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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
 

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

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-, (+)- (8CI)
  • 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/s1

InChIKey

DYDCUQKUCUHJBH-UWTATZPHSA-N

Smiles

N[C@@H]1CONC1=O

Toxicity

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.