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Acivicin

Names

[ CAS No. ]:
42228-92-2

[ Name ]:
Acivicin

[Synonym ]:
5-isoxazoleacetic acid, a-amino-3-chloro-4,5-dihydro-, (aS,5S)-
(2S)-Amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Acivicine
ACIA
5-Isoxazoleacetic acid, α-amino-3-chloro-4,5-dihydro-, (αS,5S)-
AT-125
(αS,5S)-α-Amino-3-chloro-2-isoxazoline-5-acetic acid
(S-(R*,R*))-4,5-Dihydro-a-amino-3-chloro-5-isoxazoleacetic Acid
(S-(R*,R*))-4,5-Dihydro-α-amino-3-chloro-5-isoxazoleacetic acid
Acivicinum
Antibiotic AT 125
(α-S,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid
Acivicino
(2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Acivicin
(2S)-amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]ethanoic acid
(a-S,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid

Biological Activity

[Description]:

Acivicin (AT-125), a natural product produced by Streptomyces sviceus is a γ−glutamyl transpeptidase (GGT) inhibitor. Acivicin can across the blood-brain barrier and has anti-cancer, anti-parasitic properties[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Infection

[Target]

GGT[1]


[References]

[1]. Kreuzer J, et al. Target discovery of acivicin in cancer cells elucidates its mechanism of growth inhibition†Electronic supplementary information (ESI) available: Synthesis, cloning, protein expression, purification and biochemical assays. Chem Sci. 2014 Dec 1;6(1):237-245. Epub 2014 Sep 26.

[2]. Chikhale EG, et al. Carrier-mediated transport of the antitumor agent acivicin across the blood-brain barrier. Biochem Pharmacol. 1995 Mar 30;49(7):941-5.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
341.6±48.0 °C at 760 mmHg

[ Melting Point ]:
>200ºC (dec.)

[ Molecular Formula ]:
C5H7ClN2O3

[ Molecular Weight ]:
178.574

[ Flash Point ]:
160.4±29.6 °C

[ Exact Mass ]:
178.014526

[ PSA ]:
84.91000

[ LogP ]:
-0.31

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

[ Index of Refraction ]:
1.664

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NY2103000
CHEMICAL NAME :
5-Isoxazoleacetic acid, 4,5-dihydro-alpha-amino-3-chloro-, (S-(R*,R*))-
CAS REGISTRY NUMBER :
42228-92-2
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C5-H7-Cl-N2-O3
MOLECULAR WEIGHT :
178.59

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Bird - chicken Embryo
DOSE/DURATION :
6 umol/L
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,633,1983

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
UN 3172

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds