Sofpironium bromide
Clinical data
Trade namesEcclock
Other namesBBI 4000
Routes of
administration
Topical gel
Legal status
Legal status
  • Rx-only (Japan)
Identifiers
  • [(3R)-1-(2-Ethoxy-2-oxoethyl)-1-methylpyrrolidin-1-ium-3-yl] (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate bromide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC22H32BrNO5
Molar mass470.404 g·mol−1
3D model (JSmol)
  • CCOC(=O)C[N+]1(CC[C@H](C1)OC(=O)[C@@](C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
  • InChI=1S/C22H32NO5.BrH/c1-3-27-20(24)16-23(2)14-13-19(15-23)28-21(25)22(26,18-11-7-8-12-18)17-9-5-4-6-10-17;/h4-6,9-10,18-19,26H,3,7-8,11-16H2,1-2H3;1H/q+1;/p-1/t19-,22+,23?;/m1./s1
  • Key:FIAFMTCUJCWADZ-JOFREBOKSA-M

Sofpironium bromide (trade name Ecclock; development code BBI-4000) is a drug used to treat hyperhidrosis (excessive sweating). It was approved in Japan in 2020 as a 5% gel for the treament of primary axillary hyperhidrosis (PAH).[1][2][3]

Mechanism of action

Sofpironium bromide is an anticholinergic agent that reduces sweating by inhibiting M3 muscarinic receptors in eccrine glands.[3] It is a retrometabolically-designed drug (or "soft drug") based on glycopyrronium bromide,[4][5] meaning it has been designed to exert the desired effects at the site of administration, after which it is quickly converted into an inactive non-toxic metabolite upon entering systemic circulation avoiding the typical anticholinergic side-effects caused by off-site action.

History

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Sofpironium bromide was discovered at Bodor Laboratories by Nicholas Bodor and licensed to Botanix SB, a subsidiary of Botanix Pharmaceuticals. This license was previously owned by Fresh Tracks Therapeutics, which was then sold to Botanix in 2022, exclusively in the field of hyperhidrosis, with all other uses having been retained by Bodor Laboratories. Additional sublicenses were executed with Kaken Pharmaceutical and Dong Wha Pharmaceutical.

References

  1. ^ Paik J (December 2020). "Sofpironium Bromide: First Approval". Drugs. 80 (18): 1981–1986. doi:10.1007/s40265-020-01438-1. PMID 33236266. S2CID 227155835.
  2. ^ Gregoriou S, Campanati A, Rigopoulos D, Maria Offidani A, Stratigos A, Kontochristoulos G (May 2021). "Investigational topical anticholinergics in clinical development for the treatment of hyperhidrosis". Expert Opinion on Investigational Drugs. 30 (5): 479–482. doi:10.1080/13543784.2021.1900114. PMID 33691553. S2CID 232187568.
  3. ^ a b Yokozeki H, Fujimoto T, Abe Y, Igarashi M, Ishikoh A, Omi T, et al. (March 2021). "A phase 3, multicenter, randomized, double-blind, vehicle-controlled, parallel-group study of 5% sofpironium bromide (BBI-4000) gel in Japanese patients with primary axillary hyperhidrosis". The Journal of Dermatology. 48 (3): 279–288. doi:10.1111/1346-8138.15668. PMC 7986147. PMID 33410265.
  4. ^ Huang F, Brown CE, Wu WM, Juhász A, Ji F, Bodor N (October 2003). "Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics". Pharmaceutical Research. 20 (10): 1681–9. doi:10.1023/a:1026160023030. PMID 14620526. S2CID 20657068.
  5. ^ Ji F, Wu W, Dai X, Mori N, Wu J, Buchwald P, Bodor N (November 2005). "Synthesis and pharmacological effects of new, N-substituted soft anticholinergics based on glycopyrrolate". J. Pharm. Pharmacol. 57 (11): 1427–35. doi:10.1211/jpp.57.11.0008. PMID 16259775.