Identification

Name
Indoramin
Accession Number
DB08950
Type
Small Molecule
Groups
Withdrawn
Description

Indoramin is a discontinued piperidine antiadrenergic drug with the trade names Baratol and Doralese. It is a selective alpha-1 adrenergic antagonist with no reflex tachycardia and direct myocardial depression action.

Structure
Thumb
Synonyms
  • Indoramina
  • Indoramine
External IDs
Wy 21901
Product Ingredients
IngredientUNIICASInChI Key
Indoramin HydrochlorideDQ0Z3K8W9238821-52-2AFJSFHAKSSWOKG-UHFFFAOYSA-N
International/Other Brands
Baratol (Amdipharm) / Doralese (GlaxoSmithKline) / Doralese (Chemidex) / Vidora (Leurquin) / Wydora (Riemser)
Categories
UNII
0Z802HMY7H
CAS number
26844-12-2
Weight
Average: 347.4534
Monoisotopic: 347.199762437
Chemical Formula
C22H25N3O
InChI Key
JXZZEXZZKAWDSP-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzenecarboximidic acid
SMILES
OC(=NC1CCN(CCC2=CNC3=CC=CC=C23)CC1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAlpha-1A adrenergic receptor
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
4-MethoxyamphetamineIndoramin may decrease the vasoconstricting activities of 4-Methoxyamphetamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Indoramin.
AcebutololAcebutolol may increase the orthostatic hypotensive activities of Indoramin.
AcemetacinThe therapeutic efficacy of Indoramin can be decreased when used in combination with Acemetacin.
AcepromazineIndoramin may increase the antihypertensive activities of Acepromazine.
Acetylsalicylic acidThe therapeutic efficacy of Indoramin can be decreased when used in combination with Acetylsalicylic acid.
AdrafinilIndoramin may decrease the vasoconstricting activities of Adrafinil.
AgmatineThe therapeutic efficacy of Agmatine can be decreased when used in combination with Indoramin.
AldesleukinThe risk or severity of adverse effects can be increased when Indoramin is combined with Aldesleukin.
AliskirenIndoramin may increase the hypotensive activities of Aliskiren.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,527,761

General References
Not Available
External Links
KEGG Drug
D04531
PubChem Compound
33625
PubChem Substance
310264915
ChemSpider
31014
BindingDB
50033113
ChEBI
135470
ChEMBL
CHEMBL279516
Drugs.com
Drugs.com Drug Page
Wikipedia
Indoramin
ATC Codes
C02CA02 — Indoramin
MSDS
Download (17.2 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208-210U.S. Patent 3,527,761
Predicted Properties
PropertyValueSource
Water Solubility0.00498 mg/mLALOGPS
logP4.02ALOGPS
logP3.02ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.47ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area51.62 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.46 m3·mol-1ChemAxon
Polarizability40.94 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Benzamides / Benzoyl derivatives / Aralkylamines / Substituted pyrroles / Piperidines / Heteroaromatic compounds / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives
show 5 more
Substituents
Tryptamine / 3-alkylindole / Benzamide / Benzoic acid or derivatives / Indole / Benzoyl / Aralkylamine / Monocyclic benzene moiety / Piperidine / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Foglar R, Shibata K, Horie K, Hirasawa A, Tsujimoto G: Use of recombinant alpha 1-adrenoceptors to characterize subtype selectivity of drugs for the treatment of prostatic hypertrophy. Eur J Pharmacol. 1995 Jan 16;288(2):201-7. [PubMed:7536677]
  2. Forray C, Bard JA, Wetzel JM, Chiu G, Shapiro E, Tang R, Lepor H, Hartig PR, Weinshank RL, Branchek TA, et al.: The alpha 1-adrenergic receptor that mediates smooth muscle contraction in human prostate has the pharmacological properties of the cloned human alpha 1c subtype. Mol Pharmacol. 1994 Apr;45(4):703-8. [PubMed:8183249]

Drug created on May 27, 2014 13:11 / Updated on August 02, 2018 07:48