From Wikipedia, the free encyclopedia
Chemical compound
Sofpironium bromide
Trade names Ecclock, Sofdra Other names BBI-4000, BBI 4000
License data
Routes of administration
Topical
ATC code
Legal status
[(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
Formula C 22 H 32 Br N O 5
Molar mass 470.404 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 , 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
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (
+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g.,
brompheniramine ,
buclizine ,
captodiame ,
chlorphenamine (chlorpheniramine) ,
cinnarizine ,
clemastine ,
cyproheptadine ,
dimenhydrinate ,
dimetindene ,
diphenhydramine ,
doxylamine ,
meclizine ,
mequitazine ,
perlapine ,
phenindamine ,
pheniramine ,
phenyltoloxamine ,
promethazine ,
propiomazine ,
triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g.,
clozapine ,
fluperlapine ,
olanzapine (
+fluoxetine ),
rilapine ,
quetiapine ,
tenilapine ,
zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (
+beclometasone/formoterol ,
+indacaterol ,
+neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (
+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,
femoxetine ,
paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin ,
mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g.,
amitriptyline (
+perphenazine ),
amitriptylinoxide ,
butriptyline ,
cidoxepin ,
clomipramine ,
desipramine ,
desmethyldesipramine ,
dibenzepin ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
lofepramine ,
nitroxazepine ,
northiaden (desmethyldosulepin) ,
nortriptyline ,
protriptyline ,
quinupramine ,
trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
chlorprothixene ,
cyamemazine (cyamepromazine) ,
loxapine ,
mesoridazine ,
thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )