U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H23N3O.C4H4O4
Molecular Weight 401.457
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE MALEATE

SMILES

CN(C)CCN(Cc1ccc(cc1)OC)c2ccccn2.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O

InChI

InChIKey=JXYWFNAQESKDNC-BTJKTKAUSA-N
InChI=1S/C17H23N3O.C4H4O4/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15;5-3(6)1-2-4(7)8/h4-11H,12-14H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI
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
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.
2001 Dec
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
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
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
Antihistamine antinociception is mediated by Gi-protein activation.
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
Insulin-induced up-regulation of histamine H1-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
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.
2002 Aug
Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice.
2002 Aug 15
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.
2002 Aug 21
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.
2002 Aug 23
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.
2002 Aug 9
Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction.
2002 Feb
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes.
2002 Jan
Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats.
2002 Jan
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
Role of Rho-associated protein kinase and histamine in lysophosphatidic acid-induced airway hyperresponsiveness in guinea pigs.
2002 Mar
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
Effects of the NMDA antagonist MK-801 on radial maze performance in histidine-deficient rats.
2002 Mar 22
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
Enhancement of neutrophil infiltration in histidine decarboxylase-deficient mice.
2002 Oct
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
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
Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release.
2002 Sep 1
Effects of NMDA antagonist MK-801 on radial maze performance in Zucker rats.
2002 Sep 20
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
Name Type Language
PYRILAMINE MALEATE
GREEN BOOK   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PYRILAMINE MALEATE [USP]
Common Name English
PYRILAMINE MALEATE [MI]
Common Name English
PARMAL
Brand Name English
N-(4-METHOXYBENZYL)-N',N'-DIMETHYL-N-PYRIDIN-2-YLETHANE-1,2-DIAMINE (2Z)-BUT-2-ENEDIOATE
Systematic Name English
ANTAMINE
Brand Name English
2-((2-(DIMETHYLAMINO)ETHYL)(P-METHOXYBENZYL)AMINO)PYRIDINE MALEATE (1:1)
Common Name English
MEPYRAMINE MALEATE [MART.]
Common Name English
NEO-ANTERGAN
Brand Name English
1,2-ETHANEDIAMINE, N-((4-METHOXYPHENYL)METHYL)-N',N'-DIMETHYL-N-2-PYRIDINYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
ANTHISAN
Brand Name English
PYRILAMINE MALEATE COMPONENT OF PREFRIN-A
Common Name English
PYRILAMINE MALEATE [VANDF]
Common Name English
HISTALON
Brand Name English
PYRILAMINE MALEATE [USP-RS]
Common Name English
DORANTAMIN
Brand Name English
THYLOGEN
Brand Name English
STAMINE
Brand Name English
PYRILAMINE MALEATE [ORANGE BOOK]
Common Name English
PYRAMAL
Brand Name English
HISTAN
Brand Name English
PARAMINYL
Brand Name English
MEPYRAMINE MALEATE
EP   MART.   WHO-DD  
Common Name English
STANGEN
Brand Name English
PYRILAMINE MALEATE [GREEN BOOK]
Common Name English
MEPYRAMINE MALEATE [WHO-DD]
Common Name English
ENRUMAY
Brand Name English
MEPYRAMINE MALEATE [EP MONOGRAPH]
Common Name English
HISTATEX
Brand Name English
HISTAPYRAN
Brand Name English
NSC-3604
Code English
PREFRIN-A COMPONENT PYRILAMINE MALEATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.2063
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
CFR 21 CFR 341.12
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
Code System Code Type Description
DRUG BANK
DBSALT001405
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
EPA CompTox
59-33-6
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
PUBCHEM
5284451
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
MERCK INDEX
M9367
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY Merck Index
RXCUI
82091
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL511
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
USP_CATALOG
1588004
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY USP-RS
FDA UNII
R35D29L3ZA
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-422-7
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
EVMPD
SUB14516MIG
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
NCI_THESAURUS
C61915
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY
CAS
59-33-6
Created by admin on Fri Jun 25 21:10:28 UTC 2021 , Edited by admin on Fri Jun 25 21:10:28 UTC 2021
PRIMARY