NAV

AS-8112

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
AS-8112
DrugBank Accession Number
DB09207
Background

AS-8112 is a synthetic compound that acts as a selective antagonist at the dopamine receptor subtypes D2 and D3, and the serotonin receptor 5-HT3. It has been shown to exert potent antiemetic effects in animal studies and has been investigated for potential medical use.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 399.333
Monoisotopic: 398.131739
Chemical Formula
C17H27BrN4O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDopamine D2 receptor
antagonist
Humans
UDopamine D3 receptor
antagonist
Humans
U5HT3 serotonin 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

Adverse Effects
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Toxicity

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
Integrate drug-drug
interactions in your software
ApomorphineThe therapeutic efficacy of Apomorphine can be decreased when used in combination with AS-8112.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with AS-8112.
BenzatropineThe risk or severity of adverse effects can be increased when AS-8112 is combined with Benzatropine.
BrexpiprazoleThe therapeutic efficacy of Brexpiprazole can be decreased when used in combination with AS-8112.
BromocriptineThe therapeutic efficacy of Bromocriptine can be decreased when used in combination with AS-8112.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzamides
Alternative Parents
3-halobenzoic acids and derivatives / Aminophenyl ethers / Benzamides / Methoxyanilines / 2-bromoanilines / Phenylalkylamines / Phenoxy compounds / Anisoles / Benzoyl derivatives / Methoxybenzenes
show 13 more
Substituents
1,4-diazepane / 2-bromoaniline / 3-halobenzoic acid or derivatives / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzamide / Aminophenyl ether / Aniline or substituted anilines / Anisole
show 33 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DALSFUWTAOKVTF-GFCCVEGCSA-N
InChI
InChI=1S/C17H27BrN4O2/c1-5-22-7-6-21(3)10-12(11-22)20-17(23)13-8-14(18)15(19-2)9-16(13)24-4/h8-9,12,19H,5-7,10-11H2,1-4H3,(H,20,23)/t12-/m1/s1
IUPAC Name
5-bromo-N-[(6R)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-4-(methylamino)benzamide
SMILES
[H]N(C)C1=C(Br)C=C(C(=O)N([H])[C@@H]2CN(C)CCN(CC)C2)C(OC)=C1

References

General References
  1. Yoshikawa T, Yoshida N, Oka M: The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. Br J Pharmacol. 2001 May;133(2):253-60. [Article]
  2. Yoshikawa T, Yoshida N, Oka M: Central antiemetic effects of AS-8112, a dopamine D2, D3, and 5-HT(3) receptor antagonist, in ferrets. Eur J Pharmacol. 2001 Nov 23;431(3):361-4. [Article]
  3. Hirokawa Y, Fujiwara I, Suzuki K, Harada H, Yoshikawa T, Yoshida N, Kato S: Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotonin 5-HT3 and dopamine D2 receptor antagonistic activity. J Med Chem. 2003 Feb 27;46(5):702-15. [Article]
PubChem Compound
10993014
PubChem Substance
310265115
ChemSpider
9168209
ZINC
ZINC000136358235
Wikipedia
AS-8112

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.114 mg/mLALOGPS
logP2.22ALOGPS
logP1.41Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.64Chemaxon
pKa (Strongest Basic)8.32Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area56.84 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity102.8 m3·mol-1Chemaxon
Polarizability39.04 Å3Chemaxon
Number of Rings2Chemaxon
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/MSsplash10-0002-0009000000-116ec65b3e34f516b628
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1209000000-0ee6d6443590b869ba53
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-0419000000-22b7cc99ca798083985f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9607000000-ca061001ae8bc8b6263a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-4977000000-1b8f8a21fab4efa9c5c1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9202000000-de70742ca56f4945cb46
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.85149
predicted
DeepCCS 1.0 (2019)
[M+H]+184.22946
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.66411
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dopamine D2 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Yoshikawa T, Yoshida N, Oka M: The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. Br J Pharmacol. 2001 May;133(2):253-60. [Article]
Details2. Dopamine D3 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name
DRD3
Uniprot ID
P35462
Uniprot Name
D(3) dopamine receptor
Molecular Weight
44224.335 Da
References
  1. Yoshikawa T, Yoshida N, Oka M: The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. Br J Pharmacol. 2001 May;133(2):253-60. [Article]
Details3. 5HT3 serotonin receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Not Available
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9UE69
Uniprot Name
5HT3 serotonin receptor
Molecular Weight
1285.6 Da
References
  1. Yoshikawa T, Yoshida N, Oka M: The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. Br J Pharmacol. 2001 May;133(2):253-60. [Article]

Drug created at October 19, 2015 21:26 / Updated at June 12, 2020 16:52