36945-98-9

36945-98-9 structure

Name: IcilinAG-3-5
Chemical Name: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one
CAS Number: 36945-98-9
Molecular Formula: C₁₆H₁₃N₃O₄
Molecular Weight: 311.292
Catalog: Signaling Pathways Membrane Transporter/Ion Channel TRP Channel
Create Date: 2018-12-29 14:49:08
Modify Date: 2025-08-21 10:54:51
Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.IC50 value:Target: TRPM8in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].in vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, s.c.). Shaking behavior caused by a fixed dose (2.5mg/kg) of icilin was also inhibited in a dose-related manner by clonidine pretreatment (0.03-0.15 mg/kg, s.c.) and reduced by clonidine posttreatment (0.15 mg/kg, s.c.) [3].

Name	3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one
Synonyms	MFCD01689072 Icilin 3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyrimidinone 2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)- AG-3-5 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

Description	Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.IC50 value:Target: TRPM8in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].in vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, s.c.). Shaking behavior caused by a fixed dose (2.5mg/kg) of icilin was also inhibited in a dose-related manner by clonidine pretreatment (0.03-0.15 mg/kg, s.c.) and reduced by clonidine posttreatment (0.15 mg/kg, s.c.) [3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel Research Areas >> Cancer
References	[1]. Lee S, et al. Icilin inhibits E2F1-mediated cell cycle regulatory programs in prostate cancer. Biochem Biophys Res Commun. 2013 Nov 29;441(4):1005-10. [2]. Andersson DA, et al. TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9. [3]. Kim J, et al. Icilin-evoked behavioral stimulation is attenuated by alpha-adrenoceptor activation. Brain Res. 2011 Apr 12;1384:110-7. [4]. Kim SH, et al. Icilin induces G1 arrest through activating JNK and p38 kinase in a TRPM8-independent manner. Biochem Biophys Res Commun. 2011 Mar 4;406(1):30-5.

Density	1.4±0.1 g/cm3
Boiling Point	594.8±50.0 °C at 760 mmHg
Melting Point	200-208ºC
Molecular Formula	C₁₆H₁₃N₃O₄
Molecular Weight	311.292
Flash Point	313.5±30.1 °C
Exact Mass	311.090607
PSA	98.39000
LogP	2.73
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.672
Storage condition	-20℃

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UW7397500

CHEMICAL NAME :: 2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-

CAS REGISTRY NUMBER :: 36945-98-9

BEILSTEIN REFERENCE NO. :: 0700310

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C16-H13-N3-O4

MOLECULAR WEIGHT :: 311.32

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 700 ug/plate

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 35,110,1983

Hazard Codes	Xn: Harmful;
Risk Phrases	R20/21/22
Safety Phrases	26-36
HS Code	2933599090

HS Code	2933599090
Summary	2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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