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

Stem definitionDrug idCAS RN
bronchodilators, phenethylamine derivatives 1720 586-06-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • metaproterenol
  • metaproterenol sulfate
  • orciprenaline
  • orciprenaline sulfate
A beta-2 adrenergic agonist used in the treatment of ASTHMA and BRONCHIAL SPASM.
  • Molecular weight: 211.26
  • Formula: C11H17NO3
  • CLOGP: 0.08
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 4
  • TPSA: 72.72
  • ALOGS: -1.48
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
6 mg Inhal.aerosol
60 mg O
60 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
Vd (Volume of distribution) 6.03 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 14.07 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.90 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.41 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 31, 1973 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC R03AB03 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS, INHALANTS
Non-selective beta-adrenoreceptor agonists
ATC R03CB03 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS FOR SYSTEMIC USE
Non-selective beta-adrenoreceptor agonists
ATC R03CB53 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS FOR SYSTEMIC USE
Non-selective beta-adrenoreceptor agonists
FDA MoA N0000009922 Adrenergic beta2-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
FDA EPC N0000175779 beta2-Adrenergic Agonist
CHEBI has role CHEBI:35522 beta-adrenergic receptor agonist
CHEBI has role CHEBI:35523 bronchodilator agents
CHEBI has role CHEBI:49167 anti-asthmatic agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchitis indication 32398004 DOID:6132
Pulmonary emphysema indication 87433001
Asthma indication 195967001 DOID:2841
Asthma management indication 406162001
Acute exacerbation of asthma indication 708038006
Bronchospasm Prevention indication
Tachyarrhythmia contraindication 6285003
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Chronic heart failure contraindication 48447003
Diabetes mellitus contraindication 73211009 DOID:9351
Seizure disorder contraindication 128613002
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.48 acidic
pKa2 11.49 acidic
pKa3 12.6 acidic
pKa4 8.55 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 Kd 6.30 CHEMBL CHEMBL
Beta-2 adrenergic receptor GPCR Kd 5.04 CHEMBL

External reference:

IDSource
4019817 VUID
N0000147906 NUI
D00685 KEGG_DRUG
5874-97-5 SECONDARY_CAS_RN
4018762 VANDF
4019817 VANDF
CHEBI:6792 CHEBI
CHEMBL776 ChEMBL_ID
CHEMBL1568057 ChEMBL_ID
CHEMBL1200812 ChEMBL_ID
7250 IUPHAR_LIGAND_ID
1586 INN_ID
DB00816 DRUGBANK_ID
53QOG569E0 UNII
4086 PUBCHEM_CID
6804 RXNORM
1956 MMSL
5060 MMSL
d00750 MMSL
001786 NDDF
004408 NDDF
372797004 SNOMEDCT_US
54172006 SNOMEDCT_US
6067003 SNOMEDCT_US
D009921 MESH_DESCRIPTOR_UI
C0029193 UMLSCUI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Metaproterenol Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 54838-507 SYRUP 10 mg ORAL ANDA 16 sections