Camostat (HCID 2536)

概要

Camostat is a benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients. It has a role as an anticoronaviral agent, an antiviral agent, an antineoplastic agent, an antihypertensive agent, an antifibrinolytic drug, a serine protease inhibitor and an anti-inflammatory agent. It is a tertiary carboxamide, a member of guanidines, a carboxylic ester, a benzoate ester and a diester. It is functionally related to a 4-guanidinobenzoic acid. It is a conjugate base of a camostat(1+).

名称と識別子

優先名称: Camostat
IUPAC: [4-[2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate
現地名: カモスタット
英語名: Camostat
分子式: C20H22N4O5
分子量: 398.41

名称と別名

Camostat59721-28-7camostateCamostatum0FD207WKDUDTXSID6044010CHEBI:135632p-Guanidinobenzoic acid, ester with (p-hydroxyphenyl)acetic acid, ester with N,N-dimethylglycolamide4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoate(4-(2-(2-dimethylamino-2-oxoethoxy)-2-oxoethyl)phenyl) 4-(diaminomethylideneamino)benzoate[4-[2-(2-dimethylamino-2-oxoethoxy)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate4-(2-((dimethylcarbamoyl)methoxy)-2-oxoethyl)phenyl 4-carbamimidamidobenzoate

名称をさらに表示

4-[[4-[(アミノイミノメチル)アミノ]ベンゾイル]オキシ]ベンゼン酢酸2-(ジメチルアミノ)-2-オキソエチル4-グアニジノ安息香酸4-[[[(ジメチルカルバモイル)メトキシ]カルボニル]メチル]フェニル4-グアニジノ安息香酸-4-(ジメチルカルバモイルメトキシカルボニルメチル)フェニル4-[(4-グアニジノベンゾイル)オキシ]ベンゼン酢酸2-(ジメチルアミノ)-2-オキソエチルカモスタットp-(p-グアニジノベンゾイルオキシ)フェニル酢酸=ジメチルカルバモイルメチル[4-[4-(グアニジノ)ベンゾイルオキシ]フェニル]酢酸(ジメチルアミノカルボニルメチル)4-{2-[(ジメチルカルバモイル)メトキシ]-2-オキソエチル}フェニル 4-カルバムイミドアミドベンゾアートCanostatFOY 305Ccris 7219FOY-305：FoipanUnii-0fd207wkduCamostat free baseCamostat formate saltCamostatum [inn-latin]

RefChem:573682DTXCID4024010Camostat [INN]camostat-mesilate[4-[2-[2-(dimethylamino)-2-oxoethoxy]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoateUS9199927, camostat4-(2-(2-(Dimethylamino)-2-oxoethoxy)-2-oxoethyl)phenyl 4-guanidinobenzoateDimethylcarbamoylmethyl 4-(4-guqnidinobenzoyloxy)phenylacetat

データベース識別子

CAS: 59721-28-7
PubChem CID: 2536
DTXSID: DTXSID6044010
ChEMBL: CHEMBL590799
ChEBI: CHEBI:135632
UNII: 0FD207WKDU
Nikkaji: J23.287D

物性

構造計算による物性

XLogP: 1.1
極性表面積: 137 Å²
水素結合供与体数: 2
水素結合受容体数: 6
回転可能結合数: 9
重原子数: 29
形式電荷: 0
複雑度: 602

実験および物理化学的性質

Melting Point194-198

物理化学的性質

沸点: 590.5 · 590.5±60.0 °C(Predicted)
比重(密度): 1.28 · 1.28±0.1 g/cm3(Predicted)
酸解離定数(Pka): 10.17 · 10.17±0.10(Predicted)

化学と産業

薬理情報

ATC Code · 2 件

B - Blood and blood forming organs

QB - Blood and blood forming organs

Protein BindingCamostat mesylate is 25.8-28.2% protein bound to human serum proteins _in vitro_.

Pharmacodynamics · 1 件

Camostat mesylate is a protease inhibitor used to treat chronic pancreatitis. The duration of action is not long, as it is typically given in 3 divided doses daily. Patients should be counselled regarding the risk of anaphylaxis, thrombocytopenia, hepatic dysfunction, and hyperkalemia.

Mechanism of Action · 1 件

In rats, oral camostat mesylate may increase pancreatic secretions and hypertrophy by increasing cholecystokinin release. Administration in rats has also lead to lower levels of IL-1beta, IL-6, TNF-alpha, TGF-beta, and PSC. Similar activity is seem after administration in humans, leading to reduced pain and inflammation as well as improve the function of the pancrease in chronic pancreatitis. In the case of SARS-CoV-2, camostat mesylate inhibits the action of the serine protease TMPRSS2, preventing the priming of the viral spike protein for attachment to ACE2, and entry into the cell.

Biological Half-LifeThe half life of camostat mesylate is 3.8-4.7h.

Metabolism/MetabolitesCamostat mesylate is hydrolyzed by carboxyesterate to the active 4-(4-guanidinobenzoyloxy) phenylacetate. The active metabolite is further hydrolyzed by arylesterase to 4-guanidinobenzoic acid.

上流・下流製品情報

上流原料

サプライヤー34 社

湖北万得化工有限公司15377098680 15377098680 · [email protected]

普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]

Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]

LGM Pharma1-(800)-881-8210 · [email protected]

武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]

カモスタット

基本情報

概要