Mirogabalin besylate

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MedKoo CAT#: 319552

CAS#: 1138245-21-2 (besylate)

Description: Mirogabalin, also known as DS-5565, is an α2δ-1 ligand being developed for pain associated with diabetic peripheral neuropathy, fibromyalgia, and postherpetic neuralgia. Mirogabalin was estimated to be 17-fold more potent than pregabalin. Mirogabalin is being developed by Daiichi Sankyo and related to drugs such as gabapentin and pregabalin. Similarly to these drugs, mirogabalin binds to the α2δ calcium channels (1 and 2), but with significantly higher potency than pregabalin. It has shown promising results in Phase II clinical trials for the treatment of diabetic peripheral neuropathic pain.

Chemical Structure

Mirogabalin besylate
CAS# 1138245-21-2 (besylate)

Theoretical Analysis

MedKoo Cat#: 319552
Name: Mirogabalin besylate
CAS#: 1138245-21-2 (besylate)
Chemical Formula: C18H25NO5S
Exact Mass: 367.1453
Molecular Weight: 367.46
Elemental Analysis: C, 58.84; H, 6.86; N, 3.81; O, 21.77; S, 8.72

Price and Availability

Size Price Availability Quantity
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 3450.0 2 Weeks
2.0g USD 5650.0 2 Weeks
5.0g USD 11650.0 2 Weeks
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Related CAS #: 1138245-21-2 (besylate)   1138245-13-2 (free base)    

Synonym: DS-5565; DS 5565; DS5565; A-2000700; Mirogabalin; Mirogabalin besylate.

IUPAC/Chemical Name: 2-((1R,5S,6S)-6-(aminomethyl)-3-ethylbicyclo[3.2.0]hept-3-en-6-yl)acetic acid compound with benzenesulfonic acid (1:1)


InChi Code: InChI=1S/C12H19NO2.C6H6O3S/c1-2-8-3-9-5-12(7-13,6-11(14)15)10(9)4-8;7-10(8,9)6-4-2-1-3-5-6/h4,9-10H,2-3,5-7,13H2,1H3,(H,14,15);1-5H,(H,7,8,9)/t9-,10-,12-;/m1./s1

SMILES Code: O=C(O)C[C@]1(CN)[C@]2([H])C=C(CC)C[C@]2([H])C1.O=S(C3=CC=CC=C3)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 367.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Calandre EP, Rico-Villademoros F, Slim M. Alpha(2)delta ligands, gabapentin, pregabalin and mirogabalin: a review of their clinical pharmacology and therapeutic use. Expert Rev Neurother. 2016 Nov;16(11):1263-1277. Epub 2016 Jul 7. Review. PubMed PMID: 27345098.

2: Yin OQ, Merante D, Truitt K, Miller R. Population pharmacokinetic modeling and simulation for assessing renal impairment effect on the pharmacokinetics of mirogabalin. J Clin Pharmacol. 2016 Feb;56(2):203-12. doi: 10.1002/jcph.584. Epub 2015 Sep 2. PubMed PMID: 26138993.

3: Vinik A, Rosenstock J, Sharma U, Feins K, Hsu C, Merante D; DS5565-A-U201 US Phase II Study Investigators. Efficacy and safety of mirogabalin (DS-5565) for the treatment of diabetic peripheral neuropathic pain: a randomized, double-blind, placebo- and active comparator-controlled, adaptive proof-of-concept phase 2 study. Diabetes Care. 2014 Dec;37(12):3253-61. doi: 10.2337/dc14-1044. Epub 2014 Sep 17. PubMed PMID: 25231896.

4: Hutmacher MM, Frame B, Miller R, Truitt K, Merante D. Exposure-response modeling of average daily pain score, and dizziness and somnolence, for mirogabalin (DS-5565) in patients with diabetic peripheral neuropathic pain. J Clin Pharmacol. 2016 Jan;56(1):67-77. doi: 10.1002/jcph.567. Epub 2015 Aug 20. PubMed PMID: 26073181.

5: Alcántara Montero A, Ibor Vidal PJ. [Mirogabalin: The next pregabalin?]. Semergen. 2016 Oct 20. pii: S1138-3593(16)30158-7. doi: 10.1016/j.semerg.2016.07.014. [Epub ahead of print] Spanish. PubMed PMID: 27773622.

6: Brown K, Ohwada S, Warren V, Zahir H, Dishy V. (405) A single ascending-dose study of mirogabalin in healthy subjects: safety, tolerability, pharmacokinetic, and pharmacodynamic results. J Pain. 2016 Apr;17(4S):S76. doi: 10.1016/j.jpain.2016.01.382. Epub 2016 Mar 24. PubMed PMID: 28162650.

7: Merante D, Rosenstock J, Sharma U, Feins K, Hsu C, Vinik A; DS-5565-A-U201?US Phase 2 Study Investigators. Efficacy of Mirogabalin (DS-5565) on Patient-Reported Pain and Sleep Interference in Patients with Diabetic Neuropathic Pain: Secondary Outcomes of a Phase II Proof-of-Concept Study. Pain Med. 2017 Mar 23. doi: 10.1093/pm/pnw342. [Epub ahead of print] PubMed PMID: 28371941.

8: Jansen M, Merante D, Currie A, Velinova M, Brown K, Zahir H. (403) Co-administration of mirogabalin and zolpidem in healthy subjects: results from a randomized, double-blind, drug-drug interaction study. J Pain. 2016 Apr;17(4S):S75. doi: 10.1016/j.jpain.2016.01.380. Epub 2016 Mar 24. PubMed PMID: 28162647.

Additional Information

Related CAS#
CAS#1138245-21-2 ( Mirogabalin besylate);
CAS#1138245-13-2 ( Mirogabalin free base).