4-amino-1,2-oxazolidin-3-one

• ChemBase ID: 145
• Molecular Formular: C3H6N2O2
• Molecular Mass: 102.09194
• Monoisotopic Mass: 102.04292744
• SMILES: O1NC(=O)C(N)C1
• Canonical SMILES: NC1CONC1=O
• InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)
• InChIKey: DYDCUQKUCUHJBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1,2-oxazolidin-3-one
• IUPAC Traditional name: DL-cycloserine; (+-)-4-amino-3-isoxazolidinone
• Brand Name: Closerin; Closina; Cyclomycin; Cyclorin; Cycloserin; Farmiserina; Farmiserine; Micoserina; Miroserina; Miroseryn; Novoserin; Orientomycin; Oxamicina; Oxamycin; Oxymycin; Seromycin; Tebemicina; Tisomycin; Wasserina
• Synonyms: 4-Amino-3-isoxazolidone; DL-Cycloserine; 4-Amino-3-isoxazolidinone; (R)-(+)-4-Amino-3-isoxazolidinone; D-Cycloserine; D-Cycloserine; (+/-)-3-Oxoisooxazolidin-4-amine; rac Cycloserine; 4-amino-1,2-oxazolidin-3-one; 4-Aminoisoxazolidin-3-one; alpha-Cycloserine; Cicloserina; D-CS; D-Cycloserine; D-Cycloserine synth. BP 88; D-Cycloserine, synthetic; D-Oxamicina; D-Oxamycin; DL-Cycloserine; L-Cycloserine; Cycloserine; 4-氨基-3-异噁唑烷酮; DL-环丝氨酸; D-环丝氨酸

Database IDs

• CAS Number: 68-39-3; 68-41-7
• EC Number: 200-688-4; 200-687-9
• MDL Number: MFCD00005353; MFCD00064323
• Beilstein Number: 80798
• Merck Index: 142751
• PubChem SID: 24278332; 160963608
• PubChem CID: 401

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.210087
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.4357781
• LogD (pH = 7.4): -2.4206417
• Log P: -2.4213324
• Molar Refractivity: 21.8488 cm^3
• Polarizability: 9.062646 Å^3
• Polar Surface Area: 64.35 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.31
• LOG S: 0.93
• Solubility (Water): 8.77e+02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble; Soluble in water. Slightly soluble in methanol, propylene glycol.; Water
• Apperance: crystalline; Off-White Solid
• Melting Point: >183°C (dec.); 137°C dec.
• Optical Rotation: +115 (c=2 in water)
• Hydrophobicity(logP): -0.9; -1.192

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Air Sensitive
• RTECS: NY2974900; NY2975000
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GPT(2875), GPT2(84706)

Product Information

• Purity: 95%; 95+%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C3H6N2O2

DETAILS

DrugBank - DB00260

• Drug Groups: approved
• Description: Antibiotic substance produced by Streptomyces garyphalus. [PubChem]
• Indication: Used in combination with up to 5 other drugs as a treatment for Mycobacterium avium complex (MAC) and is also used to treat tuberculosis (TB).
• Pharmacology: 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
• Toxicity: Oral LD₅₀ in mouse is 5290 mg/kg, and in rat is over 5000 mg/kg. Symptoms of a cycloserine overdose include drowsiness, confusion, headache, dizziness, irritability, numbness and tingling, difficulty speaking, paralysis, abnormal behavior, seizures, and unconsciousness.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Rapidly and almost completely absorbed (70 to 90%) from the gastrointestinal tract following oral administration.
• Half Life: Half-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - C7005

Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.

Sigma Aldrich - 862002

Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.

Toronto Research Chemicals - C988800

Antibacterial (tuberculostatic).

REFERENCES

• Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972)
• Gentry-Weeks, C., et al.: J. Biol. Chem., 268, 7298 (1972)
• Alexander, F., et al.: Eur. J. Biochem., 219, 953 (1972)
• Auger, S., et al.: Biochimie, 87, 231 (1972)