Page last updated: 2024-12-10

(S,S)-formoterol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

**(S,S)-formoterol** is a specific enantiomer of the drug **formoterol**. Let's break down what that means and why it's significant in research:

**Enantiomers**

* **Chiral molecules** are molecules that have a non-superimposable mirror image. Think of your hands – they're mirror images, but you can't make them perfectly overlap.
* **Enantiomers** are pairs of chiral molecules that are mirror images of each other.
* Drugs often exist as enantiomers.

**Formoterol**

* Formoterol is a **long-acting beta-2 adrenergic receptor agonist**. This means it relaxes the muscles in the airways, making it a key drug for treating asthma and chronic obstructive pulmonary disease (COPD).
* It's typically sold as a **racemic mixture**, meaning it contains an equal mixture of both (R,R)-formoterol and (S,S)-formoterol enantiomers.

**(S,S)-formoterol**

* **Higher potency:** Studies have shown that the (S,S)-enantiomer of formoterol is significantly more potent than the (R,R)-enantiomer. This means it's more effective at lower doses.
* **Longer duration of action:** The (S,S)-enantiomer also has a longer duration of action than the (R,R)-enantiomer.

**Importance for Research**

* **Understanding drug efficacy:** By studying (S,S)-formoterol, researchers can better understand the specific mechanisms of action of the drug and how its structure relates to its therapeutic properties. This could lead to the development of more potent and targeted therapies.
* **Development of new drugs:** The understanding gained from studying (S,S)-formoterol could be applied to the design of new drugs with improved efficacy and reduced side effects.
* **Pharmacokinetic studies:** Researchers can investigate how (S,S)-formoterol is absorbed, distributed, metabolized, and eliminated from the body. This information is crucial for optimizing drug dosage and minimizing side effects.
* **Clinical trials:** (S,S)-formoterol could be used in clinical trials to compare its effectiveness and safety to the racemic mixture of formoterol or other asthma treatments.

**In conclusion,** the study of (S,S)-formoterol is important because it allows researchers to explore the unique properties of this specific enantiomer and its potential advantages over the racemic mixture. This research could lead to advancements in asthma and COPD treatments.

formoterol : A racemate consisting of equal amounts of arformoterol (the active enantiomer) and (S,S)-formoterol (the inactive enantiomer). Its fumaric acid salt is used as a direct-acting sympathomimetic and bronchodilator for the treatment of chronic obstructive pulmonary disease (any progressive respiratory disease that makes it harder to breathe over time, such as chronic bronchitis and emphysema). [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

(S,S)-formoterol : An N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamide in which both of the stereocentres have S configuration. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3034756
CHEMBL ID1433762
CHEBI ID63081
SCHEMBL ID595410

Synonyms (24)

Synonym
BIDD:GT0743
NCGC00025167-01
tocris-1448
73573-87-2
formoterol
n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[[(2s)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide
(s,s)-formoterol
CHEBI:63081 ,
n-{2-hydroxy-5-[(1s)-1-hydroxy-2-{[(2s)-1-(4-methoxyphenyl)propan-2-yl]amino}ethyl]phenyl}formamide
(+)-formoterol
(s,s)-n-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formaldehyde
SCHEMBL595410
AB00698470-08
67346-48-9
CHEMBL1433762
AB00698470_10
DTXSID80110070
sr-01000597976
SR-01000597976-1
NCGC00025167-03
DTXSID1023077 ,
Q27132368
NCGC00025167-16
NCGC00025167-02

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-[2-hydroxy-5-(1-hydroxy-2-{[1-(4-methoxyphenyl)propan-2-yl]amino}ethyl)phenyl]formamideA phenylethanoloamine having 4-hydroxy and 3-formamido substituents on the phenyl ring and an N-(4-methoxyphenyl)propan-2-yl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (23)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLS proteinHomo sapiens (human)Potency14.12540.35487.935539.8107AID624170
thyroid stimulating hormone receptorHomo sapiens (human)Potency0.00130.001318.074339.8107AID926; AID938
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency1.99530.00207.533739.8107AID891
cytochrome P450 2C19 precursorHomo sapiens (human)Potency6.30960.00255.840031.6228AID899
mitogen-activated protein kinase 1Homo sapiens (human)Potency0.00200.039816.784239.8107AID995
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency12.58930.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency31.62280.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency12.58931.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]