sertaconazole

Modify Date: 2024-01-08 16:26:01

sertaconazole Structure
sertaconazole structure
 Common Name sertaconazole
CAS Number 99592-32-2 Molecular Weight 437.770
Density 1.4±0.1 g/cm3 Boiling Point 614.1±55.0 °C at 760 mmHg
Molecular Formula C20H15Cl3N2OS Melting Point N/A
MSDS N/A Flash Point 325.2±31.5 °C

 Use of sertaconazole


Sertaconazole (FI7056 free base) is a broad-spectrum topical antifungal agent, exhibits anti-inflammatory activity via activation of a p38-COX-2-PGE2 pathway. Sertaconazole is also a microtubule inhibitor, shows antiproliferative effect, induces apoptosis and autophagy, and can also inhibit the migration of cells[1][2][3][4].

 Names

Name 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
Synonym More Synonyms

 sertaconazole Biological Activity

Description Sertaconazole (FI7056 free base) is a broad-spectrum topical antifungal agent, exhibits anti-inflammatory activity via activation of a p38-COX-2-PGE2 pathway. Sertaconazole is also a microtubule inhibitor, shows antiproliferative effect, induces apoptosis and autophagy, and can also inhibit the migration of cells[1][2][3][4].
Related Catalog
In Vitro Sertaconazole (0.03-40 µg/mL; 24 h) inhibits 150 strains of yeasts which includes six Candida species with arithmetic mean MIC of 0.77 µg/mL[1]. Sertaconazole (1 µg/mL; 5, 10, 30, 60 min) activates p38 MAP kinase in a time-dependent manner[2]. Sertaconazole (1, 2 µg/mL; 6, 8, or 24 h) increases a twofold release of PGE2 via COX-2 in keratinocytes, which is dependent on p38 activation[2]. Cetaconazole (10, 20, 30, 40 µM; 24 h) induces strong mitotic arrest by depolymerizing interphase and spindle microtubules, thereby inducing chromosome aggregation defects and causing anti-proliferation effect[3]. Sertaconazole (20, 40 µM; 24 h) induces apoptosis through p53 pathway in HeLa cells[3]. Sertaconazole (20, 30 µM; 24, 48, and 72 h) inhibits the migration of HeLa cells in a concentration-dependent manner[3]. Sertaconazole (15, 30 µM; 24 h) induces autophagy in A549, H460 cells[4]. Cell Viability Assay[1] Cell Line: C. albicans, C. guilliermondii, C. krusei, C. parapsilosi, C. tropicalis, C. glabrata Concentration: 0.03-40 µg/m Incubation Time: 24 h Result: Againsted 150 strains of yeasts (six Candida species) which included C. albicans, C. guilliermondii, C. krusei, C. parapsilosi, C. tropicalis, C. glabrata species with arithmetic mean MIC values of 1.02, 0.51, 0.38, 0.31, 1.67 and 0.78 µg/mL, respectively. Western Blot Analysis[2] Cell Line: HaCaT cells Concentration: 1 µg/mL Incubation Time: 5, 10, 30, 60 min Result: Showed activity of activating p38 MAP kinase and Hsp27 in a time-dependent manner. Western Blot Analysis[2] Cell Line: HaCaT cells Concentration: 1, 2 µg/mL Incubation Time: 6 or 8 h Result: Induced 50% expression of COX-2 and resulted in a twofold increased in PGE2 release. Western Blot Analysis[2] Cell Line: siRNA-transfected HaCaT cells (without p38 MAP kinase expression) Concentration: 1 µg/mL Incubation Time: 24 h Result: Mediated induction of PGE2 was dependent on p38 activation. Cell Proliferation Assay[3] Cell Line: HeLa, HEK-293, MCF-7, A549 cells Concentration: 0-100 µM Incubation Time: 24 h Result: Showed antiproliferation activity with IC50s of 38, 45.1, 41.5, and 40.8 μM for HeLa, HEK-293, A549, and MCF-7 cells, respectively. Exhibited mitotic block activity and induced cell death at concentration above 30 μM, but no significant increased in the number of mitotic cells. Depolymerized interphase and spindle microtubules inducing defect in chromosomal congression. Apoptosis Analysis[3] Cell Line: HeLa cells Concentration: 10, 20, 40 µM Incubation Time: 24 h Result: Induced approximately 5%, 10%, and 21% cells apoptotic at concentrations of 10, 20 and 40 μM, respectively. Western Blot Analysis[3] Cell Line: A549 cells Concentration: 20, 40 µM Incubation Time: 24 h Result: Induced apoptosis through p53 pathway that the expression of p53 from 30% to 50% and 95% and p21 from 11 to 39% and 40% respectively. Resulted in Noxa and Puma, two direct transcriptional targets of p53 to be overexpressed. Cell Migration Assay [3] Cell Line: HeLa cells Concentration: 20, 30 µM Incubation Time: 24, 48, and 72 h Result: Inhibited the migration of HeLa cells at concentrations lesser than its IC50, which in a concentration-dependent manner. Cell Autophagy Assay[4] Cell Line: A549, H460 cells Concentration: 15, 30 µM Incubation Time: 24 h Result: Increased endogenous LC3 puncta and LC3 intensity, which indicated induction of autophagy in A549 and H460 cells.
In Vivo Sertaconazole (1% (w/v); apply to the left ear, once) suppresses of TPA-induced ear edema CD-1 mice[2]. Animal Model: CD-1 mice (TPA-induced ear edema model)[2]. Dosage: 1% (w/v) Administration: Apply to the left ear, once. Result: Exhibited a significant reduction of inflammation in mice by mediating PGE2 release.
References

[1]. Carrillo-Muñoz AJ, et al. In-vitro antifungal activity of sertaconazole, econazole, and bifonazole against Candida spp. J Antimicrob Chemother. 1995 Oct;36(4):713-6.

[2]. Sur R, et al. Anti-inflammatory activity of sertaconazole nitrate is mediated via activation of a p38-COX-2-PGE2 pathway. J Invest Dermatol. 2008 Feb;128(2):336-44.

[3]. Sebastian J, et al. Sertaconazole induced toxicity in HeLa cells through mitotic arrest and inhibition of microtubule assembly. Naunyn Schmiedebergs Arch Pharmacol. 2021 Jun;394(6):1231-1249.

[4]. Zhang W, et al. Sertaconazole provokes proapoptotic autophagy via stabilizing TRADD in nonsmall cell lung cancer cells. MedComm (2020). 2021 Dec 16;2(4):821-837.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 614.1±55.0 °C at 760 mmHg
Molecular Formula C20H15Cl3N2OS
Molecular Weight 437.770
Flash Point 325.2±31.5 °C
Exact Mass 435.997070
PSA 55.29000
LogP 7.49
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.675
Storage condition -20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NI4376750
CHEMICAL NAME :
1H-Imidazole, 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dic hlorophenyl)ethyl)-
CAS REGISTRY NUMBER :
99592-32-2
LAST UPDATED :
199707
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C20-H15-Cl3-N2-O-S
MOLECULAR WEIGHT :
437.78

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>8 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,725,1992 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
54600 mg/kg/26W-C
TOXIC EFFECTS :
Blood - other changes Blood - changes in erythrocyte (RBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,732,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
8400 mg/kg/28D-I
TOXIC EFFECTS :
Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Metabolism (Intermediary) - xanthine, purine or nucleotides including urate
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,727,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
32500 mg/kg/26W-I
TOXIC EFFECTS :
Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42,732,1992 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1950 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - hepatobiliary system
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42(1),739,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5550 mg/kg
SEX/DURATION :
female 16-31 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 42(1),739,1992

 Safety Information

Hazard Codes Xi
Safety Phrases S22-S24/25
WGK Germany 2
RTECS KM6557000

 Precursor & DownStream

Precursor  2

DownStream  0

 Synonyms

Sertaconazolum
Sertaconazol
1H-Imidazole, 1-[2-[(7-chlorobenzo[b]thien-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-
1-{2-[(7-Chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
T56 BSJ IG D1OYR BG DG&1- AT5N CNJ
Sertaconazole (INN)
MFCD00868881
Sertaconazolum [Latin]
sertaconazole
Ertaczo
Sertaconazol [Spanish]
1-{2-[(7-chloro-3-benzo[b]thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole
1-[2-(7-chlorobenzo[b]thiophene-3-yl-methoxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
7-Chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy-methyl]benzo[b]thiophene
1-[2-[(7-chlorobenzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole
(±)-1-[2,4-Dichloro-β-[(7-chlorobenzo[b]thien-3-yl)methoxy]phenethyl]imidazole
FI-7045
7-chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxymethyl]benzo[b]thiophene
1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole
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