Drug Details

General Information of the Drug (ID: DR3490)
Name
Salmeterol
Synonyms
Salmeterol; 89365-50-4; Serevent; Aeromax; Salmeterolum [Latin]; GR 33343X; SALMATEROL; 2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenol; Salmeterol free base; SN408D; 2-(hydroxymethyl)-4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)phenol; Astmerole; CHEBI:64064; 18910-65-1 (free base); GR 33343 X; Salmeterol Fluticasone Propionate Mixture; Salmeterolum; 4-hydroxy-alpha1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol; 4-(1-hydroxy-2-(6-(4-phenylbutoxy)hexylamino)ethyl)-2-(hydroxymethyl)phenol; 2-(hydroxymethyl)-4-[1-hydroxy-2-({6-[(4-phenylbutyl)oxy]hexyl}amino)ethyl]phenol; SMR000466295; HSDB 7315; SR-01000076139; Salmeterol (USAN/INN); Salmeterol [USAN:INN:BAN]; NCGC00025247-01; Fluticasonepropiponate; (+-)-4-Hydroxy-alpha'-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-m-xylene-alpha,alpha'-diol; (+-)-4-Hydroxy-alpha1-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-1,3-benzenedimethanol; CPD000466295; Prestwick3_000945; Salmeterol Dimer Impurity; ACMC-1C1VM; DSSTox_CID_3571; S 2692; SCHEMBL4767; CHEMBL1263; DSSTox_RID_77087; DSSTox_GSID_23571; Lopac0_001100; BSPBio_000910; GTPL559; cc-441; MLS000759000; MLS001424322; Salmeterol Related Compound H; BPBio1_001002; DTXSID6023571; BDBM25771; HMS2052H13; HMS2090E17; HMS2097N12; HMS3268K19; HMS3394H13; HMS3412P13; HMS3714N12; HMS3886G10; AMY37616; BCP04199; EX-A4409; Tox21_113584; CS0057; MFCD00867037; s5527; STK629186; AKOS005561914; CCG-101194; CCG-205176; DB00938; GR-33343-X; NC00444; SDCCGSBI-0633788.P001; 1,3-Benzenedimethanol, 4-hydroxy-.alpha.1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-; 1,3-Benzenedimethanol, 4-hydroxy-alpha1-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-, (+-)-; MRF-0000468; NCGC00015938-03; NCGC00025247-02; 1,3-Benzenedimethanol, 4-hydroxy-alpha(sup 1)-(((6-(4-phenylbutoxy)hexyl)amino)methyl)-, (+-)-; 1,3-Benzenedimethanol, 4-hydroxy-alpha(sup 1)-(((6-(4-phenylbutoxy)hexyl)amino)methyl-, (+-)-; AK173141; AS-56157; HY-14302; K590; Salmeterol 100 microg/mL in Acetonitrile; CAS-89365-50-4; AB00513972; FT-0674508; FT-0674509; C07241; D05792; AB00513972-07; 365S504; L000532; Q424333; Salmeterol Impurity H (Xinafoate Adduct Impurity); Q-101428; SR-01000076139-2; SR-01000076139-6; BRD-A01320529-001-05-9; 2-hydroxymethyl-4-{1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl}phenol; 4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol; 5-[2-[6-(4-Phenylbutoxy)hexylamino]-1-hydroxyethyl]-2-hydroxybenzenemethanol; ( inverted question mark) 4-Hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]m-ethyl]-1,3-benzenedimethanol; GR 33343X; 1-hydroxy-2-naphthoic acid;4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]-2-methylol-phenol
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Molecular Type
Small molecule
Disease Chronic obstructive pulmonary disease [ICD-11: CA22] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 0.156 mcgh/L
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 47.897 ng/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 0.24 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Clearance
The clearance of drug is 392 L/h in asthmatic patients
Elimination
Salmeterol is 57.4% eliminated in the feces and 23% in the urine, and less than 5% of a dose is eliminated in the urine as unchanged salmeterol
Half-life
The concentration or amount of drug in body reduced by one-half in 5.5 hours
Metabolism
The drug is metabolized via the CYP3A4 to alpha-hydroxysalmeterol
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.00337 micromolar/kg/day
Vd
The volume of distribution (Vd) of drug is 177 L
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C25H37NO4
PubChem CID
5152
Canonical SMILES
C1=CC=C(C=C1)CCCCOCCCCCCNCC(C2=CC(=C(C=C2)O)CO)O
InChI
1S/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
InChIKey
GIIZNNXWQWCKIB-UHFFFAOYSA-N
CAS Number
CAS 89365-50-4
ChEBI ID
CHEBI:64064
TTD Drug ID
D0L5YV
DrugBank ID
DB00938
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Theophylline      Camellia sinensis     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)		 Patients with COPD may benefit from combination treatment with salmeterol plus theophylline, without a resulting increase in adverse events or other adverse sequelae.
Target and Pathway
Target(s) Adrenergic receptor beta-2 (ADRB2)  Molecule Info  [3]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cGMP-PKG signaling pathway
3 cAMP signaling pathway
4 Neuroactive ligand-receptor interaction
5 Endocytosis
6 Adrenergic signaling in cardiomyocytes
7 Salivary secretion
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Beta2 adrenergic receptor signaling pathway
Pathway Interaction Database Arf6 trafficking events Click to Show/Hide
2 Arf6 signaling events
Reactome Adrenoceptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 GPCRs, Class A Rhodopsin-like
4 Vitamin D Receptor Pathway
5 GPCR ligand binding
6 GPCR downstream signaling
7 GPCRs, Other
References
Reference 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: 559).
Reference 2 Salmeterol plus theophylline combination therapy in the treatment of COPD. Chest. 2001 Jun;119(6):1661-70.
Reference 3 Pharmacogenetic tests in asthma therapy. Clin Lab Med. 2008 Dec;28(4):645-65.
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