Olodaterol HCl
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MedKoo CAT#: 329649

CAS#: 869477-96-3 (HCl)

Description: Olodaterol, also known as BI 1744, is a long acting beta-adrenoceptor agonist used as an inhalation for treating patients with chronic obstructive pulmonary disease (COPD), manufactured by Boehringer-Ingelheim. Olodaterol was approved by FDA in 2014 for the treatment of chronic obstructive pulmonary disease.

Chemical Structure

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Olodaterol HCl
CAS# 869477-96-3 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329649
Name: Olodaterol HCl
CAS#: 869477-96-3 (HCl)
Chemical Formula: C21H27ClN2O5
Exact Mass: 0.00
Molecular Weight: 422.910
Elemental Analysis: C, 59.64; H, 6.44; Cl, 8.38; N, 6.62; O, 18.92

Price and Availability

Size Price Availability Quantity
5mg USD 150 Ready to ship
10mg USD 250 Ready to ship
25mg USD 550 Ready to ship
50mg USD 950 Ready to ship
100mg USD 1650 Ready to ship
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Related CAS #: 868049-49-4 (free base)   869477-96-3 (HCl)  

Synonym: Olodaterol hydrochloride; Olodaterol HCl; BI-1744; BI 1744; BI1744; Olodaterol; Striverdi

IUPAC/Chemical Name: (R)-6-hydroxy-8-(1-hydroxy-2-((1-(4-methoxyphenyl)-2-methylpropan-2-yl)amino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one hydrochloride

InChi Key: KCEHVJZZIGJAAW-FERBBOLQSA-N

InChi Code: InChI=1S/C21H26N2O5.ClH/c1-21(2,10-13-4-6-15(27-3)7-5-13)22-11-18(25)16-8-14(24)9-17-20(16)28-12-19(26)23-17;/h4-9,18,22,24-25H,10-12H2,1-3H3,(H,23,26);1H/t18-;/m0./s1

SMILES Code: O=C1NC2=CC(O)=CC([C@@H](O)CNC(C)(C)CC3=CC=C(OC)C=C3)=C2OC1.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Olodaterol is a long acting beta-adrenoceptor agonist.
In vitro activity: The primary aim of this study was to assess the ability of olodaterol (Striverdi®, Boehringer Ingelheim), an inhaled long‐acting β 2‐adrenoceptor agonist approved for the once‐daily maintenance treatment of COPD (Bouyssou et al., 2010a; van Noord et al., 2011), to inhibit pathogenic mechanisms involved in lung fibrosis. For this purpose, different in vitro assays were performed, including fibroblast proliferation and migration, myofibroblast differentiation and pro‐fibrotic mediator release using primary human lung cells from patients with IPF and control donors. Olodaterol inhibited the contractile properties of HLFs by approximately 85%. On the contrary, for IPF‐LF, the maximal inhibitory effect of olodaterol was 47% (Figure 4A). Summarizing the in vitro part of the data, there were no significant differences regarding the efficacy of olodaterol in inhibiting pro‐fibrotic mechanisms in HLF compared to IPF‐LF. This indicates that β2‐adrenoceptors are still functional in cells from fibrotic patients and builds a rationale for the efficacy of olodaterol in IPF Br J Pharmacol. 2017 Nov; 174(21): 3848–3864. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5647188/
In vivo activity: In order to address the inhibitory activity of olodaterol to attenuate the fibrotic pathology in vivo, a mouse model of lung fibrosis induced by bleomycin was used. Treatment with inhaled olodaterol (1 mg·mL−1, q.d.) was either started at day 1 after bleomycin instillation for the preventive treatment or at day 7 for the therapeutic treatment. Bleomycin caused a maximal reduction of body weight at day 7 with a subsequent recovery phase. With preventive as well as therapeutic olodaterol treatment, the recovery back to control levels of body weight (at day 21) was accelerated (Figure 6A). On day 21, total cell counts were significantly increased in the BALF of mice stimulated with bleomycin (Figure 6B). Furthermore, the fibrosis‐relevant mediators, MMP‐9, TGF‐β and TIMP‐1, were increased in BALF of bleomycin‐treated animals (4.3‐fold, 5.6‐fold and 35.3‐fold, respectively) and were significantly inhibited by olodaterol inhalation by about 50 to 70%, regardless of treatment start (Table 2). In summary, the in vivo experiments support anti‐fibrotic actions of olodaterol both, in the bleomycin model, as well as in a model of TGFß‐induced fibrosis. In both models, the most prominent effects were seen with a preventive dosing regimen compared to the therapeutic approach. Br J Pharmacol. 2017 Nov; 174(21): 3848–3864. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5647188/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.0 189.20

Preparing Stock Solutions

The following data is based on the product molecular weight 422.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Herrmann FE, Wollin L, Wirth J, Gantner F, Lämmle B, Wex E. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017 Nov;174(21):3848-3864. doi: 10.1111/bph.13982. Epub 2017 Sep 20. PMID: 28810065; PMCID: PMC5647188. 2. Bouyssou T, Casarosa P, Naline E, Pestel S, Konetzki I, Devillier P, Schnapp A. Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models. J Pharmacol Exp Ther. 2010 Jul;334(1):53-62. doi: 10.1124/jpet.110.167007. Epub 2010 Apr 6. Erratum in: J Pharmacol Exp Ther. 2013 Jul;346(1):161. PMID: 20371707. 3. Herrmann FE, Wollin L, Wirth J, Gantner F, Lämmle B, Wex E. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017 Nov;174(21):3848-3864. doi: 10.1111/bph.13982. Epub 2017 Sep 20. PMID: 28810065; PMCID: PMC5647188. 4. Wex E, Kollak I, Duechs MJ, Naline E, Wollin L, Devillier P. The long-acting β2 -adrenoceptor agonist olodaterol attenuates pulmonary inflammation. Br J Pharmacol. 2015 Jul;172(14):3537-47. doi: 10.1111/bph.13143. Epub 2015 May 12. PMID: 25824824; PMCID: PMC4507158.
In vitro protocol: 1. Herrmann FE, Wollin L, Wirth J, Gantner F, Lämmle B, Wex E. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017 Nov;174(21):3848-3864. doi: 10.1111/bph.13982. Epub 2017 Sep 20. PMID: 28810065; PMCID: PMC5647188. 2. Bouyssou T, Casarosa P, Naline E, Pestel S, Konetzki I, Devillier P, Schnapp A. Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models. J Pharmacol Exp Ther. 2010 Jul;334(1):53-62. doi: 10.1124/jpet.110.167007. Epub 2010 Apr 6. Erratum in: J Pharmacol Exp Ther. 2013 Jul;346(1):161. PMID: 20371707.
In vivo protocol: 1. Herrmann FE, Wollin L, Wirth J, Gantner F, Lämmle B, Wex E. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017 Nov;174(21):3848-3864. doi: 10.1111/bph.13982. Epub 2017 Sep 20. PMID: 28810065; PMCID: PMC5647188. 2. Wex E, Kollak I, Duechs MJ, Naline E, Wollin L, Devillier P. The long-acting β2 -adrenoceptor agonist olodaterol attenuates pulmonary inflammation. Br J Pharmacol. 2015 Jul;172(14):3537-47. doi: 10.1111/bph.13143. Epub 2015 May 12. PMID: 25824824; PMCID: PMC4507158.

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1: O'Donnell DE, Casaburi R, Frith P, Kirsten A, De Sousa D, Hamilton A, Xue W, Maltais F. Effects of combined tiotropium/olodaterol on inspiratory capacity and exercise endurance in COPD. Eur Respir J. 2017 Apr 19;49(4). pii: 1601348. doi: 10.1183/13993003.01348-2016. Print 2017 Apr. PubMed PMID: 28424359.

2: Cataldo D. [Spiolto Respimat® : tiotropium-olodaterol fixed combination for therapy of chronic obstructive pulmonary disease (COPD)]. Rev Med Liege. 2016 Jun;71(6):308-313. Review. French. PubMed PMID: 28383865.

3: Ichinose M, Kato M, Takizawa A, Sakamoto W, Grönke L, Tetzlaff K, Fukuchi Y. Long-term safety and efficacy of combined tiotropium and olodaterol in Japanese patients with chronic obstructive pulmonary disease. Respir Investig. 2017 Mar;55(2):121-129. doi: 10.1016/j.resinv.2016.09.004. Epub 2016 Dec 22. PubMed PMID: 28274527.

4: Donohue JF, Betts KA, Du EX, Altman P, Goyal P, Keininger DL, Gruenberger JB, Signorovitch JE. Comparative efficacy of long-acting β2-agonists as monotherapy for chronic obstructive pulmonary disease: a network meta-analysis. Int J Chron Obstruct Pulmon Dis. 2017 Jan 19;12:367-381. doi: 10.2147/COPD.S119908. eCollection 2017. PubMed PMID: 28176892; PubMed Central PMCID: PMC5261557.

5: Ferguson GT, Karpel J, Bennett N, Clerisme-Beaty E, Grönke L, Voß F, Buhl R. Effect of tiotropium and olodaterol on symptoms and patient-reported outcomes in patients with COPD: results from four randomised, double-blind studies. NPJ Prim Care Respir Med. 2017 Dec;27(1):7. doi: 10.1038/s41533-016-0002-x. Epub 2017 Feb 2. PubMed PMID: 28154373.

6: Koblížek V, Svoboda M. [Current position of new fixed-dose combination of tiotropium and olodaterol - its role in the treatment of chronic obstructive pulmonary disease in the Czech Republic]. Vnitr Lek. 2016 Winter;62(12):1011-1020. Czech. PubMed PMID: 28139131.

7: Płusa T. [New bronchodilation treatment options for patients with COPD]. Pol Merkur Lekarski. 2017 Jan 23;42(247):5-12. Polish. PubMed PMID: 28134225.

8: Price D, Østrem A, Thomas M, Welte T. Dual bronchodilation in COPD: lung function and patient-reported outcomes - a review. Int J Chron Obstruct Pulmon Dis. 2016 Dec 30;12:141-168. doi: 10.2147/COPD.S116719. eCollection 2017. Review. PubMed PMID: 28115839; PubMed Central PMCID: PMC5221557.

9: An update on LAMA/LABA combinations for COPD. Drug Ther Bull. 2017 Jan;55(1):2-5. doi: 10.1136/dtb.2017.1.0451. Epub 2017 Jan 5. PubMed PMID: 28057707.

10: Derom E, Brusselle GG, Joos GF. Efficacy of tiotropium-olodaterol fixed-dose combination in COPD. Int J Chron Obstruct Pulmon Dis. 2016 Dec 13;11:3163-3177. doi: 10.2147/COPD.S92840. eCollection 2016. Review. PubMed PMID: 28008243; PubMed Central PMCID: PMC5167492.

11: Buhl R, Magder S, Bothner U, Tetzlaff K, Voß F, Loaiza L, Vogelmeier CF, McGarvey L. Long-term general and cardiovascular safety of tiotropium/olodaterol in patients with moderate to very severe chronic obstructive pulmonary disease. Respir Med. 2017 Jan;122:58-66. doi: 10.1016/j.rmed.2016.11.011. Epub 2016 Nov 14. PubMed PMID: 27993292.

12: Lee HW, Kim HJ, Lee CH. The impact of olodaterol on the risk of mortality and serious adverse events: a systematic review and meta-analysis. Br J Clin Pharmacol. 2016 Dec 13. doi: 10.1111/bcp.13210. [Epub ahead of print] PubMed PMID: 27957746.

13: Tamura T, Satoh H. Superiority of tiotropium plus olodaterol in comparison with salmeterol plus fluticasone. Int J Chron Obstruct Pulmon Dis. 2016 Nov 23;11:2909-2911. eCollection 2016. PubMed PMID: 27920517; PubMed Central PMCID: PMC5125986.

14: Tebboth A, Ternouth A, Gonzalez-Rojas N. UK-specific cost-effectiveness of tiotropium + olodaterol fixed-dose combination versus other LAMA + LABA combinations in patients with COPD. Clinicoecon Outcomes Res. 2016 Nov 7;8:667-674. eCollection 2016. PubMed PMID: 27853383; PubMed Central PMCID: PMC5106216.

15: Ferguson GT, Karpel JP, Clerisme-Beaty E, Grönke L, Voß F, Buhl R. Efficacy and safety of tiotropium + olodaterol maintenance treatment in patients with COPD in the TONADO(®) and OTEMTO(®) studies: a subgroup analysis by age. Int J Chron Obstruct Pulmon Dis. 2016 Oct 31;11:2701-2710. eCollection 2016. PubMed PMID: 27843306; PubMed Central PMCID: PMC5098524.

16: van Boven JF, Kocks JW, Postma MJ. Cost-effectiveness and budget impact of the fixed-dose dual bronchodilator combination tiotropium-olodaterol for patients with COPD in the Netherlands. Int J Chron Obstruct Pulmon Dis. 2016 Sep 19;11:2191-2201. eCollection 2016. PubMed PMID: 27703341; PubMed Central PMCID: PMC5036592.

17: Halpin DM, Kerkhof M, Soriano JB, Mikkelsen H, Price DB. Eligibility of real-life patients with COPD for inclusion in trials of inhaled long-acting bronchodilator therapy. Respir Res. 2016 Sep 23;17(1):120. PubMed PMID: 27663386; PubMed Central PMCID: PMC5034631.

18: Ichinose M, Taniguchi H, Takizawa A, Grönke L, Loaiza L, Voß F, Zhao Y, Fukuchi Y. The efficacy and safety of combined tiotropium and olodaterol via the Respimat(®) inhaler in patients with COPD: results from the Japanese sub-population of the Tonado(®) studies. Int J Chron Obstruct Pulmon Dis. 2016 Aug 29;11:2017-27. doi: 10.2147/COPD.S110389. eCollection 2016. PubMed PMID: 27621608; PubMed Central PMCID: PMC5010080.

19: Perriello EA, Sobieraj DM. The Respimat Soft Mist Inhaler, a Novel Inhaled Drug Delivery Device. Conn Med. 2016 Jun-Jul;80(6):359-64. Review. PubMed PMID: 27509644.

20: Selya-Hammer C, Gonzalez-Rojas Guix N, Baldwin M, Ternouth A, Miravitlles M, Rutten-van Mölken M, Goosens LM, Buyukkaramikli N, Acciai V. Development of an enhanced health-economic model and cost-effectiveness analysis of tiotropium + olodaterol Respimat® fixed-dose combination for chronic obstructive pulmonary disease patients in Italy. Ther Adv Respir Dis. 2016 Oct;10(5):391-401. doi: 10.1177/1753465816657272. Epub 2016 Jul 12. PubMed PMID: 27405723.