U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of INDORAMIN

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

Molecular Formula C22H25N3O
Molecular Weight 347.4542
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

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

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
BARATOL

Approved Use

Baratol Tablets are used to reduce high blood pressure.
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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
[Migraine: a disease, not a symptom].
2002 Jan 1
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
Recent advances in the pharmacotherapy of chronic anal fissure: an update.
2008 Jul
Optimizing prophylactic treatment of migraine: Subtypes and patient matching.
2008 Oct
Patents

Patents

Sample Use Guides

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 Sat Jun 26 09:59:14 UTC 2021
Edited
by admin
on Sat Jun 26 09:59:14 UTC 2021
Record UNII
0Z802HMY7H
Record Status Validated (UNII)
Record Version
  • Download
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
NCI_THESAURUS C29713
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
WHO-VATC QC02CA02
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
WHO-ATC C02CA02
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
Code System Code Type Description
MERCK INDEX
M6280
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
248-041-5
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
ChEMBL
CHEMBL279516
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
WIKIPEDIA
INDORAMIN
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
PUBCHEM
33625
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
FDA UNII
0Z802HMY7H
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
RXCUI
5784
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY RxNorm
EPA CompTox
26844-12-2
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
MESH
D007217
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
INN
3064
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
NCI_THESAURUS
C65916
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
EVMPD
SUB08184MIG
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
DRUG CENTRAL
1443
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
CAS
26844-12-2
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
DRUG BANK
DB08950
Created by admin on Sat Jun 26 09:59:14 UTC 2021 , Edited by admin on Sat Jun 26 09:59:14 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY