Alpiropride

Last updated

Alpiropride
Alpiropride.svg
Clinical data
Trade names Revistel, Rivistel, or Rivestel
Other namesIristel; RIV-2093; RIV2093; RIV 2093; Riv 2093; Riv-2093; Riv2093
Drug class Dopamine D2 receptor antagonist; Antihypertensive agent; Antimigraine agent
Identifiers
  • 4-amino-2-methoxy-5-(methylsulfamoyl)-N-[(1-prop-2-enylpyrrolidin-2-yl)methyl]benzamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.072.585 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H26N4O4S
Molar mass 382.48 g·mol−1
3D model (JSmol)
  • CNS(=O)(=O)C1=C(C=C(C(=C1)C(=O)NCC2CCCN2CC=C)OC)N
  • InChI=1S/C17H26N4O4S/c1-4-7-21-8-5-6-12(21)11-20-17(22)13-9-16(26(23,24)19-2)14(18)10-15(13)25-3/h4,9-10,12,19H,1,5-8,11,18H2,2-3H3,(H,20,22)
  • Key:QRQMZZNDJGHPHZ-UHFFFAOYSA-N

Alpiropride (INN Tooltip International Nonproprietary Name; brand name Revistel, Rivistel, or Rivestel) is a dopamine D2 receptor antagonist of the benzamide group related to sulpiride. [1] [2] [3] [4] [5] It is described as an antihypertensive agent and has been marketed for use as an antimigraine medication in Portugal. [1] [4] [2] The drug was first described by 1980 [1] and was introduced for medical use by 1989. [4] It remained marketed in Portugal as late as 2000. [2]

Related Research Articles

<span class="mw-page-title-main">Butriptyline</span> Atypical tricyclic antidepressant medication

Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed. Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

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

Corbadrine, sold under the brand name Neo-Cobefrine and also known as levonordefrin and α-methylnorepinephrine, is a catecholamine sympathomimetic used as a topical nasal decongestant and vasoconstrictor in dentistry in the United States. It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.

<span class="mw-page-title-main">Medifoxamine</span> Withdrawn atypical antidepressant drug

Medifoxamine, previously sold under the brand names Clédial and Gerdaxyl, is an atypical antidepressant with additional anxiolytic properties acting via dopaminergic and serotonergic mechanisms which was formerly marketed in France and Spain, as well as Morocco. The drug was first introduced in France sometime around 1990. It was withdrawn from the market in 1999 (Morocco) and 2000 (France) following incidences of hepatotoxicity.

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

Amidephrine, or amidefrine, sold under the brand name Fentrinol among others, is a selective α1-adrenergic receptor agonist which is described as an adrenergic or sympathomimetic, vasoconstrictor, and topical nasal decongestant used to treat allergic rhinitis. It is used as the mesylate salt, which has the generic names amidefrine mesilate and amidephrine mesylate. The drug is a substituted phenethylamine derivative and is also known as 3-methylsulfonamidyl-β-hydroxy-N-methylphenethylamine. As of 2000, it remained marketed only in Austria.

<span class="mw-page-title-main">Nemonapride</span> Antipsychotic medication

Nemonapride, also previously known as emonapride and sold under the brand name Emilace, is an atypical antipsychotic which is used in the treatment of schizophrenia. It is taken by mouth.

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

Delanterone, also known as 1α-methylandrosta-4,16-dien-3-one, is a steroidal antiandrogen described as an anti-acne agent which was never marketed. The compound showed poor efficacy as an antiandrogen in vivo in animals, suggestive of low activity or a short terminal half-life, and likely in relation to this was not further developed. It was described and characterized in the literature in 1977.

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

Oxendolone, sold under the brand names Prostetin and Roxenone, is an antiandrogen and progestin medication which is used in Japan in the treatment of enlarged prostate. However, this use is controversial due to concerns about its clinical efficacy. Oxendolone is not effective by mouth and must be given by injection into muscle.

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

Topterone, also known as 17α-propyltestosterone or as 17α-propylandrost-4-en-17β-ol-3-one, is a steroidal antiandrogen that was first reported in 1978 and was developed for topical administration but, due to poor effectiveness, was never marketed.

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

Trengestone, sold under the brand names Reteroid, Retroid, and Retrone, is a progestin medication which was formerly used to treat menstrual disorders but is now no longer marketed. It is taken by mouth.

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

Broparestrol, also known as α-bromo-α,β-diphenyl-β-p-ethylphenylethylene (BDPE), is a synthetic, nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that has been used in Europe as a dermatological agent and for the treatment of breast cancer. The drug is described as slightly estrogenic and potently antiestrogenic, and inhibits mammary gland development and suppresses prolactin levels in animals. It is structurally related to clomifene and diethylstilbestrol. Broparestrol is a mixture of E- and Z- isomers, both of which are active, and are similarly antiestrogenic but, unlike broparestrol, were never marketed.

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

Flumexadol (INN) is a drug described and researched as a non-opioid analgesic which was never marketed. It has been found to act as an agonist of the serotonin 5-HT1A and 5-HT2C receptors and, to a much lesser extent, of the 5-HT2A receptor. According to Nilsson (2006) in a paper on 5-HT2C receptor agonists as potential anorectics, "The (+)-enantiomer of this compound showed [...] affinity for the 5-HT2C receptor (Ki) 25 nM) [...] and was 40-fold selective over the 5-HT2A receptor in receptor binding studies. The racemic version [...], also known as 1841 CERM, was originally reported to possess analgesic properties while no association with 5-HT2C receptor activity was mentioned." It is implied that flumexadol might be employable as an anorectic in addition to analgesic. Though flumexadol itself has never been approved for medical use, oxaflozane is a prodrug of the compound that was formerly used clinically in France as an antidepressant and anxiolytic agent.

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

Allenestrol, or allenoestrol, also known as α,α-dimethyl-β-ethylallenolic acid or as methallenestrilphenol, is a synthetic, nonsteroidal estrogen and a derivative of allenolic acid that was never marketed. A methyl ether of allenestrol, methallenestril (methallenestrol), is also an estrogen, but, in contrast to allenestrol, has been marketed.

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

Apparicine is a monoterpenoid tricyclic indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of indole alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.

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

Estramustine is an estrogen and cytostatic antineoplastic agent which was never marketed. It is a carbamate derivative of estradiol and acts in part as a prodrug of estradiol in the body. Estramustine phosphate, the C17β phosphate ester of estramustine and a prodrug of estramustine, estromustine, estradiol, and estrone, is marketed and used in the treatment of prostate cancer.

<span class="mw-page-title-main">Perlapine</span> Sedative and hypnotic medication

Perlapine, sold under the brand names Hypnodine and Pipnodine, is a hypnotic and sedative of the tricyclic group which is marketed in Japan. It acts primarily as a potent antihistamine, and also has anticholinergic, antiserotonergic, antiadrenergic, and some antidopaminergic activity. The drug has relatively weak affinity for the dopamine D2 receptor (IC50Tooltip Half-maximal inhibitory concentration = 1,803 nM) and, in accordance, is said to be ineffective as an antipsychotic. However, it retains higher affinity for the dopamine D1 receptor (IC50 = 198 nM). Its IC50 values are 19 nM for the α1-adrenergic receptor, 4,945 nM for the α2-adrenergic receptor, and 70 nM for the serotonin 5-HT2A receptor. Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.

<span class="mw-page-title-main">Dopamantine</span> Antiparkinsonian drug

Dopamantine is an antiparkinsonian drug of the adamantane group that developed for treatment of Parkinson's disease but was never marketed. It was developed and studied in the 1970s and was said to have reached early clinical trials.

<span class="mw-page-title-main">Carmantadine</span> Abandoned antiparkinsonian drug of the adamantane group

Carmantadine is an antiparkinsonian agent of the adamantane group that was never marketed. It is structurally related to amantadine and shares some of its pharmacological actions. Another related drug is dopamantine. Carmantadine was first described by 1972 and is said to have reached early clinical trials.

<span class="mw-page-title-main">Centpropazine</span> Experimental antidepressant

Centpropazine is an experimental antidepressant which was under development for the treatment major depressive disorder in India but was never marketed. It is described as having imipramine-like clinical effects, reversing reserpine-induced effects in animals, and potentiating amphetamine-induced effects in animals. The mechanism of action of centpropazine is unknown. The drug reached phase 3 clinical trials prior to the discontinuation of its development. It was first described in the scientific literature by 1980.

<span class="mw-page-title-main">Tepirindole</span> Abandoned antipsychotic drug

Tepirindole (INNTooltip International Nonproprietary Name; developmental code names RU-27592, HR-592) is a tryptamine-related atypical antipsychotic and major tranquilizer which was never marketed. It is similar in structure to tryptamines but is not technically a tryptamine itself and is instead a piperidinyl indole. The drug is said to act on dopamine D2, serotonin 5-HT2, and α1-adrenergic receptors. It is a potent dopamine receptor antagonist but reportedly has little propensity to cause catalepsy and has been said to potentially be useful in treating the negative symptoms of schizophrenia. The drug may also act as a potent serotonin receptor agonist. Tepirindole was first described in the literature by 1979.

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

Bufenadrine, also known as 2-tert-butyldiphenhydramine, is a drug described as an antiemetic, antihistamine, anticholinergic, and antiparkinsonian agent which was never marketed. It is the 2-tert-butyl analogue of diphenhydramine. The drug was found to produce stereoselective hepatotoxicity in animals and this led to the discontinuation of its development. Bufenadrine was first described in the literature by 1967. Its INNTooltip International Nonproprietary Name suffix "-drine" is generally for sympathomimetics but bufenadrine itself is not actually a sympathomimetic or related agent.

References

  1. 1 2 3 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 33. ISBN   978-1-4757-2085-3 . Retrieved 24 October 2024.
  2. 1 2 3 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 31. ISBN   978-3-88763-075-1 . Retrieved 24 October 2024.
  3. Milne GW (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 358. ISBN   978-1-351-78990-5 . Retrieved 24 October 2024.
  4. 1 2 3 Ong HH, Allen RC (1989). "Chapter 31. To Market, To Market -1988". Annual Reports in Medicinal Chemistry. Vol. 24. Elsevier. pp. 295–315. doi:10.1016/s0065-7743(08)60553-9. ISBN   978-0-12-040524-4. ISSN   0065-7743.
  5. Ren S, Lien LL, Lien EJ (August 1997). "Molecular modeling and structural analysis of benzamide derivatives with and without extrapyramidal syndrome side effects.". Current Medicinal Chemistry. Vol. 4. Bentham Science Publishers. pp. 271-278 (275). Retrieved 24 October 2024.