Grundinformationen
- Standard-SMILES
O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c(OCC2CC2)c1- InChIKey
MNDBXUUTURYVHR-UHFFFAOYSA-N- Summenformel
- C17H14Cl2F2N2O3
- Durchschnittliche Molmasse
- 403,2 g/mol
- Monoisotopische Masse
- 402,03495411
Überblick
Roflumilast is a benzamide obtained by formal condensation of the carboxy group of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid with the amino group of 3,5-dichloropyridin-4-amine. Used for treatment of bronchial asthma and chronic obstructive pulmonary disease. It has a role as an anti-asthmatic drug and a phosphodiesterase IV inhibitor. It is a member of benzamides, an aromatic ether, an organofluorine compound, a chloropyridine and a member of cyclopropanes.
Namen und Bezeichner
- Bevorzugter Name
- Roflumilast
- IUPAC
- 3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide
- Englischer Name
- Roflumilast
- Summenformel
- C17H14Cl2F2N2O3
- Molmasse
- 403.21
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
162401-32-3- PubChem CID
- 449193
- DTXSID
DTXSID8044123- ChEMBL
CHEMBL193240- ChEBI
CHEBI:47657- UNII
- 0P6C6ZOP5U
- EC Number
- 685-382-2
- Nikkaji
- J1.365.537E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,6
- Polarare Oberfläche (TPSA)
- 60,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 475
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Respiratory system -> Nasal preparations
Human Drugs
Breast Feeding; Lactation; Milk, Human; Phosphodiesterase 4 Inhibitors
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 158 °C · 158°C
- Siedepunkt
- 430.6 · 430.6±45.0 °C(Predicted)
- Dichte
- 1.471 · 1.471±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
- pka
- 9.89 · 9.89±0.70(Predicted)
- Aggregatzustand
- powder
- Farbe
- white to beige
- Merck
- 14 · 14,8249
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
- InChI
- InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)
- InChIKey
- MNDBXUUTURYVHR-UHFFFAOYSA-N
- SMILES
- C(NC1C(Cl)=CN=CC=1Cl)(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1
- CAS Datenbank
- 162401 · 162401-32-3(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H315 (91.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Hepatotoxicity
In preregistration studies, roflumilast was not associated with serum enzyme elevations or with episodes of clinically apparent liver injury. Since approval of roflumilast, there have been no published reports of hepatotoxicity, and the product label does not mention liver injury as an adverse event.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Roflumilast
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2933.39.4100
- RTECS-Nr.
- CV3325600
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
ATC Code
R03DX07
R - Respiratory system
D - Dermatologicals
QD - Dermatologicals
QR - Respiratory system
Pharmacodynamics
Roflumilast and its active metabolite, roflumilast N-oxide, increase cyclic adenosine-3′, 5′-monophosphate (cAMP) in affected cells by inhibiting PDE4. They are highly selective for PDE4 and are effectively inactive against PDEs 1, 2, 3, 5, and 7.
Mechanism of Action
Roflumilast and its active metabolite (roflumilast N-oxide) are inhibitors of PDE4. Roflumilast and roflumilast N-oxide inhibition of PDE4 (a major cyclic 3′,5′-adenosine monophosphate (cyclic AMP) metabolizing enzyme) activity leads to accumulation of intracellular cyclic AMP. The specific mechanism(s) by which roflumilast exerts its therapeutic action is not well defined.
Metabolism/Metabolites
Roflumilast is metabolized to roflumilast N-oxide, the active metabolite of roflumilast in humans, by CYP3A4 and CYP1A2. The N-oxide metabolite is less potent than its parent drug in regards to PDE4 inhibition, but its plasma AUC is approximately 10-fold greater.
FDA Pharmacological Classification
0P6C6ZOP5U
ROFLUMILAST
Established Pharmacologic Class [EPC] - Phosphodiesterase 4 Inhibitor
Mechanisms of Action [MoA] - Phosphodiesterase 4 Inhibitors
Roflumilast is a Phosphodiesterase 4 Inhibitor. The mechanism of action of roflumilast is as a Phosphodiesterase 4 Inhibitor.
ROFLUMILAST
Absorption, Distribution and Excretion
After a 500mcg dose, the bioavailability of roflumilast is about 80%. In the fasted state, maximum plasma concentrations are reached in 0.5 to 2 hours, while in the fed state, Cmax is reduced by 40%, Tmax is increased by one hour, and total absorption is unchanged. Applied topically, the mean systemic exposure for roflumilast and its N-oxide metabolite in adults was 72.7 ± 53.1 and 628 ± 648 h∙ng/mL, respectively. The mean systemic exposure for roflumilast and its N-oxide metabolite in adolescents was 25.1 ± 24.0 and 140 ± 179 h∙ng/mL, respectively.
Roflumilast is excreted 70% in the urine as roflumilast N-oxide.
Following a single oral dose of 500 mcg, the volume of distribution of roflumilast is approximately 2.9 L/kg.
Plasma clearance of roflumilast following short-term intravenous infusion is approximately 9.6 L/h.
Anwendungen
BeschreibungRoflumilast is a selective, orally active PDE4 inhibitor thatwas approved in Germany in July 2010 as an add-on to bronchodilator treatment for maintenance therapy of severe chronic obstructive pulmonary disorder (COPD) associated with chronic bronchitis in adult patients with a history of frequent exacerbations . Roflumilast and its primary metabolite roflumilast N-oxide are potent and competitive inhibitors of PDE4 and are equipotent against PDE4A, B, andD but inactive against PDE4C and the other ten members of the PDE family (PDEs 1–3, 5–11). Despite its inhibition of PDE4D (IC50=0.80 nM, N-oxide IC50=2.0 nM), roflumilast shows the lowest incidence of nausea (3–5%) among the PDE4 inhibitors investigated in clinical trials.Anti-inflammatory effects of roflumilast have been demonstrated in preclinical cellular and animal models. Roflumilast is synthesized in four steps from 3-(cyclopropylmethoxy)-4-hydroxybenzaldehyde. The difluoromethyl ether is introduced by alkylation of the free phenolic group with chlorodifluoromethane and base. The aldehyde moiety is oxidized to the benzoic acid, which is then converted to an acid chloride and coupled with 3,5-dichloro-4-aminopyridine. Roflumilast is rapidly absorbed and metabolized to its active metabolite, roflumilast N-oxide. Metabolism is mediated by CYP3A4 and CYP1A2.
VerwendenRoflumilast (Daxas) is a selective inhibitor of PDE4 with IC50 of 0.2-4.3 nM.
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A benzamide obtained by formal condensation of the carboxy group of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid with the amino group of 3,5-dichloropyridin-4-amine. Used for treatment of bronchial asthma and chronic obstructive pulmonary disease
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