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

• ChemBase ID: 1099
• Molecular Formular: C9H8N2O2
• Molecular Mass: 176.17202
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one
• IUPAC Traditional name: pemoline
• Brand Name: 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
• Synonyms: Phenylpseudohydantoin; Pheniminooxazolidinone; Phenoxazole; Phenylisohydantoin; Pemoline; 2-Amino-5-phenyl-4(5H)-oxazolone; Azoxodone; Tradon; Volital; 2-Amino-5-phenyl4(5H)-oxazolone; Pemoline; 2-氨基-5-苯基 4(5H)-噁唑酮; 苯异妥因; 匹莫林

Database IDs

• CAS Number: 2152-34-3
• EC Number: 218-438-8
• MDL Number: MFCD00083197
• PubChem SID: 160964562; 46509085
• PubChem CID: 4723
• ATC CODE: N06BA05
• CHEMBL: 1177
• Chemspider ID: 4561
• DrugBank ID: DB01230
• KEGG ID: D00744
• Unique Ingredient Identifier: 7GAQ2332NK
• Wikipedia Title: Pemoline

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.953647
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.8000144
• LogD (pH = 7.4): 0.80002755
• Log P: 0.8000277
• Molar Refractivity: 45.7023 cm^3
• Polarizability: 17.76415 Å^3
• Polar Surface Area: 64.68 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.52
• LOG S: -2.26
• Solubility (Water): 9.79e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble28 mg/mL; Methanol
• Apperance: solid; White Solid
• Melting Point: >230°C (dec.)
• Hydrophobicity(logP): 0.7

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere
• RTECS: RQ2975000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-20/21/22; 20/21/22
• Safety Statements: 16-36-45; 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: 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
• Drug Control: 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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 50% bound to plasma proteins
• Half Life: 12 hours
• Metabolism: Hepatic
• Legal Status: Schedule IV (United States); Schedule IV (Canada); Lista II (Argentina)
• Pregnancy Category: B U.S.

Product Information

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

DETAILS

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
Pemoline is a CNS stimulant. Pemoline is used to treat attention-deficit hyperactivity disorder (ADHD). Pemoline is a Schedule IV drug and offers some advantages over other stimulants in that it does not reduce the appetite or cause dry mouth.

Sigma Aldrich - P0048

Biochem/physiol Actions
Pemoline is a CNS stimulant. Pemoline is used to treat attention-deficit hyperactivity disorder (ADHD). Pemoline is a Schedule IV drug and offers some advantages over other stimulants in that it does not reduce the appetite or cause dry mouth.

Toronto Research Chemicals - P220100

A CNS stimulant. Controlled Substance.

REFERENCES

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