Indoramin

Currently, Indoramin has become a topic of great relevance and interest for different areas of society. From academia to business, Indoramin has captured the attention of many people due to its impact and relevance today. Technological and social advances have contributed to the growth and importance of Indoramin in contemporary life, which has generated endless debates, discussions and analyzes around this topic. That is why this article will address in detail and critically the importance of Indoramin today, as well as its influence on different aspects of modern life.

Indoramin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • N-{1-piperidin-4-yl}benzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.659 Edit this at Wikidata
Chemical and physical data
FormulaC22H25N3O
Molar mass347.462 g·mol−1
3D model (JSmol)
  • O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2c3)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 names Baratol and Doralese) is a piperidine antiadrenergic agent.

It is an alpha-1 selective adrenoceptor antagonist with direct myocardial depression action; therefore, it results in no reflex tachycardia. It is also used in benign prostatic hyperplasia (BPH).

It is commonly synthesized from tryptophol.

Dosage

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

Side Effects

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

Synthesis

Tryptamine and serotonin 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 from tryptophol, to give a quaternary pyridinium salt (3); this intermediate was in turn hydrogenated with a Raney nickel catalyst to give indoramine.

Product withdrawal

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.

References

  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 from the original on July 25, 2022. Retrieved September 30, 2012.
  3. ^ Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.
  4. ^ "Indoramin hydrochloride". National Health Service (UK). Retrieved September 30, 2012.
  5. ^ "Indoramin 20mg tablets". Medicines.org.uk. Retrieved February 7, 2018.
  6. ^ ZA 6803204, Archibald JL, Jackson JO ; eidem, U.S. patent 3,527,761 (1969, 1970 both to Wyeth).
  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). Retrieved 2023-04-17.
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