Gemfibrozil

Modify Date: 2024-01-02 16:27:32

Gemfibrozil Structure
Gemfibrozil structure
 Common Name Gemfibrozil
CAS Number 25812-30-0 Molecular Weight 250.333
Density 1.0±0.1 g/cm3 Boiling Point 394.7±30.0 °C at 760 mmHg
Molecular Formula C15H22O3 Melting Point 61-63°C
MSDS Chinese USA Flash Point 141.6±18.1 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Gemfibrozil


Gemfibrozil is an activator of PPAR-α, used as a lipid-lowering drug; Gemfibrozil is also a nonselective inhibitor of several P450 isoforms, with Ki values for CYP2C9, 2C19, 2C8, and 1A2 of 5.8, 24, 69, and 82 μM, respectively.

 Names

Name gemfibrozil
Synonym More Synonyms

 Gemfibrozil Biological Activity

Description Gemfibrozil is an activator of PPAR-α, used as a lipid-lowering drug; Gemfibrozil is also a nonselective inhibitor of several P450 isoforms, with Ki values for CYP2C9, 2C19, 2C8, and 1A2 of 5.8, 24, 69, and 82 μM, respectively.
Related Catalog
Target

PPAR-α

CYP2C9:5.8 μM (Ki)

CYP2C19:24 μM (Ki)

CYP2C8:69 μM (Ki)

CYP1A2:82 μM (Ki)

In Vitro Gemfibrozil is an activator of PPAR-α, used as a lipid-lowering drug[1]; also a nonselective inhibitor of several P450 isoforms, with Ki values for CYP2C9, 2C19, 2C8, and 1A2 of 5.8, 24, 69, and 82 μM, respectively[3]. Gemfibrozil (100, 150, 200 μM) inhibits the cytokine-induced NO production in a concentration dependent manner in human U373MG astroglial cells, and such effects are not due to any change of the stability of iNOS mRNA. Gemfibrozil (50, 100, 200 μM) inhibits human iNOS promoter-derived luciferase activity in cytokine-stimulated human U373MG astroglial cells. Furthermore, Gemfibrozil (50, 100, 150, and 200 μM) shows no effects on the viability of the cells[1]. Gemfibrozil considerably inhibits both M-23 and M-1 formation (catalyzed by CYP2C8 and CYP3A4), with Ki (IC50) values of 69 μM (95 μM) and 273 μM (>250 μM), respectively, in human liver microsomes. Gemfibrozil (0-250 μM) dose dependently inhibits the formation of M-23 (IC50, 68 μM) and M-1 (IC50, 78 μM) in recombinant CYP2C8, but shows no appreciable effect on the formation of these metabolites in recombinant CYP3A4[3].
In Vivo Gemfibrozil (62 mg/kg/day, p.o.) treatment initiated 3 days before spinal cord injury (SCI) causes decreased locomotor function, and induces a trend for decreased white matter sparing after injury in mice. Gemfibrozil (62 mg/kg/day, p.o.) decreases macrophage immunoreactivity but increases T cell infiltration into spared tissue[2].
Kinase Assay Activities of CYP3A4 (testosterone 6β-hydroxylation) and CYP2C8 (paclitaxel 6α-hydroxylation) are determined. The marker substrate concentrations used, 25 μM testosterone and 1 to 5 μM paclitaxel, are comparable with or around the Km values of the reactions. Gemfibrozil is either coincubated at 37°C for 15 min with the marker substrate and NADPH (1 mM) before the reaction is initiated with human liver microsomes (0.1 mg/mL) or preincubated with human liver microsomes and NADPH for 15 min before adding the marker substrate[3].
Cell Assay Briefly, 400 μL of culture supernatant is allowed to react with 200 μL of Griess reagent and incubated at room temperature for 15 min. The optical density of the assay samples is measured spectrophotometrically at 570 nm. Fresh culture medium serves as the blank in all experiments. Nitrite concentrations are calculated from a standard curve derived from the reaction of NaNO2 in the assay[1].
Animal Admin Mice are given vehicle or gemfibrozil beginning 3 days before SCI to ensure drug availability at the time of the injury (n=5-6/group). The drug is delivered orally by dissolving it in ethanol (0.25% w/w of gemfibrozil) and coating food pellets such that each animal receives appr 62 mg/kg/day; chow for control groups is treated with ethanol. Ethanol for each group is allowed to completely evaporate before giving the food to the animals. In addition, animals receive an intraperitoneal injection of vehicle or gemfibrozil (500 µg dissolved in 200 µL PBS) 1 h after the injury, and then continued to receive the drug in their food until the end of the study (28 days post-injury)[2].
References

[1]. Pahan K, et al. Gemfibrozil, a lipid-lowering drug, inhibits the induction of nitric-oxide synthase in human astrocytes. J Biol Chem. 2002 Nov 29;277(48):45984-91. Epub 2002 Sep 18.

[2]. Almad A, et al. The PPAR alpha agonist gemfibrozil is an ineffective treatment for spinal cord injured mice. Exp Neurol. 2011 Dec;232(2):309-17.

[3]. Wang JS, et al. Gemfibrozil inhibits CYP2C8-mediated cerivastatin metabolism in human liver microsomes. Drug Metab Dispos. 2002 Dec;30(12):1352-6.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 394.7±30.0 °C at 760 mmHg
Melting Point 61-63°C
Molecular Formula C15H22O3
Molecular Weight 250.333
Flash Point 141.6±18.1 °C
Exact Mass 250.156891
PSA 46.53000
LogP 4.39
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.512
Storage condition -20°C Freezer

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YV7120000
CHEMICAL NAME :
Valeric acid, 2,2-dimethyl-5-(2,5-xylyloxy)-
CAS REGISTRY NUMBER :
25812-30-0
LAST UPDATED :
199801
DATA ITEMS CITED :
19
MOLECULAR FORMULA :
C15-H22-O3
MOLECULAR WEIGHT :
250.37
WISWESSER LINE NOTATION :
QVX1&1&3OR B1 E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
18 gm/kg/3Y-I
TOXIC EFFECTS :
Behavioral - muscle weakness Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 151,1873,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1414 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,645,1997
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
445 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (6),38,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2218 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (6),38,1995
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - nausea or vomiting Gastrointestinal - other changes
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,699,1997 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2864 mg/kg/13D-C
TOXIC EFFECTS :
Liver - changes in liver weight
REFERENCE :
JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 17,47,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
13650 mg/kg/13W-C
TOXIC EFFECTS :
Liver - other changes Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in bone marrow (not otherwise specified)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,653,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
27300 mg/kg/13-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,703,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
54600 mg/kg/1Y-I
TOXIC EFFECTS :
Liver - other changes Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 25,703,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Bird - quail
DOSE/DURATION :
5600 mg/kg/4W-I
TOXIC EFFECTS :
Endocrine - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 34,987,1996 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
218 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Reproductive - Tumorigenic effects - testicular tumors
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 67,1105,1981
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16 gm/kg/78W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 67,1105,1981
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Endocrine - tumors Reproductive - Tumorigenic effects - testicular tumors
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 67,1105,1981 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2648 mg/kg
SEX/DURATION :
female 15-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 8,454,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
18910 mg/kg
SEX/DURATION :
male 61 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 8,454,1987 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,427,1996 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,427,1996 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 66,427,1996

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn,Xi
Risk Phrases R22
Safety Phrases S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS YV7120000
HS Code 2918990090

 Synthetic Route

 Customs

HS Code 2918990090
Summary 2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

Pentanoic acid, 5-(2,5-dimethylphenoxy)-2,2-dimethyl-
GEMFIBROZIL,USP
2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeric Acid
Genlip
5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoic acid
EINECS 247-280-2
lopid
CI-7
2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic acid (2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid
gevilon
Lipttr
ci-719
2,2-Dimethyl-5-(2,5-dimethylphenoxy)pentanoic Acid
Decrelip
Gemfibrozil
MFCD00079335
C1-719
Lipozid
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Chemsrc provides Gemfibrozil(CAS#:25812-30-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Gemfibrozil are included as well.>> amp version: Gemfibrozil

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