terbutaline Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
bronchodilators, phenethylamine derivatives 2598 23031-25-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • terbutaline
  • bricaril
  • terbutalin
  • brican
  • terbutaline sulfate
  • terbutaline hemisulfate
A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.
  • Molecular weight: 225.29
  • Formula: C12H19NO3
  • CLOGP: 0.48
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 4
  • TPSA: 72.72
  • ALOGS: -1.59
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 mg Inhal.aerosol
2 mg Inhal.powder
20 mg Inhal.solution
15 mg O
15 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 213 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 56 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.11 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 14 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.75 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 15 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 25, 1974 FDA

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
Asthma 147.11 16.82 116 6813 91426 46587707
Lactic acidosis 72.30 16.82 51 6878 33858 46645275
Wheezing 52.02 16.82 51 6878 53335 46625798
Dyspnoea 44.50 16.82 172 6757 515376 46163757
Squamous cell carcinoma of the oral cavity 43.80 16.82 10 6919 302 46678831
Bronchospasm 36.68 16.82 25 6904 15682 46663451
Shock haemorrhagic 36.28 16.82 20 6909 8604 46670529
Exposure during pregnancy 35.28 16.82 60 6869 108152 46570981
Acute kidney injury 32.14 16.82 92 6837 235763 46443370
Hyperlactacidaemia 27.95 16.82 11 6918 2204 46676929
Post viral fatigue syndrome 27.64 16.82 6 6923 143 46678990
Allergy to metals 25.76 16.82 7 6922 435 46678698
Cholestasis 24.89 16.82 25 6904 26868 46652265
Hepatocellular injury 24.71 16.82 26 6903 29496 46649637
Middle insomnia 24.27 16.82 16 6913 9499 46669634
Iodine allergy 24.17 16.82 7 6922 549 46678584
Tremor 24.02 16.82 53 6876 115586 46563547
Folate deficiency 23.34 16.82 9 6920 1709 46677424
Premature separation of placenta 23.28 16.82 9 6920 1719 46677414
Phlebectomy 20.51 16.82 4 6925 55 46679078
Haematoma 19.74 16.82 24 6905 31848 46647285
Eosinophilic granulomatosis with polyangiitis 19.31 16.82 8 6921 1828 46677305
Forced expiratory volume decreased 19.20 16.82 11 6918 5093 46674040
Cough 19.05 16.82 76 6853 230173 46448960
Maternal drugs affecting foetus 18.40 16.82 11 6918 5507 46673626
Fallopian tube disorder 18.30 16.82 5 6924 317 46678816
Eosinophilia 18.03 16.82 18 6911 19199 46659934
Nasal discharge discolouration 17.60 16.82 7 6922 1441 46677692
Forced expiratory volume abnormal 17.55 16.82 4 6925 120 46679013
Asthmatic crisis 17.46 16.82 7 6922 1471 46677662
Premature labour 17.40 16.82 14 6915 11285 46667848
Obstructive airways disorder 17.30 16.82 15 6914 13397 46665736

FDA Adverse Event Reporting System (Male)

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 116.14 18.20 69 4166 36105 29912138
Wheezing 48.66 18.20 38 4197 30900 29917343
Dyspnoea 45.79 18.20 126 4109 333169 29615074
Exposure during pregnancy 44.28 18.20 23 4212 9238 29939005
Hyperkaliuria 44.26 18.20 9 4226 163 29948080
Wolff-Parkinson-White syndrome 42.73 18.20 9 4226 195 29948048
Agranulocytosis 39 18.20 29 4206 21913 29926330
Premature baby 36.43 18.20 25 4210 16666 29931577
Chest discomfort 34.29 18.20 37 4198 45443 29902800
Bronchospasm 33.83 18.20 20 4215 10318 29937925
Gastrointestinal mucosal necrosis 32.92 18.20 7 4228 159 29948084
Placental transfusion syndrome 28.69 18.20 4 4231 4 29948239
Unmasking of previously unidentified disease 28.49 18.20 8 4227 590 29947653
Forced expiratory volume decreased 27.63 18.20 12 4223 3238 29945005
Cholestasis 27.54 18.20 25 4210 24925 29923318
Pulmonary valve stenosis 27.35 18.20 7 4228 362 29947881
Penile erythema 27.22 18.20 6 4229 162 29948081
Respiratory distress 26.92 18.20 28 4207 32944 29915299
Meralgia paraesthetica 26.64 18.20 6 4229 179 29948064
Nasal inflammation 25.11 18.20 6 4229 233 29948010
Foetal distress syndrome 24.51 18.20 8 4227 983 29947260
Middle insomnia 23.82 18.20 13 4222 5760 29942483
Ductus arteriosus premature closure 23.79 18.20 5 4230 107 29948136
Obstructive airways disorder 23.21 18.20 15 4220 9044 29939199
Lactic acidosis 22.82 18.20 25 4210 31188 29917055
Prothrombin time ratio decreased 22.62 18.20 6 4229 357 29947886
Heart rate increased 21.61 18.20 27 4208 38694 29909549
Stillbirth 21.16 18.20 5 4230 185 29948058
Accelerated idioventricular rhythm 20.44 18.20 4 4231 59 29948184
Interstitial lung disease 20.30 18.20 33 4202 60164 29888079
Clonic convulsion 20.26 18.20 6 4229 535 29947708
Atrial septal defect 19.43 18.20 12 4223 6689 29941554
Gastrointestinal oedema 18.55 18.20 7 4228 1316 29946927
Patent ductus arteriosus 18.46 18.20 9 4226 3160 29945083

Pharmacologic Action:

SourceCodeDescription
ATC R03AC03 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Selective beta-2-adrenoreceptor agonists
ATC R03CC03 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS FOR SYSTEMIC USE
Selective beta-2-adrenoreceptor agonists
ATC R03CC53 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS FOR SYSTEMIC USE
Selective beta-2-adrenoreceptor agonists
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 D001993 Bronchodilator Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D012102 Reproductive Control Agents
MeSH PA D019141 Respiratory System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D015149 Tocolytic Agents
CHEBI has role CHEBI:35522 beta-adrenergic receptor agonist
CHEBI has role CHEBI:35523 bronchodilator agents
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:35526 hypoglycemic drug
CHEBI has role CHEBI:38462 acetylcholinesterase inhibitors
CHEBI has role CHEBI:49167 anti-asthmatic agents
CHEBI has role CHEBI:66993 anti-contraction drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchitis indication 32398004 DOID:6132
Tear film insufficiency indication 46152009
Pulmonary emphysema indication 87433001
Asthma indication 195967001 DOID:2841
Skin irritation indication 367466007
Asthma management indication 406162001
Itching of skin indication 418363000
Acute exacerbation of asthma indication 708038006
Chronic Obstructive Pulmonary Disease with Bronchospasms indication
Minor Skin Wound Pain indication
Bronchospasm Prevention indication
Premature labor off-label use 6383007
Bronchiectasis off-label use 12295008 DOID:9563
Keratoconjunctivitis sicca off-label use 302896008 DOID:12895
Pulmonary edema contraindication 19242006 DOID:11396
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Ketoacidosis contraindication 56051008
Diabetes mellitus contraindication 73211009 DOID:9351
Compression of umbilical cord contraindication 79222000
Hyperglycemia contraindication 80394007 DOID:4195
Decreased respiratory function contraindication 80954004
Epilepsy contraindication 84757009 DOID:1826
Open wound contraindication 125643001
Seizure disorder contraindication 128613002
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Myocardial ischemia contraindication 414795007 DOID:3393
Placental abruption contraindication 415105001
Denuded skin contraindication 418242004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.48 acidic
pKa2 11.49 acidic
pKa3 12.74 acidic
pKa4 8.66 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
Beta-2 adrenergic receptor GPCR AGONIST Ki 5.60 WOMBAT-PK CHEMBL
Beta-2 adrenergic receptor GPCR Kd 5.40 CHEMBL

External reference:

IDSource
4019941 VUID
N0000148026 NUI
D00688 KEGG_DRUG
23031-32-5 SECONDARY_CAS_RN
4018396 VANDF
4019941 VANDF
C0039542 UMLSCUI
CHEBI:9449 CHEBI
CHEMBL1760 ChEMBL_ID
CHEMBL1160544 ChEMBL_ID
CHEMBL1315867 ChEMBL_ID
D013726 MESH_DESCRIPTOR_UI
5403 PUBCHEM_CID
2616 INN_ID
DB00871 DRUGBANK_ID
N8ONU3L3PG UNII
560 IUPHAR_LIGAND_ID
10368 RXNORM
41721 MMSL
5548 MMSL
d00752 MMSL
001812 NDDF
004731 NDDF
24583009 SNOMEDCT_US
372745006 SNOMEDCT_US
45311002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
TERBUTALINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0115-2611 TABLET 2.50 mg ORAL ANDA 23 sections
TERBUTALINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0115-2622 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9375 INJECTION 1 mg SUBCUTANEOUS ANDA 22 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9746 INJECTION 1 mg SUBCUTANEOUS ANDA 22 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0527-1311 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0527-1318 TABLET 2.50 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 10135-579 TABLET 2.50 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 10135-580 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 10271-101 INJECTION 1 mg SUBCUTANEOUS ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 17478-933 INJECTION 1 mg SUBCUTANEOUS ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 21695-121 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 21695-122 TABLET 2.50 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 24979-132 TABLET 2.50 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 24979-133 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 52584-665 INJECTION, SOLUTION 1 mg SUBCUTANEOUS ANDA 11 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 53808-0312 TABLET 2.50 mg ORAL ANDA 22 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 62559-721 TABLET 2.50 mg ORAL NDA authorized generic 22 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 62559-722 TABLET 5 mg ORAL NDA authorized generic 22 sections
Terbutaline Sulfate Human Prescription Drug Label 1 63323-665 INJECTION, SOLUTION 1 mg SUBCUTANEOUS ANDA 13 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 67296-1053 TABLET 2.50 mg ORAL ANDA 13 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 71205-938 TABLET 2.50 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 71205-939 TABLET 5 mg ORAL ANDA 23 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 71872-7080 INJECTION 1 mg SUBCUTANEOUS ANDA 22 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 71872-7130 INJECTION, SOLUTION 1 mg SUBCUTANEOUS ANDA 24 sections
Terbutaline Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 72843-101 INJECTION 1 mg SUBCUTANEOUS ANDA 23 sections