Octatropine methylbromide

Last updated
Octatropine methylbromide
Octatropine methylbromide.svg
Clinical data
Other names8-Methyltropinium bromide 2- propylvalerate
Routes of
administration
Oral
ATC code
  • none
Pharmacokinetic data
Bioavailability 10 to 25% (oral)
Protein binding Unknown
Metabolism Hepatic
Elimination half-life Unknown
Identifiers
  • (endo)-8,8-dimethyl-8-azoniabicyclo[3.2.1]octan-3-yl] 2-propylpentanoate bromide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.001.169 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H32BrNO2
Molar mass 362.352 g·mol−1
3D model (JSmol)
  • CCCC(CCC)C(=O)O[C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C.[Br-]
  • InChI=1S/C17H32NO2.BrH/c1-5-7-13(8-6-2)17(19)20-16-11-14-9-10-15(12-16)18(14,3)4;/h13-16H,5-12H2,1-4H3;1H/q+1;/p-1/t14-,15+,16+; X mark.svgN
  • Key:QSFKGMJOKUZAJM-CNKDKAJDSA-M X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Octatropine methylbromide (INN) or anisotropine methylbromide (USAN), trade names Valpin, Endovalpin, Lytispasm and others, [1] is a muscarinic antagonist and antispasmodic. It was introduced to the U.S. market in 1963 as an adjunct in the treatment of peptic ulcer, [2] and promoted as being more specific to the gastrointestinal tract than other anticholinergics, although its selectivity was questioned in later studies. [3] [4]

Octatropine has been superseded by more effective agents in the treatment of peptic ulcer disease, and is no longer used. It is still sold in some countries in combination with other drugs, such as phenobarbital and metamizole.

Related Research Articles

Peptic ulcer disease is a break in the inner lining of the stomach, the first part of the small intestine, or sometimes the lower esophagus. An ulcer in the stomach is called a gastric ulcer, while one in the first part of the intestines is a duodenal ulcer. The most common symptoms of a duodenal ulcer are waking at night with upper abdominal pain, and upper abdominal pain that improves with eating. With a gastric ulcer, the pain may worsen with eating. The pain is often described as a burning or dull ache. Other symptoms include belching, vomiting, weight loss, or poor appetite. About a third of older people have no symptoms. Complications may include bleeding, perforation, and blockage of the stomach. Bleeding occurs in as many as 15% of cases.

An antispasmodic is a pharmaceutical drug or other agent that suppresses muscle spasms.

Anticholinergics are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system.

<span class="mw-page-title-main">Imidazopyridine</span> Class of compounds

An imidazopyridine is a nitrogen containing heterocycle that is also a class of drugs that contain this same chemical substructure. In general, they are GABAA receptor agonists, however recently proton pump inhibitors, aromatase inhibitors, NSAIDs and other classes of drugs in this class have been developed as well. Despite usually being similar to them in effect, they are not chemically related to benzodiazepines. As such, GABAA-agonizing imidazopyridines, pyrazolopyrimidines, and cyclopyrrones are sometimes grouped together and referred to as "nonbenzodiazepines." Imidazopyridines include:

<span class="mw-page-title-main">Gastritis</span> Stomach disease that is an inflammation of the lining of the stomach

Gastritis is inflammation of the lining of the stomach. It may occur as a short episode or may be of a long duration. There may be no symptoms but, when symptoms are present, the most common is upper abdominal pain. Other possible symptoms include nausea and vomiting, bloating, loss of appetite and heartburn. Complications may include stomach bleeding, stomach ulcers, and stomach tumors. When due to autoimmune problems, low red blood cells due to not enough vitamin B12 may occur, a condition known as pernicious anemia.

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

Cimetidine, sold under the brand name Tagamet among others, is a histamine H2 receptor antagonist that inhibits stomach acid production. It is mainly used in the treatment of heartburn and peptic ulcers.

<span class="mw-page-title-main">Indometacin</span> Anti-inflammatory drug

Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins.

Indigestion, also known as dyspepsia or upset stomach, is a condition of impaired digestion. Symptoms may include upper abdominal fullness, heartburn, nausea, belching, or upper abdominal pain. People may also experience feeling full earlier than expected when eating. Indigestion is relatively common, affecting 20% of people at some point during their life, and is frequently caused by gastroesophageal reflux disease (GERD) or gastritis.

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

Gastrointestinal perforation, also known as gastrointestinal rupture, is a hole in the wall of the gastrointestinal tract. The gastrointestinal tract is composed of hollow digestive organs leading from the mouth to the anus. Symptoms of gastrointestinal perforation commonly include severe abdominal pain, nausea, and vomiting. Complications include a painful inflammation of the inner lining of the abdominal wall and sepsis.

<span class="mw-page-title-main">Oxybutynin</span> Bladder medication

Oxybutynin, sold as under the brand names Ditropan among others, is a medication used to treat overactive bladder. It works similar to tolterodine, Darifenacin, and Solifenacin. While used for bed wetting in children, evidence to support this use is poor. It is taken by mouth or applied to the skin.

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

Chlorcyclizine is a first-generation antihistamine of the diphenylmethylpiperazine group marketed in the United States and certain other countries. It is used primarily to treat allergy symptoms such as rhinitis, urticaria, and pruritus, and may also be used as an antiemetic. In addition to its antihistamine effects, chlorcyclizine has some anticholinergic, antiserotonergic, and local anesthetic properties. It has been studied as a potential treatment for various flaviviruses like hepatitis C and Zika virus.

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

Melitracen is a tricyclic antidepressant (TCA), for the treatment of depression and anxiety. In addition to single drug preparations, it is also available as Deanxit, marketed by Lundbeck, a combination product containing both melitracen and flupentixol.

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

Niaprazine (INN) is a sedative-hypnotic drug of the phenylpiperazine group. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France, Italy, and Luxembourg. It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.

<span class="mw-page-title-main">Antihistamine</span> Drug that blocks histamine or histamine agonists

Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic drug that can be bought without a prescription and provides relief from nasal congestion, sneezing, or hives caused by pollen, dust mites, or animal allergy with few side effects. Antihistamines are usually for short-term treatment. Chronic allergies increase the risk of health problems which antihistamines might not treat, including asthma, sinusitis, and lower respiratory tract infection. Consultation of a medical professional is recommended for those who intend to take antihistamines for longer-term use.

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

Tridihexethyl is an anticholinergic, antimuscarinic and antispasmodic drug. It may be used, usually in combination with other drugs, to treat acquired nystagmus or peptic ulcer disease. Many patients discontinue the drug because of unwanted side effects.

Donnatal is a combination medication that provides natural belladonna alkaloids in a specific fixed ratio combined with phenobarbital to provide peripheral anticholinergic/antispasmodic action and mild sedation. Donnatal is manufactured for Concordia Pharmaceuticals by IriSys, LLC. It is available as tablets and 5 mL elixir. Active ingredients are listed as: phenobarbital (16.2 mg), hyoscyamine sulfate (0.1037 mg), atropine sulfate (0.0194 mg), and scopolamine hydrobromide (0.0065 mg). The latter two ingredients are found in plants of the family Solanaceae, such as belladonna.

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

Dacemazine (INN, also known as Ahistan and Histantine) is a phenothiazine derivative which acts as a histamine antagonist at the H1 subtype. First described in 1951, it was never marketed as a drug on its own, although a combination of dacemazine and di-tert-butylnaphthalenesulfonate was sold as an antispasmodic and antitussive under the trade name Codopectyl. It was also assessed as a possible anticancer drug.

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

Imipraminoxide, or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.

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

Pipofezine, sold under the brand name Azafen or Azaphen, is a tricyclic antidepressant approved in Russia for the treatment of depression. It was introduced in the late 1960s and is still used today.

<span class="mw-page-title-main">Acid peptic diseases</span> Overview of the acid peptic diseases of the stomach and gastrointestinal tract

Acid peptic diseases, such as peptic ulcers, Zollinger-Ellison syndrome, and gastroesophageal reflux disease, are caused by distinct but overlapping pathogenic mechanisms involving acid effects on mucosal defense. Acid reflux damages the esophageal mucosa and may also cause laryngeal tissue injury, leading to the development of pulmonary symptoms.

References

  1. Triggle DJ, Ganellin CR, MacDonald F (1997). Dictionary of Pharmacological Agents. Vol. 2. Boca Raton: Chapman & Hall/CRC. p. 1467. ISBN   0-412-46630-9. Retrieved on August 31, 2008 through Google Book Search.
  2. Batterman RC, Mouratoff GJ, Kaufman JE (May 1963). "Anisotropine methylbromide: a new antispasmodic for gastrointestinal disorders". Current Therapeutic Research, Clinical and Experimental. 5: 213–218. PMID   13966843.
  3. Gyermek L (1998). "Semisynthetic Derivatives of Tropane Alkaloids and o Other Atropine Esters". Pharmacology of antimuscarinic agents. Boca Raton: CRC Press. p. 183. ISBN   0-8493-8559-8. Retrieved on August 31, 2008 through Google Book Search.
  4. Bachrach WH (June 1972). "Clinical evaluation of anisotropine methyl bromide (valpin), an anticholinergic drug". The American Journal of Digestive Diseases. 17 (6): 505–512. doi:10.1007/BF02231205. PMID   4555460. S2CID   7836183.