Arformoterol

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H24N2O4
Molecular Weight	344.4049
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C[C@@H](C)NC[C@H](O)C2=CC=C(O)C(NC=O)=C2)C=C1

InChI

InChIKey=BPZSYCZIITTYBL-YJYMSZOUSA-N

InChI=1S/C19H24N2O4/c1-13(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/h3-8,10,12-13,19-20,23-24H,9,11H2,1-2H3,(H,21,22)/t13-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H24N2O4
Molecular Weight	344.4049
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14725487

Sepracor in the US is developing arformoterol [R,R-formoterol], a single isomer form of the beta(2)-adrenoceptor agonist formoterol [eformoterol]. This isomer contains two chiral canters and is being developed as an inhaled preparation for the treatment of respiratory disorders. Sepracor believes that arformoterol has the potential to be a once-daily therapy with a rapid onset of action and a duration of effect exceeding 12 hours. Sepracor stated in July 2003 that it had completed more than 100 preclinical studies and initiated or completed 15 clinical studies for arformoterol inhalation solution for the treatment of bronchospasm in patients with COPD. The pharmacologic effects of beta2-adrenoceptor agonist drugs, including arformoterol, are at least in part attributable to stimulation of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic-3′,5′-adenosine monophosphate (cyclic AMP). Increased intracellular cyclic AMP levels cause relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells. In vitro tests show that arformoterol is an inhibitor of the release of mast cell mediators, such as histamine and leukotrienes, from the human lung. Arformoterol also inhibits histamine-induced plasma albumin extravasation in anesthetized guinea pigs and inhibits allergen-induced eosinophil influx in dogs with airway hyper-responsiveness. The relevance of these in vitro and animal findings to humans is unknown.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20406080	Agonist 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 173 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf	Palliative		Approved 8360	BROVANA Approved Use BROVANA Inhalation Solution is a long-acting beta2-adrenergic agonist (beta2-agonist) indicated for: Long-term, twice daily (morning and evening) administration in the maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. (1.1) Important limitations of use: BROVANA Inhalation Solution is not indicated to treat acute deteriorations of chronic obstructive pulmonary disease. (1.2, 5.2) BROVANA Inhalation Solution is not indicated to treat asthma. (1.2) 1.1 Maintenance Treatment of COPD BROVANA (arformoterol tartrate) Inhalation Solution is indicated for the long-term, twice daily (morning and evening) maintenance treatment of bronchoconstriction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema. BROVANA Inhalation Solution is for use by nebulization only. 1.2 Important Limitations of Use BROVANA Inhalation Solution is not indicated to treat acute deteriorations of chronic obstructive pulmonary disease [see WARNINGS AND PRECAUTIONS (5.2) Launch Date 1.16009284E12

C_max

Value	Dose	Co-administered	Analyte	Population
4.3 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf	15 μg 2 times / day steady-state, respiratory dose: 15 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		ARFORMOTEROL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
26.65 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24746942	24 μg single, respiratory dose: 24 μg route of administration: Respiratory experiment type: SINGLE co-administered: BECLOMETHASONE 17-MONOPROPIONATE	BECLOMETHASONE 17-MONOPROPIONATE	FORMOTEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
22.3 nM REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022518Orig1s000ClinPharmR.pdf	10 μg single, respiratory dose: 10 μg route of administration: Respiratory experiment type: SINGLE co-administered: MOMETASONE FUROATE	MOMETASONE FUROATE	FORMOTEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
34.5 pg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf	15 μg 2 times / day steady-state, respiratory dose: 15 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		ARFORMOTEROL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
104.52 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24746942	24 μg single, respiratory dose: 24 μg route of administration: Respiratory experiment type: SINGLE co-administered: BECLOMETHASONE 17-MONOPROPIONATE	BECLOMETHASONE 17-MONOPROPIONATE	FORMOTEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
33.7 pM × h REVIEW https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022518Orig1s000ClinPharmR.pdf	10 μg single, respiratory dose: 10 μg route of administration: Respiratory experiment type: SINGLE co-administered: MOMETASONE FUROATE	MOMETASONE FUROATE	FORMOTEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
26 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf	15 μg 2 times / day steady-state, respiratory dose: 15 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		ARFORMOTEROL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
4.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24746942	24 μg single, respiratory dose: 24 μg route of administration: Respiratory experiment type: SINGLE co-administered: BECLOMETHASONE 17-MONOPROPIONATE	BECLOMETHASONE 17-MONOPROPIONATE	FORMOTEROL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
48% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021912lbl.pdf	15 μg 2 times / day steady-state, respiratory dose: 15 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		ARFORMOTEROL plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
37.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022007s004lbl.pdf			FORMOTEROL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 ug 2 times / day steady, respiratory Recommended Dose: 20 ug, 2 times / day Route: respiratory Route: steady Dose: 20 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022007s004lbl.pdf	unhealthy, 40-90 years n = 123 Health Status: unhealthy Condition: COPD Age Group: 40-90 years Sex: M+F Population Size: 123 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022007s004lbl.pdf	Other AEs: Diarrhea, Nausea... Other AEs: Diarrhea (6%) Nausea (6%) Nasopharyngitis (4%) Dry mouth (4%) Vomiting (3%) Dizziness (3%) Insomnia (3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022007s004lbl.pdf
25 ug 2 times / day multiple, respiratory Highest studied dose Dose: 25 ug, 2 times / day Route: respiratory Route: multiple Dose: 25 ug, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20214460 Page: p.21	unhealthy, 63.8 n = 147 Health Status: unhealthy Condition: Chronic obstructive pulmonary disease Age Group: 63.8 Sex: M+F Population Size: 147 Sources: https://pubmed.ncbi.nlm.nih.gov/20214460 Page: p.21	Sources: https://pubmed.ncbi.nlm.nih.gov/20214460 Page: p.21
30 ug 2 times / day multiple, respiratory (total) Recommended Dose: 30 ug, 2 times / day Route: respiratory Route: multiple Dose: 30 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021912s013lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Chronic obstructive pulmonary disease Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021912s013lbl.pdf Page: p.1	Disc. AE: Bronchospasm paradoxical... AEs leading to discontinuation/dose reduction: Bronchospasm paradoxical (grade 4) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021912s013lbl.pdf Page: p.1
15 ug 2 times / day steady, respiratory Dose: 15 ug, 2 times / day Route: respiratory Route: steady Dose: 15 ug, 2 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT00909779	unhealthy n = 420 Health Status: unhealthy Condition: COPD Population Size: 420 Sources: https://clinicaltrials.gov/ct2/show/NCT00909779	Other AEs: Angina pectoris, Angina unstable... Other AEs: Angina pectoris (serious, 3 patients) Angina unstable (serious, 1 patient) Atrial fibrillation (serious, 3 patients) Cardio-respiratory arrest (serious, 2 patients) Cor pulmonale (serious, 1 patient) Coronary artery disease (serious, 3 patients) Myocardial ischaemia (serious, 1 patient) Vertigo (serious, 1 patient) Iridocyclitis (serious, 1 patient) Barrett's oesophagus (serious, 1 patient) Diverticular perforation (serious, 1 patient) Gastric ulcer haemorrhage (serious, 1 patient) Gastritis erosive (serious, 1 patient) Hiatus hernia (serious, 1 patient) Intestinal perforation (serious, 1 patient) Pancreatitis acute (serious, 1 patient) Non-cardiac chest pain (serious, 3 patients) Oedema peripheral (serious, 1 patient) Cholecystitis (serious, 1 patient) Bronchopneumonia (serious, 1 patient) Clostridial infection (serious, 1 patient) Clostridium difficile colitis (serious, 1 patient) Gastroenteritis bacterial (serious, 1 patient) Osteomyelitis (serious, 1 patient) Osteotomy (serious, 1 patient) Osteomyelitis acute (serious, 1 patient) Postoperative wound infection (serious, 1 patient) Sepsis (serious, 3 patients) Urinary tract infection (serious, 1 patient) Accidental overdose (serious, 1 patient) Ankle fracture (serious, 1 patient) Cervical vertebral fracture (serious, 1 patient) Head injury (serious, 1 patient) Incisional hernia (serious, 1 patient) Open wound (serious, 1 patient) Tibia fracture (serious, 1 patient) Muscular weakness (serious, 1 patient) Rotator cuff syndrome (serious, 1 patient) Brain neoplasm (serious, 1 patient) Metastases to lymph nodes (serious, 1 patient) Oesophageal carcinoma (serious, 1 patient) Squamous cell carcinoma (serious, 1 patient) Throat cancer (serious, 1 patient) Carotid artery disease (serious, 1 patient) Headache (serious, 1 patient) Ischaemic stroke (serious, 1 patient) Sensory disturbance (serious, 1 patient) Transient ischaemic attack (serious, 1 patient) Major depression (serious, 2 patients) Mental status changes (serious, 1 patient) Nephropathy (serious, 1 patient) Renal artery stenosis (serious, 1 patient) Renal failure (serious, 1 patient) Acute respiratory distress syndrome (serious, 1 patient) Bronchiectasis (serious, 1 patient) Hypoxia (serious, 1 patient) Respiratory arrest (serious, 1 patient) Urticaria (serious, 1 patient) Aortic aneurysm (serious, 1 patient) Hypertensive crisis (serious, 1 patient) Hypotension (serious, 1 patient) Iliac artery stenosis (serious, 2 patients) Peripheral arterial occlusive disease (serious, 1 patient) Bronchitis (below serious, 43 patients) Nasopharyngitis (below serious, 38 patients) Upper respiratory tract infection (below serious, 22 patients) Headache (below serious, 35 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00909779

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709	substrate 1010 inhibitor 1752	substrate 1193 inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2A6 704 CYP2C19 1463 CYP2E1 876 CYP3A4/5 273 CYP4A9/11 37 P-gp 1437 CYP 110 BSEP 401 MRP2 367 MRP3 157 MRP4 203	CYP2C19 985 UGT1A1 418 UGT2B17 213 UGT1A9 380 UGT2B7 389 UGT1A7 236 P-gp 1527 CYP2A6 523 CYP1A2 1032 CYP2E1 648 UGT1A8 283 UGT2B15 203 MRP1 106

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
P-gp 1626	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 38.0	inconclusive
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P1.pdf#page=11, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm1) 11, 14, (ClinPharm2) 4-7	moderate [Ki 33 uM]
BSEP 402	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP2 459	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP3 208	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
CYP 146	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 37, 52	no
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP2A6 736	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 37, 52	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 37, 52	no
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP2E1 964	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 37.0	no
CYP3A4/5 330	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP3A4/5 330	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 37.0	no
CYP4A9/11 37	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=4 Page: (ClinPharm2) 4-7	no
CYP4A9/11 37	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 37.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 37, 52	no	no (co-administration study) Comment: coadministration with paroxetine did not affect exposure to either drug Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 37, 52

Drug as victim

Target	Modality	Activity	Clinical evidence
P-gp 1527	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 38.0	inconclusive
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_prntlbl.pdf#page=4, https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210595lbl.pdf#page=14, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P1.pdf#page=11, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (Label1) 4, (Label2) 14, (ClinPharm1) 11, 14, (ClinPharm2) 2-3	major
CYP2A6 523	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_prntlbl.pdf#page=4, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P1.pdf#page=11, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (Label1) 4, (ClinPharm1) 11, 14, (ClinPharm2) 2-3	minor
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_prntlbl.pdf#page=4, https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210595lbl.pdf#page=14, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P1.pdf#page=11, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (Label1) 4, (Label2) 14, (ClinPharm1) 11, 14, (ClinPharm2) 2-3	minor
CYP2C9 1010	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_prntlbl.pdf#page=4, https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210595lbl.pdf#page=14, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P1.pdf#page=11, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (Label1) 4, (Label2) 14, (ClinPharm1) 11, 14, (ClinPharm2) 2-3	minor
CYP1A2 1032	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (ClinPharm2) 2-3, , (PMDA) 16	no
CYP2E1 648	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (ClinPharm2) 2-3, (PMDA) 16	no
CYP3A4 1709	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/20831_Foradil_clinphrmr_P2.pdf#page=2 Page: (ClinPharm2) 2-3, (PMDA) 16	no
MRP1 106	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/18990976/	weak
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 17.0	yes
UGT1A1 418	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022007s015lbl.pdf#page=12, https://go.drugbank.com/drugs/DB00983 Page: (Label) 12	yes
UGT1A1 418	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	yes
UGT1A7 236	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	yes
UGT1A8 283	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022007s015lbl.pdf#page=12, https://go.drugbank.com/drugs/DB00983 Page: (Label) 12	yes
UGT1A9 380	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022007s015lbl.pdf#page=12, https://go.drugbank.com/drugs/DB00983 Page: (Label) 12	yes
UGT1A9 380	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	yes
UGT2B15 203	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022007s015lbl.pdf#page=12, https://go.drugbank.com/drugs/DB00983 Page: (Label) 12	yes
UGT2B17 213	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	yes
UGT2B7 389	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/022007s015lbl.pdf#page=12, https://go.drugbank.com/drugs/DB00983 Page: (Label) 12	yes
UGT2B7 389	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 28.0	yes
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 17, 37	yes	no (co-administration study) Comment: coadministration with paroxetine caused a slight increase in paroxetine; dose adjustment is not required when coadministered with therapeutic agents that are potent inhibitors of CYP2D6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_ClinPharmR_P1.pdf Page: 17, 37

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021912s000_PharmR_P1.pdf Page: 25, 29

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific, Inc. (AKSCI)	X5000	http://www.aksci.com/item_detail.php?cat=X5000
Achemo Scientific Limited	AC-13762	http://www.achemo.com/search/?Keyword= 73573-87-2
Achemtek	0102-022140	http://www.achemtek.com/67346-49-0
Allbio Pharm Co., Ltd	AD02530	http://www.allbiopharm.com/product/n/AD02530
Aurum Pharmatech LLC	W-5127	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5127
BioCrick	BCC1293	http://www.biocrick.com/-R-R-Formoterol-BCC1293.html
Chem Scene	CS-1413	http://www.chemscene.com/67346-49-0.html
ChemMol	49423907	http://www.chemmol.com/chemmol/49423907.html
ChemMol	99141668	http://www.chemmol.com/chemmol/99141668.html
ChemicalBook	CB7722411	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7722411
Chemspace	CSSB00020619539	https://chem-space.com/CSSB00020619539
Combi-Blocks	QA-9564	http://www.combi-blocks.com/cgi-bin/find.cgi?QA-9564
Glentham Life Sciences	GP2396	http://www.glentham.com/products/product/GP2396/
LGC Standards	MM0447.12	https://www.lgcstandards.com/US/en/p/MM0447.12
Lab Network	LN00196799	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196799
MedChem Express	HY-B0010A	https://www.medchemexpress.com/Formoterol.html
MolPort	MolPort-003-847-486	https://www.molport.com/shop/molecule-link/MolPort-003-847-486
MuseChem	I004530	https://www.musechem.com/product/I004530.html
OChem	10387	http://www.ocheminc.com/index.php?act=psearch&pid=73F872
Smolecule	S612938	https://www.smolecule.com/products/s612938
Synblock Inc	SB17482	http://www.synblock.com/product/67346-49-0.html
THE BioTek	bt-333293	https://www.thebiotek.com/product/others/bt-333293
abcr GmbH	AB479021	http://www.abcr.com/shop/en/AB479021
eNovation Chemicals	D393614	https://www.enovationchem.com/ProductDetails.asp?ProductID=D393614
eNovation Chemicals	Y1053969	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1053969
iChemical	EBD43239	http://www.ichemical.com/chemicals/cas-67346-49-0

PubMed

Title	Date	PubMed
Long-acting beta-agonist treatment in patients with persistent asthma already receiving inhaled corticosteroids.	2001	11437672
Nocturnal asthma uncontrolled by inhaled corticosteroids: theophylline or long-acting beta2 agonists?	2001	11293649
Inhaled budesonide/formoterol combination.	2001	11217872
Onset of action of single doses of formoterol administered via Turbuhaler in patients with stable COPD.	2001	11162418
Similar efficacy following four weeks treatment of asthmatics with formoterol 12 micrograms b.d. delivered by two different dry powder inhalers: differences in inhaler handling.	2001 Apr	11351769
Formoterol used as needed--clinical effectiveness.	2001 Aug	11534891
Improved asthma control with budesonide/formoterol in a single inhaler, compared with budesonide alone.	2001 Aug	11529282
Safety of formoterol Turbuhaler at cumulative dose of 90 microg in patients with acute bronchial obstruction.	2001 Dec	11829098
Development of a lyophilized formulation for (R,R)-formoterol (L)-tartrate.	2001 Jan	11247540
Decreased bronchodilating effect of salbutamol in relieving methacholine induced moderate to severe bronchoconstriction during high dose treatment with long acting beta2 agonists.	2001 Jul	11413351
Adding formoterol to budesonide in moderate asthma--health economic results from the FACET study.	2001 Jun	11421509
Reversing acute bronchoconstriction in asthma: the effect of bronchodilator tolerance after treatment with formoterol.	2001 Mar	11405513
Single-isomer beta-agonists.	2001 Mar	11253864
In patients with COPD, treatment with a combination of formoterol and ipratropium is more effective than a combination of salbutamol and ipratropium : a 3-week, randomized, double-blind, within-patient, multicenter study.	2001 May	11348938
A placebo-controlled clinical trial of regular monotherapy with short-acting and long-acting beta(2)-agonists in allergic asthmatic patients.	2001 May	11348933
[Precise direction or flexible self-control. How strictly must the asthma patient adhere to medical advice?].	2001 May 10	11400630
Formoterol (Foradil Aerolizer) for asthma.	2001 May 14	11353924
Glaucoma associated with metered-dose bronchodilator therapy.	2001 Oct	11601753
Statistical issues in bioequivalence [correction of bioequivalance].	2001 Sep 15-30	11523083
Formoterol Turbuhaler 4.5 microg (delivered dose) has a rapid onset and 12-h duration of bronchodilation.	2002	12090792
Biological actions of formoterol isomers.	2002	12090787
Onset of action following formoterol Turbuhaler and salbutamol pMDI in reversible chronic airway obstruction.	2002	12090782
Formoterol as dry powder oral inhalation compared with salbutamol metered-dose inhaler in acute exacerbations of chronic obstructive pulmonary disease.	2002 Apr	12017404
Cost-effectiveness of eformoterol Turbohaler versus salmeterol Accuhaler in children with symptomatic asthma.	2002 Apr	12000004
Dose-related effects of formoterol on airway responsiveness to adenosine 5'-monophosphate and histamine.	2002 Apr	11998988
A randomized, double-blind trial of the effect of glucocorticoid, antileukotriene and beta-agonist treatment on IL-10 serum levels in children with asthma.	2002 Feb	11929492
The role of inflammation and anti-inflammatory medication in asthma.	2002 Feb	11858564
Symbicort: controlling asthma in adults.	2002 Feb	11858561
The safety and efficacy of formoterol (Oxis) turbuhaler plus budesonide (Pulmicort) turbuhaler in mild to moderate asthma: a comparison with budesonide Turbuhaler alone and current non-corticosteroid therapy in Russia.	2002 Jan-Feb	11833550
Low-dose budesonide improved asthma control in mild asthma; adding formoterol improved control in corticosteroid-treated patients.	2002 Jul-Aug	12093218
Beta-adrenoceptor agonists and asthma--100 years of development.	2002 Jun 7	12065188
[Effect of triamcinolone acetonide, montelukast, nedocromil sodium and formoterol on eosinophil blood counts, ECP serum levels and clinical progression of asthma in children].	2002 Mar	12053590
Additive anti-inflammatory effect of formoterol and budesonide on human lung fibroblasts.	2002 Mar	11867828
New therapeutic drugs in the management of chronic obstructive pulmonary disease.	2002 Mar	11845005
Quantification of terbutaline in urine by enzyme-linked immunosorbent assay and capillary electrophoresis after oral and inhaled administrations.	2002 Mar 5	11888060
Comparison of second controller medications in addition to inhaled corticosteroid in patients with moderate asthma.	2002 May	12113382
Formoterol in patients with chronic obstructive pulmonary disease: a randomized, controlled, 3-month trial.	2002 May	12030736
Acute protection against exercise-induced bronchoconstriction by formoterol, salmeterol and terbutaline.	2002 May	12030726
Comparison of the effects of salmeterol and formoterol in patients with severe asthma.	2002 May	12006420

Patents

Sample Use Guides

In Vivo Use Guide

15 ug administered twice a day (morning and evening) by nebulization. A total daily dose greater than 30 ug (15 ug twice daily) is not recommended. BROVANA (arformoterol tartrate) should be administered by the inhaled route via a standard jet nebulizer connected to an air compressor

Route of Administration: Respiratory

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Thu Jul 06 22:53:45 UTC 2023` Edited by `admin` on `Thu Jul 06 22:53:45 UTC 2023`
Record UNII	F91H02EBWT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Arformoterol

Official Name

English

(-)-N-(2-HYDROXY-5-((1R)-1-HYDROXY-2-(((1R)-2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)FORMAMIDE HYDROGEN (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE

Systematic Name

English

ARFORMOTEROL [VANDF]

Common Name

English

(R,R)-FORMOTEROL

Common Name

English

N-[2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide

Systematic Name

English

(-)-Formoterol

Common Name

English

Formamide, N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-

Systematic Name

English

arformoterol [INN]

Common Name

English

FORMAMIDE, N-(2-HYDROXY-5-((1R)-1-HYDROXY-2-(((1R)-2-(4-METHOXYPHENYL)-1-METHYLETHYL)AMINO)ETHYL)PHENYL)-

Systematic Name

English

Arformoterol [WHO-DD]

Common Name

English

FORMOTEROL R,R-FORM [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000009922