Atosiban acetate

- Overview
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    Background
    
    Atosibana is a mixed antagonist of oxytocin and vasopressin receptors [1]. Atosibana is a peptide and is a dual antagonist of oxytocin receptor (OTR) and vasopressin receptors (V1aR, V1bR, V2R). When acted as an OTR antagonist, atosibana showed pKi values of 7.9 and 7.2 for human OTR and rat OTR, respectively. Treatment of atosibana significantly inhibited cell growth in MDCK and HEK293 cells stably transfected with the human OTR with IC50 values of 15.4 nM and 20.8 nM, respectively. When acted as a vasopressin receptor antagonist, atosibana exerted pKi values of 9.8, 7.4 and 6.5 for hV1aR, hV1bR and hV2R, respectively. Atosibana has been shown to have efficacy in inhibiting uterine contractions and delaying preterm delivery. However, atosibana can not be used for long-term maintenance treatment since it is not orally bioavailable [1].
    
    [1] Borthwick A D. Oral oxytocin antagonists. Journal of medicinal chemistry, 2010, 53(18): 6525-6538.
    [2] Reversi A, Rimoldi V, Marrocco T, et al. The oxytocin receptor antagonist atosiban inhibits cell growth via a “biased agonist” mechanism. Journal of Biological Chemistry, 2005, 280(16): 16311-16318.
- Properties
  - Categories
    
    mixed antagonist of oxytocin and vasopressin receptors
    
    Alternative Name
    
    RW22164 acetate; RWJ22164 acetate; (2S)-N-((S)-5-amino-1-((2-amino-2-oxoethyl)amino)-1-oxopentan-2-yl)-1-((4R,7S,13S,16R)-7-(2-amino-2-oxoethyl)-13-((S)-sec-butyl)-16-(4-ethoxybenzyl)-10-((R)-1-hydroxyethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrr
    
    CAS Number
    
    914453-95-5
    
    Molecular Formula
    
    C45H71N11O14S2
    
    Molecular Weight
    
    1054.24
    
    Appearance
    
    A crystalline solid
    
    Purity
    
    98.00%
    
    Solubility
    
    ≥30 mg/mL in EtOH; ≥32.7 mg/mL in H2O; ≥59.6 mg/mL in DMSO
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    O=C(N1CCC[[email protected]]1C(N[[email protected]](C(NCC(N)=O)=O)CCCN)=O)[[email protected]@H](NC([[email protected]](CC(N)=O)NC(C([[email protected]@H](C)O)NC([[email protected]]([H])([[email protected]](CC)C)N2)=O)=O)=O)CSSCCC(N[[email protected]](CC3=CC=C(C=C3)OCC)C2=O)=O.OC(C)=O
    
    * For Research Use Only