PYRILAMINE

US Approved OTC

First approved in 1948

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 Search

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

Description
Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 300 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22918191	Antagonist 2575		0.8 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html	Primary	Approved 7968	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
Upper respiratory allergies 13 Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html	Primary	Approved 7968	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
Premenstrual syndrome 36 Sources: https://www.drugs.com/drp/pyrilamine-maleate.html	Primary	Approved 7968	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

C_max

Value	Dose	Co-administered	Analyte	Population
36.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/	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

Value	Dose	Co-administered	Analyte	Population
54.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.85 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19161458/	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

Dose	Population	Adverse events
50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/8079504/	healthy, 32-38 years n = 3 Health Status: healthy Age Group: 32-38 years Sex: M Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/8079504/	Sources: https://pubmed.ncbi.nlm.nih.gov/8079504/
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: https://pubmed.ncbi.nlm.nih.gov/1687324/	unhealthy, adult Health Status: unhealthy Condition: Allergic conjunctivitis Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/1687324/	Sources: https://pubmed.ncbi.nlm.nih.gov/1687324/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1421	inhibitor 1359

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCTN2 40

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1455	inhibitor 2612 Sources: https://pubmed.ncbi.nlm.nih.gov/7853212/	yes [IC50 0.034 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 40	substrate 2751 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/bdd.681	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1391	inhibitor 1373 Sources: https://pubmed.ncbi.nlm.nih.gov/16278312/ Page: 3.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY579206	https://www.001chemical.com/chem/91-84-9
3B Scientific (Wuhan) Corp	3B2-6096	http://www.3bsc.com/index/pro_info.php?id=101018
Aurora Fine Chemicals LLC	A17.996.209	http://online.aurorafinechemicals.com/info?ID=A17.996.209
BLD Pharm	BD149819	http://www.bldpharm.com/products/91-84-9.html
ChemMol	99173757	http://www.chemmol.com/chemmol/99173757.html
Clearsynth	CS-O-01879	http://www.clearsynth.com/en/CSO01879.html
DC Chemicals	DC37035	http://www.dcchemicals.com//product_show-Mepyramine.html
Finetech	FT-0628211	http://www.finetechnology-ind.com/prod/detail/pub/91-84-9.html
Hairui	HR137269	http://www.hairuichem.com/en/product/91-84-9.html
MolPort	MolPort-001-794-651	https://www.molport.com/shop/molecule-link/MolPort-001-794-651
Molcore	MC579206	https://www.molcore.com/product/91-84-9
Parchem	29372	http://www.parchem.com/chemical-supplier-distributor/Mepyramine-Maleate-019372.aspx
Sigma-Aldrich	S347108_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s347108
Smolecule	S534993	http://www.smolecule.com/products/s534993
THE BioTek	bt-274773	https://www.thebiotek.com/product/inhibitors/bt-274773
eNovation Chemicals	Y1089293	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1089293
iChemical	EBD4056537	http://www.ichemical.com/products/102206-59-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
iChemical	EBD76116	http://www.ichemical.com/products/91-84-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Role of L-arginine/nitric oxide pathway in the antinociceptive activities of morphine and mepyramine in mice.	2001	11799845
Effect of clobenpropit on regional cerebral blood flow in rat hippocampus.	2001 Apr	11742589
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.	2001 Dec	11903961
Mechanism underlying histamine-induced intracellular Ca2+ movement in PC3 human prostate cancer cells.	2001 Dec	11735364
Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.	2001 Dec	11724747
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.	2001 Jul	11749824
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex.	2001 Jul-Aug	11990086
Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells.	2001 Nov	11817705
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture.	2001 Nov	11678636
Preclinical comparison of ebastine and other second generation H1-antihistamines.	2001 Oct	11881966
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.	2001 Oct	11606024
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	11640976
Pharmacological characterization of cyclosporine A-induced kaolin intake in rats.	2001 Oct-Nov	11701197
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.	2002	12113215
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine.	2002	12056651
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	12013195
Characterisation of the calcium responses to histamine in capsaicin-sensitive and capsaicin-insensitive sensory neurones.	2002	11958874
Impact of soil movement on carbon sequestration in agricultural ecosystems.	2002	11822721
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	12027381
Elevated nasal mucosal G protein levels and histamine receptor affinity in a guinea pig model of nasal hyperresponsiveness.	2002 Apr	12021547
Mouse mammary epithelial cells bear histamine receptors.	2002 Apr	12013422
Contractile response of horse deep dorsal penile vein to histamine.	2002 Apr	11979322
Stimulation of protein kinase B and p70 S6 kinase by the histamine H1 receptor in DDT1MF-2 smooth muscle cells.	2002 Apr	11959800
Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats.	2002 Apr	11931695
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	11927170
GBR compounds and mepyramines as cocaine abuse therapeutics: chemometric studies on selectivity using grid independent descriptors (GRIND).	2002 Apr 11	11931612
The control effect of histamine on body temperature and respiratory function in IgE-dependent systemic anaphylaxis.	2002 Aug	12170272
Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery.	2002 Aug	12163355
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.	2002 Aug 21	12191794
Biochemical characterization of desloratadine, a potent antagonist of the human histamine H(1) receptor.	2002 Aug 9	12167464
Urothelium derived inhibitory factor and cross-talk among receptors in the trigone of the bladder of the pig.	2002 Feb	11792964
Orexins activate histaminergic neurons via the orexin 2 receptor.	2002 Feb 1	11811995
Effects of brain histamine on memory deficit induced by nucleus basalis-lesion in rats.	2002 Jan	11860740
L-Carnitine transport in mouse renal and intestinal brush-border and basolateral membrane vesicles.	2002 Jan 2	11750267
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.	2002 Jan-Feb	11812538
A novel phenylaminotetralin radioligand reveals a subpopulation of histamine H(1) receptors.	2002 Jul	12065734
Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf.	2002 Jul	12065152
The antianaphylactic effects of Crinum glaucum aqueous extract.	2002 Jul	12065149
Suppression of spontaneous scratching in hairless rats by sedatives but not by antipruritics.	2002 Jul-Aug	12218283
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.	2002 Jun	12166087
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.	2002 Jun	12065605
Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States.	2002 Mar	11927027
The recovery of the neurally evoked secretory response of rat colonic mucosa after irradiation is independent of mast cells.	2002 Mar	11839088
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.	2002 Mar 8	11852180
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	12384422
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.	2002 Oct	12392093
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.	2002 Oct	12235264
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa.	2002 Sep	12208781
Tryptase activates the mitogen-activated protein kinase/activator protein-1 pathway in human peripheral blood eosinophils, causing cytokine production and release.	2002 Sep 1	12193739
Mediators of adenosine- and ovalbumen-induced bronchoconstriction of sensitized guinea-pig isolated airways.	2002 Sep 6	12223233

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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Name

Type

Language

PYRILAMINE

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

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