α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile

Product Name: α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
CAS No.: 218136-59-5
Chemical Name: α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
Synonyms: CS-117;SC 26196;PF-o6341724;SC26196;SC 26196;SC 26196 - PF 06341724;α,α-Diphenyl-4-[(3-pyridinylMethylene)aMino]-1-piperazine;a,a-diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile;α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile;1-Piperazinepentanenitrile, α,α-diphenyl-4-[(3-pyridinylmethylene)amino]-;2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile
CBNumber: CB12518849
Molecular Formula: C27H29N5
Formula Weight: 423.55
MOL File: 218136-59-5.mol

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α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Property

storage temp.: 2-8°C
solubility: DMSO: ≥10mg/mL
form: powder
color: white to tan

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PZ0176
Product name: SC-26196
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $151
Updated: 2025/07/31

Sigma-Aldrich

Product number: PZ0176
Product name: SC-26196
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $405
Updated: 2025/07/31

Cayman Chemical

Product number: 10792
Product name: SC 26196
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 10792
Product name: SC 26196
Purity: ≥98%
Packaging: 5mg
Price: $122
Updated: 2024/03/01

Cayman Chemical

Product number: 10792
Product name: SC 26196
Purity: ≥98%
Packaging: 10mg
Price: $169
Updated: 2024/03/01

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α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Chemical Properties,Usage,Production

Description

The enzyme Δ⁶ desaturase mediates the conversion of linoleic acid to γ-linolenic acid (GLA), which can then be elongated to dihomo-γ-linolenic acid (DGLA). DGLA can then be used as a substrate for Δ⁵ desaturase to produce arachidonic acid (AA), the fatty acid that is used to generate eicosanoids. SC 26196 is an inhibitor of Δ⁶ desaturase (IC₅₀ = 0.2 μM in a rat liver microsomal assay) that completely blocks the conversion of linoleic acid to arachidonic acid (AA). It is selective for Δ⁶ desaturase, as IC₅₀ values for Δ⁵ and Δ⁹ desaturases exceed 200 μM and it has no effect on the conversion of dihomo-γ-linolenic acid to AA. SC 26196 is orally active in vivo, decreasing edema in the carrageenan paw edema model in mice. It also blocks aging-related increases in AA in myocardial cardiolipin in mice, attenuating contractile dysfunction without impacting mitochondrial oxidative stress.

Uses

SC-26196 has been used as an inhibitor of delta6 (Δ6) fatty acid desaturase:

in mouse inner medullary?collecting duct?(IMCD3) and human (female) embryonic kidney (HEK) 293 cell culture as Dulbecco′s modified eagle′s medium (DMEM) component
in hepatic HepG2 cells
in glioblastoma cell lines to test its effect post-radiation treatments

Uses

A selective Δ6 desaturase inhibitor (IC50 = 0.2 μM in vitro). Displays selectivity over Δ5 and Δ9 desaturases (IC50 values are >200 μM in vitro). It exhibits anti-inflammatory properties in a mouse edema model.

Biochem/physiol Actions

SC-26196 is a Delta6 fatty acid desaturase (Delta6D) inhibitor. It specifically inhibited Delta6D activity with an IC(50) value of 100 nM. The rate-limiting step in arachidonic acid synthesis is the desaturation of dietary linoleic acid by Delta6D. SC-26196 completely prevented this conversion of linoleic acid to arachidonic acid.

in vivo

SC-26196 ( included in the diet at 0, 0.07, 0.21, or 0.7 mg/kg diet to achieve dosages of 0, 10, 30, and 100 mg/kg per day) causes a decrease in the calculated Δ6-desaturase index in both adipose tissue and liver. Feeding 100 mg SC-26196 per kg BW per day inhibits the Δ6-desaturase enzyme^[3].

Animal Model:	Male mice (12- or 15-week-old)^[3]
Dosage:	0, 10, 30, and 100 mg/kg per day
Administration:	Included in the diet at 0, 0.07, 0.21, or 0.7mg/kg diet to achieve dosages of 0, 10, 30, and 100mg/kg per day.
Result:	Caused a decrease in the calculated Δ6-desaturase index in both adipose tissue and liver.

storage

Store at -20°C

References

[1] M. OBUKOWICZ. Novel, selective Δ6 or Δ5 fatty acid desaturase inhibitors as antiinflammatory agents in mice[J]. Lipids, 1999, 34 S1Part2: S149. DOI: 10.1007/bf02562269
[2] SHAWN D. HARMON. Effect of the Δ6-desaturase inhibitor SC-26196 on PUFA metabolism in human cellsinhibitor SC-26196 on PUFA metabolism in human cells[J]. Lipids, 2003, 38 4: 469-476. DOI: 10.1007/s11745-003-1086-9
[3] CHRISTOPHER M MULLIGAN. Inhibition of delta-6 desaturase reverses cardiolipin remodeling and prevents contractile dysfunction in the aged mouse heart without altering mitochondrial respiratory function.[J]. Journals of Gerontology Series A-Biological Sciences and Medical Sciences, 2014, 69 7: 799-809. DOI: 10.1093/gerona/glt209
[4] T. LAVAL. De novo synthesized polyunsaturated fatty acids operate as both host immunomodulators and nutrients for Mycobacterium tuberculosis[J]. eLife, 2021. DOI: 10.1101/2021.07.08.451715

α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Preparation Products And Raw materials

Raw materials

Preparation Products

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α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Suppliers

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218136-59-5, α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrileRelated Search:

Nicotinamide SC-43 SC-1 SC-560 4-[5-(4-CHLOROPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-1-YL]BENZENESULFONAMIDE 4-ThiazolecarboxaMide, N-(6-benzoyl-1H-benziMidazol-2-yl)-2-(1-thieno[3,2-d]pyriMidin-4-yl-4-piperidinyl)- 2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester SC-514 SC 57461A SC 66

SC 26196

α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile

alpha,alpha-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile

α,α-Diphenyl-4-[(3-pyridinylMethylene)aMino]-1-piperazine

2,2-diphenyl-5-{4-[(E)-(pyridin-3-ylMethylidene)aMino]piperazin-1-yl}pentanenitrile

PF-o6341724

(E)-2,2-diphenyl-5-(4-((pyridin-3-ylMethylene)aMino)piperazin-1-yl)pentanenitrile

2,2-diphenyl-5-(4-[[(1 E)-pyridin-3-yl-methylidene]amino]piperazin-1-yl)pentanenitrile

a,a-diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile

SC 26196 - PF 06341724

CS-117

SC26196;SC 26196

1-Piperazinepentanenitrile, α,α-diphenyl-4-[(3-pyridinylmethylene)amino]-

2,2-Diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile

218136-59-5

C27H29N5

Selective Δ6 desaturase inhibitor.