Guanidinosuccinic acid

Names

[ Name ]:
Guanidinosuccinic acid

[Synonym ]:
N-Carbamimidoyl-L-asparaginsaeure
N-amidinoaspartic acid
L-Aspartic acid, N-(aminoiminomethyl)-
aspartic acid, N-(aminoiminomethyl)-
N-Amidino-L-aspartic acid
2-Guanidinosuccinic acid
GUANIDINOSUCCINIC ACID
(2S)-2-carbamimidamidobutanedioic acid
Aspartic acid, N-(diaminomethylene)-
N-Carbamimidoyl-L-aspartic acid
N-(Diaminomethylene)aspartic acid
N-Carbamimidoylaspartic acid
n-amidino-asparticaci

Biological Activity

[Description]:

Guanidinosuccinic acid is a nitrogenous metabolite isolated in excess from serum and urine.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vivo]

Guanidinosuccinic acid, a constituent of normal urine, is elevated in the urine and serum of azotemic patients[1]. Guanidinosuccinic acid (GSA), a guanidino compound found to be greatly increased in uremia, is administered by intraperitoneal (i.p.) injection to adult albino mice and to young mice 7, 14 and 21 days old. Epileptogenic and toxic properties are assessed and Guanidinosuccinic acid brain levels following i.p. injection ae determined. In adult mice, Guanidinosuccinic acid induces long-lasting generalized clonic and clonic-tonic convulsions in a dose-dependent manner with a CD50 (and 95% confidence interval) of 363 (287-458) mg/kg (n=35), and an LD50 of 579 (445-756) mg/kg. The CD50 of Guanidinosuccinic acid corresponded with a brain concentration of 56 nmol/g tissue. Electrocorticographic recording in five adult mice revealed epileptiform discharges (spikes, spike-waves, and polyspike-waves) which appeared concomitant with the convulsions, When young mice are i.p. injected with a (for adults) subconvulsive dose of Guanidinosuccinic acid (250 mg/kg), an age-dependent decrease is noted in Guanidinosuccinic acid-induced convulsions and in the resulting brain concentration[2].

[Animal admin]

Mice[2] Randomly bred Swiss mice (male and female, body weight 13-25 g for the first series of experiments) are housed under standard environmentally controlled conditions. For another series of experiments, young Swiss mice 7, 14 and 21 days old are used. Injections of Guanidinosuccinic acid suspensions are delivered in volumes of 0.1 mL per 10 g body weight, i.p. and in doses between 250 and 1000 mg/kg (5 mice per dose, in duplicate). After injection, the mice are put in individual cylindrical transparent cages and observed for 1 h (for 2 h in the case of the young mice). Both CD50 and LD50 are calculated by probit analysis or moving average interpolation[2].

[References]

[1]. Milstien S, et al. Role of intestinal microflora in the metabolism of guanidinosuccinic acid. J Bacteriol. 1973 May;114(2):641-4.

[2]. D'Hooge R, et al. Behavioral toxicity of guanidinosuccinic acid in adult and young mice. Toxicol Lett. 1992 Dec;64-65 Spec No:773-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
344.5±52.0 °C at 760 mmHg

[ Molecular Formula ]:
C₅H₉N₃O₄

[ Molecular Weight ]:
175.143

[ Flash Point ]:
162.1±30.7 °C

[ Exact Mass ]:
175.059311

[ PSA ]:
136.50000

[ LogP ]:
-1.50

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.633

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CI9098875

CHEMICAL NAME :: L-Aspartic acid, N-(aminoiminomethyl)-

CAS REGISTRY NUMBER :: 6133-30-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C5-H9-N3-O4

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 :: 579 mg/kg

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

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 64,773,1992

Safety Information

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

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2925290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2925290090

[ Summary ]:
2925290090 other imines and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Uraemic guanidino compounds inhibit gamma-aminobutyric acid-evoked whole cell currents in mouse spinal cord neurones.

Neurosci. Lett. 265(2) , 83-6, (1999)

Guanidine, creatinine (CTN), methylguanidine (MG) and guanidinosuccinic acid (GSA) are four endogenous guanidino compounds with proven neuroexcitatory actions, and putative pathophysiological signific...

Effect of NaCN on currents evoked by uremic retention solutes in dissociated mouse neurons.

Brain Res. 1008(1) , 107-12, (2004)

Uremic retention solutes possibly contribute to neuronal hypoxia/ischemia and its consequences in patients with renal failure. We examined the in vitro effects of several uremic retention solutes on m...

Accumulation of methylguanidine and changes in guanidino compound levels in plasma, urine, and kidneys of furosemide-treated rats.

Metab. Clin. Exp. 57(6) , 802-10, (2008)

Antidiuresis and renal diseases alter the levels of guanidino compounds (GCs) in various tissues. Therefore, we hypothesized that diuresis could also disturb GC metabolism, storage, and elimination. I...

Related Compounds

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