(R)-4-Aminoisoxazolidin-3-one, 98%

Name: (R)-4-Aminoisoxazolidin-3-one
Brand: Chempure

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CAS Number

68-41-7

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IUPAC name	(4R)-4-amino-1,2-oxazolidin-3-one
inchi	InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
inchi key	DYDCUQKUCUHJBH-UWTATZPHSA-N
molecular formula	C3H6N2O2
synonyms	D-cycloserine cycloserine 68-41-7 Seromycin orientomycin
Compound Description	D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase and D-alanine--D-alanine ligase . It has a role as an antitubercular agent, an antiinfective agent, an antimetabolite, a metabolite and a NMDA receptor agonist. It is an organooxygen heterocyclic antibiotic, an organonitrogen heterocyclic antibiotic and a 4-amino-1,2-oxazolidin-3-one. It is a conjugate base of a D-cycloserine. It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion. Antibiotic substance produced by Streptomyces garyphalus. Cycloserine is a broad spectrum antibiotic used as a second line agent for treatment of drug resistant tuberculosis, always in combination with other antituberculosis agents. Cycloserine is appears to have little or no hepatotoxic potential, but it is usually used in combination with agents that are known to be hepatotoxic, and its role in the reported cases of liver injury with combination therapy cannot always be excluded. Cycloserine has been reported in Streptomyces garyphalus and Streptomyces lavendulae with data available. Cycloserine is an analogue of the amino acid D-alanine with broad-spectrum antibiotic and glycinergic activities. D-cycloserine interferes with bacterial cell wall synthesis by competitively inhibiting two enzymes, L-alanine racemase and D-alanine:D-alanine ligase, thereby impairing peptidoglycan formation necessary for bacterial cell wall synthesis. This agent may be bactericidal or bacteriostatic, depending on its concentration at the infection site and the susceptibility of the organism. In addition, D-cycloserine is an excitatory amino acid and partial agonist at the glycine binding site of the NMDA receptor in the central nervous system ; binding to the central NMDA receptor may result in amelioration of neuropathic pain. CYCLOSERINE is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1964 and is indicated for extrapulmonary tuberculosis and tuberculosis and has 29 investigational indications. Antibiotic substance produced by Streptomyces garyphalus.

Computed Properties

Molecular Weight:	102.09 g/mol
XLogP3:	-1.5
Hydrogen Bond Donor Count:	2
Hydrogen Bond Acceptor Count:	3
Rotatable Bond Count:	0
Exact Mass:	102.042927438 g/mol
Monoisotopic Mass:	102.042927438 g/mol
Topological Polar Surface Area:	64.4 Å²
Heavy Atom Count:	7
Formal Charge:	0
Complexity:	92.9
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	1
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Acute Tox. 4 (20%) Skin Irrit. 2 (20%) Eye Irrit. 2A (20%) STOT SE 3 (20%)
precautionary statement codes	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (20%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation] H335 (20%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

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About this item

IUPAC name	(4R)-4-amino-1,2-oxazolidin-3-one
inchi	InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
inchi key	DYDCUQKUCUHJBH-UWTATZPHSA-N
molecular formula	C3H6N2O2
synonyms	D-cycloserine cycloserine 68-41-7 Seromycin orientomycin
Compound Description	D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase and D-alanine--D-alanine ligase . It has a role as an antitubercular agent, an antiinfective agent, an antimetabolite, a metabolite and a NMDA receptor agonist. It is an organooxygen heterocyclic antibiotic, an organonitrogen heterocyclic antibiotic and a 4-amino-1,2-oxazolidin-3-one. It is a conjugate base of a D-cycloserine. It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion. Antibiotic substance produced by Streptomyces garyphalus. Cycloserine is a broad spectrum antibiotic used as a second line agent for treatment of drug resistant tuberculosis, always in combination with other antituberculosis agents. Cycloserine is appears to have little or no hepatotoxic potential, but it is usually used in combination with agents that are known to be hepatotoxic, and its role in the reported cases of liver injury with combination therapy cannot always be excluded. Cycloserine has been reported in Streptomyces garyphalus and Streptomyces lavendulae with data available. Cycloserine is an analogue of the amino acid D-alanine with broad-spectrum antibiotic and glycinergic activities. D-cycloserine interferes with bacterial cell wall synthesis by competitively inhibiting two enzymes, L-alanine racemase and D-alanine:D-alanine ligase, thereby impairing peptidoglycan formation necessary for bacterial cell wall synthesis. This agent may be bactericidal or bacteriostatic, depending on its concentration at the infection site and the susceptibility of the organism. In addition, D-cycloserine is an excitatory amino acid and partial agonist at the glycine binding site of the NMDA receptor in the central nervous system ; binding to the central NMDA receptor may result in amelioration of neuropathic pain. CYCLOSERINE is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1964 and is indicated for extrapulmonary tuberculosis and tuberculosis and has 29 investigational indications. Antibiotic substance produced by Streptomyces garyphalus.

Computed Properties

Molecular Weight:	102.09 g/mol
XLogP3:	-1.5
Hydrogen Bond Donor Count:	2
Hydrogen Bond Acceptor Count:	3
Rotatable Bond Count:	0
Exact Mass:	102.042927438 g/mol
Monoisotopic Mass:	102.042927438 g/mol
Topological Polar Surface Area:	64.4 Å²
Heavy Atom Count:	7
Formal Charge:	0
Complexity:	92.9
Isotope Atom Count:	0
Defined Atom Stereocenter Count:	1
Undefined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
Covalently-Bonded Unit Count:	1
Compound Is Canonicalized:	Yes

hazard signal	Warning
hazard classes and categories	Acute Tox. 4 (20%) Skin Irrit. 2 (20%) Eye Irrit. 2A (20%) STOT SE 3 (20%)
precautionary statement codes	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
hazard statements	H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (20%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation] H335 (20%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Product No: CL4954

(R)-4-Aminoisoxazolidin-3-one, 98%

Product No: CL4954

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

About this item

Documentation

Certificate of Analysis

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Product No: CL4954

About this item

NAME AND IDENTIFIERS

CHEMICAL AND PHYSICAL PROPERTIES

SAFETY AND HAZARDS

Require a Sample Certificate of Analysis (COA) ?