General Information of Drug (ID: DMIEU69)

Drug Name
Salmeterol Drug Info
Synonyms
Aeromax; Astmerole; SALMATEROL; Salmeterolum; Serevent; Glaxo Wellcome brand of salmeterol xinafoate; Salmeterolum [Latin]; GR 33343X; S 2692; GR-33343X; Serevent (TN); Salmeterol (USAN/INN); Salmeterol [USAN:BAN:INN]; (+-)-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; (inverted question mark) 4-Hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]m-ethyl]-1,3-benzenedimethanol; 2-(hydroxymethyl)-4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)phenol; 2-(hydroxymethyl)-4-[1-hydroxy-2-({6-[(4-phenylbutyl)oxy]hexyl}amino)ethyl]phenol; 2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]ethyl]phenol
Indication
Disease Entry ICD 11 Status REF
Allergic asthma CA23.0 Approved [1]
Chronic obstructive pulmonary disease CA22 Approved [2]
Intrinsic asthma Approved [1]
Pulmonary emphysema CA21.Z Approved [1]
Therapeutic Class
Bronchodilator Agents
Cross-matching ID
PubChem CID
5152
ChEBI ID
CHEMBL1263
CAS Number
CAS 89365-50-4
TTD Drug ID
DMIEU69
INTEDE Drug ID
DR1460

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Indacaterol DMQJHR7 Chronic obstructive pulmonary disease CA22 Approved [10]
Formoterol DMSOURV Allergic asthma CA23.0 Approved [11]
Salbutamol DMN9CWF Acute asthma CA23 Approved [12]
Arformoterol DMYM974 Chronic obstructive pulmonary disease CA22 Approved [13]
Isoproterenol DMK7MEY Atrioventricular block Approved [14]
Clenbuterol DMCKYZ5 Chronic breathing disorder 7A4Z Approved [15]
Ritodrine DM4V6RL Premature labour JB00 Approved [16]
Olodaterol DM62B78 Chronic obstructive pulmonary disease CA22 Approved [17]
Fenoterol DMIP3ZV Asthma CA23 Approved [18]
Vilanterol DMF5EK1 Chronic obstructive pulmonary disease CA22 Approved [19]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [20]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [21]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [22]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [24]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [25]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [26]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [21]
Verapamil DMA7PEW Angina pectoris BA40 Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A5 (CYP3A5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [29]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [30]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [31]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [5]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [32]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [33]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [34]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [35]
Verapamil DMA7PEW Angina pectoris BA40 Approved [36]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [5]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A7 (CYP3A7)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [37]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [5]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [5]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [5]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [38]
Verapamil DMA7PEW Angina pectoris BA40 Approved [39]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [5]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [5]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [5]
Metronidazole DMTIVEN Abscess Approved [40]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Bambuterol DMKLSHF Asthma CA23 Approved [41]
Terbutaline DMD4381 Asthma CA23 Approved [42]
Salbutamol DMN9CWF Acute asthma CA23 Approved [43]
Imipramine DM2NUH3 Depression 6A70-6A7Z Approved [44]
Methotrexate DM2TEOL Anterior urethra cancer Approved [45]
Epinephrine DM3KJBC Acute asthma CA23 Approved [46]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [47]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [48]
Ergotidine DM78IME Osteoarthritis FA00-FA05 Approved [49]
Propranolol DM79NTF Angina pectoris BA40 Approved [50]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [51]
Cyclophosphamide DM4O2Z7 Advanced cancer 2A00-2F9Z Approved [52]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [53]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [54]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [55]
Cytarabine DMZD5QR Acute lymphoblastic leukaemia 2A85 Approved [56]
Beclomethasone dipropionate DM5NW1E Allergic rhinitis CA08.0 Phase 4 [8]
Urethane DM7NSI0 N. A. N. A. Phase 4 [57]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [58]
Milchsaure DM462BT Pruritus EC90 Investigative [59]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [51]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [54]
Zafirlukast DMHNQOG Asthma CA23 Approved [60]
Budesonide DMJIBAW Allergic rhinitis CA08.0 Approved [60]
Diphenylpyraline DMW4X37 Allergic rhinitis CA08.0 Approved [61]
Arformoterol DMYM974 Chronic obstructive pulmonary disease CA22 Approved [62]
Beclomethasone dipropionate DM5NW1E Allergic rhinitis CA08.0 Phase 4 [63]
PHENCYCLIDINE DMQBEYX Discovery agent N.A. Investigative [64]
⏷ Show the Full List of 8 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Epinephrine DM3KJBC Acute asthma CA23 Approved [65]
Ergotidine DM78IME Osteoarthritis FA00-FA05 Approved [65]
Norepinephrine DMOUC09 Alopecia ED70 Approved [65]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [66]
Quercetin DM3NC4M Obesity 5B81 Approved [67]
Phenoxybenzamine DM8KSQH Malignant essential hypertension BA00 Approved [68]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [69]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [70]
Enzalutamide DMGL19D Prostate cancer 2C82.0 Approved [71]
Mifepristone DMGZQEF Cushing disease 5A70 Approved [72]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adrenergic receptor beta-2 (ADRB2) TT2CJVK ADRB2_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [5]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [6]
Eosinophil cationic protein (RNASE3) OTVE2XD1 ECP_HUMAN Gene/Protein Processing [7]
Non-secretory ribonuclease (RNASE2) OT8Z4FNE RNAS2_HUMAN Gene/Protein Processing [8]
Solute carrier family 22 member 3 (SLC22A3) OTQYGVXX S22A3_HUMAN Regulation of Drug Effects [9]

References

1 Salmeterol FDA Label
2 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).
3 Pharmacogenetic tests in asthma therapy. Clin Lab Med. 2008 Dec;28(4):645-65.
4 Clinical pharmacokinetics of salmeterol. Clin Pharmacokinet. 2002;41(1):19-30.
5 Drug Interactions Flockhart Table
6 Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity. Am J Respir Cell Mol Biol. 2007 Feb;36(2):236-43. doi: 10.1165/rcmb.2006-0257OC. Epub 2006 Sep 15.
7 Salmeterol decreases eosinophilic cationic protein and rescue medication in patients inhaling beclomethasone dipropionate: preliminary study in mild and moderate asthma in Trinidad, West Indies. Int J Clin Pharmacol Res. 2003;23(2-3):69-74.
8 Comparison of anti-inflammatory and clinical effects of beclomethasone dipropionate and salmeterol in moderate asthma. Eur Respir J. 2002 Jul;20(1):66-72. doi: 10.1183/09031936.02.00094202.
9 The effect of corticosteroids on the disposal of long-acting beta2-agonists by airway smooth muscle cells. J Allergy Clin Immunol. 2007 Nov;120(5):1103-9. doi: 10.1016/j.jaci.2007.08.034. Epub 2007 Oct 17.
10 Emerging drugs in chronic obstructive pulmonary disease. Expert Opin Emerg Drugs. 2009 Mar;14(1):181-94.
11 Long-acting beta2-agonists for chronic obstructive pulmonary disease patients with poorly reversible airflow limitation. Cochrane Database Syst Rev. 2002;(3):CD001104.
12 Potential of beta2-adrenoceptor agonists as add-on therapy for multiple sclerosis: focus on salbutamol (albuterol). CNS Drugs. 2002;16(1):1-8.
13 Arformoterol tartrate in the treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease. Drugs Today (Barc). 2009 Jan;45(1):3-9.
14 Current therapeutic uses and potential of beta-adrenoceptor agonists and antagonists. Eur J Clin Pharmacol. 1998 Feb;53(6):389-404.
15 Postischemic brain injury is attenuated in mice lacking the beta2-adrenergic receptor. Anesth Analg. 2009 Jan;108(1):280-7.
16 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
17 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
18 Functional alpha1- and beta2-adrenergic receptors in human osteoblasts. J Cell Physiol. 2009 Jul;220(1):267-75.
19 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: 7353).
20 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
21 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
22 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
23 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
24 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
25 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
26 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
27 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
28 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
29 Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95.
30 Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81.
31 Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
32 Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8.
33 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
34 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
35 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
36 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
37 The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. J Steroid Biochem Mol Biol. 1993 Jan;44(1):61-7.
38 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
39 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
40 The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
41 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.
42 Beta2-adrenergic receptor polymorphisms in African American children with status asthmaticus. Pediatr Crit Care Med. 2006 Jan;7(1):15-8. doi: 10.1097/01.pcc.0000194010.63115.a2.
43 beta2-adrenergic receptor polymorphisms and salbutamol-stimulated energy expenditure. J Clin Endocrinol Metab. 2005 Apr;90(4):2301-7. doi: 10.1210/jc.2004-1356. Epub 2005 Feb 1.
44 Neutrophil beta(2)-adrenoceptor function in major depression: G(s) coupling, effects of imipramine and relationship to treatment outcome. Eur J Pharmacol. 1999 Dec 15;386(2-3):135-44. doi: 10.1016/s0014-2999(99)00749-9.
45 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
46 Myocardial ischaemia and ventricular arrhthymias precipitated by physiological concentrations of adrenaline in patients with coronary artery disease. Br Heart J. 1992 May;67(5):419-20. doi: 10.1136/hrt.67.5.419-b.
47 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
48 Hormonal regulation of beta2-adrenergic receptor level in prostate cancer. Prostate. 2008 Jul 1;68(10):1133-42. doi: 10.1002/pros.20778.
49 Histamine augments beta2-adrenoceptor-induced cyclic AMP accumulation in human prostate cancer cells DU-145 independently of known histamine receptors. Biochem Pharmacol. 2007 Mar 15;73(6):814-23. doi: 10.1016/j.bcp.2006.11.022. Epub 2006 Dec 1.
50 Expression of inwardly rectifying potassium channels (GIRKs) and beta-adrenergic regulation of breast cancer cell lines. BMC Cancer. 2004 Dec 16;4:93. doi: 10.1186/1471-2407-4-93.
51 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
52 Comparative gene expression analysis of a chronic myelogenous leukemia cell line resistant to cyclophosphamide using oligonucleotide arrays and response to tyrosine kinase inhibitors. Leuk Res. 2007 Nov;31(11):1511-20.
53 Integrative "-Omics" analysis in primary human hepatocytes unravels persistent mechanisms of cyclosporine A-induced cholestasis. Chem Res Toxicol. 2016 Dec 19;29(12):2164-2174.
54 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
55 Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
56 The DNA methyltransferase inhibitors azacitidine, decitabine and zebularine exert differential effects on cancer gene expression in acute myeloid leukemia cells. Leukemia. 2009 Jun;23(6):1019-28.
57 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
58 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
59 Transcriptional profiling of lactic acid treated reconstructed human epidermis reveals pathways underlying stinging and itch. Toxicol In Vitro. 2019 Jun;57:164-173.
60 Effects of different anti-asthmatic agents on induced sputum and eosinophil cationic protein in mild asthmatics. Respirology. 2004 Nov;9(4):514-20. doi: 10.1111/j.1440-1843.2004.00631.x.
61 Asthma therapy modulates priming-associated blood eosinophil responsiveness in allergic asthmatics. Eur Respir J. 1999 Oct;14(4):915-22. doi: 10.1034/j.1399-3003.1999.14d31.x.
62 Formoterol compared with beclomethasone and placebo on allergen-induced asthmatic responses. Am Rev Respir Dis. 1992 Nov;146(5 Pt 1):1156-60. doi: 10.1164/ajrccm/146.5_Pt_1.1156.
63 Effect of inhaled beclomethasone dipropionate and budesonide dry powder on pulmonary function and serum eosinophil cationic protein in adult asthmatics. J Investig Allergol Clin Immunol. 1999 Jul-Aug;9(4):241-7.
64 Differential response of Mono Mac 6, BEAS-2B, and Jurkat cells to indoor dust. Environ Health Perspect. 2007 Sep;115(9):1325-32.
65 Selective transport of monoamine neurotransmitters by human plasma membrane monoamine transporter and organic cation transporter 3. J Pharmacol Exp Ther. 2010 Dec;335(3):743-53. doi: 10.1124/jpet.110.170142. Epub 2010 Sep 21.
66 Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Toxicology. 2013 Apr 5;306:24-34.
67 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
68 Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36.
69 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
70 Gene Expression Regulation and Pathway Analysis After Valproic Acid and Carbamazepine Exposure in a Human Embryonic Stem Cell-Based Neurodevelopmental Toxicity Assay. Toxicol Sci. 2015 Aug;146(2):311-20. doi: 10.1093/toxsci/kfv094. Epub 2015 May 15.
71 LSD1 activates a lethal prostate cancer gene network independently of its demethylase function. Proc Natl Acad Sci U S A. 2018 May 1;115(18):E4179-E4188.
72 Mifepristone induced progesterone withdrawal reveals novel regulatory pathways in human endometrium. Mol Hum Reprod. 2007 Sep;13(9):641-54.