Cyclazodone

{{Short description|Chemical compound}}

{{Distinguish|Cyclexanone}}

{{Drugbox

| IUPAC_name = (RS)-2-(cyclopropylamino)-5-phenyl-1,3-oxazol-4-one

| image = Cyclazodone structure.svg

| image_class = skin-invert-image

| width = 180px

| chirality = Racemic mixture

| drug_name =

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Legal

| routes_of_administration = Oral

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 14461-91-7

| ATC_prefix = none

| PubChem = 26701

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 2106536

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = O8U55ZRL9K

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 24875

| C=12 | H=12 | N=2 | O=2

| smiles = C1CC1NC2=NC(=O)C(O2)C3=CC=CC=C3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H12N2O2/c15-11-10(8-4-2-1-3-5-8)16-12(14-11)13-9-6-7-9/h1-5,9-10H,6-7H2,(H,13,14,15)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DNRKTAYPGADPGW-UHFFFAOYSA-N

}}

Cyclazodone is a centrally acting stimulant drug developed by American Cyanamid Company in the 1960s.{{cite patent | country = US | number = 3321470 | title = 5-Arylidene-2-Amino-2-Oxazolin-4-Ones | assign1 = American Cyanamid | inventor = Howell Jr CF, Hardy RA, Quinones N | gdate = 23 May 1967 }} The drug is related to other drugs such as pemoline and thozalinone. It displayed a favorable therapeutic index and margin of safety in comparison to pemoline and other N-lower-alkyl-substituted pemoline derivatives.{{cite patent | country = US | number = 3609159 | title = 5-Phenyl-2-Cyclopropylamino-4-Oxazolinone | inventor = De Marne V, Pierre D, Guidicelli RL, Najer H | assign1 = Les Laboratoires Dausse | gdate = 28 September 1971 }} The patents concluded that cyclazodone possessed properties efficacious in reducing fatigue and as a potential anorectic.{{cite patent | country = GB | number = 1005738 | title = 5-Phenyl-2-Cyclopropylamino-4-Oxazolinone | inventor = De Marne V, Pierre D, Guidicelli RL, Najer H | assign1 = Les Laboratoires Dausse | gdate = 29 September 1965 }} Structural congeners of pemoline have been described as "excitants with unique properties distinguishing them from the sympathomimetic amines" whilst displaying less stimulatory activity and toxicity compared to amphetamine.{{cite journal | vauthors = Greenblatt EN, Osterberg AC | title = Some pharmacologic properties of thozalinone, a new excitant | journal = Toxicology and Applied Pharmacology | volume = 7 | issue = 4 | pages = 566–78 | date = July 1965 | pmid = 4378772 | doi = 10.1016/0041-008x(65)90042-6 }}

It is included under the World Anti-Doping Agency prohibited list.{{cite web | url = https://www.wada-ama.org/sites/default/files/resources/files/WADA_Prohibited_List_2008_EN.pdf | title = World Anti-Doping Agency 2008 Prohibited List | date = 22 September 2007 | work = World Anti-Doping Agency }}