| Identification | Back Directory | [Name]
2-((1R,5S,6S)-6-(aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl)acetic acid | [CAS]
1138245-13-2 | [Synonyms]
DS5565
A200-0700
Miluobalin
Asapiprant
Mirogabalin
DS5565;A200-0700
MIROGABALIN; DS-5565
DS 5565;DS-5565;DS5565
[(1R,5S,6S)-6-(Aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid
2-((1R,5S,6S)-6-(aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl)acetic acid
Bicyclo[3.2.0]hept-3-ene-6-acetic acid, 6-(aminomethyl)-3-ethyl-, (1R,5S,6S)-
2-[(1R,5S,6S)-6-(aminomethyl)-3-ethyl-6-bicyclo[3.2.0]hept-3-enyl]acetic acid | [Molecular Formula]
C12H19NO2 | [MDL Number]
MFCD28411425 | [MOL File]
1138245-13-2.mol | [Molecular Weight]
209.28 |
| Chemical Properties | Back Directory | [Boiling point ]
357.5±15.0 °C(Predicted) | [density ]
1.104±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF:0.5(Max Conc. mg/mL);2.39(Max Conc. mM)
Ethanol:1.25(Max Conc. mg/mL);5.97(Max Conc. mM)
PBS (pH 7.2):0.5(Max Conc. mg/mL);2.39(Max Conc. mM)
Water:5.36(Max Conc. mg/mL);25.61(Max Conc. mM) | [form ]
A crystalline solid | [pka]
4.65±0.10(Predicted) | [color ]
Light yellow to light brown | [InChI]
InChI=1S/C12H19NO2/c1-2-8-3-9-5-12(7-13,6-11(14)15)10(9)4-8/h4,9-10H,2-3,5-7,13H2,1H3,(H,14,15)/t9-,10-,12-/m1/s1 | [InChIKey]
FTBQORVNHOIASH-CKYFFXLPSA-N | [SMILES]
[C@]12([H])[C@]([H])([C@@](CN)(CC(O)=O)C1)C=C(CC)C2 |
| Hazard Information | Back Directory | [Description]
Mirogabalin is a calcium channel blocker with analgesic effects.1 It binds to the α2δ-1 and α2δ-2 subunits of voltage-dependent Ca2+ channels. Mirogabalin has potent and sustained analgesic effects (ED50 = 2.5 mg/kg) in rats with diabetes induced by streptozotocin (STZ; Item No. 13104). Mirogabalin does not inhibit activities associated with CNS adverse effects of analgesics, such as rotarod performance (ID50 = 9.4 mg/kg) or locomotor activity (ID50 = 43.9 mg/kg), at its effective dose. Formulations containing mirogabalin are in clinical trials for diabetic peripheral neuropathic pain.2 | [Uses]
Mirogabalin is a two alpha2delta ligand which is investigated for the treatment of peripheral neuropathic pain, postherpetic neuralgia and fibromyalgia, showing promising results in patients with diabetic peripheral neuropathy. | [Brand name]
Mirogabalin (brand name Tarlige; developmental code name DS-5565) is a gabapentinoid medication developed by Daiichi Sankyo. | [Side effects]
The most typical clinical adverse reactions of mirogabalin were dizziness (7.6%) and somnolence (5.1%). However, the occurrence rate was lower than with pregabalin, whose adverse effects were reported to include somnolence, balance disorder, fatigue, and peripheral edema, with an occurrence rate of 8.0%, 4.0%, 4.0%, and 4.0%, respectively[1]. | [storage]
Store at -20°C | [Mode of action]
Mirogabalin is an analog of the neurotransmitter, gamma-aminobutyric acid (GABA). It is a potent and specific ligand of the α2δ subunit of voltage-dependent Ca2+channels, which reduces calcium (Ca2+) influx and neurotransmission in dorsal root ganglia (DRGs), inhibiting neurotransmitter release in presynaptic neuron endings. | [References]
[1] Hui Tang. “The Clinical Application and Progress of Mirogabalin on Neuropathic Pain as a Novel Selective Gabapentinoids.” Mediators of Inflammation 2023 (2023): 4893436.
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