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Substance Name: Cycloserine [USP:INN:BAN:JAN]
RN: 68-41-7
UNII: 95IK5KI84Z
InChIKey: DYDCUQKUCUHJBH-UWTATZPHSA-N
Note
- Antibiotic substance produced by Streptomyces garyphalus.
Molecular Formula
- C3-H6-N2-O2
Molecular Weight
- 102.0924
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterial (Tuberculostatic)
- Antibiotics, Antitubercular
- Antimetabolites
- Antitubercular Agents
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Natural Product
- Noxae
- Renal Agents
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Names and Synonyms
Name of Substance
- Cycloserine
- Cycloserine [USP:INN:BAN:JAN]
MeSH Heading
- Cycloserine
Synonyms
- (+)-4-Amino-3-isoxazolidinone
- 3-Isoxazolidinone, 4-amino-, (+)-
- 3-Isoxazolidinone, 4-amino-, (R)-
- 3-Isoxazolidinone, 4-amino-, D-
- 4-27-00-05549 (Beilstein Handbook Reference)
- AI3-50153
- BRN 0080798
- Cicloserina
- Cicloserina [INN-Spanish]
- Cicloserina [Italian]
- Closina
- Cyclo-D-serine
- Cyclorin
- Cycloserine
- Cycloserinum
- Cycloserinum [INN-Latin]
- D-4-Amino-3-isossazolidone
- D-4-Amino-3-isossazolidone [Italian]
- D-4-Amino-3-isoxazolidinone
- D-4-Amino-3-isoxazolidone
- D-Cycloserine
- DCS
- E-733-A
- EINECS 200-688-4
- Farmiserina
- HSDB 3218
- I-1431
- K-300
- Miroserina
- Miroseryn
- Novoserin
- NSC 154851
- Orientomycin
- Oxamicina
- Oxamicina [Italian]
- Oxamycin
- PA 94
- PA-94
- Ro-1-9213
- Seromycin
- Tebemicina
- Tisomycin
- UNII-95IK5KI84Z
- Wasserina
Systematic Names
- 3-Isoxazolidinone, 4-amino-, (+)-
- 3-Isoxazolidinone, 4-amino-, (R)-
- 3-Isoxazolidinone, 4-amino-, D-
- Cycloserine
Registry Numbers
CAS Registry Number
- 68-41-7
FDA UNII
- 95IK5KI84Z
System Generated Number
- 0000068417
Structure Descriptors
InChI
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1InChIKey
DYDCUQKUCUHJBH-UWTATZPHSA-NSmiles
N[C@@H]1CONC1=OToxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | > 2gm/kg (2000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
dog | LDLo | subcutaneous | 2gm/kg (2000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR GASTROINTESTINAL: NAUSEA OR VOMITING | Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956. |
guinea pig | LD50 | oral | > 2gm/kg (2000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. | |
guinea pig | LD50 | subcutaneous | > 1gm/kg (1000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. | |
human | TDLo | oral | 560mg/kg/4W-I (560mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: WAKEFULNESS | Diseases of the Chest. Vol. 29, Pg. 241, 1956. |
man | TDLo | unreported | 64mg/kg/4D-I (64mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SLEEP | Antibiotics Annual. Vol. 3, Pg. 148, 1955/1956. |
monkey | LDLo | subcutaneous | 4gm/kg (4000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: ATAXIA | Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956. |
mouse | LD50 | intraperitoneal | 180mg/kg (180mg/kg) | "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 238, 1967. | |
mouse | LD50 | intravenous | 560mg/kg (560mg/kg) | Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980. | |
mouse | LD50 | oral | 5290mg/kg (5290mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
mouse | LD50 | subcutaneous | 1400mg/kg (1400mg/kg) | Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980. | |
rabbit | LD | oral | > 2gm/kg (2000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 382, 1956. | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
rat | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
women | TDLo | oral | 60mg/kg (60mg/kg) | BEHAVIORAL: COMA | British Medical Journal. Vol. 1, Pg. 907, 1965. |
women | TDLo | oral | 5gm/kg/71W-I (5000mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES | Rinsho Shinkeigaku. Clinical Neurology. Vol. 7, Pg. 357, 1967. |
women | TDLo | unreported | 40mg/kg/2D-I (40mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Tubercle. Vol. 38, Pg. 297, 1957. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 155.5 dec | deg C | EXP | |
log P (octanol-water) | -1.720 | (none) | EST | |
Atmospheric OH Rate Constant | 3.76E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.