zoxazolamine

{{Short description|Withdrawn muscle relaxant drug}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = 5-Chloro-1,3-benzoxazol-2-amine

| image = Zoxazolamine.svg

| width = 200px

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| routes_of_administration = Oral

| bioavailability =

| protein_bound =

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| CAS_number_Ref =

| CAS_number = 61-80-3

| ChEBI = 35053

| ChEMBL = 472566

| CAS_supplemental =

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| ATC_suffix =

| PubChem = 6103

| DrugBank_Ref =

| DrugBank =

| UNII = 9DOW362Q29

| KEGG = C13841

| ChemSpiderID_Ref =

| ChemSpiderID = 5878

| C=7 | H=5 | Cl=1 | N=2 | O=1

| smiles = C1=CC2=C(C=C1Cl)N=C(O2)N

| StdInChI_Ref =

| StdInChI = InChI=1S/C7H5ClN2O/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3H,(H2,9,10)

| StdInChIKey_Ref =

| StdInChIKey = YGCODSQDUUUKIV-UHFFFAOYSA-N

| synonyms = McN-485

}}

Zoxazolamine (INN, USAN, BAN) (brand name Contrazole, Deflexol, Flexin, Miazol, Uri-Boi, Zoxamine, Zoxine) is a muscle relaxant that is no longer marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA48|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=48–}}{{cite book| vauthors = Kar A |title=Medicinal Chemistry |url= https://books.google.com/books?id=07g30rxCA0EC&pg=PA185 |date=1 January 2005|publisher=New Age International|isbn=978-81-224-1565-0|pages=185–}} It was synthesized in 1953 and introduced clinically in 1955 but was withdrawn due to hepatotoxicity.{{cite book| vauthors = Lowry W |title=Forensic Toxicology: Controlled Substances and Dangerous Drugs|url=https://books.google.com/books?id=szDnBwAAQBAJ&pg=PA166|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-3444-6|pages=166–}} One of its active metabolites, chlorzoxazone, was found to show less toxicity, and was subsequently marketed in place of zoxazolamine. These drugs activate IK_Ca channels.{{cite book| vauthors = Offermanns S |title=Encyclopedia of Molecular Pharmacology|date=14 August 2008|url=https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA996|publisher=Springer Science & Business Media|isbn=978-3-540-38916-3|pages=996–}}