INDORAMIN HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H25N3O.ClH
Molecular Weight	383.914
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AFJSFHAKSSWOKG-UHFFFAOYSA-N

InChI=1S/C22H25N3O.ClH/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);1H

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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	Potency
Alpha-1a adrenergic receptor 66 Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2778	8.4 null [pKi]
Alpha-1b adrenergic receptor 44 Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2778	7.4 null [pKi]
Alpha-1d adrenergic receptor 36 Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028	Antagonist 2778	6.8 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con509423.pdf	Primary	Approved 8429	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 567 Sources: https://www.drugs.com/uk/indoramin-hydrochloride-25-mg-tablets-leaflet.html	Primary	Approved 8429	BARATOL Approved Use Baratol Tablets are used to reduce high blood pressure.
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3543093	Primary	Not Provided 504	Unknown Approved Use Unknown
Migraine 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/49624	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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
Use of alpha-blockers and the risk of hip/femur fractures.	2003 Dec	14641795
Drug-related hyperprolactinemia.	2003 Feb	12602384
5-Alpha reductase inhibition provides superior benefits to alpha blockade by preventing AUR and BPH-related surgery.	2004 May	15082205
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
Prokinetic effect of alpha-adrenergic antagonist, and beta-adrenergic antagonist on gall-bladder motility in humans with gall-stone disease.	2007 Jul	17556905
Pharmacological causes of hyperprolactinemia.	2007 Oct	18473017
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 HYDROCHLORIDE

Official Name

English

INDORAMIN HYDROCHLORIDE [MART.]

Common Name

English

Indoramin hydrochloride [WHO-DD]

Common Name

English

BENZAMIDE, N-(1-(2-(1H-INDOL-3-YL)ETHYL)-4-PIPERIDINYL)-, MONOHYDROCHLORIDE

Common Name

English

INDORAMIN HYDROCHLORIDE [MI]

Common Name

English

WY-21,901 HCL

Code

English

INDORAMIN HCL

Common Name

English

INDORAMIN HYDROCHLORIDE [USAN]

Common Name

English

N-[1-(2-Indol-3-ylethyl)-4-piperidyl]benzamide monohydrochloride

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID1046504