基本情報
- CAS
68-41-7- 標準SMILES
N[C@@H]1CONC1=O- InChIKey
DYDCUQKUCUHJBH-UWTATZPHSA-N- 分子式
- C3H6N2O2
- 平均分子量
- 102.09 g/mol
- 単同位体質量
- 102.04292744
概要
D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanineD-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). It has a role as a metabolite, an antitubercular agent, an antimetabolite, an antiinfective agent and a NMDA receptor agonist. It is a 4-amino-1,2-oxazolidin-3-one, an organonitrogen heterocyclic antibiotic and an organooxygen heterocyclic antibiotic. It is a conjugate base of a D-cycloserine(1+). It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion.
名称と識別子
- 優先名称
- Cycloserine
- IUPAC
- (4R)-4-amino-1,2-oxazolidin-3-one
- 現地名
- D-(+)-シクロセリン
- 英語名
- D-Cycloserine
- 分子式
- C3H6N2O2
- 分子量
- 102.09
名称と別名
D-cycloserinecycloserine68-41-7SeromycinorientomycinOxamycinCyclo-D-serineCicloserinaFarmiserinaTisomycinWasserinaCyclorin
名称をさらに表示
D-(+)-シクロセリン[R,(+)]-4-アミノイソオキサゾリジン-3-オンチソミシンノボセリンシクロセリンセロマイシンワセリナ(+)-シクロセリンオリエントマイシンD-4-アミノ-3-オキソ-1,2-オキサゾリジン(4R)-4α-アミノイソオキサゾリジン-3-オンD-4-アミノ-3-イソオキサゾロンサイクロセリンオキサマイシンD-シクロセリンCS【シクロセリン】ファルミセリナ(R)-4-アミノイソオキサゾリジン-3-オン(R)-(+)-4-アミノ-3-イソオキサゾリジノンサイクロセリン (JP17)(R)-4-AMINO-ISOXAZOLIDIN-3-ONECycloserin(+)-Cycloserinepa94NJ-21PA 94106-7
MiroserynClosinaD-4-amino-3-isoxazolidinoneCycloserinum(4R)-4-amino-1,2-oxazolidin-3-onealpha-CycloserineNovoserin(+)-4-Amino-3-isoxazolidinone
物性
構造計算による物性
- XLogP
- -1.5
- 極性表面積
- 64.4 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 0
- 重原子数
- 7
- 形式電荷
- 0
- 複雑度
- 92.9
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Lipids
Polyketides [PK] -> Non-ribosomal peptide/polyketide hybrids [PK14]
Polyketides [PK] -> Non-ribosomal peptide/polyketide hybrids [PK14]
pHAQ SOLN HAVE PH OF ABOUT 6
LogP-0.9
OdorODORLESS OR HAS FAINT ODOR
Color/Form
CRYSTALS
WHITE TO PALE YELLOW, CRYSTALLINE POWDER
Solubility
Soluble
SOL IN WATER; SLIGHTLY SOL IN METHANOL, PROPYLENE GLYCOL
8.77e+02 g/L
Human Drugs
Breast Feeding; Lactation; Anti-infective Agents; Antibiotics, Antitubercular
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Antituberculosis medicines
Melting Point
155-156 °C (decomposes)
147 °C
Optical Rotation
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 80% (4 of 5) of all reports.
Warning
H302 (20%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information3-Isoxazolidinone, 4-amino-, (4R)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 3-Isoxazolidinone, 4-amino-, (R)-: Environment tier I assessment
FDA Requirements
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).
Hazard Classes and CategoriesAcute Tox. 4 (20%)
安全と保護具
Storage ConditionsStore below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in tight container.
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.
化学と産業
薬理情報
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
J04AB01
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.
EXCRETION OF B-ALANINE & D-BETA-AMINOISOBUTYRIC ACID WAS INCR IN PT WITH TUBERCULOSIS RECEIVING CLINICAL DOSES OF D-CYCLOSERINE.
Cycloserine is inhibitory for Mycobacterium tuberculosis in concentrations of 5 to 20 ug/ml in vitro. There is no cross-resistance between cycloserine and other tuberculostatic agents. While the antibiotic is effective in experimental infections caused by other microorganisms, studies in vitro reveal no suppression of growth in cultures made in conventional media, which contain D-alanine; this amino acid blocks the antibacterial activity of cycloserine. ... Cycloserine inhibits reactions in which D-alanine is involved in bacterial cell-wall synthesis. The use of media free of D-alanine reveals that the antibiotic inhibits the growth in vitro of enterococci, E. coli, Staph. aureus, Nocardia species, and Chlamydia.
Biological Half-Life
Half-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
Normal renal function - 10 hours. Impaired renal function - prolonged.
Metabolism/MetabolitesAPPROX 35% OF ANTIBIOTIC IS METABOLIZED TO AS-YET-UNIDENTIFIED SUBSTANCE.
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