Daltroban

Names

[ Name ]:
Daltroban

[Synonym ]:
4-[2-(4-Chlorobenzene-sulfonamido)ethyl]benzeneacetic acid
[4-[2-(4-chlorobenzenesulfonamido)ethyl]phenyl]acetic acid
2-[4-[2-(4-chlorophenylsulphonylamino)-ethyl]-phenyl]-acetic acid
4-[2-[(4-CHLOROPHENYLSULFONYL)AMINO]ETHYL]BENZENEACETIC ACID
DatelliptiumChloride
2-[4-[2-(4-chlorophenyl)sulfonylaminoethyl]phenyl]acetic acid
4-[2-(4-chlorobenzenesulphonamido)-ethyl]-phenylacetic acid
4-((((4-chlorophenyl)sulfonyl)amino)ethyl)benzene acetic acid
MFCD00868295

Biological Activity

[Description]:

Daltroban (BM-13505) is a selective and specific thromboxane A2 (TXA2) receptor antagonist. Daltroban increase intracellular calcium in vascular smooth muscle cells. Daltroban shows protective effect in reperfusion injury[1][2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

[Target]

TXA2

[In Vivo]

Daltroban (BM-13505) (1 mg/kg; i.v.; per hour) exerts protective effect in reperfusion injury following acute myocardial ischemia in cats[2]. In comparison with vehicle (physiological saline)-treated cats, Daltroban (20 mg/kg per hour i.v.) reduces the ischaemia-induced rise in the ST segment and prevented the development of a Q-wave in the ECG during reperfusion. Daltroban protects the myocardium from ischaemic injury and that this effect involves prevention of ischaemia-induced leukocytosis[3]. Animal Model: Adult male cats (2.8 to 4.6 kg; anesthetized cat model)[2] Dosage: 1 mg/kg Administration: i.v.; 30 minutes before reperfusion at a rate of 1 mg/kg followed by 1 mg/kg/hour Result: Significantly reduced the area of ischemic tissue as a percent of total left ventricular mass and total area at risk, without altering basic hemodynamics and thereby not influencing myocardial oxygen demand.

[References]

[1]. Miki I, et al. Differences in activities of thromboxane A2 receptor antagonists in smooth muscle cells. Eur J Pharmacol. 1992 Oct 1;227(2):199-204.

[2]. Thiemermann C, et al. The thromboxane receptor antagonist, daltroban, protects the myocardium from ischaemic injury resulting in suppression of leukocytosis. Eur J Pharmacol. 1988 Oct 11;155(1-2):57-67.

[3]. Bhat AM, et al. Protective effect of the specific thromboxane receptor antagonist, BM-13505, in reperfusion injury following acute myocardial ischemia in cats. Am Heart J. 1989 Apr;117(4):799-803.

Chemical & Physical Properties

[ Density]:
1.378g/cm3

[ Boiling Point ]:
555.3ºC at 760 mmHg

[ Melting Point ]:
132.5-137.4 °C(lit.)

[ Molecular Formula ]:
C₁₆H₁₆ClNO₄S

[ Molecular Weight ]:
353.82100

[ Flash Point ]:
289.6ºC

[ Exact Mass ]:
353.04900

[ PSA ]:
91.85000

[ LogP ]:
3.95980

[ Appearance of Characters ]:
white

[ Vapour Pressure ]:
3.63E-13mmHg at 25°C

[ Index of Refraction ]:
1.609

[ Water Solubility ]:
DMSO: 22 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Cyclooxygenase-2 inhibition and thromboxane A(2) receptor antagonism attenuate hypoxic pulmonary vasoconstriction in a porcine model.

Acta Physiol. (Oxf.) 205(4) , 507-19, (2012)

Hypoxic pulmonary vasoconstriction (HPV) causes pulmonary hypertension that may lead to right heart failure. We hypothesized that the COX-2 inhibitor nimesulide and the thromboxane A(2) receptor antag...

Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets.

Thromb. Haemost. 87(1) , 114-21, (2002)

Arachidonic acid (AA) is a potent inducer of platelet aggregation in vitro; this activity is due to its conversion to biologically active metabolites, prostaglandin (PG) endoperoxides and thromboxane ...

Increase by anaphylatoxin C5a of glucose output in perfused rat liver via prostanoids derived from nonparenchymal cells: direct action of prostaglandins and indirect action of thromboxane A(2) on hepatocytes.

Hepatology 30 , 454-461, (1999)

In the perfused rat liver the anaphylatoxin C5a enhanced glucose output, reduced flow, and elevated prostanoid overflow. Because hepatocytes (HCs) do not express C5a receptors, the metabolic C5a actio...