mepyramine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
2331 91-84-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pyrilamine
  • pyrilamine maleate
  • pyranisamine
  • mepyramine
A histamine H1 antagonist. 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.
  • Molecular weight: 285.39
  • Formula: C17H23N3O
  • CLOGP: 3.23
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 28.60
  • ALOGS: -2.56
  • ROTB: 7
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

ADMET properties:

None

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.467 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.641 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 28.314 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 131.826 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 58.490 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 71.760 % High 1
herg hERG pIC50 5.411 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 13.964 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 31.696 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 51.900 % High 1
kinase-safety-class ACVR2A,ACVR2B,AKT2,AKT3,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,MAP3K21,MAP3K7,MAPK10,MAPK12,MAPK7,MAPK9,MET,MTOR,NTRK2,PDK2,PDK4,PDPK1,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK 41
kinase-selectivity-class AXL,BRAF,EIF2AK3,ERBB2,GRK2 5
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.314 High 1
mh-clint Mouse hepatocyte intrinsic clearance 219.786 High 1
mppb Mouse plasma protein binding (% unbound) 56.920 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.984 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 74.990 % High 1
rh-clint Rat hepatocyte intrinsic clearance 276.694 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 77.850 % High 1
rppb Rat plasma protein binding (% unbound) 56.860 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 963.829 uM High 1

Approvals:

DateAgencyCompanyOrphan
Aug. 7, 1973 FDA IMPAX LABS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Bronchopulmonary aspergillosis allergic 124.41 32.82 26 1916 3740 90622765
Total lung capacity decreased 124.21 32.82 26 1916 3769 90622736
Lung opacity 111.91 32.82 26 1916 6076 90620429
Blood calcium increased 94.33 32.82 26 1916 12032 90614473
Pleuritic pain 88.53 32.82 24 1918 10437 90616068
Aspiration 87.55 32.82 26 1916 15667 90610838
Pulmonary mass 87.39 32.82 30 1912 28742 90597763
Rales 87.34 32.82 26 1916 15801 90610704
Sputum discoloured 80.84 32.82 26 1916 20365 90606140
Blood test abnormal 80.15 32.82 26 1916 20926 90605579
Pneumococcal infection 80.06 32.82 15 1927 1230 90625275
Bronchiectasis 78.52 32.82 26 1916 22304 90604201
Transaminases increased 76.24 32.82 29 1913 37163 90589342
Obstructive airways disorder 74.77 32.82 26 1916 25843 90600662
Haemoptysis 68.35 32.82 26 1916 33294 90593211
Hypoxia 51.85 32.82 27 1915 72372 90554133
Liver function test increased 45.14 32.82 26 1916 84829 90541676
Upper respiratory tract infection 44.63 32.82 30 1912 128288 90498217
Blood creatinine increased 40.86 32.82 26 1916 101360 90525145
Tremor 39.85 32.82 30 1912 153143 90473362
Pulmonary fibrosis 39.46 32.82 26 1916 107477 90519028
Pleural effusion 38.50 32.82 26 1916 111965 90514540
Constipation 34.70 32.82 36 1906 280359 90346146

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Total lung capacity decreased 133.74 49.62 29 1639 7085 110580546
Bronchopulmonary aspergillosis allergic 128.85 49.62 29 1639 8397 110579234
Lung opacity 119.50 49.62 29 1639 11623 110576008
Blood calcium increased 106.92 49.62 29 1639 18011 110569620
Pulmonary mass 102.25 49.62 33 1635 37268 110550363
Pleuritic pain 100.60 49.62 27 1641 16113 110571518
Rales 97.86 49.62 29 1639 24710 110562921
Sputum discoloured 94.37 49.62 29 1639 27916 110559715
Blood test abnormal 93.76 49.62 29 1639 28525 110559106
Aspiration 91.84 49.62 29 1639 30504 110557127
Bronchiectasis 86.76 49.62 29 1639 36464 110551167
Obstructive airways disorder 80.10 49.62 29 1639 46120 110541511
Pneumococcal infection 79.65 49.62 15 1653 1804 110585827
Transaminases increased 71.15 49.62 29 1639 63361 110524270
Haemoptysis 67.83 49.62 29 1639 71325 110516306
Upper respiratory tract infection 64.95 49.62 34 1634 131294 110456337
Liver function test increased 61.83 49.62 29 1639 88519 110499112
Pulmonary fibrosis 57.91 49.62 29 1639 102013 110485618
Hypoxia 51.41 49.62 29 1639 129486 110458145

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D04AA02 DERMATOLOGICALS
ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
Antihistamines for topical use
ATC R06AC01 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Substituted ethylene diamines
MeSH PA D000068776 Sleep Aids, Pharmaceutical
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018926 Anti-Allergic Agents
CHEBI has role CHEBI:37955 H<small><sub>1</sub></small>-receptor antagonist

Related Drugs by ATC class:

D04AA Antihistamines for topical use 13 drugs
bamipinechloropyraminechlorphenoxamineclemastinedimetindenediphenhydramineisothipendylpheniraminepromethazinethenalidinethonzylaminetolpropamine show all 13 →
R06AC Substituted ethylene diamines 5 drugs
chloropyraminehistapyrrodinemethapyrilenethonzylaminetripelennamine

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Dermatographic urticaria indication 7632005 DOID:743
Vasomotor rhinitis indication 8229003 DOID:4730
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Urticaria indication 126485001
Dysmenorrhea indication 266599000
Influenza-like symptoms indication 315642008
Seasonal allergic rhinitis indication 367498001
Itching of skin indication 418363000
Allergic conjunctivitis indication 473460002 DOID:11204
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Hyperkalemia contraindication 14140009
Constipation contraindication 14760008 DOID:2089
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Myocardial infarction contraindication 22298006 DOID:5844
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acidosis contraindication 51387008
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Acute nephropathy contraindication 58574008
Metabolic acidosis contraindication 59455009
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Arteriosclerotic vascular disease contraindication 72092001
Diabetes mellitus contraindication 73211009 DOID:9351
Urethral stricture contraindication 76618002
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Cor pulmonale contraindication 83291003 DOID:8515
Epilepsy contraindication 84757009 DOID:1826
Pulmonary emphysema contraindication 87433001
Kidney disease contraindication 90708001 DOID:557
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Gastrointestinal obstruction contraindication 126765001
Neoplasm of brain contraindication 126952004 DOID:1319
Seizure disorder contraindication 128613002
Drug-induced psychosis contraindication 191483003 DOID:1742
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Hyporeninemic hypoaldosteronism contraindication 236464008
Bladder outflow obstruction contraindication 236645006
Morbid obesity contraindication 238136002 DOID:11981
Rhabdomyolysis contraindication 240131006
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Exacerbation of asthma contraindication 281239006
Lesion of brain contraindication 301766008
Panic disorder contraindication 371631005 DOID:594
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000
Breastfeeding (mother) contraindication 413712001
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Traumatic injury contraindication 417746004
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Dysfunction of sphincter of Oddi contraindication 430887001
Hypertensive urgency contraindication 443482000
Acute exacerbation of asthma contraindication 708038006




🐶 Veterinary Drug Use

SpeciesUseRelation
Horses Antihistaminic therapy Indication

🐶 Veterinary products

ProductApplicantIngredients
Histavet-P Intervet Inc. 1
Pyrilamine Maleate Injection Bimeda Animal Health Limited 1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.62 Basic
pKa2 4.33 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Histamine H1 receptor GPCR ANTAGONIST Ki 9.10 CHEMBL CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.18 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.96 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 7.60 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 5.70 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 5.75 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.23 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.16 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.52 DRUG MATRIX
Adenosine receptor A3 GPCR IC50 8.89 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 5.95 DRUG MATRIX
Histamine H1 receptor GPCR Kd 9.50 CHEMBL
Histamine H1 receptor GPCR IC50 8.24 CHEMBL

External reference:

IDSource
4019923 VUID
N0000148008 NUI
D05660 KEGG_DRUG
59-33-6 SECONDARY_CAS_RN
4018202 VANDF
4019923 VANDF
CHEBI:6762 CHEBI
Y5E PDB_CHEM_ID
CHEMBL511 ChEMBL_ID
CHEMBL1201006 ChEMBL_ID
1227 IUPHAR_LIGAND_ID
DB06691 DRUGBANK_ID
82091 RXNORM
4998 MMSL
5394 MMSL
d00782 MMSL
003377 NDDF
004791 NDDF
349962001 SNOMEDCT_US
36516003 SNOMEDCT_US
387087002 SNOMEDCT_US
C0034282 UMLSCUI
D011738 MESH_DESCRIPTOR_UI
106 INN_ID
4992 PUBCHEM_CID
HPE317O9TL UNII
HPE317O9TL INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Midol Complete Caffeine Free HUMAN OTC DRUG LABEL 3 0280-0078 TABLET 15 mg ORAL OTC Monograph Drug 17 sections
Midol Complete HUMAN OTC DRUG LABEL 3 0280-8005 TABLET 15 mg ORAL OTC Monograph Drug 17 sections
Midol CompleteGelcaps HUMAN OTC DRUG LABEL 3 0280-8015 TABLET, COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual ReliefMaximum Strength HUMAN OTC DRUG LABEL 3 0363-0252 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Acetaminophen 500mg Caffeine 60mg Pyrilamine maleate 15mg HUMAN OTC DRUG LABEL 3 0363-2310 TABLET 15 mg ORAL OTC Monograph Drug 11 sections
Menstrual Pain Relief HUMAN OTC DRUG LABEL 3 0363-3900 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 0363-3909 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual Complete Pain Relief HUMAN OTC DRUG LABEL 3 0363-9390 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Midol Complete HUMAN OTC DRUG LABEL 3 0924-6010 TABLET 15 mg ORAL OTC Monograph Drug 17 sections
Multi-Symptom Menstrual Relief HUMAN OTC DRUG LABEL 3 11673-363 TABLET 15 mg ORAL OTC Monograph Drug 17 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 11673-390 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 11673-967 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual CompleteMaximum Strength HUMAN OTC DRUG LABEL 3 11822-0390 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
MENSTRUAL COMPLETE HUMAN OTC DRUG LABEL 3 11822-3900 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
menstrual pain reliefmaximum strength HUMAN OTC DRUG LABEL 3 11822-6790 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 21130-930 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Ninjacof HUMAN OTC DRUG LABEL 2 23359-032 SOLUTION 12.50 mg ORAL OTC Monograph Drug 12 sections
Ninjacof-A HUMAN OTC DRUG LABEL 3 23359-033 LIQUID 12.50 mg ORAL OTC monograph final 12 sections
Ninjacof-D HUMAN OTC DRUG LABEL 3 23359-034 LIQUID 12.50 mg ORAL OTC Monograph Drug 15 sections
Midol Complete HUMAN OTC DRUG LABEL 3 29485-2802 TABLET 15 mg ORAL OTC Monograph Drug 16 sections
Midol Complete HUMAN OTC DRUG LABEL 3 29485-7358 TABLET 15 mg ORAL OTC Monograph Drug 16 sections
Midol Complete HUMAN OTC DRUG LABEL 3 29485-7964 TABLET 15 mg ORAL OTC Monograph Drug 16 sections
Capron Max HUMAN OTC DRUG LABEL 2 29978-123 LIQUID 15 mg ORAL OTC Monograph Drug 13 sections
Capron DM HUMAN OTC DRUG LABEL 2 29978-127 LIQUID 7.50 mg ORAL OTC Monograph Drug 14 sections
Capron DMT HUMAN OTC DRUG LABEL 2 29978-128 TABLET 30 mg ORAL unapproved drug other 14 sections
Histanaz HUMAN OTC DRUG LABEL 2 29978-129 TABLET 30 mg ORAL OTC Monograph Drug 13 sections
Menstrual Complete HUMAN OTC DRUG LABEL 3 30142-390 TABLET, FILM COATED 15 mg ORAL OTC Monograph Drug 16 sections
Kroger Allergy Relief HUMAN OTC DRUG LABEL 2 30142-773 LIQUID 50 mg ORAL OTC monograph final 16 sections
Acetaminophen , Caffeine and pyrilamine maleate HUMAN OTC DRUG LABEL 3 35916-0710 CAPSULE, LIQUID FILLED 15 mg ORAL OTC Monograph Drug 15 sections
Acetaminophen , Caffeine and pyrilamine maleate HUMAN OTC DRUG LABEL 3 35916-0710 CAPSULE, LIQUID FILLED 15 mg ORAL OTC Monograph Drug 15 sections