". Lancet. 371 (9629): 2013–2018. doi:10.1016/S0140-6736(08)60869-7. PMID   18555912. S2CID   43278410.
  3. Yasuda H, Yamaya M, Sasaki T, Inoue D, Nakayama K, Tomita N, Yoshida M, Sasaki H (2006). "Carbocisteine reduces frequency of common colds and exacerbations in patients with chronic obstructive pulmonary disease". Journal of the American Geriatrics Society. 54 (2): 378–380. doi:10.1111/j.1532-5415.2005.00592_9.x. PMID   16460403. S2CID   1580116.
  4. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 544. ISBN   9783527607495.
  5. Karlheinz Drauz; Ian Grayson; Axel Kleemann; Hans‐Peter Krimmer; Wolfgang Leuchtenberger; Christoph Weckbecker (2007). "Amino Acids". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_057.pub2.