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28822-58-4

28822-58-4 structure
28822-58-4 structure
Name 3-isobutyl-1-methyl-7H-xanthine
Synonyms 3-Isobutyl-1-methyxanthine
3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione
3-Isobutyl-1-methylxanthine (IBMX)
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-
IBMX
EINECS 249-259-3
Xanthine,3-isobutyl-1-methyl
MFCD00005584
1-METHYL-3-ISOBUTYLXANTHINE
1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
3-Isobutyl-1-methylxanthine
isobutylmethylxanthine
Methylisobutylxanthine
Methylergometrine maleate
3-isobutylmethylxanthine
3-isobutyl-1-methyl-7H-xanthine
NSC165960
SC2964
Description IBMX is a broad-spectrum phosphodiesterase (PDE) inhibitor, with IC50s of 6.5, 26.3 and 31.7 μM for PDE3, PDE4 and PDE5, respectively.
Related Catalog
Target

IC50: 6.5±1.2 μM(PDE3), 26.3±3.9 μM (PDE4), 31.7±5.3 μM (PDE5)[1]

In Vitro At 100 μM, KMUP-1 (a xanthine derivative) and IBMX are the most effective at inducing tracheal relaxation; the magnitude of the relaxation responses induced by KMUP-1 and IBMX are not significantly different[1]. IBMX (100 μM) activates renal outer medullary K+ (ROMK) channels (n=6, P<0.05) and prevents further channel activation by ANG II (n=6, P=NS) or cGMP. Of note is that pretreatment of cortical collecting duct (CCDs) isolated from high-K+ (HK)-fed rats with IBMX (100 μM) for 20 min leads to a significant increase in tubular cAMP content to 1.43±0.35 pg/mm tubule length (n=14) compare with that measured in vehicle-treated controls (0.61±0.13 pg/mm tubule length, n=12, P<0.05)[2].
In Vivo IBMX, a non-selective PDE inhibitor significantly decreases the liver glycogen storage (mg/g, IBMX 22±1.5 P<0.001). IBMX potentiates insulin release and in hepatocytes and adipocytes, they increase glycogenolysis and lipolysis. In comparison with the control group, IBMX and mc5 significantly increase plasma glucose (blood glucose, mg/dl, control=141±3, IBMX=210±17 P<0.001 and mc5=191±13 P<0.01) while other test compounds (mc1, mc6, MCPIP and milrinone) do not produce significant effect (control=141±3, mc1 160±7, mc6 175±9, MCPIP 179±8 and milrinone 116±2 P>0.05) also mc2 does not change plasma glucose (control=141±3 and mc2=145±5). IBMX has the highest efficacy on increasing plasma glucose[3]. Treatments with IBMX and Apocynin significantly decrease cold-induced elevation of right ventricular (RV) systolic pressure (23.5±1.8 and 24.2±0.6 mmHg, respectively) although they do not decrease RV pressure to the warm control levels. IBMX or Apocynin significantly reduces medial layer thickness (19.0±0.9, and 16.9±0.8 μm, respectively) and increases lumen diameter (62.7±4.2, and 59.5±4.3 μm, respectively) of small PAs in cold-exposed rats[4].
Cell Assay Cells are grown in 24-well plates 105 cells per well. At confluence, monolayer cells are washed with phosphate buffer solution (PBS) and then incubated with KMUP-1 (0.1-100 μM) in the presence of 100 μM IBMX for 20 min. Incubation is terminated by the addition of 10% trichloroacetic acid (TCA). Cell suspensions are sonicated and then centrifuged at 2500× g for 15 min at 4°C. To remove TCA, the supernatants are extracted three times with 5 volumes of water-saturated diethyl ether. Then, the supernatants are lyophilized and the cyclic GMP or AMP of each sample is determined by using commercially available radioimmunoassay kits[2].
Animal Admin Mice[3] Male mice (25-35 g) are used. For the experiment, the test compound (IBMX, milrinone, MCPIP, mc1, mc2, mc5 or mc6) or solvent (control) is injected subcutaneously to mice at 1 mg/kg dosage twice a day (8:00 a.m. and 8:00 p.m.) for 7 days. On day 8, animals are anesthetized with intraperitoneal injection of thiopental (80 mg/kg) and blood samples are obtained from their hearts and then the liver is dissected. Each sample is centrifuged for 5 min and its serum is separated. The serum and the liver of each animal are kept frozen in less than -18 oC for the following measurements. Rats[4] Six groups of male Sprague-Dawley rats are used (150-180g, 6 rats/group). Three groups of rats are exposed to a climate-controlled walk-in chamber maintained at moderate cold (5.0±1°C). The remaining groups are kept in an identical chamber maintained at room temperature (23.5±1°C, warm) and served as controls. After eight weeks of exposure to cold, 3 groups in each temperature condition received continuous IV infusion of IBMX (PDE-1 inhibitor, 8.5 mg/kg/day), Apocynin (NADPH oxidase inhibitor, 25 mg/kg/day) and vehicle (DMSO, 50%), respectively. The doses of drugs have been validated for effective inhibition of PDE-1 and NADPH oxidase activity, respectively. Body weight is measured weekly. After one week of drug infusion, the animals’ right ventricular systolic blood pressure (RVBP) is measured under anesthesia. The RVP is a reliable indicator of pulmonary arterial blood pressure (PAP) and has been used by numerous investigators for evaluating PH.
References

[1]. Wu BN, et al. KMUP-1, a xanthine derivative, induces relaxation of guinea-pig isolated trachea: the role of the epithelium, cyclic nucleotides and K+ channels. Br J Pharmacol. 2004 Aug;142(7):1105-14

[2]. Wei Y, et al. Angiotensin II type 2 receptor regulates ROMK-like K+ channel activity in the renal cortical collecting duct during high dietary K+ adaptation. Am J Physiol Renal Physiol. 2014 Oct 1;307(7):F833-43

[3]. Hosseini A, et al. Differential metabolic effects of novel cilostamide analogs, methyl carbostiryl derivatives, on mouse and hyperglycemic rat. Iran J Basic Med Sci. 2012 Jul;15(4):916-25.

[4]. Crosswhite P, et al. Inhibition of phosphodiesterase-1 attenuates cold-induced pulmonary hypertension. Hypertension. 2013 Mar;61(3):585-92.
Density 1.3±0.1 g/cm3
Boiling Point 445.6±37.0 °C at 760 mmHg
Melting Point 200-201 °C(lit.)
Molecular Formula C10H14N4O2
Molecular Weight 222.244
Flash Point 223.3±26.5 °C
Exact Mass 222.111679
PSA 72.68000
LogP 1.24
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.569
Storage condition −20°C
Water Solubility DMSO: 1 M with gentle warming

CHEMICAL IDENTIFICATION

RTECS NUMBER :
ZD8500000
CHEMICAL NAME :
Xanthine, 3-isobutyl-1-methyl-
CAS REGISTRY NUMBER :
28822-58-4
LAST UPDATED :
199706
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C10-H14-N4-O2
MOLECULAR WEIGHT :
222.28
WISWESSER LINE NOTATION :
T56 BM DN FNVNVJ F1Y1&1 H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
44 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
20 mg/kg
REFERENCE :
RCOCB8 Research Communications in Chemical Pathology and Pharmacology. (PJD Pub. Ltd., P.O. Box 966, Westbury, NY 11590) V.1- 1970- Volume(issue)/page/year: 54,121,1986 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6639 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 198 (estimated) No. of Female Employees: 151 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS ZD8500000
HS Code 2942000000
HS Code 2942000000

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