Formoterol Hemifumarate (CGP-25827A, NSC-299587, YM-08316; Eformoterol; Aformoterol; Atock; Foradil Aerolizer), the Hemifumarate salt of formoterol, is a selective and long-acting β2-adrenoceptor agonist with airway smooth muscle relaxing effects. It has been used in the management of asthma and chronic obstructive pulmonary disease (COPD with high efficacy, and very high affinity and selectivity for the beta 2-adrenoceptor.
Physicochemical Properties
| Molecular Formula | C19H24N2O4.1/2C4H4O4 | |
| Molecular Weight | 402.40 | |
| Exact Mass | 460.184 | |
| CAS # | 43229-80-7 | |
| Related CAS # | Formoterol hemifumarate hydrate; 183814-30-4; Arformoterol; 67346-49-0; Formoterol-1; 73573-87-2; (S,S)-Formoterol; 67346-48-9; Arformoterol tartrate; 200815-49-2; Formoterol-d6; 1020719-45-2 | |
| PubChem CID | 53477580 | |
| Appearance | White to off-white solid powder | |
| Boiling Point | 603.2ºC at 760mmHg | |
| Melting Point | 138-140ºC | |
| Flash Point | 318.6ºC | |
| LogP | 3.034 | |
| Hydrogen Bond Donor Count | 10 | |
| Hydrogen Bond Acceptor Count | 14 | |
| Rotatable Bond Count | 18 | |
| Heavy Atom Count | 58 | |
| Complexity | 507 | |
| Defined Atom Stereocenter Count | 4 | |
| SMILES | C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=CC(=C(C=C2)O)NC=O)O.C(=C/C(=O)O)\C(=O)O |
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| InChi Key | OBRNDARFFFHCGE-PERKLWIXSA-N | |
| InChi Code | InChI=1S/2C19H24N2O4.C4H4O4/c2*1-13(9-14-3-6-16(25-2)7-4-14)20-11-19(24)15-5-8-18(23)17(10-15)21-12-22;5-3(6)1-2-4(7)8/h2*3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*13-,19+;/m00./s1 | |
| Chemical Name | (E)-but-2-enedioic acid;N-[2-hydroxy-5-[(1S)-1-hydroxy-2-[[(2S)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide | |
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| 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. |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | β2-adrenergic receptor | ||
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Although no published data exist on the use of formoterol by inhaler during lactation, data from the related drug, terbutaline, indicate that very little is expected to be excreted into breastmilk. The authors of several reviews and expert guidelines 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. |
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| References |
[1]. Life Sci . 1993;52(26):2145-60. [2]. Eur J Pharmacol . 1994 Jan 14;251(2-3):127-35. [3]. Br J Pharmacol . 1993 Oct;110(2):613-8. |
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| Additional Infomation |
Arformoterol fumarate is a fumarate salt prepared from arformoterol by reaction of one molecule of fumaric acid for every two molecules of arformoterol. It has a role as a beta-adrenergic agonist and a bronchodilator agent. It contains an arformoterol(1+). It is an enantiomer of a (S,S)-formoterol fumarate. Formoterol Fumarate is the fumarate salt form of formoterol, a long-acting and selective sympathomimetic beta-receptor agonist with bronchodilator activity. Formoterol fumarate binds beta 2 adrenergic receptors in bronchial smooth muscle and stimulates intracellular adenyl cyclase, thereby increasing the production of cyclic adenosine monophosphate (cAMP). Increased cAMP levels cause relaxation of bronchial smooth muscle, improve mucociliary clearance and reduce mediator substance release in inflammatory cells, especially from mast cells. (NCI05) An ADRENERGIC BETA-2 RECEPTOR AGONIST with a prolonged duration of action. It is used to manage ASTHMA and in the treatment of CHRONIC OBSTRUCTIVE PULMONARY DISEASE. See also: Formoterol Fumarate (annotation moved to). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 3: 2.5 mg/mL (6.21 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4851 mL | 12.4254 mL | 24.8509 mL | |
| 5 mM | 0.4970 mL | 2.4851 mL | 4.9702 mL | |
| 10 mM | 0.2485 mL | 1.2425 mL | 2.4851 mL |