Phenprobamate

{{Short description|Muscle relaxant drug}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 464200713

| IUPAC_name = 3-Phenylpropylcarbamate

| image = Phenprobamate.svg

| image_class = skin-invert-image

| width = 200

| tradename =

| Drugs.com = {{drugs.com|international|phenprobamate}}

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK =

| legal_US =

| legal_EU =

| legal_UN =

| elimination_half-life = 5–8 hours

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 673-31-4

| ATC_prefix = M03

| ATC_suffix = BA01

| PubChem = 4770

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

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

| ChemSpiderID = 4606

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

| UNII = UJZ473TPS0

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01824

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

| ChEMBL = 1079576

| C=10 | H=13 | N=1 | O=2

| smiles = O=C(OCCCc1ccccc1)N

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

| StdInChI = 1S/C10H13NO2/c11-10(12)13-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H2,11,12)

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

| StdInChIKey = CAMYKONBWHRPDD-UHFFFAOYSA-N

}}

Phenprobamate (Gamaquil, Isotonil, Actozine) is a centrally acting skeletal muscle relaxant, with additional sedative and anticonvulsant effects.{{cite journal | vauthors = Demir B, Demir Y, Aksoy I, Kilic OH, Gucyetmez V, Savas HA | title = Phenprobamate dependence: a case report | journal = Addictive Behaviors | volume = 45 | pages = 232–3 | date = June 2015 | pmid = 25727392 | doi = 10.1016/j.addbeh.2015.01.037 }}{{Unreliable source?|date=March 2024}} Its mechanism of action is probably similar to meprobamate. Phenprobamate has been used in humans as an anxiolytic, and is still sometimes used in general anesthesia and for treating muscle cramps and spasticity. Phenprobamate is still used and available OTC in some European countries, but it has generally been replaced by newer drugs. It has been sold labeled as a nootropic. Phenprobamate is metabolized by oxidative degradation of the carbamate group and ortho-hydroxylation of the benzene ring, and is eliminated in urine by the kidneys.{{Citation needed|date=March 2024}}

Doses range from 400 to 800 mg, up to 3 times a day.{{cite web |title=(meprobamate) dosing, indications, interactions, adverse effects, and more |url=https://reference.medscape.com/drug/meprobamate-342920 |website=Medscape |publisher=WebMD LLC |access-date=21 March 2024}}