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Details

Stereochemistry ACHIRAL
Molecular Formula C22H25N3O
Molecular Weight 347.4534
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDORAMIN

SMILES

O=C(NC1CCN(CCC2=CNC3=C2C=CC=C3)CC1)C4=CC=CC=C4

InChI

InChIKey=JXZZEXZZKAWDSP-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Indoramin is an alpha-1 selective antagonist of adrenergic receptor, sold under trade names Baratol and Doralese, and now available as a generic. It has no reflex tachycardia and direct myocardial depression action and is used to treat benign prostate hyperplasia (as 20 mg tablets) or reduce blood pressure (as 25 mg strength tablets). It was also investigated as a treatment of a migraine and congestive heart failure.

CNS Activity

Originator

PMID

PMID

TitleDatePMID
A double-blind comparison of indoramin and propranolol in the treatment of moderate to severe essential hypertension.
1983
Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin.
1986 Feb
The alpha 1-adrenergic receptor that mediates smooth muscle contraction in human prostate has the pharmacological properties of the cloned human alpha 1c subtype.
1994 Apr
Use of recombinant alpha 1-adrenoceptors to characterize subtype selectivity of drugs for the treatment of prostatic hypertrophy.
1995 Jan 16
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.
1997 Jul
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies.
1999 Apr 16
A double-blind randomized placebo-controlled trial of oral indoramin to treat chronic anal fissure.
2001 May
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.
2002 Feb
[Migraine: a disease, not a symptom].
2002 Jan 1
Prokinetic effect of indoramin, an alpha-adrenergic antagonist, on human gall-bladder.
2002 Oct
The medical and surgical management of chronic anal fissure.
2002 Sep
Use of alpha-blockers and the risk of hip/femur fractures.
2003 Dec
Drug-related hyperprolactinemia.
2003 Feb
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.
2003 Jul
[Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database].
2003 Mar-Apr
Effect of cyproterone acetate on alpha1-adrenoceptor subtypes in rat vas deferens.
2003 Nov
Current treatment options for fissure-in-ano.
2004 Jan-Mar
5-Alpha reductase inhibition provides superior benefits to alpha blockade by preventing AUR and BPH-related surgery.
2004 May
Khat chewing and arterial blood pressure. A randomized controlled clinical trial of alpha-1 and selective beta-1 adrenoceptor blockade.
2005 Apr
Pharmacological advancements in the treatment of chronic anal fissure.
2005 Nov
Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod.
2006 Feb 23
Non surgical therapy for anal fissure.
2006 Oct 18
Multiple GPCR conformations and signalling pathways: implications for antagonist affinity estimates.
2007 Aug
Prokinetic effect of alpha-adrenergic antagonist, and beta-adrenergic antagonist on gall-bladder motility in humans with gall-stone disease.
2007 Jul
Pharmacological causes of hyperprolactinemia.
2007 Oct
Alpha antagonists and intraoperative floppy iris syndrome: A spectrum.
2008 Dec
Recent advances in the pharmacotherapy of chronic anal fissure: an update.
2008 Jul
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008 Oct
Torsade de pointes: a severe and unknown adverse effect in indoramin self-poisoning.
2009 Apr 3
[Acute bilateral angle-closure glaucoma induced by topiramate: contribution of Visante OCT].
2010 May
Patent

Patent

Sample Use Guides

In Vivo Use Guide
The recommended dose is one tablet (20 mg) twice a day. The tablet should be swallowed with water. Some elderly patients may need just one tablet at night. The patient’s doctor may increase their dose to a maximum total daily dose of 100 mg. The patient must not take more than their doctor has recommended.
Route of Administration: Oral
In Vitro Use Guide
Binding of indoramin to alpha1 receptors was studied using rat cerebral cortex membranes with [3H]prazosin to label alpha1 adrenoreceptors. Indoramin displaces prozasin with IC50 pKi of 7.61.
Name Type Language
INDORAMIN
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
INDORAMIN [USAN]
Common Name English
INDORAMIN [INN]
Common Name English
INDORAMIN [MI]
Common Name English
N-(1-(2-INDOL-3-YLETHYL)-4-PIPERIDYL)BENZAMIDE
Systematic Name English
BENZAMIDE, N-(1-(2-(1H-INDOL-3-YL)ETHYL)-4-PIPERIDINYL)-
Systematic Name English
INDORAMIN [WHO-DD]
Common Name English
WY-21901
Code English
WY 21901
Code English
Classification Tree Code System Code
WHO-VATC QC02CA02
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
WHO-ATC C02CA02
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
Code System Code Type Description
MERCK INDEX
M6280
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
248-041-5
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
ChEMBL
CHEMBL279516
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
WIKIPEDIA
INDORAMIN
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
PUBCHEM
33625
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY SWITZERF
RXCUI
5784
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY RxNorm
EPA CompTox
26844-12-2
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
MESH
D007217
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
INN
3064
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
NCI_THESAURUS
C65916
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
EVMPD
SUB08184MIG
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY
CAS
26844-12-2
Created by admin on Tue Mar 06 11:42:47 UTC 2018 , Edited by admin on Tue Mar 06 11:42:47 UTC 2018
PRIMARY