| 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]. | [Synthesis]
1. (1R,5S,6S)-[6-(tert-butoxycarbonylaminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (9.82 g, 23.7 mmol) was added to 100 mL of 4N hydrochloric acid-ethyl acetate solution.
2. The reaction mixture was stirred at room temperature for 1 hour.
3. After completion of the reaction, the solvent was removed by distillation under reduced pressure.
4. The residue was dissolved in dichloromethane. 5.
5. Triethylamine was added dropwise to the above solution and the resulting white powder was subsequently collected by filtration.
6. The collected powder was washed with dichloromethane and then dried to give 4.02 g of white powder.
7. Finally, the powder was washed with ethanol and ethyl acetate to afford the target compound 2-((1R,5S,6S)-6-(aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl)acetic acid as a white powder (2.14 g, 43% yield). | [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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