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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 of INDORAMIN HYDROCHLORIDE

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

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C22H25N3O
Molecular Weight 347.4534
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Wyeth
116
Curator's Comment: # Wyeth John & Brother Ltd

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 8.4 null [pKi]
Antagonist
2778
 7.4 null [pKi]
Antagonist
2778
 6.8 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
Primary
Approved
8429
BARATOL

Approved Use

Baratol Tablets are used to reduce high blood pressure.
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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
Patents

Patents

04162252
2

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:09:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:39 GMT 2023
Record UNII
DQ0Z3K8W92
Record Status Validated (UNII)
Record Version
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Name Type Language
INDORAMIN HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
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
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
DRUG BANK
DBSALT001077
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
EVMPD
SUB02679MIG
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
FDA UNII
DQ0Z3K8W92
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
CAS
38821-52-2
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL279516
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
RXCUI
235773
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY RxNorm
SMS_ID
100000086406
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
PUBCHEM
38102
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
NCI_THESAURUS
C170066
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
USAN
W-109
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
MERCK INDEX
m6280
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
254-136-2
Created by admin on Fri Dec 15 15:09:39 GMT 2023 , Edited by admin on Fri Dec 15 15:09:39 GMT 2023
PRIMARY
Related Record Type Details
Structure of INDORAMIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of INDORAMIN
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