Details of the Drug

General Information of Drug (ID: DMIP3ZV)

Drug Name
Fenoterol
Synonyms
Berotec; Berotek; Fenoterolum; Phenoterol; TH 1165A; Berotec (TN); Fenoterolum [INN-Latin]; P-Hydroxyphenylorciprenaline; Th-1165a; Fenoterol (USAN/INN); Fenoterol [USAN:BAN:INN]; P-Hydroxyphenyl-orciprenaline; 1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-((4-hydroxyphenyl)isopropylamino)ethane; 1-(p-Hydroxyphenyl)-2-((beta-hydroxy-beta-(3',5'-dihydroxyphenyl))ethyl)aminopropane; 3,5-Dihydroxy-alpha-(((p-hydroxy-alpha-methylphenethyl)amino)methyl)benzyl alcohol; 5-(1-hydroxy-2-{[1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)benzene-1,3-diol; 5-(1-hydroxy-2-{[2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)benzene-1,3-diol; 5-[1-hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol; 5-{1-Hydroxy-2-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-benzene-1,3-diol
Indication
Disease Entry ICD 11 Status REF
Asthma CA23 Approved [1]
Therapeutic Class
Bronchodilator Agents
Affected Organisms
Humans and other mammals
ATC Code
G02CA03: Fenoterol
G02CA: Sympathomimetics, labour repressants
G02C: OTHER GYNECOLOGICALS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
R03AC04: Fenoterol
R03AC: Selective beta-2-adrenoreceptor agonists
R03A: ADRENERGICS, INHALANTS
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
R03AC04: Fenoterol
R03AC: Selective beta-2-adrenoreceptor agonists
R03A: ADRENERGICS, INHALANTS
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
R03AC04: Fenoterol
R03AC: Selective beta-2-adrenoreceptor agonists
R03A: ADRENERGICS, INHALANTS
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
R03CC04: Fenoterol
R03CC: Selective beta-2-adrenoreceptor agonists
R03C: ADRENERGICS FOR SYSTEMIC USE
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
R03CC04: Fenoterol
R03CC: Selective beta-2-adrenoreceptor agonists
R03C: ADRENERGICS FOR SYSTEMIC USE
R03: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 303.35
Logarithm of the Partition Coefficient (xlogp) 2
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 29 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.87 hours [3]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.07544 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.53% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.2 L/kg [3]
Chemical Identifiers
Formula
C17H21NO4
IUPAC Name
5-[1-hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol
Canonical SMILES
CC(CC1=CC=C(C=C1)O)NCC(C2=CC(=CC(=C2)O)O)O
InChI
InChI=1S/C17H21NO4/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13/h2-5,7-9,11,17-22H,6,10H2,1H3
InChIKey
LSLYOANBFKQKPT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3343
ChEBI ID
CHEBI:149226
CAS Number
13392-18-2
UNII
22M9P70OQ9
DrugBank ID
DB01288
TTD ID
D04XEG
VARIDT ID
DR01356

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor beta-2 (ADRB2) TT2CJVK ADRB2_HUMAN Agonist [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [7]
Endothelin receptor type B (EDNRB) OTLLZV3P EDNRB_HUMAN Gene/Protein Processing [8]
Erythropoietin (EPO) OTZ90CN4 EPO_HUMAN Gene/Protein Processing [9]
Leptin (LEP) OT5Q7ODW LEP_HUMAN Protein Interaction/Cellular Processes [10]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Asthma
ICD Disease Classification CA23
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Adrenergic receptor beta-2 (ADRB2) DTT ADRB2 4.88E-01 -0.05 -0.12
Adrenergic receptor beta-2 (ADRB2) DTT ADRB2 7.10E-01 0.06 0.09
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 1.48E-01 6.33E-02 3.20E-01
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 1.74E-02 1.21E-01 4.40E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 557).
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Functional alpha1- and beta2-adrenergic receptors in human osteoblasts. J Cell Physiol. 2009 Jul;220(1):267-75.
6 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
7 Development of 3D-QSAR models for predicting the activities of chemicals to stimulate muscle growth via (2)-adrenoceptor. Toxicol In Vitro. 2021 Dec;77:105251. doi: 10.1016/j.tiv.2021.105251. Epub 2021 Sep 30.
8 beta2-Adrenoceptor agonist modulates endothelin-1 receptors in human isolated bronchi. Am J Respir Cell Mol Biol. 2006 Apr;34(4):410-6. doi: 10.1165/rcmb.2005-0091OC. Epub 2005 Dec 9.
9 Fenoterol but not dobutamine increases erythropoietin production in humans. Clin Pharmacol Ther. 1997 Jun;61(6):669-76. doi: 10.1016/S0009-9236(97)90102-8.
10 Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors. Eur J Endocrinol. 2000 Sep;143(3):439-45. doi: 10.1530/eje.0.1430439.