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Details

Stereochemistry ACHIRAL
Molecular Formula C22H25N3O.ClH
Molecular Weight 383.9151
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDORAMIN HYDROCHLORIDE

SMILES

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

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 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H25N3O
Molecular Weight 347.4542
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
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
The medical and surgical management of chronic anal fissure.
2002 Sep
Use of alpha-blockers and the risk of hip/femur fractures.
2003 Dec
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
Increased cholinergic contractions of jejunal smooth muscle caused by a high cholesterol diet are prevented by the 5-HT4 agonist--tegaserod.
2006 Feb 23
Prokinetic effect of alpha-adrenergic antagonist, and beta-adrenergic antagonist on gall-bladder motility in humans with gall-stone disease.
2007 Jul
Alpha antagonists and intraoperative floppy iris syndrome: A spectrum.
2008 Dec
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 16:33:18 UTC 2021
Edited
by admin
on Sat Jun 26 16:33:18 UTC 2021
Record UNII
DQ0Z3K8W92
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDORAMIN HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
INDORAMIN HYDROCHLORIDE [MART.]
Common Name English
BENZAMIDE, N-(1-(2-(1H-INDOL-3-YL)ETHYL)-4-PIPERIDINYL)-, MONOHYDROCHLORIDE
Common Name English
INDORAMIN HYDROCHLORIDE [MI]
Common Name English
INDORAMIN HYDROCHLORIDE [WHO-DD]
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
38821-52-2
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
DRUG BANK
DBSALT001077
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
EVMPD
SUB02679MIG
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
FDA UNII
DQ0Z3K8W92
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
CAS
38821-52-2
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL279516
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
RXCUI
235773
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY RxNorm
PUBCHEM
38102
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
NCI_THESAURUS
C170066
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
MERCK INDEX
M6280
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
254-136-2
Created by admin on Sat Jun 26 16:33:18 UTC 2021 , Edited by admin on Sat Jun 26 16:33:18 UTC 2021
PRIMARY
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