salmeterol Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
bronchodilators, phenethylamine derivatives 2419 89365-50-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • serevent
  • salmeterol
  • salmeterol xinafoate
Salmeterol is a selective long acting beta2-adrenoceptor agonist. In vitro studies show salmeterol to be at least 50 times more selective for beta2-adrenoceptors than albuterol. Although beta2-adrenoceptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-adrenoceptors are the predominant receptors in the heart, there are also beta2-adrenoceptors in the human heart comprising 10% to 50% of the total beta-adrenoceptors. The precise function of these receptors has not been established, but their presence raises the possibility that even selective beta2-agonists may have cardiac effects. The pharmacologic effects of beta2-adrenoceptor agonist drugs, including salmeterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3',5'-adenosine monophosphate (cyclic AMP). Increased cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. In vitro tests show that salmeterol is a potent and long-lasting inhibitor of the release of mast cell mediators, such as histamine, leukotrienes, and prostaglandin D2, from human lung. Salmeterol inhibits histamine-induced plasma protein extravasation and inhibits platelet-activating factor-induced eosinophil accumulation in the lungs of guinea pigs when administered by the inhaled route. In humans, single doses of salmeterol administered via inhalation aerosol attenuate allergen-induced bronchial hyper-responsiveness.
  • Molecular weight: 415.57
  • Formula: C25H37NO4
  • CLOGP: 3.06
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 4
  • TPSA: 81.95
  • ALOGS: -5.26
  • ROTB: 16

Drug dosage:

DoseUnitRoute
0.10 mg Inhal.aerosol
0.10 mg Inhal.powder

Approvals:

DateAgencyCompanyOrphan
Feb. 4, 1994 FDA

FDA Adverse Event Reporting System

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
Asthma 1300.22 29.26 290 2073 12112 3371384
Dyspnoea 1059.14 29.26 391 1972 102543 3280953
Chronic obstructive pulmonary disease 810.99 29.26 194 2169 10815 3372681
Product quality issue 750.30 29.26 219 2144 26516 3356980
Drug ineffective 634.81 29.26 282 2081 115808 3267688
Pneumonia 610.48 29.26 238 2125 69905 3313591
Cough 389.79 29.26 148 2215 39710 3343786
Dysphonia 297.21 29.26 81 2282 7423 3376073
Malaise 258.08 29.26 128 2235 65049 3318447
Wheezing 245.12 29.26 71 2292 8100 3375396
Drug hypersensitivity 231.79 29.26 99 2264 35581 3347915
Inhalation therapy 189.18 29.26 25 2338 21 3383475
Drug administration error 181.28 29.26 53 2310 6223 3377273
Bronchitis 165.58 29.26 61 2302 14784 3368712
Candida infection 154.61 29.26 42 2321 3770 3379726
Device use error 143.52 29.26 30 2333 866 3382630
Underdose 142.80 29.26 45 2318 6789 3376707
Status asthmaticus 142.02 29.26 24 2339 206 3383290
Chest discomfort 132.12 29.26 54 2309 17231 3366265
Ill-defined disorder 131.13 29.26 36 2327 3358 3380138
Condition aggravated 128.28 29.26 68 2295 39165 3344331
Asphyxia 127.81 29.26 30 2333 1486 3382010
Hospitalisation 122.67 29.26 54 2309 20671 3362825
Emphysema 115.04 29.26 29 2334 1939 3381557
Arteriosclerosis coronary artery 113.18 29.26 31 2332 2863 3380633
Respiratory failure 110.74 29.26 52 2311 23089 3360407
Productive cough 104.76 29.26 35 2328 6336 3377160
Drug dose omission 99.09 29.26 57 2306 38375 3345121
Throat irritation 98.77 29.26 32 2331 5262 3378234
Oral candidiasis 97.58 29.26 27 2336 2587 3380909
Lung disorder 96.92 29.26 36 2327 8881 3374615
Intentional product use issue 96.21 29.26 25 2338 1885 3381611
Tremor 89.64 29.26 48 2315 28096 3355400
Adverse event 87.85 29.26 36 2327 11521 3371975
Treatment noncompliance 82.36 29.26 32 2331 8913 3374583
Dyspnoea exertional 79.23 29.26 29 2334 6857 3376639
Fall 76.85 29.26 57 2306 58826 3324670
Pulmonary mass 73.31 29.26 21 2342 2279 3381217
Loss of consciousness 73.13 29.26 42 2321 28105 3355391
Hypoxia 72.99 29.26 30 2333 9661 3373835
Aphonia 70.02 29.26 18 2345 1299 3382197
Nasopharyngitis 68.62 29.26 37 2326 21910 3361586
Bronchospasm 68.22 29.26 23 2340 4271 3379225
Dizziness 65.71 29.26 58 2305 76454 3307042
Oxygen saturation decreased 65.16 29.26 28 2335 10063 3373433
Asthenia 64.97 29.26 54 2309 65611 3317885
Chest pain 64.01 29.26 44 2319 40231 3343265
Lung neoplasm malignant 63.36 29.26 23 2340 5305 3378191
Overdose 63.34 29.26 41 2322 33937 3349559
Pyrexia 62.79 29.26 58 2305 81057 3302439
Investigation 61.55 29.26 17 2346 1615 3381881
Heart rate increased 61.43 29.26 30 2333 14456 3369040
Fatigue 61.36 29.26 65 2298 107175 3276321
Increased upper airway secretion 60.01 29.26 15 2348 966 3382530
Oropharyngeal pain 59.99 29.26 28 2335 12206 3371290
Expired product administered 59.72 29.26 17 2346 1802 3381694
Pain 58.94 29.26 53 2310 71504 3311992
Cardiac arrest 58.50 29.26 36 2327 27283 3356213
Choking 58.34 29.26 17 2346 1958 3381538
Cushing's syndrome 57.70 29.26 15 2348 1131 3382365
Muscle spasms 56.45 29.26 35 2328 26868 3356628
Dry mouth 56.09 29.26 25 2338 9797 3373699
Lung hyperinflation 55.01 29.26 10 2353 135 3383361
Laryngitis 54.83 29.26 15 2348 1375 3382121
Oxygen therapy 54.45 29.26 11 2352 266 3383230
Weight increased 54.12 29.26 34 2329 26706 3356790
Palpitations 53.63 29.26 30 2333 19053 3364443
Cataract 53.29 29.26 22 2341 7154 3376342
Eosinophilic granulomatosis with polyangiitis 53.15 29.26 13 2350 765 3382731
Tachycardia 53.11 29.26 32 2331 23339 3360157
Influenza 53.04 29.26 26 2337 12620 3370876
Insomnia 51.84 29.26 37 2326 35861 3347635
Lung infection 51.56 29.26 20 2343 5533 3377963
Myocardial infarction 51.47 29.26 40 2323 44093 3339403
Diabetes mellitus 51.04 29.26 25 2338 12108 3371388
Death 50.49 29.26 70 2293 152254 3231242
Pulmonary function test decreased 50.19 29.26 12 2351 641 3382855
Cataract operation 50.12 29.26 13 2350 971 3382525
Headache 49.46 29.26 54 2309 91926 3291570
Glaucoma 49.28 29.26 16 2347 2640 3380856
Atrial fibrillation 47.33 29.26 30 2333 23911 3359585
Surgery 47.24 29.26 20 2343 6920 3376576
Respiratory distress 46.77 29.26 21 2342 8367 3375129
Sinusitis 46.13 29.26 26 2337 16742 3366754
Adrenal insufficiency 45.74 29.26 14 2349 1907 3381589
Breath sounds abnormal 44.38 29.26 12 2351 1052 3382444
Anxiety 44.20 29.26 35 2328 39594 3343902
Inability to afford medication 44.14 29.26 8 2355 106 3383390
Intentional underdose 43.92 29.26 10 2353 431 3383065
Emergency care 43.73 29.26 8 2355 112 3383384
Respiratory disorder 43.24 29.26 18 2345 5972 3377524
Hypersensitivity 43.14 29.26 30 2333 27870 3355626
Nervousness 42.57 29.26 18 2345 6206 3377290
Weight decreased 41.70 29.26 34 2329 40077 3343419
Hip fracture 41.55 29.26 17 2346 5398 3378098
Acute respiratory failure 40.82 29.26 16 2347 4546 3378950
Memory impairment 40.64 29.26 23 2340 14915 3368581
Stomatitis 39.86 29.26 21 2342 11831 3371665
Medication error 39.83 29.26 21 2342 11850 3371646
Cushingoid 39.20 29.26 10 2353 699 3382797
Multiple allergies 38.95 29.26 10 2353 717 3382779
Oropharyngeal candidiasis 38.89 29.26 8 2355 212 3383284
Feeling abnormal 38.86 29.26 28 2335 27497 3355999
Gait disturbance 38.43 29.26 28 2335 27964 3355532
Drug interaction 37.14 29.26 34 2329 46778 3336718
Back pain 36.96 29.26 31 2332 37974 3345522
Cerebrovascular accident 36.85 29.26 30 2333 35258 3348238
Hypertension 36.64 29.26 31 2332 38435 3345061
Therapeutic response decreased 36.10 29.26 19 2344 10679 3372817
Infection 33.94 29.26 25 2338 25377 3358119
Arrhythmia 33.77 29.26 18 2345 10379 3373117
Pruritus 33.27 29.26 32 2331 46801 3336695
Nasal congestion 33.24 29.26 16 2347 7451 3376045
Cyanosis 32.70 29.26 14 2349 4972 3378524
Drug dispensing error 32.49 29.26 13 2350 3895 3379601
Vision blurred 32.47 29.26 22 2341 19567 3363929
Cardiac disorder 31.69 29.26 19 2344 13700 3369796
Hypoxic-ischaemic encephalopathy 31.62 29.26 10 2353 1515 3381981
Hypokalaemia 31.58 29.26 19 2344 13786 3369710
Adrenal suppression 31.34 29.26 7 2356 276 3383220
Visual impairment 31.15 29.26 19 2344 14127 3369369
Obstructive airways disorder 30.85 29.26 10 2353 1639 3381857
Disability 30.49 29.26 9 2354 1082 3382414
Rhinorrhoea 29.82 29.26 15 2348 7674 3375822
Cardio-respiratory arrest 29.62 29.26 19 2344 15421 3368075
Respiratory arrest 29.56 29.26 17 2346 11351 3372145
Seizure 29.44 29.26 28 2335 40372 3343124

Pharmacologic Action:

SourceCodeDescription
ATC R03AC12 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Selective beta-2-adrenoreceptor agonists
ATC R03AK06 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
ATC R03AK12 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Adrenergics in combination with corticosteroids or other drugs, excl. anticholinergics
FDA MoA N0000009922 Adrenergic beta2-Agonists
FDA EPC N0000175779 beta2-Adrenergic Agonist
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058666 Adrenergic beta-2 Receptor Agonists
MeSH PA D000318 Adrenergic beta-Agonists
MeSH PA D018927 Anti-Asthmatic Agents
MeSH PA D001337 Autonomic Agents
MeSH PA D001993 Bronchodilator Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents
CHEBI has role CHEBI:35523 bronchodilator agent
CHEBI has role CHEBI:35522 beta-adrenergic agonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pulmonary emphysema indication 87433001
Non-allergic asthma indication 266361008 DOID:9360
Allergic asthma indication 389145006 DOID:9415
Adjunct Therapy to Achieve Long-term Asthma Control indication
Bronchospasm Prevention with COPD indication
Exercise-Induced Bronchospasm Prevention indication
COPD Associated with Chronic Bronchitis indication
Mycosis contraindication 3218000 DOID:1564
Disease caused by parasite contraindication 17322007
Glaucoma contraindication 23986001 DOID:1686
Acute tuberculosis contraindication 25629007
Hypertensive disorder contraindication 38341003 DOID:10763
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Ketoacidosis contraindication 56051008
Osteoporosis contraindication 64859006 DOID:11476
Diabetes mellitus contraindication 73211009 DOID:9351
Hypopituitarism contraindication 74728003 DOID:9406
Candidiasis of mouth contraindication 79740000 DOID:14262
Hyperglycemia contraindication 80394007 DOID:4195
Thyrotoxicosis contraindication 90739004 DOID:7997
Bilateral cataracts contraindication 95722004
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002 DOID:1826
Ophthalmic herpes simplex contraindication 186542001
Exacerbation of asthma contraindication 281239006
Osteopenia contraindication 312894000
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Congenital long QT syndrome contraindication 442917000
Uncontrolled Bacterial Infections contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.07 acidic
pKa2 9.28 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 0.014MG BASE/INH AIRDUO RESPICLICK TEVA PHARM N208799 Jan. 27, 2017 RX POWDER INHALATION 9066957 Oct. 6, 2034 TREATMENT OF ASTHMA
EQ 0.014MG BASE/INH AIRDUO RESPICLICK TEVA PHARM N208799 Jan. 27, 2017 RX POWDER INHALATION 9415008 Oct. 6, 2034 TREATMENT OF ASTHMA

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 0.014MG BASE/INH AIRDUO RESPICLICK TEVA PHARM N208799 Jan. 27, 2017 RX POWDER INHALATION Jan. 27, 2020 NEW PRODUCT
EQ 0.05MG BASE/INH ADVAIR DISKUS 100/50 GLAXO GRP LTD N021077 Aug. 24, 2000 RX POWDER INHALATION Dec. 20, 2020 INFORMATION ADDED TO THE CLINICAL TRIALS SECTION OF THE LABELING REGARDING A POSTMARKETING SAFETY AND EFFICACY STUDY EVALUATING THE RISK OF SERIOUS ASTHMA-RELATED EVENTS
EQ 0.05MG BASE/INH ADVAIR DISKUS 250/50 GLAXO GRP LTD N021077 Aug. 24, 2000 RX POWDER INHALATION Dec. 20, 2020 INFORMATION ADDED TO THE CLINICAL TRIALS SECTION OF THE LABELING REGARDING A POSTMARKETING SAFETY AND EFFICACY STUDY EVALUATING THE RISK OF SERIOUS ASTHMA-RELATED EVENTS
EQ 0.05MG BASE/INH ADVAIR DISKUS 500/50 GLAXO GRP LTD N021077 Aug. 24, 2000 RX POWDER INHALATION Dec. 20, 2020 INFORMATION ADDED TO THE CLINICAL TRIALS SECTION OF THE LABELING REGARDING A POSTMARKETING SAFETY AND EFFICACY STUDY EVALUATING THE RISK OF SERIOUS ASTHMA-RELATED EVENTS

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-2 adrenergic receptor GPCR AGONIST Ki 9.41 CHEMBL CHEMBL
Aldehyde oxidase Enzyme IC50 5.00 WOMBAT-PK
Beta-1 adrenergic receptor GPCR Ki 6.10 CHEMBL
Beta-3 adrenergic receptor GPCR EC50 6 CHEMBL
D(3) dopamine receptor GPCR Ki 5.98 CHEMBL
Beta-2 adrenergic receptor GPCR EC50 7.50 CHEMBL

External reference:

IDSource
559 IUPHAR_LIGAND_ID
4023955 VUID
N0000021960 NUI
C0073992 UMLSCUI
D00687 KEGG_DRUG
2I4BC502BT UNII
5578 INN_ID
94749-08-3 SECONDARY_CAS_RN
DB00938 DRUGBANK_ID
4023955 VANDF
N0000021960 NDFRT
004036 NDDF
d03759 MMSL
36117 RXNORM
108605008 SNOMEDCT_US
372515005 SNOMEDCT_US
CHEMBL1263 ChEMBL_ID
5152 PUBCHEM_CID
CHEMBL1082607 ChEMBL_ID
D000068299 MESH_DESCRIPTOR_UI
CHEBI:9011 CHEBI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fluticasone Propionate and Salmeterol HUMAN PRESCRIPTION DRUG LABEL 2 0093-3607 POWDER, METERED 14 ug RESPIRATORY (INHALATION) NDA AUTHORIZED GENERIC 19 sections
Fluticasone Propionate and Salmeterol HUMAN PRESCRIPTION DRUG LABEL 2 0093-3608 POWDER, METERED 14 ug RESPIRATORY (INHALATION) NDA AUTHORIZED GENERIC 19 sections
Fluticasone Propionate and Salmeterol HUMAN PRESCRIPTION DRUG LABEL 2 0093-3609 POWDER, METERED 14 ug RESPIRATORY (INHALATION) NDA AUTHORIZED GENERIC 19 sections
SEREVENT HUMAN PRESCRIPTION DRUG LABEL 1 0173-0520 POWDER, METERED 50 ug RESPIRATORY (INHALATION) NDA 19 sections
SEREVENT HUMAN PRESCRIPTION DRUG LABEL 1 0173-0521 POWDER, METERED 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 0173-0695 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 0173-0696 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 0173-0697 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HFA HUMAN PRESCRIPTION DRUG LABEL 2 0173-0715 AEROSOL, METERED 21 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HFA HUMAN PRESCRIPTION DRUG LABEL 2 0173-0716 AEROSOL, METERED 21 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HFA HUMAN PRESCRIPTION DRUG LABEL 2 0173-0717 AEROSOL, METERED 21 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 21695-196 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 21695-197 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 21695-361 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 33261-873 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 33261-874 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 49999-819 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 49999-984 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 49999-985 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 50090-0730 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 50090-0731 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 50090-0732 POWDER 50 ug RESPIRATORY (INHALATION) NDA 18 sections
ADVAIR DISKUS HUMAN PRESCRIPTION DRUG LABEL 2 54868-4516 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR DISKUS HUMAN PRESCRIPTION DRUG LABEL 2 54868-4517 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR DISKUS HUMAN PRESCRIPTION DRUG LABEL 2 54868-4518 POWDER 50 ug RESPIRATORY (INHALATION) NDA 19 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 58437-000 POWDER 50 ug RESPIRATORY (INHALATION) Approved Drug Product Manufactured Under Contract 1 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 58437-001 POWDER 50 ug RESPIRATORY (INHALATION) Approved Drug Product Manufactured Under Contract 1 sections
ADVAIR HUMAN PRESCRIPTION DRUG LABEL 2 58437-002 POWDER 50 ug RESPIRATORY (INHALATION) Approved Drug Product Manufactured Under Contract 1 sections
AirDuo RespiClick HUMAN PRESCRIPTION DRUG LABEL 2 59310-805 POWDER, METERED 14 ug RESPIRATORY (INHALATION) NDA 19 sections
AirDuo RespiClick HUMAN PRESCRIPTION DRUG LABEL 2 59310-812 POWDER, METERED 14 ug RESPIRATORY (INHALATION) NDA 19 sections