Olodaterol HCl

Alias: Olodaterol hydrochloride BI 1744 BI1744BI-1744 Olodaterol StriverdiOlodaterol HCl

Cat No.:V8325 Purity: ≥98%

COA Product Data Instructions for use SDS

Olodaterol HCl, the hydrochloride salt of Olodaterol (BI-1744; BI1744;STRIVERDI RESPIMAT), is a ultra-long acting β-adrenergic receptor agonist approved in 2014 as an inhalation for the treatment of patients with chronic obstructive pulmonary disease (COPD).

Olodaterol HCl Chemical Structure CAS No.: 869477-96-3
Product category: Adrenergic Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Olodaterol HCl:

Olodaterol

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Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Olodaterol HCl, the hydrochloride salt of Olodaterol (BI-1744; BI1744; STRIVERDI RESPIMAT), is a ultra-long acting β-adrenergic receptor agonist approved in 2014 as an inhalation for the treatment of patients with chronic obstructive pulmonary disease (COPD).

Biological Activity I Assay Protocols (From Reference)

ln Vitro	Olodaterol (0.001~10 nM; fibroblasts) hydrochloride initiates growth factor-induced motility and proliferation [2]. Olodaterol (0.1~10 nM; fibroblasts) hydrochloride interferes with FGF-induced phosphorylation of the signaling cascade [2]. Olodaterol (0.001~1000). nM; 30 min; fibroblasts) hydrochloric acid concentration raises intracellular cAMP in a dependent manner. Olodaterol (0 to 10 nM; 30 minutes; fibroblasts) hydrochloric acid concentration reduces the increase in PICP, with maximal effectiveness at 10 nM. Olodaterol hydrochloride exhibits subnanomolar affinity for β2-AR (pKi=9.14 ), olodaterol hydrochloride is selective for this receptor compared with β1-AR and β3-AR subtypes [2].
ln Vivo	Olodaterol hydrochloride (1 mg/kg; inhalation; day 21) accelerates weight return to control levels (day 21) and attenuates TGF-β-induced pulmonary fibrosis [2]. Olodaterol (0.1 to 3 μg/kg; inhalation; Olodaterol (0.3 and 0.6 μg/kg; inhalation; 24 hours)) induces approximately 60% anesthetic protection after 0.5 hours [3].
Cell Assay	Western Blot analysis [2] Cell Types: fibroblasts Tested Concentrations: 0.1~10 nM Incubation Duration: Experimental Results: Interference with FGF-induced signaling cascade phosphorylation. Cell proliferation analysis[2] Cell Types: Fibroblasts Tested Concentrations: 0.001~10 nM Incubation Duration: Experimental Results: Growth factor-induced motility and proliferation were attenuated.
Animal Protocol	Animal/Disease Models: Pulmonary fibrosis C57BL/6 mice Doses: 1 mg/mL Route of Administration: inhalation; 21-day Experimental Results: Accelerated body weight recovery to control level (day 21) and attenuated TGF-β-induced pulmonary fibrosis. Animal/Disease Models: guinea pig Doses: 0.1~3 μg/kg Route of Administration: inhalation; 5 hrs (hrs (hours)) Experimental Results: Induced dose-dependent bronchial protection. Animal/Disease Models: Dog Doses: 0.3 and 0.6 μg/kg Route of Administration: Inhalation; 24 hrs (hrs (hours)) Experimental Results: Olodaterol (0.6 μg/kg) induced approximately 60% of maximal bronchial protection after 0.5 hrs (hrs (hours)).
Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Although no published data exist on the use of olodaterol during lactation, data from the related drug, terbutaline, indicate that very little is expected to be excreted into breastmilk. The authors of several reviews agree that use of inhaled bronchodilators is acceptable during breastfeeding because of the low bioavailability and maternal serum levels after use. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date.
References	[1]. Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists. Bioorg Med Chem. 2020;28(1):115178. [2]. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017;174(21):3848-3864. [3]. Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models [published correction appears in J Pharmacol Exp Ther. 2013 Jul;346(1):161]. J Pharmacol Exp Ther. 2010;334(1):53-62.
Additional Infomation	Olodaterol hydrochloride is a hydrochloride obtained by combining olodaterol with one equivalent of hydrochloric acid. Used for long-term treatment of airflow obstruction in patients with chronic obstructive pulmonary disease including chronic bronchitis and/or emphysema. It has a role as a beta-adrenergic agonist and a bronchodilator agent. It contains an olodaterol(1+). See also: Olodaterol (has active moiety); Olodaterol hydrochloride; tiotropium bromide (component of) ... View More ... Drug Indication Treatment of cystic fibrosis

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C21H27CLN2O5
Molecular Weight	422.906
Exact Mass	422.161
Elemental Analysis	C, 59.64; H, 6.44; Cl, 8.38; N, 6.62; O, 18.92
CAS #	869477-96-3
Related CAS #	Olodaterol;868049-49-4
PubChem CID	11711522
Appearance	White to light yellow solid powder
LogP	3.654
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Heavy Atom Count	29
Complexity	521
Defined Atom Stereocenter Count	1
SMILES	[C@H](C1C=C(O)C=C2NC(COC=12)=O)(O)CNC(C)(C)CC1C=CC(OC)=CC=1.Cl
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
Chemical Name	6-hydroxy-8-[(1R)-1-hydroxy-2-[[1-(4-methoxyphenyl)-2-methylpropan-2-yl]amino]ethyl]-4H-1,4-benzoxazin-3-one;hydrochloride
Synonyms	Olodaterol hydrochloride BI 1744 BI1744BI-1744 Olodaterol StriverdiOlodaterol HCl
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	H2O : ~250 mg/mL (~591.16 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 14.29 mg/mL (33.79 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.3646 mL	11.8228 mL	23.6457 mL
	5 mM	0.4729 mL	2.3646 mL	4.7291 mL
	10 mM	0.2365 mL	1.1823 mL	2.3646 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
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In vivo Formulation Calculator (Clear solution)

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Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT02682862	COMPLETED	Drug: olodaterol hydrochloride 2.5mcg, tiotropium bromide 2.5mcg Drug: olodaterol 2.5 mcg	Asthma	University of Dundee	2016-07-11	Phase 4
NCT02799784	COMPLETEDWITH RESULTS	Drug: UMEC/VI Drug: TIO/OLO Drug: Albuterol/salbutamol	Pulmonary Disease, Chronic Obstructive	GlaxoSmithKline	2016-07-14	Phase 4<

Biological Data

β2‐adrenoceptor function and protein expression in primary HLF. Intracellular cAMP increase was measured in fibroblasts from control donors (HLF) (A) and patients with IPF (IPF‐LF) (B) upon stimulation with different concentrations of olodaterol. Fibroblasts were pre‐incubated for 30 min with 30 nM ICI‐118,551 or 100 nM CGP‐20712A, respectively, before stimulation with olodaterol for another 30 min. Intracellular cAMP increase was measured by a bioluminescent cAMP assay. Dotted line represents the highest cAMP concentration reached. Control cells without stimulation were defined as 1. The EC50 value was calculated with a nonlinear regression fit by GraphPad Prism software. Levels of β2‐adrenoceptor (β2‐AR) protein in healthy and IPF fibroblasts (C). Expression of β2‐adrenoceptor protein was normalized to cell count. Each dot or square represents a different donor. Data shown are means ± SEM of n = 5 different donors each for HLF and IPF‐LF.[2]. Herrmann FE, et al. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017;174(21):3848-3864.

Olodaterol attenuates TGF‐β‐stimulated protein expression of primary HLF. Fibroblasts from control donors (HLF) and patients with IPF (IPF‐LF) were pre‐incubated with different concentrations of olodaterol and subsequently stimulated with TGF‐β (4 ng·mL−1) for 48 h in the presence of the compound. α‐SMA protein expression was measured in cell lysates by an MSD Western replacement assay (A). Pro‐collagen I C‐peptide (B), fibronectin (C) and ET‐1 (D) expression was measured in supernatants by elisa. Basal levels of 16 ng·mL−1, 1.5 μg·mL−1 and 0.2 pg·mL−1 increased to 40 ng·mL−1, 2.5 μg·mL−1 and 5 pg·mL−1 respectively. Effect of olodaterol on ET‐1 protein expression in HLF and IPF‐LF in the presence of ICI‐118,551 (30 nM) (D). Data are expressed as normalized protein expression (100% is expression with TGF‐β stimulation). Data shown are means ± SEM of n = 5 different donors for HLF and n = 5 different donors for IPF cells. Horizontal dotted line is 50% inhibition of the TGF‐β‐induced effect. Representative image of TGF‐β‐induced collagen I assembly and inhibition by 10 nM olodaterol in HLF in a ‘scar‐in‐a‐jar’ assay (E). Unstimulated cells (Ctr) were compared to TGF‐β‐stimulated cells (TGFβ) and TGFβ‐stimulated and olodaterol‐treated cells (10 nM Olodaterol).[2]. Herrmann FE, et al. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017;174(21):3848-3864.

Olodaterol attenuates growth factor‐induced motility and proliferation of primary HLF. The motility of fibroblasts from control donors (HLF) and patients with IPF (IPF‐LF) after FGF or PDGF stimulation was measured by time‐lapse microscopy and manual single cell tracking. Cells were stimulated with FGF (20 ng·mL−1) or PDGF (50 ng·mL−1) for 72 h. Effect of olodaterol on FGF (A) and PDGF (B) induced motility. Data expressed as normalized migration (100% is defined as the migration measured after treatment with the respective stimulus). Data are shown as means ± SEM of n = 3 different donors for HLFs and IPFs. Cell proliferation was measured by BrdU incorporation. For proliferation, cells were stimulated with EGF (3 ng·mL−1), FCS (1%), FGF (20 ng·mL−1) or PDGF (50 ng·mL−1) for 92 h in the presence of the compound. Effect of olodaterol on EGF (C), FCS (D), FGF (E) or PDGF (F) induced proliferation. Data are shown as means ± SEM of n = 5 different donors for HLFs and n = 5 different donors for IPF‐LFs. Horizontal dotted line is 50% inhibition of the induced effect. *P < 0.05, significantly different from HLF data; unpaired Student's t‐test.[2]. Herrmann FE, et al. Olodaterol shows anti-fibrotic efficacy in in vitro and in vivo models of pulmonary fibrosis. Br J Pharmacol. 2017;174(21):3848-3864.