2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one

• ChemBase编号: 1099
• 分子式: C9H8N2O2
• 平均质量: 176.17202
• 单一同位素质量: 176.05857751
• SMILES: O1C(c2ccccc2)C(=O)N=C1N
• Canonical SMILES: O=C1N=C(OC1c1ccccc1)N
• InChI: InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)
• InChIKey: NRNCYVBFPDDJNE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one
• IUPAC传统名: pemoline
• 商标名: Azoksodon; Azoxodon; Azoxodone; Betanamin; Centramin; Constimol; Cylert; Cylert Chewable; Dantromin; Deltamin; Deltamine; Endolin; Fenoxazol; Fio; Hyton; Hyton asa; Juston-Wirkstoff; Kethamed; Myamin; NPL 1; Nitan; Notair; Okodon; PIO; Pemolin; Pemolina; Phenalone; Phenilone; Pioxol; Pomoline; Pondex; Ronyl; Senior; Sigmadyn; Sistra; Sistral; Stimul; Stimulol; Tradon; Tradone; Volital; Volitol; Yh 1
• 别名: 2-氨基-5-苯基 4(5H)-噁唑酮; 苯异妥因; 匹莫林; Phenylpseudohydantoin; Pheniminooxazolidinone; Phenoxazole; Phenylisohydantoin; Pemoline; 2-Amino-5-phenyl-4(5H)-oxazolone; Azoxodone; Tradon; Volital; 2-Amino-5-phenyl4(5H)-oxazolone; Pemoline

登记号

• CAS号: 2152-34-3
• EC号: 218-438-8
• MDL号: MFCD00083197
• PubChem SID: 160964562; 46509085
• PubChem CID: 4723
• ATC码: N06BA05
• CHEMBL: 1177
• Chemspider ID: 4561
• DrugBank ID: DB01230
• KEGG ID: D00744
• 美国药典/FDA物质标识码: 7GAQ2332NK
• 维基百科标题: Pemoline

理论计算性质

JChem

• Acid pKa: 14.953647
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 0.8000144
• LogD (pH = 7.4): 0.80002755
• Log P: 0.8000277
• 摩尔折射率: 45.7023 cm^3
• 极化性: 17.76415 Å^3
• 极化表面积: 64.68 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -2.26
• 溶解度: 9.79e-01 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble28 mg/mL; Methanol
• 外观: solid; White Solid
• 熔点: >230°C (dec.)
• 疏水性(logP): 0.7

安全信息

• 保存条件: -20°C Freezer, Under inert atmosphere
• RTECS编号: RQ2975000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1230
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-20/21/22; 20/21/22
• 安全公开号: 16-36-45; 36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P2 (EN 143) respirator cartridges, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1230 3/PG 2
• 毒品管制信息: USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; Home Office Schedule 4.2; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 生物利用度: 50% bound to plasma proteins
• 半衰期: 12 hours
• 代谢: Hepatic
• 法定药品分级: Schedule IV (United States); Schedule IV (Canada); Lista II (Argentina)
• 妊娠期药物分类: B U.S.

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H8N2O2

详细说明

DrugBank - DB01230

• Drug Groups: illicit; withdrawn
• Description: In 2005, the Food and Drug Administration (FDA) withdrew approval for pemoline. In March 2005, Abbott Laboratories (Cylert marketer) had discontinued the production of Cylert arguing economic reasons.
• Indication: For treatment of Attention Deficit Hyperactivity Disorder (ADHD)
• Pharmacology: Pemoline belongs to the group of medicines called central nervous system (CNS) stimulants. It is used to treat attention deficit hyperactivity disorder (ADHD). Pemoline stimulates the brain, probably by affecting neurotransmitters, the chemicals in the brain that nerves use to communicate with each other.
• Toxicity: Side effects include insomnia, anorexia, stomach ache, skin rashes, increased irritability, mild depression, nausea, dizziness, headache, drowsiness, and hallucinations
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Pemoline is rapidly absorbed from the gastrointestinal tract
• Half Life: The serum half-life of pemoline is approximately 12 hours.
• Protein Binding: Approximately 50% (bound to plasma proteins).
• Elimination: Pemoline is excreted primarily by the kidneys with approximately 50% excreted unchanged and only minor fractions present as metabolites.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P6260

Biochem/physiol Actions
匹莫林为中枢神经兴奋剂。匹莫林用于治疗注意缺陷多动障碍 (ADHD)。匹莫林为第 IV 类精神药品，因其不会造成食欲下降或导致口干而比其他兴奋剂具有优势。

Sigma Aldrich - P0048

Biochem/physiol Actions
匹莫林为中枢神经兴奋剂。匹莫林用于治疗注意缺陷多动障碍 (ADHD)。匹莫林为第 IV 类精神药品，因其不会造成食欲下降或导致口干而比其他兴奋剂具有优势。

Toronto Research Chemicals - P220100

A CNS stimulant. Controlled Substance.

参考文献

• Connors, C.K., et al.: Psychopharacolgia, 26, 321 (1972)
• Schafer, E.W., et al.: Toxicol. Appl. Pharmacol., 21, 315 (1972)