Sofpironium bromide

Sofpironium bromide
Clinical data
Trade names	Ecclock
Other names	BBI 4000
Routes of; administration	Topical gel
Legal status
Legal status	Rx-only (Japan);
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 data
Formula	C22H32BrNO5
Molar mass	470.404 g·mol−1
3D 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 (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]

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.[3]

References

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.
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.
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. PMID 14620526.
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.

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[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.

[Yokozeki-3] 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.

[pmid14620526-4] 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. PMID 14620526.

[pmid16259775-5] 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.