5-Methyl-1H-pyrazole-3-carboxylic acid

Names

[ CAS No. ]:
402-61-9

[ Name ]:
5-Methyl-1H-pyrazole-3-carboxylic acid

[Synonym ]:
5-Methyl-1H-pyrazole-3-carboxylic acid
MFCD00462235
3-Methyl-1H-pyrazole-5-carboxylic acid
AS057278 5-Methylpyrazole-3-carboxylic acid MPC

Biological Activity

[Description]:

AS057278 is a potent, selective, orally active and blood-brain barrier (BBB) penetrant non-peptidic D-amino acid oxidase (DAAO) inhibitor with an IC50 value of 0.91 μM and EC50 of 2.2-3.95 μM. AS057278 can normalize phencyclidine (PCP)-induced prepulse inhibition in mice. AS057278 can be used for researching schizophrenia[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[Target]

IC50: 0.91 μM (DAAO)[1]

[In Vivo]

AS057278 (PO; 20 mg/kg b.i.d for 28 days; 80 mg/kg single dosage) normalizes phencyclidine (PCP)-induced prepulse inhibition[1]. AS057278 (10 mg/kg; PO and IV; single dosage) exhibits good pharmacokinetic effects[1]. Pharmacokinetic Parameters of AS057278 in male Sprague-Dawley rats[1]. IV (10 mg/kg) PO (10 mg/kg) C0 (ng/mL) 100,557.3 Cmax (ng/mL) 73,559.8 8088.8 tmax (h) 0.083 1 CZ (ng/mL) 26.8 40.5 tZ (h) 24 24 AUCZ (ng/mL·h) 45,596.2 18,254.4 λZ (h^-1) 0.124 0.096 AUC (ng/mL·h) 45,810.9 18,649.9 VZ (L/kg) 1.76 VSS (L/kg) 0.24 CL (L/kg/h) 0.22 MRT (h) 1.087 F 0.407 Animal Model: Males C57BL/6J mice[1] Dosage: 80 mg/kg, 20 mg/kg Administration: PO; 20 mg/kg b.i.d for 28 days; 80 mg/kg single dosage Result: Normalized phencyclidine (PCP)-induced prepulse inhibition after acute (80 mg/kg) and chronic (20 mg/kg b.i.d.) oral administration in mice. Animal Model: Male Sprague-Dawley rats[1] Dosage: 10 mg/kg Administration: PO and IV; single dosage (Pharmacokinetics Analysis) Result: Exhibited good pharmacokinetic effect.

[References]

[1]. Adage T, et al. In vitro and in vivo pharmacological profile of AS057278, a selective d-amino acid oxidase inhibitor with potential anti-psychotic properties. Eur Neuropsychopharmacol. 2008;18(3):200-214.

Chemical & Physical Properties

[ Density]:
1.404g/cm3

[ Boiling Point ]:
388.8ºC at 760mmHg

[ Melting Point ]:
241 °C

[ Molecular Formula ]:
C₅H₆N₂O₂

[ Molecular Weight ]:
126.11

[ Flash Point ]:
188.9ºC

[ Exact Mass ]:
126.04300

[ PSA ]:
65.98000

[ LogP ]:
0.41630

[ Index of Refraction ]:
1.595

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ6407500

CHEMICAL NAME :: Pyrazole-3-carboxylic acid, 5-methyl-

CAS REGISTRY NUMBER :: 402-61-9

BEILSTEIN REFERENCE NO. :: 0002906

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C5-H6-N2-O2

MOLECULAR WEIGHT :: 126.13

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

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

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 27,295,1964

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UQ6407500

[ HS Code ]:
2933199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933199090

[ Summary ]:
2933199090. other compounds containing an unfused pyrazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Changes in the plasma concentrations of D-kynurenine and kynurenic acid in rats after intraperitoneal administration of tryptophan enantiomers.

Chirality 22 , 901-916, (2010)

An aqueous solution of enantiomerically pure tryptophan (Trp), namely, D-Trp or L-Trp (100 mg/kg), was administered intraperitoneally to male Sprague-Dawley rats. The time-course profiles of the rat p...

A series of D-amino acid oxidase inhibitors specifically prevents and reverses formalin-induced tonic pain in rats.

J. Pharmacol. Exp. Ther. 336 , 282-293, (2011)

We have found that mutation of D-amino acid oxidase (DAO) diminished formalin-induced tonic pain. The present research further studied the analgesic effects of a series of DAO inhibitors in this model...

In vitro and in vivo pharmacological profile of AS057278, a selective d-amino acid oxidase inhibitor with potential anti-psychotic properties.

Eur. Neuropsychopharmacol. 18(3) , 200-14, (2008)

Non-competitive N-methyl-d-aspartate (NMDA) blockers induce schizophrenic-like behavior in healthy volunteers and exacerbate symptomatology in schizophrenic patients. Hence, a compound able to enhance...