PYRILAMINE MALEATE

US Approved OTC

First approved in 1948

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H23N3O.C4H4O4
Molecular Weight	401.4562
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1

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

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22918191	Antagonist 2778		0.8 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.drugs.com/cdi/phenylephrine-pyrilamine.html	Primary	Approved 8429	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 8429	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 8429	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 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCTN2 50

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 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 3367 Sources: https://onlinelibrary.wiley.com/doi/abs/10.1002/bdd.681	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
Activation of the p38 and p42/p44 mitogen-activated protein kinase families by the histamine H(1) receptor in DDT(1)MF-2 cells.	2001 Aug	11498525
The effects of histamine and its antagonists on the cochlear microphonic and the compound action potential of the guinea pig.	2001 Aug	11489364
Comparative effect of Phoneutria nigriventer spider venom and capsaicin on the rat paw oedema.	2001 Aug 17	11554618
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
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.	2001 Jul	11749824
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
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
Histamine H(1)-receptor activation of nuclear factor-kappa B: roles for G beta gamma- and G alpha(q/11)-subunits in constitutive and agonist-mediated signaling.	2001 Nov	11641442
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
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
Antihistamine antinociception is mediated by Gi-protein activation.	2002	11927163
Impact of soil movement on carbon sequestration in agricultural ecosystems.	2002	11822721
Insulin-induced up-regulation of histamine H1-receptors.	2002 Apr	12013418
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
Effects of histamine on the contractile and electrical activity in isolated lymphatic vessels of the guinea-pig mesentery.	2002 Aug	12163355
Functional analysis of histamine receptor subtypes involved in endothelium-mediated relaxation of the human uterine artery.	2002 Aug	12100006
Accelerated clearance of Escherichia coli in experimental peritonitis of histamine-deficient mice.	2002 Aug 15	12165523
Yawning/cortical activation induced by microinjection of histamine into the paraventricular nucleus of the rat.	2002 Aug 21	12191794
Modulation of formalin-induced behaviors and edema by local and systemic administration of dextromethorphan, memantine and ketamine.	2002 Aug 23	12206853
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
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation.	2002 Jan 18	11790377
L-Carnitine transport in mouse renal and intestinal brush-border and basolateral membrane vesicles.	2002 Jan 2	11750267
Antinociceptive and smooth muscle contracting activities of the methanolic extract of Cassia tora leaf.	2002 Jul	12065152
Modulation of the discriminative stimulus effects of cocaine and methamphetamine by the histaminergic system.	2002 Jun	12166087
Role of Rho-associated protein kinase and histamine in lysophosphatidic acid-induced airway hyperresponsiveness in guinea pigs.	2002 Mar	11949879
The recovery of the neurally evoked secretory response of rat colonic mucosa after irradiation is independent of mast cells.	2002 Mar	11839088
Effects of the NMDA antagonist MK-801 on radial maze performance in histidine-deficient rats.	2002 Mar 22	12002811
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
Enhancement of neutrophil infiltration in histidine decarboxylase-deficient mice.	2002 Oct	12383201
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.	2002 Oct	12235264
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
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
Effects of NMDA antagonist MK-801 on radial maze performance in Zucker rats.	2002 Sep 20	12231236
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 Dec 15 15:06:58 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:58 UTC 2023`
Record UNII	R35D29L3ZA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRILAMINE MALEATE

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

Mepyramine maleate [WHO-DD]

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

Common Name

English

PYRILAMINE MALEATE [USP MONOGRAPH]

Common Name

English

STANGEN

Brand Name

English

PYRILAMINE MALEATE [GREEN BOOK]

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