SALMETEROL XINAFOATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C25H37NO4.C11H8O3
Molecular Weight	603.745
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C2C=CC=CC2=C1O.OCC3=C(O)C=CC(=C3)C(O)CNCCCCCCOCCCCC4=CC=CC=C4

InChI

InChIKey=XTZNCVSCVHTPAI-UHFFFAOYSA-N

InChI=1S/C25H37NO4.C11H8O3/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;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2;1-6,12H,(H,13,14)

HIDE SMILES / InChI

Molecular Formula	C11H8O3
Molecular Weight	188.1794
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C25H37NO4
Molecular Weight	415.5656
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20236s030,20692s026lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/salmeterol-inhalation.html http://www.rxlist.com/serevent-diskus-drug.htm http://www.wikidoc.org/index.php/Salmeterol

Salmeterol is a long-acting beta2-adrenergic agonist. Although beta2-adrenoceptors are the predominant adrenergic receptors in bronchial smooth muscle and beta1-adrenoceptors are the predominant receptors in the heart, there are also beta2-adrenoceptors in the human heart comprising 10% to 50% of the total beta-adrenoceptors. The precise function of these is not yet established, but they raise the possibility that even highly selective beta2-agonists may have cardiac effects. It is FDA approved for the treatment of asthma, prevention of exercise-induced bronchospasm, maintenance treatment of chronic obstructive pulmonary disease. Common adverse reactions include musculoskeletal pain, headache, influenza, nasal/sinus congestion, pharyngitis, rhinitis, tracheitis/bronchitis, cough, throat irritation, viral respiratory infection. Salmeterol should be administered with extreme caution to patients being treated with monoamine oxidase inhibitors or tricyclic antidepressants, or within 2 weeks of discontinuation of such agents, because the action of salmeterol on the vascular system may be potentiated by these agents. Coadministration of salmeterol and ketoconazole was associated with more frequent increases in QTc duration compared with salmeterol and placebo administration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20236s030,20692s026lbl.pdf	Agonist 2752		1.5 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20236s030,20692s026lbl.pdf	Palliative	Approved 8583	SEREVENT Approved Use ADVAIR DISKUS is a combination product containing a corticosteroid and a LABA indicated for: Treatment of asthma in patients aged 4 years and older. (1.1) Maintenance treatment of airflow obstruction and reducing exacerbations in patients with chronic obstructive pulmonary disease (COPD). (1.2) Important limitation: Not indicated for the relief of acute bronchospasm. (1.1, 1.2) 1.1 Treatment of Asthma ADVAIR DISKUS is indicated for the treatment of asthma in patients aged 4 years and older. Long-acting beta2-adrenergic agonists (LABAs), such as salmeterol, one of the active ingredients in ADVAIR DISKUS, increase the risk of asthma-related death. Available data from controlled clinical trials suggest that LABAs increase the risk of asthma-related hospitalization in pediatric and adolescent patients [see Warnings and Precautions (5.1) Launch Date 1994
Chronic obstructive pulmonary disease 175 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20236s030,20692s026lbl.pdf	Palliative	Approved 8583	SEREVENT Approved Use ADVAIR DISKUS is a combination product containing a corticosteroid and a LABA indicated for: Treatment of asthma in patients aged 4 years and older. (1.1) Maintenance treatment of airflow obstruction and reducing exacerbations in patients with chronic obstructive pulmonary disease (COPD). (1.2) Important limitation: Not indicated for the relief of acute bronchospasm. (1.1, 1.2) 1.1 Treatment of Asthma ADVAIR DISKUS is indicated for the treatment of asthma in patients aged 4 years and older. Long-acting beta2-adrenergic agonists (LABAs), such as salmeterol, one of the active ingredients in ADVAIR DISKUS, increase the risk of asthma-related death. Available data from controlled clinical trials suggest that LABAs increase the risk of asthma-related hospitalization in pediatric and adolescent patients [see Warnings and Precautions (5.1) Launch Date 1994
Exercise-induced bronchospasm 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/20236s030,20692s026lbl.pdf	Preventing	Approved 8583	SEREVENT Approved Use ADVAIR DISKUS is a combination product containing a corticosteroid and a LABA indicated for: Treatment of asthma in patients aged 4 years and older. (1.1) Maintenance treatment of airflow obstruction and reducing exacerbations in patients with chronic obstructive pulmonary disease (COPD). (1.2) Important limitation: Not indicated for the relief of acute bronchospasm. (1.1, 1.2) 1.1 Treatment of Asthma ADVAIR DISKUS is indicated for the treatment of asthma in patients aged 4 years and older. Long-acting beta2-adrenergic agonists (LABAs), such as salmeterol, one of the active ingredients in ADVAIR DISKUS, increase the risk of asthma-related death. Available data from controlled clinical trials suggest that LABAs increase the risk of asthma-related hospitalization in pediatric and adolescent patients [see Warnings and Precautions (5.1) Launch Date 1994

C_max

Value	Dose	Co-administered	Analyte	Population
319 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29493402/	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: FLUTICASONE PROPIONATE	FLUTICASONE PROPIONATE	SALMETEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
167 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020692s028lbl.pdf	50 μg 2 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered:		SALMETEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
464 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29493402/	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: FLUTICASONE PROPIONATE	FLUTICASONE PROPIONATE	SALMETEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29493402/	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: FLUTICASONE PROPIONATE	FLUTICASONE PROPIONATE	SALMETEROL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020692s028lbl.pdf	50 μg 2 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered:		SALMETEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020692s028lbl.pdf	50 μg 2 times / day multiple, oral dose: 50 μg route of administration: Oral experiment type: MULTIPLE co-administered:		SALMETEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
84 ug 2 times / day multiple, respiratory Dose: 84 ug, 2 times / day Route: respiratory Route: multiple Dose: 84 ug, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7909285/	unhealthy, 30 Health Status: unhealthy Age Group: 30 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7909285/	Other AEs: Headache, Dizziness... Other AEs: Headache (5 patients) Dizziness (2 patients) Tremor (5 patients) Palpitations (1 patient) Muscle cramps (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7909285/
400 ug single, respiratory Dose: 400 ug Route: respiratory Route: single Dose: 400 ug Sources: https://pubmed.ncbi.nlm.nih.gov/1349491/	healthy, 34.3 Health Status: healthy Age Group: 34.3 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/1349491/	Other AEs: Headache, Tremor... Other AEs: Headache (5 patients) Tremor (5 patients) Palpitations (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/1349491/
50 ug 2 times / day multiple, respiratory Recommended Dose: 50 ug, 2 times / day Route: respiratory Route: multiple Dose: 50 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	unhealthy, 4-11 Health Status: unhealthy Age Group: 4-11 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	Other AEs: Ear disorder, Pharyngitis... Other AEs: Ear disorder (4%) Pharyngitis (6%) Headache (17%) Asthma (4%) Skin rash (4%) Urticaria (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf
50 ug 2 times / day multiple, respiratory Recommended Dose: 50 ug, 2 times / day Route: respiratory Route: multiple Dose: 50 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	unhealthy, >12 Health Status: unhealthy Age Group: >12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	Other AEs: Nasal sinus congestion, Rhinitis... Other AEs: Nasal sinus congestion (9%) Rhinitis (5%) Headache (13%) Asthma (3%) Tracheobronchitis (7%) Influenza (5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf
50 ug 2 times / day multiple, respiratory Recommended Dose: 50 ug, 2 times / day Route: respiratory Route: multiple Dose: 50 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf	Other AEs: Hypertension, Throat irritation... Other AEs: Hypertension (4%) Throat irritation (7%) Congestion nasal (4%) Sinusitis (4%) Ear disorder (3%) Nausea and vomiting (3%) Cough (5%) Rhinitis (4%) Respiratory tract infection viral (5%) Musculoskeletal pain (12%) Muscle cramps (3%) Headache (14%) Dizziness (4%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499 MRP3 246 MRP4 290 OCT3 159 P-gp 1741 CYP2C8 1057 CYP2B6 926 OCT1 620 OCT2 779 BSEP 550 ALDH1 41	CYP1A2 1197 CYP2C8/9 2 CYP2E1 729 CYP3A5 446 CYP3A7 109

Drug as perpetrator

Target	Modality	Activity
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
OCT2 782	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00938, https://pubmed.ncbi.nlm.nih.gov/25751092/	weak
OCT3 161	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00938, https://pubmed.ncbi.nlm.nih.gov/25751092/	weak
ALDH1 41	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODI2MDcifX0%3D	yes [Activation 25.1189 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	yes [IC50 1.87 uM]
OCT1 656	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00938, https://pubmed.ncbi.nlm.nih.gov/25751092/	yes [IC50 47.8 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	yes
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8723736/	no
CYP2C8/9 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8723736/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8723736/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8723736/	unlikely
CYP3A5 446	substrate 4014 Sources: https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.02d&code=C29443&ns=ncit&type=relationship&key=null&b=1&n=0&vse=null	yes
CYP3A7 109	substrate 4014 Sources: https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.02d&code=C29443&ns=ncit&type=relationship&key=null&b=1&n=0&vse=null	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf#page=13, https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.02d&code=C29443&ns=ncit&type=relationship&key=null&b=1&n=0&vse=null Page: 13-14, 21-22	yes	yes (co-administration study) Comment: Coadministration of inhaled Salmetrol and oral ketoconazole (strong CYP3A4 inhibitor) for 7 days increased Salmetrol AUC by 16-fold and Cmax by 1.4-fold. Coadministration of Erythromycin (moderate CYP3A4 inhibitor) increased inhaled Salmeterol Cmax,ss by 40% (3.6-beat/min in heart rate, 5.8-msec increase in QTc interval). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf#page=13, https://ncit-stage.nci.nih.gov/ncitbrowser/pages/concept_details.jsf?dictionary=NCI_Thesaurus&version=21.02d&code=C29443&ns=ncit&type=relationship&key=null&b=1&n=0&vse=null Page: 13-14, 21-22

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTA4MjYwNyJ9fQ%3D%3D, https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020692s047lbl.pdf#page=22 Page: (Label) 22

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY447694	https://www.001chemical.com/chem/89365-50-4
AA Blocks	AA003AUE	https://www.aablocks.com/goods/Goods/detail?id=AA003AUE
Aaron Chemicals	AR003BM6	http://www.aaronchem.com/89365-50-4
abcr GmbH	AB492509	http://www.abcr.com/shop/en/AB492509
Achemica	ACMC-1C1VM	http://www.achemica.com/prodinfo/?id=79389
Achemtek	0104-001738	http://www.achemtek.com/89365-50-4
Acorn PharmaTech	ACN-040075	http://www.acornpharmatech.com/
AEchem Scientific Corp., USA	AE1-000626	http://www.aechemsc.com/info_products/AE1-000626.php
AHH Chemical co.,ltd	MT-01629	http://www.ahhchemical.com/product/MT-01629.html
AHH Chemical co.,ltd	MT-22224	http://www.ahhchemical.com/product/MT-22224.html
AK Scientific, Inc. (AKSCI)	K590	http://www.aksci.com/item_detail.php?cat=K590
Alfa Chemistry	136112-01-1	https://www.alfa-chemistry.com/cas_136112-01-1.htm
Alfa Chemistry	AP1330076522	https://reagents.alfa-chemistry.com/product/salmeterol-related-compound-h-cas-1330076-52-2-3896.html
Ambeed	A728769	https://www.ambeed.com/products/94749-08-3.html
Angel Pharmatech	AG153148	http://www.angelpharmatech.com/89365-50-4.html
Angene	AGN-PC-0VOWRZ	http://www.angenechemical.com/productshow/AGN-PC-0VOWRZ.html
Ark Pharm	AK173141	http://www.arkpharminc.com/products/89365-50-4.html
Ark Pharma Scientific Limited	N-2877	http://www.arkpharmtech.com/product/244416.html
Aurora Fine Chemicals LLC	A12.866.668	http://online.aurorafinechemicals.com/info?ID=A12.866.668
AvaChem Scientific	2784B	http://www.avachem.com/productSearch.asp?2784B
BioChemPartner	BCP04199	http://www.biochempartner.com/89365-50-4-BCP04199
BioSynth	Q-101428	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-101428.html
BLD Pharm	BD150785	http://www.bldpharm.com/products/94749-08-3.html
BOC Sciences	497063-94-2	https://www.bocsci.com/salmeterol-d3-cas-497063-94-2-item-482701.html
Boerchem	BC202639	http://www.boerchem.com/?product_34051.html
Chem Scene	CS-2815	http://www.chemscene.com/89365-50-4.html
ChemMol	44001319	http://www.chemmol.com/chemmol/44001319.html
ChemMol	49401177	http://www.chemmol.com/chemmol/49401177.html
ChemMol	97900683	http://www.chemmol.com/chemmol/97900683.html
ChemMol	99162002	http://www.chemmol.com/chemmol/99162002.html
Chemspace	CSSB00000047424	https://chem-space.com/CSSB00000047424
Clearsynth	CS-T-61226	https://www.clearsynth.com/en/CST61226.html
Clearsynth	CS-T-85804	https://www.clearsynth.com/en/CST85804.html
CSNpharm	CSN11887	https://www.csnpharm.com/products/salmeterol-xinafoate.html
DC Chemicals	DC8610	http://www.dcchemicals.com/product_show-Salmeterol.html
eNovation Chemicals	D371569	http://www.enovationchem.com/productDetails.asp?productID=D371569
eNovation Chemicals	D565765	https://www.enovationchem.com/ProductDetails.asp?ProductID=D565765
eNovation Chemicals	D633111	https://www.enovationchem.com/ProductDetails.asp?ProductID=D633111
Excenen	EX-A4409	https://www.excenen.com/searchresultlist.php?id=EX-A4409
Finetech	FT-0674508	http://www.finetechnology-ind.com/prod/detail/pub/497063-94-2.html
Finetech	FT-0674509	http://www.finetechnology-ind.com/prod/detail/pub/1330076-52-2.html
Hairui	HR132921	http://www.hairuichem.com/en/product/89365-50-4.html
iChemical	EBD39669	http://www.ichemical.com/products/89365-50-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01295079	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01295079
LGC Standards	DRE-A16904900AL-100	https://www.lgcstandards.com/US/en/p/DRE-A16904900AL-100
LGC Standards	DRE-C16904900	https://www.lgcstandards.com/US/en/p/DRE-C16904900
MedChem Express	HY-14302	https://www.medchemexpress.com/Salmeterol.html
Molcore	MC447694	https://www.molcore.com/product/89365-50-4
MuseChem	I005348	https://www.musechem.com/product/I005348.html
MuseChem	R052751	https://www.musechem.com/product/R052751.html
OChem	5082	http://www.ocheminc.com/index.php?act=psearch&pid=365S504
Smolecule	S542353	http://www.smolecule.com/products/s542353
Smolecule	S793339	https://www.smolecule.com/products/s793339
THE BioTek	bt-281527	https://www.thebiotek.com/product/inhibitors/bt-281527
THE BioTek	bt-459092	https://www.thebiotek.com/product/others/bt-459092
TripleBond	CS0057	http://www.triplebond-canada.com/prod/1591/
Yuhao Chemical	RT12961	http://www.chemyuhao.com/136112-01-1.html
Yuhao Chemical	RT2765	http://www.chemyuhao.com/1391051-88-9.html
Yuhao Chemical	YH93795	http://www.chemyuhao.com/89365-50-4.html

PubMed

Title	Date	PubMed
[Cushing's syndrome during HIV treatment: pharmacological interaction during use of ritonavir].	2013	23548184
Budesonide/formoterol maintenance and reliever therapy in Asian patients (aged ≥16 years) with asthma: a sub-analysis of the COSMOS study.	2012-07-01	22607479
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.	2010-07	20590599
The preclinical toxicology of salmeterol hydroxynaphthoate.	2010-05	20219844
Budesonide prevents cytokine-induced decrease of the relaxant responses to formoterol and terbutaline, but not to salmeterol, in mouse trachea.	2010-04	20061444
The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells.	2007-11	17920670
Inhaled corticosteroids and long-acting beta 2-agonists in treatment of patients with chronic bronchiolitis following exposure to sulfur mustard.	2007-08	17687719
An increase in murine skeletal muscle peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1alpha) mRNA in response to exercise is mediated by beta-adrenergic receptor activation.	2007-07	17446185
Combination therapy with a long-acting beta-agonist and a leukotriene antagonist in moderate asthma.	2007-02-01	16973987
Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity.	2007-02	16980553
Comparative safety of long-acting inhaled bronchodilators: a cohort study using the UK THIN primary care database.	2007	18035867
Meta-analysis: effect of long-acting beta-agonists on severe asthma exacerbations and asthma-related deaths.	2006-06-20	16754916
Agonist-specific activation of the beta2-adrenoceptor/Gs-protein and beta2-adrenoceptor/Gi-protein pathway in adult rat ventricular cardiomyocytes.	2006-04	16474418
Glucocorticoid receptor nuclear translocation in airway cells after inhaled combination therapy.	2005-09-15	15860753
Heat-induced degradation of overexpressed glucocorticoid receptor Separate protective roles of hsp90 and hsp70.	2005-02	15862954
Outcomes associated with initiation of different controller therapies in a Medicaid asthmatic population: a retrospective data analysis.	2005-02	15801326
Differential regulation of chemokine expression by peroxisome proliferator-activated receptor gamma agonists: interactions with glucocorticoids and beta2-agonists.	2005-01-28	15531761
Examination of 209 drugs for inhibition of cytochrome P450 2C8.	2005-01	15601807
Synergistic effects of fluticasone propionate and salmeterol on in vitro T-cell activation and apoptosis in asthma.	2004-11	15536434
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.	2004-02	14730417
Characterization of agonist stimulation of cAMP-dependent protein kinase and G protein-coupled receptor kinase phosphorylation of the beta2-adrenergic receptor using phosphoserine-specific antibodies.	2004-01	14722251
Long-acting beta2-adrenergic formoterol and salmeterol induce the apoptosis of B-chronic lymphocytic leukaemia cells.	2004-01	14687023
Effects of low dose fluticasone/salmeterol combination on surrogate inflammatory markers in moderate persistent asthma.	2003-07	12823118
Stimulation of beta 2-adrenergic receptor increases cystic fibrosis transmembrane conductance regulator expression in human airway epithelial cells through a cAMP/protein kinase A-independent pathway.	2003-05-09	12621035
Salmeterol decreases eosinophilic cationic protein and rescue medication in patients inhaling beclomethasone dipropionate: preliminary study in mild and moderate asthma in Trinidad, West Indies.	2003	15025036
[Contribution of salmeterol in ambulatory practice to the improvement of asthma and quality of life in childhood].	2002-10	12449667
Comparison of anti-inflammatory and clinical effects of beclomethasone dipropionate and salmeterol in moderate asthma.	2002-07	12166584
Serum potassium levels, CPK-MB and ECG in children suffering asthma treated with beclomethasone or beclomethasone-salmeterol.	2001-07-14	11449530
Comparison of the bronchodilating effect of salmeterol and zafirlukast in combination with that of their use as single treatments in asthma and chronic obstructive pulmonary disease.	2001	11694805
Comparative effects of long-acting beta2-agonists, leukotriene receptor antagonists, and a 5-lipoxygenase inhibitor on exercise-induced asthma.	2000-09	10984370
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.	2000-08	10982225
Asthma therapy modulates priming-associated blood eosinophil responsiveness in allergic asthmatics.	1999-10	10573242
Effects of a range of beta2 adrenoceptor agonists on changes in intracellular cyclic AMP and on cyclic AMP driven gene expression in cultured human airway smooth muscle cells.	1999-10	10516654
Comparative study of extended release albuterol sulfate and long-acting inhaled salmeterol xinafoate in the treatment of nocturnal asthma.	1999-08	10480584
Comparison of inhaled salmeterol and oral zafirlukast in patients with asthma.	1999-06	10359889
Oral bambuterol compared to inhaled salmeterol in patients with partially reversible chronic obstructive pulmonary disease.	1999-01	10027655
Formoterol and salmeterol in partially reversible chronic obstructive pulmonary disease: A crossover, placebo-controlled comparison of onset and duration of action.	1999	10516540
Potential masking effects of salmeterol on airway inflammation in asthma.	1998-09	9731027
Onset of bronchodilation and finger tremor induced by salmeterol and salbutamol in asthmatic patients.	1998-08-26	9707465
ACE inhibitors: a possible cause of unexplained anemia.	1998-01	9434678
A comparison of beclomethasone, salmeterol, and placebo in children with asthma. Canadian Beclomethasone Dipropionate-Salmeterol Xinafoate Study Group.	1997-12-04	9385125
Salmeterol versus theophylline in the treatment of asthma.	1997-05	9164358
Salmeterol inhibits the allergen-induced mononuclear cell proliferation and downregulates GM-CSF release and HLA-DR expression by monocytes.	1997	9344832
Effects of salmeterol and terbutaline on IgE-mediated dermal reactions and inflammatory events in skin chambers in atopic patients.	1996-09	8899116
[Salmeterol-induced enuresis in children].	1996-05-22	8649105
Salmeterol-induced vertigo.	1994-11	7875287
Dose-response study with high-dose inhaled salmeterol in healthy subjects.	1992-03	1349491
Salmeterol: a four week study of a long-acting beta-adrenoceptor agonist for the treatment of reversible airways disease.	1991-11	1687131

Patents

Sample Use Guides

In Vivo Use Guide

Asthma and Chronic Obstructive Pulmonary Disease: the usual dosage for adults and children 4 years of age and older is 1 inhalation (50 mcg) twice daily (morning and evening, approximately 12 hours apart). Exercise-Induced Bronchospasm: One inhalation of SEREVENT DISKUS at least 30 minutes before exercise.

Route of Administration: Respiratory

In Vitro Use Guide

Since fibroblasts express beta2-adrenoreceptors, the effects of different concentrations (0.1-100 nM) of salmeterol on lung fibroblast proliferation and adhesion molecule expression were evaluated. A significant downregulation of ICAM-1 or H-CAM expression was demonstrated in the presence of Salmeterol, at all concentrations tested (0.1-100 nM; p<0.01).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:25:49 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:49 GMT 2025`
Record UNII	6EW8Q962A5
Record Status	`Validated (UNII)`
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Name

Type

Language

ADVAIR HFA COMPONENT SALMETEROL XINAFOATE

Preferred Name

English

SALMETEROL XINAFOATE

Official Name

English

SALMETEROL XINAFOATE [EP MONOGRAPH]

Common Name

English

GR-33343 G

Code

English

SALMETEROL XINAFOATE [USP-RS]

Common Name

English

GR 33343 G

Code

English

SALMETEROL 1-HYDROXY-2-NAPHTHOATE [MI]

Common Name

English

SALMETEROL XINAFOATE [JAN]

Common Name

English

SALMETEROL XINAFOATE [USP MONOGRAPH]

Common Name

English

SALMETEROL XINAFOATE [EP IMPURITY]

Common Name

English

SEREVENT

Brand Name

English

SALMETEROL XINAFOATE [MART.]

Common Name

English

ADVAIR COMPONENT SALMETEROL XINAFOATE

Brand Name

English

SALMETEROL XINAFOATE [USAN]

Common Name

English

AIRDUO RESPICLICK COMPONENT SALMETEROL XINAFOATE

Brand Name

English

(±)-4-HYDROXY-.ALPHA.(SUP 1)-(((6-(4-PHENYLBUTOXY)HEXYL)AMINO)METHYL)-M-XYLENE-.ALPHA.,.ALPHA.'-DIOL 1-HYDROXY-2-NAPHTHOATE

Common Name

English

SALMETEROL XINAFOATE [ORANGE BOOK]

Common Name

English

LIPO-102 COMPONENT SALMETEROL XINAFOATE

Common Name

English

GR-33343X

Code

English

SALMETEROL 1-HYDROXY-2-NAPHTHOATE

Common Name

English

1,3-BENZENEDIMETHANOL, 4-HYDROXY-.ALPHA.(SUP 1)-(((6-(4-PHENYLBUTOXY)HEXYL)AMINO)METHYL)-, (±)-, 1-HYDROXY-2-NAPHTHALENECARBOXYLATE

Common Name

English

SALMETEROL XINAFOATE [VANDF]

Common Name

English

Salmeterol xinafoate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319