Formoterol Fumarate
Basic information
- CAS
43229-80-7- Standard SMILES
COc1ccc(C[C@@H](C)NC[C@H](O)c2ccc(O)c(NC=O)c2)cc1.COc1ccc(C[C@@H](C)NC[C@H](O)c2ccc(O)c(NC=O)c2)cc1.O=C(O)/C=C/C(=O)O- InChIKey
OBRNDARFFFHCGE-QDSVTUBZSA-N- Molecular formula
- C42H52N4O12
- Average molar mass
- 804.9 g/mol
- Monoisotopic mass
- 804.35817311
Overview
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.
Names & identifiers
- Preferred name
- Formoterol Fumarate
- IUPAC
- (E)-but-2-enedioic acid;bis(N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide)
- English name
- Formoterol fumarate
- Molecular formula
- C42H52N4O12
- Molecular weight
- 804.88
Names & synonyms
FORMOTEROL FUMARATE43229-80-7AtockForadil CertihalerPerforomistPerformistFomoterol fumarateP3T5QA5J9NFormoterol fumarate (superceded)ForadilFormoterol fumarate anhydrousYM-08316
Show more names
FORMOTEROL HEMIFUMARATEAformoterolYM 08316FarMeterolNSC 299587CGP-25827A-eFumarate dihydrateFORMAMIDE FUMARATEFORMOTEROL
BD 40ACGP 25827AW34SHF8J2KOxezeNSC-299587Atimos moduliteBD-40A3-formylamino-4-hydroxy-alpha-(N-1-methyl-2-p-methoxyphenethylaminomethyl)benzyl alcohol.hemifumarate
Database identifiers
- CAS
43229-80-7- PubChem CID
- 53477580
- DTXSID
DTXSID5044239- ChEMBL
CHEMBL1200811、CHEMBL3184383、CHEMBL3989798- ChEBI
Properties
Computed structural properties
- Topological polar surface area
- 256 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 18
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 507
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Asthmatic Agents; Bronchodilator Agents; Beta Adrenergic Agonists
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 138 · 138-140°C
- storage temp.
- Room temperature
- solubility
- 2 · Slightly soluble in water, soluble in methanol, slightly soluble in 2-propanol, practically insoluble in acetonitrile.
- pka
- 1 · pKa1 7.9; pKa2 9.2(at 25℃)
- form
- Solid
- color
- White to off-white
- λmax
- 284 nm · 284nm(lit.)
- Merck
- 14 · 14,4245
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- Major Application
- pharmaceutical
- InChIKey
- OBRNDARFFFHCGE-WXXKFALUSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (29.2%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P264, P270, P271, P273, P280, P301+P316, P304+P340, P308+P316, P317, P318, P319, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 89 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (29.2%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- rtecs
- LQ2988000
- ridadr
- 3249
- Toxicity
- LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida)
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- II
- Hazard statements
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
FORMOTEROL FUMARATE
Adrenergic beta2-Agonists [MoA]; beta2-Adrenergic Agonist [EPC]
MeSH Pharmacological Classification
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS.
Applications
DescriptionFormoterol 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.
Useslong-acting β 2-agonist, anti-asthmatic
UsesFormoterol fumarate is a potent β2-AR agonist.
UsesA selective 2-adrenergic receptor agonist. Used as an antiasthmatic
Usesantiasthmatic;2-agonist
Additional notes
DefinitionChEBI: (S,S)-formoterol fumarate is a fumarate salt prepared from (S,S)-formoterol by reaction of one molecule of fumaric acid for every two molecules of (S,S)-formoterol. It contains a (S,S)-formoterol(1+). It is an enantiomer of an arformoterol fumarate.
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Compound notes
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