Identification

Name
Thonzylamine
Accession Number
DB11235
Type
Small Molecule
Groups
Approved
Description

Thonzylamine is an antihistamine and anticholinergic drug. It is available as combination products with Clofedanol or Phenylephrine for temporary relief of symptoms of common cold, hay fever (allergic rhinitis) or other upper respiratory allergies.

Structure
Thumb
Synonyms
  • neohetramine
Product Ingredients
IngredientUNIICASInChI Key
Thonzylamine hydrochloride6K9YKD48Y463-56-9HRYJPHOTGFERGT-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Nasopen PEThonzylamine hydrochloride (50 mg/15mL) + Phenylephrine hydrochloride (10 mg/15mL)LiquidOralGm Pharmaceuticals2012-10-03Not applicableUs
Poly Hist PDThonzylamine hydrochloride (6.25 mg/mL) + Chlophedianol hydrochloride (6.25 mg/mL)LiquidOralPoly Pharmaceuticals2013-07-01Not applicableUs
Poly-Hist DMThonzylamine hydrochloride (25 mg/5mL) + Dextromethorphan hydrobromide (10 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralPoly Pharmaceuticals2013-06-22Not applicableUs
TexaClear Kids Sinus ReliefThonzylamine hydrochloride (50 mg/30mL) + Phenylephrine hydrochloride (5 mg/30mL)LiquidOralGm Pharmaceuticals2015-06-15Not applicableUs
Categories
UNII
R79646H5Z8
CAS number
91-85-0
Weight
Average: 286.379
Monoisotopic: 286.179361344
Chemical Formula
C16H22N4O
InChI Key
GULNIHOSWFYMRN-UHFFFAOYSA-N
InChI
InChI=1S/C16H22N4O/c1-19(2)11-12-20(16-17-9-4-10-18-16)13-14-5-7-15(21-3)8-6-14/h4-10H,11-13H2,1-3H3
IUPAC Name
N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine
SMILES
COC1=CC=C(CN(CCN(C)C)C2=NC=CC=N2)C=C1

Pharmacology

Indication

Thozylamine is indicated for use in the symptomatic control of allergic rhinitis or other upper respiratory allergic symptoms [Label]. It is typically a part of combination over the counter products.

Pharmacodynamics

Thonzylamine is a first-generation antihistamine. It antagonizes the action of histamine to relief allergic symptoms like nasal congestion, runny nose, itchy eyes, itchy nose and throat, and sneezing [Label]

Mechanism of action

Thonzylamine competes with histamine for binding to the H1 histamine receptor [1]. Binding of histamine to this receptor stimulates vasodilation and increased vascular permeability leading to nasal congestion and runny nose [3]. Histamine also produces itchiness by stimulating nerve endings which can result in sneezing. By blocking these effects, thonzylamine can reduce or eliminate symptoms of allergic rhinitis.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
UMuscarinic acetylcholine receptor M1
antagonist
Human
UMuscarinic acetylcholine receptor M2
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
UMuscarinic acetylcholine receptor M4
antagonist
Human
UMuscarinic acetylcholine receptor M5
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

Doses of up to 300 mg/day for up to 4 days have produces no observable toxic effects in humans [2]. In a chronic toxicity study, rats were given up to 200 mg/kg/day orally for 91 days with no observable toxic effects [1].

Affected organisms
Not Available
Pathways
PathwayCategory
Thonzylamine H1-Antihistamine ActionDrug action
Thonzylamine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Thonzylamine.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Thonzylamine.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Thonzylamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Thonzylamine.Experimental, Illicit
AgmatineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Agmatine.Experimental, Investigational
AmphetamineAmphetamine may decrease the sedative activities of Thonzylamine.Approved, Illicit, Investigational
AtropineThe risk or severity of adverse effects can be increased when Atropine is combined with Thonzylamine.Approved, Vet Approved
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Thonzylamine.Approved
BenzphetamineBenzphetamine may decrease the sedative and stimulatory activities of Thonzylamine.Approved, Illicit
Benzylpenicilloyl PolylysineThonzylamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Thonzylamine.Approved, Investigational
BisacodylThe therapeutic efficacy of Bisacodyl can be decreased when used in combination with Thonzylamine.Approved
BrompheniramineThe risk or severity of adverse effects can be increased when Brompheniramine is combined with Thonzylamine.Approved
BupropionThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Bupropion.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Thonzylamine.Illicit, Withdrawn
CodeineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Codeine.Approved, Illicit
DextroamphetamineDextroamphetamine may decrease the sedative activities of Thonzylamine.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Dextromethorphan.Approved
DiethylpropionDiethylpropion may decrease the sedative and stimulatory activities of Thonzylamine.Approved, Illicit
DiphenhydramineThe risk or severity of adverse effects can be increased when Diphenhydramine is combined with Thonzylamine.Approved, Investigational
DocusateThe therapeutic efficacy of Docusate can be decreased when used in combination with Thonzylamine.Approved
DoxylamineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Doxylamine.Approved, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Fluoxetine.Approved, Vet Approved
GepefrineGepefrine may decrease the sedative activities of Thonzylamine.Experimental
GlycerinThe therapeutic efficacy of Glycerin can be decreased when used in combination with Thonzylamine.Approved, Investigational
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Thonzylamine.Approved, Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Thonzylamine.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Hydrocodone.Approved, Illicit
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Thonzylamine.Approved
HyoscyamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Thonzylamine.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Thonzylamine.Approved
IpratropiumThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Ipratropium.Approved
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Thonzylamine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Lamotrigine.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Thonzylamine.Approved, Investigational
Magnesium carbonateThe therapeutic efficacy of Magnesium carbonate can be decreased when used in combination with Thonzylamine.Approved, Investigational
Magnesium citrateThe therapeutic efficacy of Magnesium citrate can be decreased when used in combination with Thonzylamine.Approved
Magnesium hydroxideThe therapeutic efficacy of Magnesium hydroxide can be decreased when used in combination with Thonzylamine.Approved, Investigational
Magnesium sulfateThe therapeutic efficacy of Magnesium sulfate can be decreased when used in combination with Thonzylamine.Approved, Investigational, Vet Approved
MephedroneMephedrone may decrease the sedative activities of Thonzylamine.Investigational
MephentermineMephentermine may decrease the sedative activities of Thonzylamine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Thonzylamine.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Thonzylamine.Experimental
MetoclopramideThe therapeutic efficacy of Thonzylamine can be decreased when used in combination with Metoclopramide.Approved, Investigational
MidomafetamineMidomafetamine may decrease the sedative activities of Thonzylamine.Experimental, Illicit, Investigational
Mineral oilThe therapeutic efficacy of Mineral oil can be decreased when used in combination with Thonzylamine.Approved, Vet Approved
MMDAMMDA may decrease the sedative activities of Thonzylamine.Experimental, Illicit
NicardipineThe risk or severity of adverse effects can be increased when Nicardipine is combined with Thonzylamine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Otilonium is combined with Thonzylamine.Experimental, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Oxymorphone.Approved, Investigational, Vet Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Thonzylamine.Approved, Investigational
PhenobarbitalThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Phenobarbital.Approved, Investigational
PhenterminePhentermine may decrease the sedative activities of Thonzylamine.Approved, Illicit
Potassium ChlorideThe risk or severity of gastrointestinal ulceration can be increased when Thonzylamine is combined with Potassium Chloride.Approved, Withdrawn
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Thonzylamine.Approved, Investigational
PseudoephedrinePseudoephedrine may decrease the sedative and stimulatory activities of Thonzylamine.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Thonzylamine.Approved
RitobegronRitobegron may decrease the sedative activities of Thonzylamine.Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Thonzylamine.Approved, Investigational
Sodium phosphate, monobasicThe therapeutic efficacy of Sodium phosphate, monobasic can be decreased when used in combination with Thonzylamine.Approved
TopiramateThe risk or severity of hyperthermia and oligohydrosis can be increased when Thonzylamine is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Tramadol.Approved, Investigational
TrimebutineThe risk or severity of adverse effects can be increased when Thonzylamine is combined with Trimebutine.Approved
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Thonzylamine.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Vecuronium is combined with Thonzylamine.Approved
WIN 55212-2The risk or severity of Tachycardia and drowsiness can be increased when Thonzylamine is combined with WIN 55212-2.Experimental
Food Interactions
Not Available

References

General References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
  3. Chapter 39: Histamine, Bradykinin, and Their Antagonists. (2018). In Goodman & Gilman's: The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education. [ISBN:978-1-25-958473-2]
External Links
Human Metabolome Database
HMDB0240222
PubChem Compound
5457
PubChem Substance
347827947
ChemSpider
5258
ChEBI
104017
ChEMBL
CHEMBL1623738
Wikipedia
Thonzylamine
ATC Codes
R01AC06 — ThonzylamineD04AA01 — ThonzylamineR06AC06 — Thonzylamine
FDA label
Download (190 KB)
MSDS
Download (82.2 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)173-176Scudi JV, Reinhard JF, Dreyer NB. Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948;19(3):184-99.
water solubilityHighly SolubleScudi JV, Reinhard JF, Dreyer NB. Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948;19(3):184-99.
Predicted Properties
PropertyValueSource
Water Solubility0.733 mg/mLALOGPS
logP2.4ALOGPS
logP2.42ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area41.49 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity86.19 m3·mol-1ChemAxon
Polarizability32.42 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-05fr-9720000000-8a7d4d036feab1e4ee54
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 anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Dialkylarylamines / Benzylamines / Aminopyrimidines and derivatives / Alkyl aryl ethers / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 1 more
Substituents
Phenoxy compound / Anisole / Benzylamine / Methoxybenzene / Dialkylarylamine / Alkyl aryl ether / Aminopyrimidine / Monocyclic benzene moiety / Pyrimidine / Heteroaromatic compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Thonzylamine is known to have weak parasympatholytic activity. No binding studies have been performed.
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Thonzylamine is known to have weak parasympatholytic activity. No binding studies have been performed.
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Thonzylamine is known to have weak parasympatholytic activity. No binding studies have been performed.
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Thonzylamine is known to have weak parasympatholytic activity. No binding studies have been performed.
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Thonzylamine is known to have weak parasympatholytic activity. No binding studies have been performed.
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. SCUDI JV, REINHARD JF, DREYER NB: Pharmacologic characteristics of neohetramine, a new antihistaminic drug. J Allergy. 1948 May;19(3):184-99. [PubMed:18858080]
  2. AARON TH, CRIEP LH: Neohetramine and thephorin; two new antihistaminic drugs. Can Med Assoc J. 1948 Nov;59(5):438-41. [PubMed:18888474]

Drug created on December 03, 2015 09:51 / Updated on August 02, 2018 07:55