Clomacran

{{Short description|Antipsychotic medication}}

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{{Infobox drug

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| IUPAC_name = 3-(2-Chloro-9,10-dihydroacridin-9-yl)-N,N-dimethylpropan-1-amine

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| image = Clomacran no stereo.png

| image_class = skin-invert-image

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| tradename = Devryl, Olaxin,{{Cite web |title=Clomacran {{!}} 5310-55-4 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61178346.htm |access-date=2023-08-25 |website=ChemicalBook |language=en}} Develar{{Cite book |url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA297 |title=Dictionary of Drugs |date=1990 |publisher=Springer US |isbn=978-1-4757-2087-7 | veditors = Elks J, Ganellin CR |location=Boston, MA |pages=297 |language=en |doi=10.1007/978-1-4757-2085-3 }}{{Cite news |date=1986-11-05 |title=Substâncias e remédios sob controle |language=pt-br |trans-title=Substances and drugs under control |pages=14 |work=Jornal do Brasil |url=https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |url-status=live |access-date=2023-08-08 |archive-url=https://web.archive.org/web/20230808230340/https://memoria.bn.br/pdf/030015/per030015_1986_00211.pdf |archive-date=2023-08-08}}

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| ATC_prefix = N05A

| ATC_suffix = X

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| 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=2023-08-03 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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| legal_UK= Withdrawn{{Cite journal | vauthors = Dixit N, Patel C, Bhavsar M, Patel S, Rawal R, Solanki H |date=2022-05-02 |title=Quantitative Structure-activity Relationship (QSAR) study of Liver Toxic Drugs |journal=International Association of Biologicals and Computational Digest |volume=1 |pages=63–71 |doi=10.56588/iabcd.v1i1.17 |eissn=2583-3995 |doi-access=free}}

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| CAS_number = 5310-55-4

| PubChem = 21382

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

| ChemSpiderID = 20095

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

| UNII = 5B1UZF65WW

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| ChEBI = 135273

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

| ChEMBL = 1615350

| C = 18| H = 21| Cl = 1| N = 2

| SMILES = CN(C)CCCC1C2=CC=CC=C2NC3=C1C=C(C=C3)Cl

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

| StdInChI = 1S/C18H21ClN2/c1-21(2)11-5-7-14-15-6-3-4-8-17(15)20-18-10-9-13(19)12-16(14)18/h3-4,6,8-10,12,14,20H,5,7,11H2,1-2H3

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

| StdInChIKey = JFRLWWDJCFYFSU-UHFFFAOYSA-N

| density = 1.120 g/cm³

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Clomacran is an antipsychotic drug of the dihydroacridine class, developed in the 1970s by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) under the brand names Devryl and Olaxin.

It was used to treat schizophrenia in the 1970s.{{cite journal | vauthors = Pecknold JC, Ban TA, Lehmann HE, Climan M | title = Clomacran in the treatment of schizophrenic patients: a comparison of two assessment methods | journal = International Journal of Clinical Pharmacology and Biopharmacy | volume = 11 | issue = 4 | pages = 299–303 | date = June 1975 | pmid = 1099021 }} It was withdrawn from the market in the UK, due to liver toxicity, in 1982.{{Cite web |title=Clomacran |url= https://pubchem.ncbi.nlm.nih.gov/compound/21382 |access-date=2023-08-25 | work = PubChem |language=en | publisher = U.S. National Library of Medicine }}{{Cite book |title=Mann's Pharmacovigilance |date=2014 |publisher=Wiley |isbn=978-0-470-67104-7 | veditors = Andrews EB, Moore N |edition=1st |language=en |doi=10.1002/9781118820186 }}