Indoramin

Indoramin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	C02CA02 (WHO) ;
Identifiers
	IUPAC name N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide;
CAS Number	26844-12-2 ;
PubChem CID	33625;
IUPHAR/BPS	501;
DrugBank	DB08950 ;
ChemSpider	31014 ;
UNII	0Z802HMY7H;
KEGG	D04531 ;
ChEMBL	ChEMBL279516 ;
CompTox Dashboard (EPA)	DTXSID7048370 ;
ECHA InfoCard	100.043.659
Chemical and physical data
Formula	C22H25N3O
Molar mass	347.462 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2[nH]c3)CC4;
	InChI 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) ; Key:JXZZEXZZKAWDSP-UHFFFAOYSA-N ;

Indoramin (trade names Baratol and Doralese) is a piperidine antiadrenergic agent.

It is an alpha-1 selective adrenoceptor antagonist^[1] with direct myocardial depression action; therefore, it results in no reflex tachycardia. It is also used in benign prostatic hyperplasia (BPH).^[2]

It is commonly synthesized from tryptophol.^[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, and palpitations.^[5]

Synthesis[edit]

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.^[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]

^ 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.
^ "Indoramin 20mg tablets". Medicines.org.uk. April 20, 2011. Archived from the original on July 25, 2022. Retrieved September 30, 2012.
^ Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.
^ "Indoramin hydrochloride". National Health Service (UK). Retrieved September 30, 2012.
^ "Indoramin 20mg tablets". Medicines.org.uk. Retrieved February 7, 2018.
^ ZA 6803204, Archibald JL, Jackson JO ; eidem, U.S. patent 3,527,761 (1969, 1970 both to Wyeth).
^ 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.
^ "Actualités". ANSM (in French). Retrieved 2023-04-17.

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[pmid3955309-1] 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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