T3DB: Salmeterol

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Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-09-11 05:13:58 UTC

Update Date

2014-12-24 20:26:56 UTC

Accession Number

T3D4734

Identification

Common Name

Salmeterol

Class

Small Molecule

Description

Salmeterol is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD.

Compound Type

Adrenergic beta-2 Receptor Agonist
Amine
Bronchodilator Agent
Drug
Ether
Organic Compound
Sympathomimetic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Aeromax Diskus
Arial
GR-33343-X
GR-33343X
Salmaterol
Salmetedur
Salmeterolum
Serevent
Serevent diskus

Chemical Formula

C₂₅H₃₇NO₄

Average Molecular Mass

415.566 g/mol

Monoisotopic Mass

415.272 g/mol

CAS Registry Number

89365-50-4

IUPAC Name

4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol

Traditional Name

salmeterol

SMILES

OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1

InChI Identifier

InChI=1/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2

InChI Key

InChIKey=GIIZNNXWQWCKIB-UHFFFAOYNA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyl alcohols

Direct Parent

Benzyl alcohols

Alternative Parents

Substituents

Benzyl alcohol
Phenol
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Secondary alcohol
1,2-aminoalcohol
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:64064 )
phenols (CHEBI:64064 )
secondary amino compound (CHEBI:64064 )
ether (CHEBI:64064 )
primary alcohol (CHEBI:64064 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	75.5-76.5°C
Boiling Point	Not Available
Solubility	Sparingly soluble
LogP	4.2

Predicted Properties

Property	Value	Source
Water Solubility	0.0023 g/L	ALOGPS
logP	3.82	ALOGPS
logP	3.61	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	81.95 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	122.39 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl4-1931000000-aebe04422bbfbd21a187	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-02tc-5973658000-6d357698fc40226d221a	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0001900000-3c44a8f19551abbbb83a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001j-0029000000-43896c08fd5ce2a060e8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-4972000000-23117c7d5dc844d67897	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-6910000000-2afb08aff0a51fff0532	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-9800000000-5575125dd87cfbd258a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00kb-0229500000-3598d6091893d5b1aa38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-5972000000-a6ca754a34913f88d108	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-9800000000-5575125dd87cfbd258a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-01ot-0009300000-d3f77d91978dfaf39955	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-9800000000-7adc8cf858bfb5e724b0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001j-2479100000-524fb5341c41f1eb3c0b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0029000000-43896c08fd5ce2a060e8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6910000000-2afb08aff0a51fff0532	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-4972000000-23117c7d5dc844d67897	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0001900000-3c44a8f19551abbbb83a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-5972000000-aee8f4bebdf8839cdaf4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6910000000-8fb698226990601c85fd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0029000000-8305c8a339d3428f74c3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-6910000000-126c3afedc2ab8218bbc	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00l2-0239300000-048a637b7c1acf79f394	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-2986000000-c7d8a74f19032d089bf5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f8c-4920000000-a6c163078dfcde75e91f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0435900000-cc06b9723667c55e1a58	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0898200000-63660974abcc88edf138	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006t-1920000000-5acac3c6e55225ea19ba	JSpectraViewer

Toxicity Profile

Route of Exposure

Because of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.

Mechanism of Toxicity

Salmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.

Metabolism

Hepatic, metabolized by hydroxylation via CYP3A4 Half Life: 5.5 hours

Toxicity Values

By the oral route, no deaths occurred in rats at 1,000 mg/kg (approximately 81,000 times the maximum recommended daily inhalation dose in adults and approximately 38,000 times the maximum recommended daily inhalation dose in children on a mg/m² basis).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

DB00938

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Salmeterol

References

Synthesis Reference

Panayiotis Procopiou, “Novel process for preparing salmeterol.” U.S. Patent US20030162840, issued August 28, 2003.

MSDS

Not Available

General References

Salpeter SR, Buckley NS, Ormiston TM, Salpeter EE: Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths. Ann Intern Med. 2006 Jun 20;144(12):904-12. Epub 2006 Jun 5. [16754916 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Beta-2 adrenergic receptor

General Function:: Protein homodimerization activity
Specific Function:: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular Weight:: 46458.32 Da

References

Rong Y, Arbabian M, Thiriot DS, Seibold A, Clark RB, Ruoho AE: Probing the salmeterol binding site on the beta 2-adrenergic receptor using a novel photoaffinity ligand, [(125)I]iodoazidosalmeterol. Biochemistry. 1999 Aug 31;38(35):11278-86. [10471277 ]
Finney PA, Donnelly LE, Belvisi MG, Chuang TT, Birrell M, Harris A, Mak JC, Scorer C, Barnes PJ, Adcock IM, Giembycz MA: Chronic systemic administration of salmeterol to rats promotes pulmonary beta(2)-adrenoceptor desensitization and down-regulation of G(s alpha). Br J Pharmacol. 2001 Mar;132(6):1261-70. [11250877 ]
Green SA, Rathz DA, Schuster AJ, Liggett SB: The Ile164 beta(2)-adrenoceptor polymorphism alters salmeterol exosite binding and conventional agonist coupling to G(s). Eur J Pharmacol. 2001 Jun 15;421(3):141-7. [11516429 ]
Meliton AY, Munoz NM, Liu J, Lambertino AT, Boetticher E, Myo S, Myou S, Zhu X, Johnson M, Leff AR: Blockade of LTC4 synthesis caused by additive inhibition of gIV-PLA2 phosphorylation: Effect of salmeterol and PDE4 inhibition in human eosinophils. J Allergy Clin Immunol. 2003 Aug;112(2):404-10. [12897749 ]
Brogden RN, Faulds D: Salmeterol xinafoate: a review of its pharmacological properties and therapeutic potential in reversible obstructive airways disease. Allergol Immunopathol (Madr). 1992 Mar-Apr;20(2):72-84. [1359777 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]

Salmeterol (T3D4734)

Structure for T3D4734: Salmeterol

Targets

References