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 184.13 16.23 140 7479 108832 53232615
Wheezing 74.69 16.23 67 7552 65208 53276239
Lactic acidosis 69.73 16.23 51 7568 37202 53304245
Dyspnoea 65.12 16.23 207 7412 586025 52755422
Squamous cell carcinoma of the oral cavity 44.03 16.23 10 7609 307 53341140
Allergy to metals 38.55 16.23 10 7609 540 53340907
Iodine allergy 36.35 16.23 10 7609 677 53340770
Shock haemorrhagic 35.83 16.23 20 7599 9163 53332284
Exposure during pregnancy 34.48 16.23 63 7556 124797 53216650
Acute kidney injury 33.00 16.23 95 7524 253773 53087674
Sputum discoloured 32.31 16.23 22 7597 14317 53327130
Bronchospasm 31.66 16.23 23 7596 16575 53324872
Forced expiratory volume decreased 29.82 16.23 15 7604 5570 53335877
Hyperlactacidaemia 29.54 16.23 12 7607 2713 53338734
Tremor 29.25 16.23 59 7560 125677 53215770
Post viral fatigue syndrome 27.37 16.23 6 7613 156 53341291
Obstructive airways disorder 26.30 16.23 21 7598 17408 53324039
Rubber sensitivity 26.22 16.23 10 7609 1915 53339532
Cough 25.85 16.23 88 7531 256805 53084642
Middle insomnia 25.49 16.23 17 7602 10691 53330756
Folate deficiency 25.36 16.23 10 7609 2094 53339353
Hepatocellular injury 25.21 16.23 26 7593 29960 53311487
Cholestasis 24.34 16.23 25 7594 28670 53312777
Nasal discharge discolouration 24.11 16.23 9 7610 1625 53339822
Asthmatic crisis 23.06 16.23 9 7610 1834 53339613
Premature separation of placenta 22.94 16.23 9 7610 1858 53339589
Food allergy 21.89 16.23 14 7605 8204 53333243
Rheumatoid arthritis 21.54 16.23 9 7610 314522 53026925
Heart rate increased 20.79 16.23 40 7579 82275 53259172
Phlebectomy 20.66 16.23 4 7615 55 53341392
Sleep disorder due to a general medical condition 20.60 16.23 13 7606 7444 53334003
Pleural rub 20.59 16.23 4 7615 56 53341391
Exposure to allergen 20.23 16.23 5 7614 222 53341225
Haematoma 19.32 16.23 24 7595 33820 53307627
Respiratory rate increased 18.85 16.23 15 7604 12368 53329079
Eosinophilia 18.84 16.23 19 7600 21316 53320131
Maternal drugs affecting foetus 18.74 16.23 11 7608 5535 53335912
Fallopian tube disorder 18.46 16.23 5 7614 319 53341128
Eosinophilic granulomatosis with polyangiitis 18.22 16.23 8 7611 2191 53339256
Premature baby 18.16 16.23 18 7601 19783 53321664
Respiratory distress 17.74 16.23 23 7596 33804 53307643
Forced expiratory volume abnormal 17.64 16.23 4 7615 122 53341325
Productive cough 17.41 16.23 30 7589 56699 53284748
Premature labour 16.76 16.23 14 7605 12348 53329099

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 132.62 18.65 81 4577 43984 32464884
Wheezing 61.20 18.65 47 4611 36827 32472041
Dyspnoea 53.77 18.65 142 4516 361903 32146965
Chest discomfort 46.69 18.65 46 4612 50184 32458684
Cholestasis 46.03 18.65 35 4623 26998 32481870
Hyperkaliuria 44.14 18.65 9 4649 163 32508705
Exposure during pregnancy 44.07 18.65 23 4635 9206 32499662
Forced expiratory volume decreased 43.17 18.65 17 4641 3539 32505329
Wolff-Parkinson-White syndrome 42.10 18.65 9 4649 207 32508661
Agranulocytosis 39.09 18.65 30 4628 23447 32485421
Bronchospasm 35.08 18.65 21 4637 10934 32497934
Premature baby 33.79 18.65 25 4633 18493 32490375
Nasal disorder 32.16 18.65 11 4647 1539 32507329
Gastrointestinal mucosal necrosis 31.92 18.65 7 4651 182 32508686
Placental transfusion syndrome 28.63 18.65 4 4654 4 32508864
Pulmonary valve stenosis 27.22 18.65 7 4651 364 32508504
Unmasking of previously unidentified disease 27.04 18.65 8 4650 701 32508167
Penile erythema 26.79 18.65 6 4652 172 32508696
Meralgia paraesthetica 26.56 18.65 6 4652 179 32508689
Respiratory distress 25.07 18.65 28 4630 35218 32473650
Bronchospasm paradoxical 24.82 18.65 5 4653 85 32508783
Nasal inflammation 24.51 18.65 6 4652 255 32508613
Obstructive airways disorder 23.75 18.65 17 4641 11944 32496924
Foetal distress syndrome 23.66 18.65 8 4650 1081 32507787
Heart rate increased 22.78 18.65 29 4629 41799 32467069
Middle insomnia 22.25 18.65 13 4645 6471 32502397
Prothrombin time ratio decreased 22.09 18.65 6 4652 386 32508482
Lactic acidosis 21.08 18.65 25 4633 33511 32475357
Stillbirth 20.77 18.65 5 4653 198 32508670
Ductus arteriosus premature closure 20.15 18.65 5 4653 225 32508643
Lung disorder 19.32 18.65 24 4634 33730 32475138
Clonic convulsion 19.01 18.65 6 4652 653 32508215
Accelerated idioventricular rhythm 18.88 18.65 4 4654 88 32508780
Atrial septal defect 18.76 18.65 12 4646 7013 32501855

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 acetylcholine esterase inhibitor
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
DB00871 DRUGBANK_ID
CHEMBL1315867 ChEMBL_ID
CHEMBL1160544 ChEMBL_ID
D013726 MESH_DESCRIPTOR_UI
5403 PUBCHEM_CID
2616 INN_ID
560 IUPHAR_LIGAND_ID
N8ONU3L3PG UNII
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 0404-9962 INJECTION, SOLUTION 1 mg SUBCUTANEOUS ANDA 11 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