sofpironium   Click here for help

GtoPdb Ligand ID: 13426

Synonyms: BBI-4000 (sofpironium bromide) | Ecclock® | Sofdra®
Approved drug
sofpironium is an approved drug (Japan (2020))
Compound class: Synthetic organic
Comment: Sofpironium is an anticholinergic drug. It is a structural analogue of glycopyrrolate which was modified to be rapidly converted to an inactive metabolite in the circulation so as to restrict action to local sites of administration (i.e. it is a so-called retrometabolic or "soft" drug) and minimise potential systemic side-effects. In relation to its use to reduce sweating in axillary hyperhidrosis its effect is mediated by antagonism of M3 muscarinic acetylcholine receptors in eccrine glands.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 72.83
Molecular weight 390.49
XLogP 2.1
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOC(=O)C[N+]1(C)CC[C@H](C1)OC(=O)[C@](C2=CC=CC=C2)(C3CCCC3)O
Isomeric SMILES CCOC(=O)C[N+]1(CC[C@H](C1)OC(=O)[C@@](C2CCCC2)(C3=CC=CC=C3)O)C
InChI InChI=1S/C22H32NO5/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/q+1/t19-,22+,23?/m1/s1
InChI Key SEVCTUCCZYBJER-BSJAROSPSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Sofpironium (bromide) was first approved in Japan (September 2020) for the topical treatment of primary axillary hyperhidrosis, following successful phase 3 clinical evaluation [1-3]. FDA approval for this indication was granted in June 2024.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03836287 Safety and Efficacy Study of Sofpironium Bromide in Subjects With Axillary Hyperhidrosis (BBI-4000-CL-301) Phase 3 Interventional Botanix Pharmaceuticals
NCT03948646 Safety and Efficacy Study of Sofpironium Bromide in Subjects With Axillary Hyperhidrosis (BBI-4000-CL-302) Phase 3 Interventional Botanix Pharmaceuticals
NCT03627468 A Safety Study of BBI-4000 Gel in Patients With Axillary Hyperhidrosis Phase 3 Interventional Botanix Pharmaceuticals