Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Indoramin

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Indoramin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.043.659Edit this at Wikidata
Chemical and physical data
FormulaC22H25N3O
Molar mass347.462 g·mol−1
3D model (JSmol)
  • O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2[nH]c3)CC4
  • InChI=1S/C22H25N3O/c26-22(17-6-2-1-3-7-17)24-19-11-14-25(15-12-19)13-10-18-16-23-21-9-5-4-8-20(18)21/h1-9,16,19,23H,10-15H2,(H,24,26) checkY
  • Key:JXZZEXZZKAWDSP-UHFFFAOYSA-N checkY

Indoramin (trade namesBaratol andDoralese) is apiperidineantiadrenergic agent.

It is analpha-1 selective adrenoceptor antagonist[1] with direct myocardial depression action; therefore, it results in no reflextachycardia. It is also used inbenign prostatic hyperplasia (BPH).[2]

It is commonly synthesized fromtryptophol.[3]

Dosage

[edit]

Indoramin is commonly prescribed as 20 mg tablets when used in BPH.[4]

Side Effects

[edit]

Drowsiness, dizziness, dry mouth, nasal congestion, headache, fatigue, weight gain,hypotension,postural hypotension, depression, problems with ejaculation, diarrhoea, nausea, increased need to pass urine, andpalpitations.[5]

Synthesis

[edit]

Tryptamine andserotonin are naturally occurring indole ethylamino compounds with pronounced pharmacological activities. They have served as the inspiration for synthesis of numerous analogues.

One such study involved alkylation of 4-benzamidopyridine (2) with a bromoethyy compound (1) derived fromtryptophol, to give a quaternarypyridinium salt (3); this intermediate was in turn hydrogenated with aRaney nickel catalyst to give indoramine.[6][7]

Product withdrawal

[edit]

On May 31, 2013, the French National Agency for the Safety of Medicines and Health Products (ANSM) concluded that the benefit/risk ratio of this product was unfavorable and withdrew Vidora's marketing authorization and recalled its batches from the market on June 3, 2013.[8]

References

[edit]
  1. ^Pierce V, Shepperson NB, Todd MH, Waterfall JF (February 1986)."Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin".British Journal of Pharmacology.87 (2):433–441.doi:10.1111/j.1476-5381.1986.tb10834.x.PMC 1916533.PMID 3955309.
  2. ^"Indoramin 20mg tablets". Medicines.org.uk. April 20, 2011. Archived fromthe original on July 25, 2022. RetrievedSeptember 30, 2012.
  3. ^Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.
  4. ^"Indoramin hydrochloride". National Health Service (UK). RetrievedSeptember 30, 2012.
  5. ^"Indoramin 20mg tablets". Medicines.org.uk. RetrievedFebruary 7, 2018.
  6. ^ZA 6803204, Archibald JL, Jackson JO ; eidem,U.S. patent 3,527,761 (1969, 1970 both toWyeth).
  7. ^Archibald JL, Alps BJ, Cavalla JF, Jackson JL (November 1971). "Synthesis and hypotensive activity of benzamidopiperidylethylindoles".Journal of Medicinal Chemistry.14 (11):1054–1059.doi:10.1021/jm00293a009.PMID 5115203.
  8. ^"Actualités".ANSM (in French). Retrieved2023-04-17.
Sympatholytic (and closely related)antihypertensives (C02)
Sympatholytics
(antagonizeα-adrenergic
vasoconstriction)
Central
α2-Adrenergic receptor agonists
Adrenergic release inhibitors
Imidazoline receptor agonists
Ganglion-blocking/nicotinic antagonists
Peripheral
Indirect
Monoamine oxidase inhibitors
VMAT inhibitors
Tyrosine hydroxylase inhibitors
Direct
α1-Adrenergic receptor blockers
Non-selective α-adrenergic receptor blockers
Otherantagonists
Serotonin receptor antagonists
Endothelin receptor antagonists (forPHTooltip Pulmonary hypertension)
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Stub icon

Thisantihypertensive-related article is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Indoramin&oldid=1282584561"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp