PYRILAMINE

US Approved OTC

First approved in 1948

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 Search

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

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 312 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22918191	Antagonist 2737		0.8 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html	Primary	Approved 8307	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 8 Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html	Primary	Approved 8307	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 37 Sources: https://www.drugs.com/drp/pyrilamine-maleate.html	Primary	Approved 8307	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 1789	inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCTN2 50

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1826	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/7853212/	yes [IC50 0.034 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 50	substrate 3264 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/bdd.681	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1603	inhibitor 1584 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
Comparison of cedar pollen-induced allergic rhinitis in passively and actively sensitized guinea pigs.	2001 Apr	11388645
Effects of two newly synthesized analogues of lidocaine on rat arterial blood pressure and heart rate.	2001 Apr	11352535
Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells.	2001 Feb	11693169
Histamine alters gene expression in cultured human nasal epithelial cells.	2001 Feb	11174198
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.	2001 Jul	11749824
Identification of two distinct vasodilator pathways activated by ATP in the mesenteric bed of the rat.	2001 Jul	11454655
Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats.	2001 Jul 6	11448481
Effects of histamine on phosphoinositide metabolism in chick cerebral cortex.	2001 Jul-Aug	11990086
Pharmacologic properties of brewery dust extracts in vitro.	2001 Jun	11399717
VUF-K-8788, a periphery-selective histamine H1 antagonist with anti-pruritic activities.	2001 May	11430473
Standard treatment: the role of antihistamines.	2001 Nov	11764306
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture.	2001 Nov	11678636
Regulation of IL-13 production by histamine in cloned murine T helper type 2 cells.	2001 Oct	11606024
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons.	2001 Oct	11591447
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
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	11530103
Antiallergic anti-inflammatory effects of H1-antihistamines in humans.	2002	12113215
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
Antihistamine antinociception is mediated by Gi-protein activation.	2002	11927163
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
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
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.	2002 Aug	12100006
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.	2002 Aug 23	12206853
Role of mast cells in the development of pancreatitis-induced multiple organ dysfunction.	2002 Feb	11856129
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation.	2002 Jan 18	11790377
Histamine H(2) -like receptors in chick cerebral cortex: effects on cyclic AMP synthesis and characterization by [(3) H]tiotidine binding.	2002 Jun	12065605
Histamine excites GABAergic cells in the rat substantia nigra and ventral tegmental area in vitro.	2002 Mar 8	11852180
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.	2002 Oct 4	12354569
Ligands for histamine H(3) receptors modulate cell proliferation and migration in rat oxyntic mucosa.	2002 Sep	12208781
Cosensitivity of vagal mucosal afferents to histamine and 5-HT in the rat jejunum.	2002 Sep	12181174

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 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

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

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