INDORAMIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H25N3O
Molecular Weight	347.4542
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(cc1)C(=NC2CCN(CCc3c[nH]c4ccccc34)CC2)O

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
Sources: https://www.drugbank.ca/drugs/DB08950

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-1a adrenergic receptor 64 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2577	Benign prostatic hyperplasia Hypertension Congestive heart failure	8.40000000000000036 null [pKi]
Alpha-1b adrenergic receptor 42 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2577		7.40000000000000036 null [pKi]
Alpha-1d adrenergic receptor 34 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2577		6.79999999999999982 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con509423.pdf	Primary	Alpha-1a adrenergic receptor	Approved 7997	DORALESE Approved Use Indoramin 20 mg Tablets are used for a condition called ‘benign prostatic hyperplasia’ or BPH. The prostate is a gland found underneath the bladder in men. It surrounds the tube (called the urethra) which carries urine from the bladder to the outside of the body.
Hypertension 513 Sources: https://www.drugs.com/uk/indoramin-hydrochloride-25-mg-tablets-leaflet.html	Primary	Alpha-1a adrenergic receptor	Approved 7997	BARATOL Approved Use Baratol Tablets are used to reduce high blood pressure.
Congestive heart failure 48 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3543093	Primary	Alpha-1a adrenergic receptor	Not Provided 523
Migraine 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/49624	Primary		Not Provided 523

PubMed

Title	Date	PubMed
A double-blind comparison of indoramin and propranolol in the treatment of moderate to severe essential hypertension.	1983	6365463
Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin.	1986 Feb	3955309
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	8183249
Use of recombinant alpha 1-adrenoceptors to characterize subtype selectivity of drugs for the treatment of prostatic hypertrophy.	1995 Jan 16	7536677
Pharmacological pleiotropism of the human recombinant alpha1A-adrenoceptor: implications for alpha1-adrenoceptor classification.	1997 Jul	9249248
Human cloned alpha1A-adrenoceptor isoforms display alpha1L-adrenoceptor pharmacology in functional studies.	1999 Apr 16	10334511
A double-blind randomized placebo-controlled trial of oral indoramin to treat chronic anal fissure.	2001 May	12790983
The use of alpha-adrenoceptor antagonists in lower urinary tract disease.	2002 Feb	11829730
[Migraine: a disease, not a symptom].	2002 Jan 1	11852766
Prokinetic effect of indoramin, an alpha-adrenergic antagonist, on human gall-bladder.	2002 Oct	12269974
The medical and surgical management of chronic anal fissure.	2002 Sep	12469422
Use of alpha-blockers and the risk of hip/femur fractures.	2003 Dec	14641795
Drug-related hyperprolactinemia.	2003 Feb	12602384
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.	2003 Jul	12845422
[Drug-induced hyperprolactinemia: a case-non-case study from the national pharmacovigilance database].	2003 Mar-Apr	12942857
Effect of cyproterone acetate on alpha1-adrenoceptor subtypes in rat vas deferens.	2003 Nov	14576912
Current treatment options for fissure-in-ano.	2004 Jan-Mar	15881700
5-Alpha reductase inhibition provides superior benefits to alpha blockade by preventing AUR and BPH-related surgery.	2004 May	15082205
Khat chewing and arterial blood pressure. A randomized controlled clinical trial of alpha-1 and selective beta-1 adrenoceptor blockade.	2005 Apr	15900355
Pharmacological advancements in the treatment of chronic anal fissure.	2005 Nov	16259578
Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod.	2006 Feb 23	16504074
Non surgical therapy for anal fissure.	2006 Oct 18	17054170
Multiple GPCR conformations and signalling pathways: implications for antagonist affinity estimates.	2007 Aug	17629959
Pharmacological causes of hyperprolactinemia.	2007 Oct	18473017
Alpha antagonists and intraoperative floppy iris syndrome: A spectrum.	2008 Dec	19668424
Recent advances in the pharmacotherapy of chronic anal fissure: an update.	2008 Jul	18658016
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.	2008 Oct	19209286
Torsade de pointes: a severe and unknown adverse effect in indoramin self-poisoning.	2009 Apr 3	18191476
[Acute bilateral angle-closure glaucoma induced by topiramate: contribution of Visante OCT].	2010 May	20434235

Patents

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

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

NCI_THESAURUS

C29713