Treprostinil (diethanolamine salt)

Treprostinil is a derivative of prostaglandin I2 (PGI2/prostacyclin, Cay-18220) and an agonist of PGI2, PGD2, and PGE2 receptors IP2, DP2, and EP2. It binds selectively to IP2, DP2, and EP2 over EP1, EP3, and EP4 receptors with Ki values of 32, 4.4, 3.6, 212, 2,505, and 826 nM, respectively, in radioligand binding assays. Treprostinil inhibits LPS-induced production of TNF-alpha, IL-1beta, IL-6, and granulocyte macrophage colony-stimulating factor (GM-CSF) in isolated human alveolar macrophages when used at a concentration of 200 ng/ml. It also prevents LPS-induced nuclear translocation and activation of NF-kappaB in the same cells. Treprostinil relaxes isolated small pulmonary arteries and veins precontracted with the thromboxane A2 (TP) receptor antagonist U-46619 (Cay-16450), an effect that can be blocked by IP receptor antagonists in the arteries and reduced by IP receptor antagonists in the veins. It reduces right ventricular systolic pressure, but not right ventricular hypertrophy, compared to hypoxic and sham control animals in a mouse model of chronic hypoxic pulmonary hypertension. Formulations containing treprostinil have been used in the treatment of primary pulmonary hypertension.Formal Name: 2-[[(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]-acetic acid compd. with 2,2'-iminobis[ethanol], diethanolamine salt. CAS Number: 830354-48-8. Synonyms: Treprostinil diolamine, UT 15C. Molecular Formula: C23H33O5 . C4H12NO2. Formula Weight: 495.7. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 5 mg/ml, Ethanol: 13 mg/ml, PBS (pH 7.2): 5 mg/ml. SMILES: O=C([O-])COC1=C(C[C@](C[C@@H](O)[C@@H]2CC[C@@H](O)CCCCC)([H])[C@]2([H])C3)C3=CC=C1.OCC[NH2+]CCO. InChi Code: InChI=1S/C23H34O5.C4H11NO2/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25,6-3-1-5-2-4-7/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27),5-7H,1-4H2/t16-,17-,18+,19-,21+,/m0./s1. InChi Key: RHWRWEUCEXUUAV-ZSESPEEFSA-N.