Formoterol fumarate
- Iupac Name：(E)-but-2-enedioic acid;N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide
- CAS No.: 43229-80-7
- Molecular Weight：804.88
- Modify Date.: 2022-12-10 08:48
- Introduction: A selective 2-adrenergic receptor agonist. Used as an antiasthmatic
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1. Names and Identifiers
- 1.1 Name
- Formoterol fumarate
- 1.2 Synonyms
(+/-)-(R*,R*)-N-[2-HYDROXY-5-[1-HYDROXY-2-[[2-(4-METHOXYPHENYL)-1-METHYLETHYL]AMINO]ETHYL]PHENYL] FORMAMIDE HEMIFUMARATE (R*,R*)-(+)-N-[2-HYDROXY-5-[1-HYDROXY-2-[[2-(4-METHOXYPHENYL)-1-METHYLETHYL]AMINO]ETHYL]-PHENYL]FORMAMIDE FUMARATE (R*,R*)-N-[2-HYDROXY-5-[1-HYDROXY-2-[[2-(4-METHOXYPHENYL)-1-METHYLETHYL]AMINO]ETHYL]PHENYL]FORMAMIDE FUMARATE Aformoterol Atock BD 40A CGP 25827A Eformoterol fumarate Foradil Foradil Acrolizer Foradil Aerolizer Foradil Certihaler Formamide, N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, rel-, (2E)-2-butenedioate (2:1) (salt) Formamide, N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (R*,R*)-(±)-, (E)-2-butenedioate (2:1) (salt) Formamide, N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, (R*,R*)-, (E)-2-butenedioate (2:1) (salt) formamide,n-(2-hydroxy-5-(1-hydroxy-2-((2-(4-methoxyphenyl)-1-methylethyl)amin FORMATEROL FUMATATE Formoterol fumarate 50 gram Formoterol fumarate JP13 NSC 299587 o)ethyl)phenyl)-,(e)-2-butenedioate(2:1)(salt),dihydrate Oxis pMDi YM 08316
- 1.3 CAS No.
- 43229-80-7
- 1.4 CID
- 9832292
- 1.5 EINECS(EC#)
- 1308068-626-2
- 1.6 Molecular Formula
- C42H52N4O12 (isomer)
- 1.7 Inchi
- InChI=1/2C19H24N2O4.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)
- 1.8 InChkey
- OBRNDARFFFHCGE-UHFFFAOYNA-N
- 1.9 Canonical Smiles
- OC(=O)C=CC(O)=O.COC1=CC=C(CC(C)NCC(O)C2=CC(NC=O)=C(O)C=C2)C=C1.COC1=CC=C(CC(C)NCC(O)C2=CC(NC=O)=C(O)C=C2)C=C1
- 1.10 Isomers 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
2. Properties
- 2.1 Melting point
- 138-140°C
- 2.1 Boiling point
- 603.2ºC at 760mmHg
- 2.1 Flash Point
- 318.6ºC
- 2.1 Precise Quality
- 460.18500
- 2.1 PSA
- 165.42000
- 2.1 logP
- 3.03490
- 2.1 Λmax
- 284nm(lit.)
- 2.2 Appearance
- White powder
- 2.3 Chemical Properties
- Crystalline Solid
- 2.4 pKa
- pKa1 7.9; pKa2 9.2(at 25℃)
- 2.5 Water Solubility
- Slightly soluble in water, soluble in methanol, slightly soluble in 2-propanol, practically insoluble in acetonitrile.
- 2.6 StorageTemp
- Room temperature
3. Use and Manufacturing
- 3.1 Usage
- A selective 2-adrenergic receptor agonist. Used as an antiasthmatic
4. Safety and Handling
- 4.1 Safety Statements
- S36/37
- 4.1 Packing Group
- II
- 4.1 Hazard Class
- 6.1(b)
- 4.1 RIDADR
- 3249
- 4.1 RTECS
- LQ2988000
- 4.1 Safety
-
Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Experimental teratogenic and reproductive effects. Used as a bronchodilator. When heated to decomposition it emits toxic fumes of NOx.
- 4.2 Specification
-
Crystalline Solid
usageEng:A selective 2-adrenergic receptor agonist. Used as an antiasthmatic
- 4.3 Toxicity
-
| 1. |
??? |
orl-rat LD50:3130?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 2. |
??? |
ipr-rat LD50:170?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 3. |
??? |
scu-rat LD50:1000?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 4. |
??? |
ivn-rat LD50:98?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 5. |
??? |
orl-mus LD50:6700?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 6. |
??? |
ipr-mus LD50:210?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 7. |
??? |
scu-mus LD50:640?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
| 8. |
??? |
ivn-mus LD50:71?mg/kg
|
??? |
OYYAA2 ?? Oyo Yakuri. Pharmacometrics. 26 (1983),811. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 2
Reproductive toxicity, Category 2
Specific target organ toxicity \u2013 single exposure, Category 1
Specific target organ toxicity \u2013 repeated exposure, Category 2
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Danger |
| Hazard statement(s) | H300 Fatal if swallowed H370 Causes damage to organs H373 May cause damage to organs through prolonged or repeated exposure H412 Harmful to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment. |
| Response | P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P308+P313 IF exposed or concerned: Get medical advice/ attention. P308+P311 IF exposed or concerned: Call a POISON CENTER/doctor/... P314 Get medical advice/attention if you feel unwell. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
43229-80-7Total: 1 Synthesis Route
8. Other Information
- 8.0 Merck
- 14,4245
- 8.1 Target
- Value
- 8.2 Description
- Formoterol fumarate is a β2-selective adrenergic agonist useful in the treatment of bronchial asthma. It s potency and duration of action a r e reported to exceed those of salbutamol, as is its ability to inhibit allergic and non-allergic histamine release.
- 8.3 Chemical Properties
- Crystalline Solid
- 8.4 Originator
- Yarnanouchi (Japan)
- 8.5 Uses
- Formoterol fumarate is a potent β2-AR agonist.
- 8.6 Uses
- A potent β2-AR agonist
- 8.7 Uses
- long-acting β 2-agonist, anti-asthmatic
- 8.8 Uses
- A selective 2-adrenergic receptor agonist. Used as an antiasthmatic
- 8.9 Uses
- antiasthmatic;?2-agonist
- 8.10 Brand name
- Foradil (Novartis);ATOCK.
- 8.11 Mechanism of action
- This is believed to result from formoterol's greater water solubility, allowing it to get to the receptor sites faster, whereas its moderate lipophilicity keeps it in the lungs longer. It is indicated for the long-term maintenance treatment of asthma and for patients with symptoms of nocturnal asthma who require regular treatment with inhaled, short-acting, β2-agonists. It is not indicated for patients whose asthma can be managed by occasional use of inhaled, short-acting, β2-agonists. Formoterol is available only as a powder in a capsule for administration via the aerosolizer. Patients should be cautioned not to take the capsules orally and to keep them in a safe place to avoid accidental oral administration.
- 8.12 Clinical Use
- Formoterol has a β-directing N-isopropyl-p-methoxyphenyl group and a unique m-formamide and p-hydroxyphenyl ring, which provides selectivity for β2-receptors. It is resistant to MAO and COMT, making it a long-acting agonist. Formoterol has a more rapid onset as compared to salmeterol while maintaining the same long duration of action.
- 8.13 References
- 1) Anderson et al. (1993), Formoterol: pharmacology, molecular basis of agonism and mechanism of long duration of a highly potent and selective beta 2-adrenoceptor agonist bronchodilator; Life Sciences, 52 2145 2) Teng et al. (2005), Structure-activity relationship study of novel necroptosis inhibitors; Bioorg. Med. Chem. Lett., 15 5039 3) Noguchi et al. (2015), Effect of beta2-adrenergic agonist on eosinophil adhesion, superoxide anion generation, and degranulation; Allergol. Int., 64 S46 4)Busquets et al. (2004), Anticachectic effects of formoterol: a drug for potential treatment of muscle wasting; Cancer Res., 64 6725 5) O’Neill et al. (2020), Pharmacological targeting of ?2-adrenoceptors is neuroprotective in the LPS inflammatory rat model of Parkinson’s disease; Br. J. Pharmacol., 177 282
9. Computational chemical data
- Molecular Weight: 804.88g/mol
- Molecular Formula: C42H52N4O12
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 804.35817311
- Monoisotopic Mass: 804.35817311
- Complexity: 507
- Rotatable Bond Count: 18
- Hydrogen Bond Donor Count: 10
- Hydrogen Bond Acceptor Count: 14
- Topological Polar Surface Area: 256
- Heavy Atom Count: 58
- Defined Atom Stereocenter Count: 4
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 1
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 3
- CACTVS Substructure Key Fingerprint: AAADcfB/vAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGAAAAAAAABVAAAHgAQCAAADDzhmAYyzoLABgCIAiTS2ACCCAAhIgAIiIAPbMgONiLWsZuEcChk1BHY+Yew4KQOIAAAQAAAEABAAACAAAAgAAAAAAAAAA==
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11. Realated Product Infomation
skype
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