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3-Isoxazolidinone,4-amino-, (4R)-(CAS No. 68-41-7)

3-Isoxazolidinone,4-amino-, (4R)- C3H6N2O2 (cas 68-41-7) Molecular Structure

68-41-7 Structure

Identification and Related Records

【Name】
3-Isoxazolidinone,4-amino-, (4R)-
【Iupac name】
(4R)-4-amino-1,2-oxazolidin-3-one
【CAS Registry number】
68-41-7
【Synonyms】
3-Isoxazolidinone,4-amino-, (+)- (8CI)
3-Isoxazolidinone, 4-amino-, (R)-
(+)-Cycloserine
(4R)-4-Amino-3-isoxazolidinone
(R)-4-Amino-3-isoxazolidinone
(R)-Cycloserine
Cyclo-D-serine
Cycloserine
D-4-Amino-3-isoxazolidinone
D-4-Amino-3-isoxazolidone
D-CS
Farmiserina
Micoserina
Miroseryn
NSC 154851
Novoserin
Orientomycin
Oxamycin
Seromycin
Tisomycin
Wasserina
【EINECS(EC#)】
200-688-4
【Molecular Formula】
C3H6N2O2 (Products with the same molecular formula)
【Molecular Weight】
102.09
【Inchi】
InChI=1/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
【Canonical SMILES】
C1C(C(=O)NO1)N
【Isomers smiles】
C1[C@H](C(=O)NO1)N
【MOL File】
68-41-7.mol

Chemical and Physical Properties

【Appearance】
white to off-white powder
【Density】
1.278 g/cm3
【Melting Point】
147℃
【Boiling Point】
267
【Alpha】
111 o (C=5, 2N NAOH)
【Water】
SOLUBLE
【Solubilities】
SOLUBLE IN WATER
【Color/Form】
CRYSTALS
WHITE TO PALE YELLOW, CRYSTALLINE POWDER
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
?20°C
【Spectral properties】
INDEX OF REFRACTION: 1.583 (ALPHA), 1.630 (GAMMA)
MAX ABSORPTION: 226 NM (E= 402, 1%, 1 CM)
SPECIFIC OPTICAL ROTATION: +116 DEG @ 23 DEG C/D (1.17%); +137 DEG @ 25 DEG C/546 NM (2 N NAOH, 5%)
IR: 9803 (Sadtler Research Laboratories IR Grating Collection)
UV: 651 (Absorption Spectra in the UV and visible Regions, Academic Press, New York)
【Computed Properties】
Molecular Weight:102.09194 [g/mol]
Molecular Formula:C3H6N2O2
XLogP3-AA:-1.5
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:0
Tautomer Count:5
Exact Mass:102.042927
MonoIsotopic Mass:102.042927
Topological Polar Surface Area:64.4
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
Feature 3D Acceptor Count:1
Feature 3D Donor Count:2
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:0.8
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn
【Risk Statements】
R5
【Safety Statements 】
S24/25
【Safety】
Poison by intraperitoneal route. Moderately toxic by intravenous and subcutaneous routes. Mildly toxic by ingestion. Human systemic effects by ingestion and possibly other routes: wakefulness, sleep, altered sleep time, hallucinations, distorted perceptions, tremors, convulsions, and coma. An antibiotic used in the treatment of human pulmonary tuberculosis. When heated to decomposition it emits toxic fumes of NOx.
【Sensitive】
Air Sensitive
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

ANTIBIOTIC SUBSTANCE PRODUCED BY STREPTOMYCES GARYPHALUSSIVE ORCHIDACEUS.
【Usage】

In the treatment of nocardiosis, sulfonamides have been used with cycloserine.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
- Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic.
- Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
【Therapeutic Uses】
Anti-Infective Agents, Urinary; Antibiotics, Antitubercular; Antimetabolites
INHIBITS WIDE VARIETY OF BOTH GRAM-POSITIVE & GRAM-NEGATIVE BACTERIA, INCL MYCOBACTERIA. ... IT HAS BEEN USED SUCCESSFULLY AGAINST STUBBORN URINARY TRACT INFECTIONS CAUSED BY STREPTOCOCCI, STAPHYLOCOCCI, E COLI & AEROBACTER AEROGENES.
Cycloserine is indicated in combination with other antituberculars in the treatment of tuberculosis after failure of the primary medications (pyrazinamide, streptomycin, isoniazid, rifampin, and ethambutol). /Included in US product labeling/
Cycloserine is used in the treatment of atypical mycobacterial infections, such as mycobacterium avium complex. /NOT included in US product labeling/
Although cycloserine has been used for the treatment of urinary tract infections, it has been superseded by newer, safer, and/or more effective agents (eg, aminoglycosides, beta-lactams, quinolones, trimethoprim).
Cycloserine is used particularly for tuberculosis of the lungs and for leprosy with p-aminosalicylic acid or isonicotinic acid hydrazide.
【Biomedical Effects and Toxicity】
VALUE OF CYCLOSERINE IS ENHANCED BY FACT THAT IT DIFFUSES INTO CELLS & CROSSES BLOOD-BRAIN BARRIER, EVEN IN ABSENCE OF DISEASE.
When given orally, 70% to 90% of cycloserine is rapidly absorbed. Peak concentrations in plasma are reached 3 to 4 hours after a single dose and are in the range of 20 to 35 ug/ml in children who receive 20 mg/kg; only small quantities are present after 12 hours.
Cycloserine is distributed throughout body fluids and tissues. There is no appreciable blood-brain barrier to the drug, and CSF concentrations in all patients are approximately the same as those in plasma. About 50% of a parenteral dose of cycloserine is excreted unchanged in the urine in the first 12 hours; a total of 65% is recoverable in the active form over a period of 72 hours.

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