Tropanserin

Last updated
Tropanserin
Tropanserin.svg
Clinical data
ATC code
  • None
Identifiers
  • [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3,5-dimethylbenzoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H23NO2
Molar mass 273.376 g·mol−1
3D model (JSmol)
  • CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)c2cc(C)cc(C)c2
  • InChI=1S/C17H23NO2/c1-11-6-12(2)8-13(7-11)17(19)20-16-9-14-4-5-15(10-16)18(14)3/h6-8,14-16H,4-5,9-10H2,1-3H3/t14-,15+,16+
  • Key:HDDNYFLPWFSBLN-ZSHCYNCHSA-N

Tropanserin (INN; MDL-72,422) is a drug which acts as a potent and selective 5-HT3 receptor antagonist. [1] It was investigated in clinical trials for the treatment of migraine in the 1980s but was never marketed. [2]

Contents

Synthesis

Tropanserin can be prepared by the reaction of tropine with 3,5-dimethylbenzoyl chloride.

Tropanserin synthesis Tropanserin synthesis.svg
Tropanserin synthesis

See also

Related Research Articles

Metoclopramide Medication used for stomach and related problems

Metoclopramide is a medication used for stomach and esophageal problems. It is commonly used to treat and prevent nausea and vomiting, to help with emptying of the stomach in people with delayed stomach emptying, and to help with gastroesophageal reflux disease. It is also used to treat migraine headaches.

Ergoline

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.

Cimetidine Medicine that reduces stomach acid

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.

Nefazodone

Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant which was first marketed by Bristol-Myers Squibb in 1994 but has since largely been discontinued. BMS withdrew it from the market by 2004 due to decreasing sales due to the rare incidence of severe liver damage and the onset of generic competition. The incidence of severe liver damage is approximately 1 in every 250,000 to 300,000 patient-years. Generic versions were introduced in 2003.

Phenoxybenzamine

Phenoxybenzamine is a non-selective, irreversible alpha blocker.

Methylergometrine

Methylergometrine, also known as methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in the treatment of migraine. It reportedly produces psychedelic effects similar to those of lysergic acid diethylamide (LSD) at high doses.

Methysergide

Methysergide, sold under the brand names Deseril and Sansert, is a monoaminergic medication of the ergoline and lysergamide groups which is used in the prophylaxis and treatment of migraine and cluster headaches. It has been withdrawn from the market in the United States and Canada due to adverse effects. It is taken by mouth.

Ritanserin

Ritanserin is a serotonin receptor antagonist which was never marketed for clinical use but has been used in scientific research.

Lisuride

Lisuride, sold under the brand name Dopergin among others, is a monoaminergic medication of the ergoline class which is used in the treatment of Parkinson's disease, migraine, and high prolactin levels. It is taken by mouth.

Cyproheptadine

Cyproheptadine, sold under the brand name Periactin among others, is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties.

Tropisetron

Tropisetron is a serotonin 5-HT3 receptor antagonist used mainly as an antiemetic to treat nausea and vomiting following chemotherapy, although it has been used experimentally as an analgesic in cases of fibromyalgia.

Antimigraine drug

Antimigraine drugs are medications intended to reduce the effects or intensity of migraine headache. They include drugs for the treatment of acute migraine symptoms as well as drugs for the prevention of migraine attacks.

A serotonin antagonist, or serotonin receptor antagonist, is a drug used to inhibit the action at serotonin (5-HT) receptors.

Telcagepant

Telcagepant (INN) is a calcitonin gene-related peptide receptor antagonist which was an investigational drug for the acute treatment and prevention of migraine, developed by Merck & Co..

Calcitonin gene-related peptide (CGRP) receptor antagonists are a class of drugs that act as antagonists of the calcitonin gene-related peptide receptor (CGRPR).

Zanoterone

Zanoterone, also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinical trials, and also showed an unacceptable incidence rate and severity of side effects. As such, it was not further developed.

Filorexant

Filorexant (INN, USAN) (code name MK-6096) is an orexin antagonist which is or was under development by Merck for the treatment of insomnia. It is a dual antagonist of the OX1 and OX2 receptors. As of March 2014, filorexant has completed phase II clinical trials. It was also investigated as a migraine prophylaxis, but was not found effective, and in major depressive disorder and painful diabetic neuropathy. As of May 2015, filorexant is no longer listed on Merck's online development pipeline.

Selurampanel

Selurampanel is a drug closely related to the quinoxalinedione series which acts as a competitive antagonist of the AMPA and kainate receptors and, as of 2015, is being investigated in clinical trials by Novartis for the treatment of epilepsy. It has also been studied in the acute treatment of migraine, and was found to produce some pain relief, but with a relatively high rate of side effects.

Amesergide

Amesergide is a serotonin receptor antagonist of the ergoline and lysergamide families related to methysergide which was under development by Eli Lilly and Company for the treatment of a variety of conditions including depression, anxiety, schizophrenia, male sexual dysfunction, migraine, and thrombosis but was never marketed. It reached phase II clinical trials for the treatment of depression, erectile dysfunction, and premature ejaculation prior to the discontinuation of its development.

Ubrogepant

Ubrogepant, sold under the brand name Ubrelvy, is a medication used for the acute (immediate) treatment of migraine with or without aura in adults. It is not indicated for the preventive treatment of migraine. It is the first drug in the class of oral calcitonin gene-related peptide receptor antagonists approved for the acute treatment of migraine.

References

  1. King FD, Jones BJ, Sanger GJ (22 October 1993). 5-Hydroxytryptamine-3 Receptor Antagonists. CRC Press. p. 244. ISBN   978-0-8493-5463-2 . Retrieved 6 May 2012.
  2. Johnson G (1 August 1987). "Recent Advances in Migraine Research". In Bailey DM (ed.). Annual Reports in Medicinal Chemistry. 22. Academic Press. p. 44. doi:10.1016/S0065-7743(08)61153-7. ISBN   978-0-08-058366-2.
  3. US 4563465,Fozard JR, Gittos MW,"Treatment of migraine with substituted tropyl benzoate derivatives",issued 7 January 1986, assigned to Merrell Dow Pharma