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Details

Stereochemistry ABSOLUTE
Molecular Formula C76H52O46.C17H23N3O
Molecular Weight 1986.5861
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRILAMINE TANNATE

SMILES

c1c(cc(c(c1O)O)O)C(=O)Oc2cc(cc(c2O)O)C(=O)OC[C@]3([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O3)OC(=O)c4cc(c(c(c4)OC(=O)c5cc(c(c(c5)O)O)O)O)O)OC(=O)c6cc(c(c(c6)OC(=O)c7cc(c(c(c7)O)O)O)O)O)OC(=O)c8cc(c(c(c8)OC(=O)c9cc(c(c(c9)O)O)O)O)O)OC(=O)c%10cc(c(c(c%10)OC(=O)c%11cc(c(c(c%11)O)O)O)O)O.CN(C)CCN(Cc1ccc(cc1)OC)c2ccccn2

InChI

InChIKey=FPPPOGQYQQBHQR-HBNMXAOGSA-N
InChI=1S/C76H52O46.C17H23N3O/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h1-20,52,63-65,76-101H,21H2;4-11H,12-14H2,1-3H3/t52-,63-,64+,65-,76+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C76H52O46
Molecular Weight 1701.2015
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
QSAR study on binding affinity of PATs (rodenticides) to the [3H]-mepyramine-labelled H1 receptor in rat and guinea pig brain.
2001
Effect of clobenpropit on regional cerebral blood flow in rat hippocampus.
2001 Apr
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
The effects of histamine and its antagonists on the cochlear microphonic and the compound action potential of the guinea pig.
2001 Aug
Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.
2001 Dec
Enhancement by histamine of vascular endothelial growth factor production in granulation tissue via H(2) receptors.
2001 Dec
Characterization of histamine-induced increases in intracellular free Ca2+ concentrations in Chang liver cells.
2001 Feb
Effect of H1-antagonists on spatial memory deficit evaluated by 8-arm radial maze in rats.
2001 Jul
The H3 receptor is involved in cholecystokinin inhibition of food intake in rats.
2001 Jun 15
Histamine H1 receptor activation stimulates mitogenesis in human astrocytoma U373 MG cells.
2001 Nov
Standard treatment: the role of antihistamines.
2001 Nov
The role of central histaminergic neuron system as an anticonvulsive mechanism in developing brain.
2001 Nov
The kinetics, function, and regulation of P-selectin expressed by human brain microvessel endothelial cells in primary culture.
2001 Nov
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
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Inhibitory effect of histamine on axonal transport in cultured mouse dorsal root ganglion neurons.
2001 Oct
Pharmacological characterization of cyclosporine A-induced kaolin intake in rats.
2001 Oct-Nov
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
Histochemical and biochemical studies on the secretory mechanisms of some glands of guinea-pigs treated with histamine.
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
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
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
Orexins activate histaminergic neurons via the orexin 2 receptor.
2002 Feb 1
Histamine-induced IL-6 and IL-8 production are differentially modulated by IFN-gamma and IL-4 in human keratinocytes.
2002 Jan
ReN 1869, a novel tricyclic antihistamine, is active against neurogenic pain and inflammation.
2002 Jan 18
Mouse light/dark box test reveals anxiogenic-like effects by activation of histamine H1 receptors.
2002 Jan-Feb
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
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
Predicting the risk of Lyme disease: habitat suitability for Ixodes scapularis in the north central United States.
2002 Mar
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
Histamine h(4) and h(2) receptors control histamine-induced interleukin-16 release from human CD8(+) T cells.
2002 Oct
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
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:18:44 UTC 2021
Edited
by admin
on Sat Jun 26 13:18:44 UTC 2021
Record UNII
A9310LW34B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRILAMINE TANNATE
VANDF  
Common Name English
MEPYRAMINE TANNATE
WHO-DD  
Common Name English
PYRILAMINE TANNATE [VANDF]
Common Name English
2-((2-(DIMETHYLAMINO)ETHYL)(P-METHOXYBENZYL)AMINO)PYRIDINE TANNATE
Common Name English
MEPYRAMINE TANNATE [WHO-DD]
Common Name English
Code System Code Type Description
EVMPD
SUB03164MIG
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY
RXCUI
221152
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY RxNorm
PUBCHEM
72941740
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY
DRUG BANK
DBSALT002726
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY
FDA UNII
A9310LW34B
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY
CAS
183969-60-0
Created by admin on Sat Jun 26 13:18:44 UTC 2021 , Edited by admin on Sat Jun 26 13:18:44 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY