Identification

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Name
Indoramin
Accession Number
DB08950
Type
Small Molecule
Groups
Approved, Withdrawn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
  • Indoramin
  • Indoramina
  • Indoramine
  • Indoraminum
External IDs
WY 21901 / WY-21901 / WY21901
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}benzamide
SMILES
O=C(NC1CCN(CCC2=CNC3=C2C=CC=C3)CC1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAlpha-1A adrenergic receptor
antagonist
Humans
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Indoramin.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Indoramin.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Indoramin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Indoramin can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe therapeutic efficacy of Indoramin can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamineThe therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Indoramin.
4-MethoxyamphetamineThe therapeutic efficacy of 4-Methoxyamphetamine can be decreased when used in combination with Indoramin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Indoramin is combined with 5-methoxy-N,N-dimethyltryptamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Indoramin.
AbediterolThe therapeutic efficacy of Abediterol can be decreased when used in combination with Indoramin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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 Solubility0.00863 mg/mLALOGPS
logP3.4ALOGPS
logP3.19ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)15.09ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.94 m3·mol-1ChemAxon
Polarizability40.72 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
Humans
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 January 15, 2020 03:38