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Details

Stereochemistry ACHIRAL
Molecular Formula C17H23N3O
Molecular Weight 285.3847
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE

SMILES

CN(C)CCN(Cc1ccc(cc1)OC)c2ccccn2

InChI

InChIKey=YECBIJXISLIIDS-UHFFFAOYSA-N
InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C17H23N3O
Molecular Weight 285.3847
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pyrilamine (also known as Mepyramine) is a first generation antihistamine, targeting the H1 receptor. However, it rapidly permeates the brain and so often causes drowsiness as a side effect. It is used in over-the-counter combination products for colds and menstrual symptoms. Mepyramine is a histamine H1 receptor inverse agonist. It binds to a G protein-coupled form of the receptor and promotes a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling. Mepyramine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of Mepyramine occur at the subcortical level of the CNS. It has mild hypnotic properties and some local anesthetic action and is used for allergies (including skin eruptions) both parenterally and locally. It is a common ingredient of cold remedies.

CNS Activity

Curator's Comment:: The sedative properties of Pyrilamine occur at the subcortical level of the CNS.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phenylephrine/ pyrilamine

Approved Use

Uses Temporarily relieves nasal congestion due to hay fever (allergic rhinitis) runny nose sneezing, itching of nose or throat and itchy, watery eyes due to hay fever or upper respiratory allergies

Launch Date

4.04697612E11
Primary
Phenylephrine/ pyrilamine

Approved Use

Uses Temporarily relieves nasal congestion due to hay fever (allergic rhinitis) runny nose sneezing, itching of nose or throat and itchy, watery eyes due to hay fever or upper respiratory allergies

Launch Date

4.04697612E11
Primary
MIDOL PMS

Approved Use

Uses: For the temporary relief of these symptoms associated with menstrual periods: bloating water-weight gain cramps breast tenderness headache backache

Launch Date

4.04697612E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36.6 ng/mL
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PYRILAMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
54.6 ng × h/mL
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PYRILAMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.85 h
300 mg single, intravenous
dose: 300 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PYRILAMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
50 mg single, oral
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
healthy, 32-38 years
n = 3
Health Status: healthy
Age Group: 32-38 years
Sex: M
Population Size: 3
Sources:
0.3 % 1 times / day steady, ophthalmic
Recommended
Dose: 0.3 %, 1 times / day
Route: ophthalmic
Route: steady
Dose: 0.3 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: Allergic conjunctivitis
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.034 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Role of L-arginine/nitric oxide pathway in the antinociceptive activities of morphine and mepyramine in mice.
2001
Effect of clobenpropit on regional cerebral blood flow in rat hippocampus.
2001 Apr
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.
2001 Dec
Mechanism underlying histamine-induced intracellular Ca2+ movement in PC3 human prostate cancer cells.
2001 Dec
Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.
2001 Dec
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.
2001 Jul
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex.
2001 Jul-Aug
Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells.
2001 Nov
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture.
2001 Nov
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001 Oct
Histamine H(3)-receptor antagonism improves memory retention and reverses the cognitive deficit induced by scopolamine in a two-trial place recognition task.
2001 Oct 15
Pharmacological characterization of cyclosporine A-induced kaolin intake in rats.
2001 Oct-Nov
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.
2002
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine.
2002
Topically applied aspirin decreases histamine-induced wheal and flare reactions in normal and SLS-inflamed skin, but does not decrease itch. A randomized, double-blind and placebo-controlled human study.
2002
Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones.
2002
Impact of soil movement on carbon sequestration in agricultural ecosystems.
2002
The initial inositol 1,4,5-trisphosphate response induced by histamine is strongly amplified by Ca(2+) release from internal stores in smooth muscle.
2002 Apr
Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness.
2002 Apr
Mouse mammary epithelial cells bear histamine receptors.
2002 Apr
Contractile response of horse deep dorsal penile vein to histamine.
2002 Apr
Stimulation of protein kinase B and p70 S6 kinase by the histamine H1 receptor in DDT1MF-2 smooth muscle cells.
2002 Apr
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.
2002 Apr
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate).
2002 Apr
GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND).
2002 Apr 11
The control effect of histamine on body temperature and respiratory function in IgE-dependent systemic anaphylaxis.
2002 Aug
Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery.
2002 Aug
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.
2002 Aug 21
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.
2002 Aug 9
Urothelium derived inhibitory factor and cross-talk among receptors in the trigone of the bladder of the pig.
2002 Feb
Orexins activate histaminergic neurons via the orexin 2 receptor.
2002 Feb 1
Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats.
2002 Jan
L-Carnitine transport in mouse renal and intestinal brush-border and basolateral membrane vesicles.
2002 Jan 2
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.
2002 Jan-Feb
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.
2002 Jul
Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf.
2002 Jul
The antianaphylactic effects of Crinum glaucum aqueous extract.
2002 Jul
Suppression of spontaneous scratching in hairless rats by sedatives but not by antipruritics.
2002 Jul-Aug
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.
2002 Jun
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States.
2002 Mar
The recovery of the neurally evoked secretory response of rat colonic mucosa after irradiation is independent of mast cells.
2002 Mar
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.
2002 Mar 8
LPS-induced platelet response and rapid shock in mice: contribution of O-antigen region of LPS and involvement of the lectin pathway of the complement system.
2002 Nov 1
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa.
2002 Sep
Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release.
2002 Sep 1
Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways.
2002 Sep 6
Patents

Sample Use Guides

Usual Adult Dose for Allergic Rhinitis phenylephrine-pyrilamine 25 mg-60 mg oral tablet: 1 or 2 tablets orally every 12 hours as needed. phenylephrine-pyrilamine 20 mg-16 mg oral tablet, chewable, extended release: 1 or 2 tablets orally every 12 hours as needed. phenylephrine-pyrilamine 5 mg-16 mg/5 mL oral suspension, extended release: 5 to 10 mL orally every 12 hours as needed. phenylephrine-pyrilamine 9 mg-12 mg/5 mL oral suspension, extended release: 5 to 10 mL orally every 12 hours as needed, not to exceed 20 mL in 24 hours.
Route of Administration: Oral
Pretreatment with the histamine H1 receptor antagonist pyrilamine (1 uM) could reduce the beta-lactoglobulin-induced response in the in vitro guinea pig mesenteric preparation
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:38:10 UTC 2021
Edited
by admin
on Fri Jun 25 23:38:10 UTC 2021
Record UNII
HPE317O9TL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRILAMINE
MI   VANDF  
Common Name English
PYRILAMINE [VANDF]
Common Name English
NSC-13136
Code English
MEPYRAMINE [INN]
Common Name English
1,2-ETHANEDIAMINE, N-((4-METHOXYPHENYL)METHYL)-N',N'-DIMETHYL-N-2-PYRIDINYL-
Systematic Name English
MEPYRAMINE [HSDB]
Common Name English
MEPYRAMINE [MART.]
Common Name English
MEPYRAMINE
HSDB   INN   MART.   WHO-DD  
INN  
Official Name English
MEPYRAMINE [WHO-DD]
Common Name English
2-((2-(DIMETHYLAMINO)ETHYL)(P-METHOXYBENZYL)AMINO)PYRIDINE
Common Name English
PYRILAMINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC D04AA02
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
WHO-ATC R06AC01
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
WHO-VATC QD04AA02
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
WHO-VATC QR06AC01
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
Code System Code Type Description
MERCK INDEX
M9367
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL511
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
IUPHAR
1227
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
PUBCHEM
4992
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
CAS
91-84-9
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
MESH
D011738
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
EVMPD
SUB08762MIG
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
RXCUI
9009
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY RxNorm
HSDB
5187
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-102-2
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
INN
106
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
LACTMED
Pyrilamine
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
NCI_THESAURUS
C76676
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
FDA UNII
HPE317O9TL
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
DRUG CENTRAL
2331
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
EPA CompTox
91-84-9
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
DRUG BANK
DB06691
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
WIKIPEDIA
MEPYRAMINE
Created by admin on Fri Jun 25 23:38:10 UTC 2021 , Edited by admin on Fri Jun 25 23:38:10 UTC 2021
PRIMARY
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