Roflumilast

HCID 449193CAS 162401-32-3

기본 정보

표준 SMILES
O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c(OCC2CC2)c1
InChIKey
MNDBXUUTURYVHR-UHFFFAOYSA-N
분자식
C17H14Cl2F2N2O3
평균 분자량
403.2 g/mol
단동위원소 질량
402.03495411

개요

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.

이름 및 식별자

우선 이름
Roflumilast
IUPAC
3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide
영어명
Roflumilast
분자식
C17H14Cl2F2N2O3
분자량
403.21

이름 및 동의어

Roflumilast162401-32-3DAXAS3-(CYCLOPROPYLMETHOXY)-N-(3,5-DICHLOROPYRIDIN-4-YL)-4-(DIFLUOROMETHOXY)BENZAMIDEDalirespBY217BYK20869ZORYVEBenzamide, 3-(cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)-BY-2170P6C6ZOP5UBYK-20869
이름 더 보기
BY 217RosterCS-1960RoflostBYK 20869APTA 2217B 9302-107RofluMilas
roflumilastumB9302-107ARQ-154 (Roflumilast foam)DTXSID8044123ARQ-151CHEBI:476573-cyclopropylmethoxy-4-difluoromethoxy-N-(3,5-di-chloropyrid-4-yl)benzamide3-Cyclopropylmethoxy-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
4.6
극성 표면적
60.5 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
6
회전 가능 결합 수
7
무거운 원자 수
26

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Respiratory system -> Nasal preparations

SolubilitySparingly soluble
Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Phosphodiesterase 4 Inhibitors

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Dissociation Constants8.74

물리화학적 성질

녹는점
158 °C · 158°C
끓는 점
430.6 · 430.6±45.0 °C(Predicted)
밀도
1.471 · 1.471±0.06 g/cm3(Predicted)
저장 조건
-20 °C · -20°C
용해도
20 mg/mL, · DMSO: 용해성20mg/mL, 투명
산도 계수 (pKa)
9.89 · 9.89±0.70(Predicted)

화학적 성질

Crystallin Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesSkin Irrit. 2 (91.1%)

독성 정보

Hepatotoxicity · 1건

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 · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Roflumilast

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
CV3325600
HS 번호
2933.39.4100
risk_code
36/37/38
hazard_code
Xi
safety_code
26

화학 및 산업

약리 정보

ATC Code · 5건

R03DX07

R - Respiratory system

D - Dermatologicals

QD - Dermatologicals

QR - Respiratory system

Protein BindingPlasma protein binding of roflumilast and its N-oxide metabolite is approximately 99% and 97%, respectively.
Pharmacodynamics · 1건

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 · 1건

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.

Biological Half-LifeFollowing oral administration, the plasma half-lives of roflumilast and roflumilast N-oxide are 17 hours and 30 hours, respectively.
Metabolism/Metabolites · 1건

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.

응용 분야 · 2건

개요Roflumilast 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.

용도Roflumilast (Daxas) is a selective inhibitor of PDE4 with IC50 of 0.2-4.3 nM.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
安徽倍瑞药业科技有限公司0551-68665055 18130089676
LGM Pharma1-(800)-881-8210 · [email protected]
南部县诚信科技有限公司0838-5675166 15883665058 · [email protected]
추가 설명 · 1건

정의ChEBI: 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

관련 반응

7건

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