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Details

Stereochemistry ACHIRAL
Molecular Formula C17H23N3O
Molecular Weight 285.384
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE

SMILES

COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1

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 285.384
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
Comparison of cedar pollen-induced allergic rhinitis in passively and actively sensitized guinea pigs.
2001 Apr
Effects of two newly synthesized analogues of lidocaine on rat arterial blood pressure and heart rate.
2001 Apr
Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells.
2001 Feb
Histamine alters gene expression in cultured human nasal epithelial cells.
2001 Feb
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.
2001 Jul
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat.
2001 Jul
Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats.
2001 Jul 6
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex.
2001 Jul-Aug
Pharmacologic properties of brewery dust extracts in vitro.
2001 Jun
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.
2001 May
Standard treatment: the role of antihistamines.
2001 Nov
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture.
2001 Nov
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.
2001 Oct
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons.
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
Role of adenosine in ischemic preconditioning in rats depends critically on the duration of the stimulus and involves both A(1) and A(3) receptors.
2001 Sep
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.
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
Antihistamine antinociception is mediated by Gi-protein activation.
2002
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
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
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.
2002 Aug
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.
2002 Aug 23
Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction.
2002 Feb
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation.
2002 Jan 18
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.
2002 Jun
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.
2002 Mar 8
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.
2002 Oct 4
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa.
2002 Sep
Cosensitivity of vagal mucosal afferents to histamine and 5-HT in the rat jejunum.
2002 Sep
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 Dec 16 16:53:54 UTC 2022
Edited
by admin
on Fri Dec 16 16:53:54 UTC 2022
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
Mepyramine [WHO-DD]
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
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 Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
WHO-ATC R06AC01
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
WHO-VATC QD04AA02
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
WHO-VATC QR06AC01
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
NCI_THESAURUS C29578
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
Code System Code Type Description
MERCK INDEX
M9367
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL511
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
IUPHAR
1227
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
PUBCHEM
4992
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
CAS
91-84-9
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
MESH
D011738
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
EVMPD
SUB08762MIG
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
RXCUI
9009
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY RxNorm
HSDB
5187
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
ECHA (EC/EINECS)
202-102-2
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
INN
106
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
LACTMED
Pyrilamine
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
NCI_THESAURUS
C76676
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
FDA UNII
HPE317O9TL
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
CHEBI
6762
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
DRUG CENTRAL
2331
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
DAILYMED
HPE317O9TL
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
NSC
13136
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
EPA CompTox
DTXSID9023542
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
DRUG BANK
DB06691
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
WIKIPEDIA
MEPYRAMINE
Created by admin on Fri Dec 16 16:53:54 UTC 2022 , Edited by admin on Fri Dec 16 16:53:54 UTC 2022
PRIMARY
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