(4R)-4-ammonio-3-oxo-1,2-oxazolidin-2-ide
Basic information
- CAS
68-41-7- Standard SMILES
[NH3+][C@@H]1CON=C1[O-]- InChIKey
DYDCUQKUCUHJBH-UWTATZPHSA-N- Molecular formula
- C3H6N2O2
- Average molar mass
- 102.09 g/mol
- Monoisotopic mass
- 102.04292744
Overview
D-cycloserine zwitterion is a zwitterion resulting from the transfer of a proton from the ring nitrogen to the primary amino group of D-cycloserine. The major species at pH 7.3. It is a tautomer of a D-cycloserine.
Names & identifiers
- Preferred name
- (4R)-4-ammonio-3-oxo-1,2-oxazolidin-2-ide
- IUPAC
- (4R)-4-azaniumyl-4,5-dihydro-1,2-oxazol-3-olate
- English name
- D-Cycloserine
- Molecular formula
- C3H6N2O2
- Molecular weight
- 102.09
Names & synonyms
cycloserine zwitterionD-cycloserine zwitterionalpha-cycloserine zwitterionCHEBI:74159D-4-amino-3-isoxazolidinone zwitterion(+)-4-amino-3-isoxazolidinone zwitterion(4R)-4-aminoisoxazolidin-3-one zwitterion(4R)-4-ammonio-3-oxo-1,2-oxazolidin-2-ideCYCLOSERINE(R)-4-AMINO-ISOXAZOLIDIN-3-ONED-4-AMINO-3-ISOXAZOLIDINONESEROMYCIN
Show more names
Cycloserin(+)-Cycloserinepa94NJ-21PA 94106-7
Database identifiers
- CAS
68-41-7- PubChem CID
- 51670069
- ChEBI
CHEBI:74159
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 72.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 101
Experimental & physicochemical properties
Lipids
Polyketides [PK] -> Non-ribosomal peptide/polyketide hybrids [PK14]
Polyketides [PK] -> Non-ribosomal peptide/polyketide hybrids [PK14]
LogP-0.9
Solubility
Soluble
8.77e+02 g/L
Melting Point147 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 147 °C · 147 °C (dec.)(lit.)
- alpha
- 111 · 111 º (C=5, 2N NaOH)
- Boiling point
- 191.38 °C · 191.38°C (rough estimate)
- Density
- 1.3516 · 1.3516 (rough estimate)
- refractive index
- 1.511 · 1.5110 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- NY2975000
- hs_code
- 29419090
- risk_code
- 5-20
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 38-36/37-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P271-P261-P280
- Hazardous Substances Data
- 68-41-7(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Pharmacodynamics
Cycloserine, a broad-spectrum antibiotic, may be bactericidal or bacteriostatic, depending on its concentration at the site of infection and the susceptibility of the organism. Cycloserine works by blocking the formation of these peptidoglycans. By doing this the walls of the bacteria become weak and it results in the death of the bacteria
Mechanism of Action
Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis.
Biological Half-LifeHalf-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
Absorption, Distribution and ExcretionRapidly and almost completely absorbed (70 to 90%) from the gastrointestinal tract following oral administration.
Cellular LocationsCytoplasm
Applications
UsesUsed as an antibiotic medicine in the treatment of drug-resistant Mycobacterium tuberculosis infection. Biochemical research
DescriptionD-Cycloserine (68-41-7) is a partial agonist at the glycine modulatory site of NMDA glutamatergic receptors.1Blocks kainate-induced seizures2and displays anticonvulsant effects3in rat models. D-Cycloserine facilitates synaptic plasticity but impairs glutamatergic neurotransmission in rat hippocampal slices.4Second-line drug for the treatment of tuberculosis. Enhances activity-dependent plasticity in human adults.5
UsesD-cycloserine has been used to inhibit serine hydroxymethyltransferase.
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