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]
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Therapeutic Class

Bronchodilator Agents

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)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
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]

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Drug Transporter (DTP)

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

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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)

MEA Detail

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.