Sofpironium bromide

Chemical compound

US DailyMed: Sofpironium bromide

Routes of
administrationTopicalATC code

None

Legal statusLegal status

US: ℞-only^[1]
JP: Rx-only

Identifiers

IUPAC name

[(3R)-1-(2-Ethoxy-2-oxoethyl)-1-methylpyrrolidin-1-ium-3-yl] (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate bromide

CAS Number

1628106-94-4

PubChem CID

86301316

ChemSpider

52085312

UNII

7B2Y1932XU

KEGG

D10989

ChEMBL

ChEMBL3707223

Chemical and physical dataFormulaC₂₂H₃₂BrNO₅Molar mass470.404 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CCOC(=O)C[N+]1(CC[C@H](C1)OC(=O)[C@@](C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]

InChI

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, sold under the brand name Ecclock among others, is a medication used to treat hyperhidrosis (excessive sweating).^[1] It is an anticholinergic and is applied to the skin.^[1]

It was approved in Japan in 2020, for the treatment of primary axillary hyperhidrosis.^[2]^[3]^[4] It was approved for medical use in the United States in June 2024.^[1]^[5]

Medical uses

Sofpironium bromide is indicated for the treatment of primary axillary hyperhidrosis.^[1]

Mechanism of action

Sofpironium bromide is an anticholinergic agent that reduces sweating by inhibiting M₃ muscarinic receptors in eccrine glands.^[4] It is a retrometabolically-designed drug (or "soft drug") based on glycopyrronium bromide,^[6]^[7] 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.

Society and culture

Brand names

Sofpironium bromide is the international nonproprietary name.^[8]

It is marketed as Ecclock in Japan and as Sofdra in the US.

References

^ ^a ^b ^c ^d ^e "Sofdra (sofpironium) topical gel, 12.45%" (PDF). Archived (PDF) from the original on 20 June 2024. Retrieved 20 June 2024.
^ Paik J (December 2020). "Sofpironium Bromide: First Approval". Drugs. 80 (18): 1981–1986. doi:10.1007/s40265-020-01438-1. PMID 33236266. S2CID 227155835.
^ 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.
^ ^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.
^ "FDA Approves Sofdra topical gel" (Press release). Botanix Pharmaceuticals. 20 June 2024. Archived from the original on 20 June 2024. Retrieved 20 June 2024.
^ 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.
^ Ji F, Wu W, Dai X, Mori N, Wu J, Buchwald P, et al. (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.
^ World Health Organization (2017). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 77". WHO Drug Information. 31 (1). hdl:10665/330984.

External links

"Sofpironium Bromide (Code C152384)". NCI Thesaurus.
Clinical trial number NCT03836287 for "Safety and Efficacy Study of Sofpironium Bromide in Subjects With Axillary Hyperhidrosis (BBI-4000-CL-301) (CardiganI)" at ClinicalTrials.gov
Clinical trial number NCT03948646 for "Safety and Efficacy Study of Sofpironium Bromide in Subjects With Axillary Hyperhidrosis (BBI-4000-CL-302) (CARDIGANII)" at ClinicalTrials.gov