112665-43-7 Usage
Description
Seratrodast, a novel benzoquinone derivative, is the first thromboxane A2
(TxA2) receptor antagonist to reach the market. It is orally active for the treatment of
bronchospastic disorders such as asthma. TxA2, a metabolite of the arachidonate
cascade, is involved in several cardiovascular and respiratory diseases through its
potent biological effects on platelet aggregation and constriction of vascular and
respiratory smooth muscles. Seratrodast potently inhibits platelet aggregation and
bronchoconstriction induced by a TxA2 mimic and by a variety of spasmogenic
prostanoids including PGF2α, PGD2 and 9α,11β-PGF2. Seratrodast shows excellent
efficacy in asthma and has been reported to be potentially useful in hyper-responsive
disorder. The R-(+)- seratrodast was reported to be the active isomer.
Chemical Properties
Pale Orange Solid
Originator
Takeda (Japan)
Uses
Different sources of media describe the Uses of 112665-43-7 differently. You can refer to the following data:
1. Thromboxane A2-receptor antagonist. Antiasthmatic.
2. Thromboxane A2-receptor antagonist. Antiasthmatic
3. antibacterial
Brand name
Bronica
Biological Activity
Thromboxane A 2 (TP) receptor antagonist. Antiasthmatic agent; inhibits platelet aggregation and bronchoconstriction induced by a TXA 2 mimetic in guinea pigs.
in vitro
seratrodast was found to inhibit the aggregation of guinea pig platelets induced by a prostaglandin endoperoxide analogue, u-44069 and the specific binding of another analogue, [3h]u-46619 to washed guinea pig platelets. seratrodast could competitively inhibit the contraction of rabbit aorta and pig coronary arteries induced by u-44069. seratrodast also inhibited the contraction of rabbit aorta induced by pgf2 alpha and the contraction of pig coronary arteries. however, seratrodast had no effect on the antiaggregatory effect of guinea pig platelets [1].
in vivo
in experiments with guinea pigs, oral seratrodast at 0.1-1 mg/kg could dose-dependently inhibit the platelet aggregation induced by u-44069; the inhibition at 1 mg/kg was 100% at 1 hr and was 89% even at 24 hr after seratrodast administration [1].
IC 50
7.4 nm for guinea pig platelets
references
[1] imura, y. ,terashita, z.,shibouta, y., et al. antagonistic action of aa-2414 on thromboxane a2/prostaglandin endoperoxide receptor in platelets and blood vessels. japanese journal of pharmacology 52(1), 35-53 (1990).
Check Digit Verification of cas no
The CAS Registry Mumber 112665-43-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,6,6 and 5 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 112665-43:
(8*1)+(7*1)+(6*2)+(5*6)+(4*6)+(3*5)+(2*4)+(1*3)=107
107 % 10 = 7
So 112665-43-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H9N3O2/c1-9-5(7)4(3-8-9)6(10)11-2/h3H,7H2,1-2H3
112665-43-7Relevant articles and documents
Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids
Xu, Xiao-Long,Li, Zhi
, p. 5078 - 5081 (2019/09/03)
Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.
Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
Kuninobu, Yoichiro,Kawata, Atsushi,Noborio, Taihei,Yamamoto, Syun-Ichi,Matsuki, Takashi,Takata, Kazumi,Takai, Kazuhiko
scheme or table, p. 941 - 945 (2010/07/07)
Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.
Process for preparing diphenylmethane compounds
-
, (2008/06/13)
A diphenylmethane compound (III) can be produced in a good yield by allowing a phenol compound (I) to react with a stilbene compound (II) in the presence of methanesulfonic acid STR1
