:Tamibarotene

{{chembox

| ImageFile = Tamibarotene2DACS.svg

| ImageSize =

| PIN = 4-[(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid

| OtherNames =

|Section1={{Chembox Identifiers

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

| UNII = 08V52GZ3H9

| IUPHAR_ligand = 2648

| CASNo = 94497-51-5

| ChEMBL = 25202

| ChEBI = 32181

| KEGG = D01418

| PubChem = 108143

| ChemSpiderID = 97231

| Beilstein = 3564473

| DrugBank = DB04942

| SMILES = O=C(O)c1ccc(cc1)C(=O)Nc2ccc3c(c2)C(CCC3(C)C)(C)C

| InChI = InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

}}

|Section2={{Chembox Properties

| C=22 | H=25 | N=1 | O=3

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Tamibarotene (brand name: Amnolake), also called retinobenzoic acid, is orally active, synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity against acute promyelocytic leukaemia (APL) .{{Cite journal |year=2004 |title=Tamibarotene: AM 80, retinobenzoic acid, Tamibaro |journal=Drugs in R&D |volume=5 |issue=6 |pages=359–62 |doi=10.2165/00126839-200405060-00010 |pmid=15563242 |s2cid=34546131}} It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA.{{Cite journal |last=Miwako, I |last2=Kagechika, H |date=August 2007 |title=Tamibarotene |journal=Drugs of Today |volume=43 |issue=8 |pages=563–568 |doi=10.1358/dot.2007.43.8.1072615 |pmid=17925887}} Tamibarotene has been tested in many other cancer types, including Acute Myeloid Leukemia where it shows no benefit,{{Cite web |date=2024-08-12 |title=Syros Provides Update on SELECT-AML-1 Phase 2 Clinical Trial :: Syros Pharmaceuticals, Inc. (SYRS) |url=https://ir.syros.com/press-releases/detail/308/syros-provides-update-on-select-aml-1-phase-2-clinical-trial |access-date=2024-08-15 |website=Syros Pharmaceuticals, Inc. |language=en}} and lung cancer, where it accelerated the cancer growth and increased mortality.{{Cite journal |last=Arrieta |first=Oscar |last2=Levitt |first2=Daniel J. |last3=Pendergrass |first3=Kelly B. |last4=Gladkov |first4=Oleg |last5=Bondarenko |first5=Igor |last6=Jain |first6=Minish Mahendra |last7=Wieland |first7=Scott |date=2015-05-20 |title=Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer. |url=https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034 |journal=Journal of Clinical Oncology |language=en |volume=33 |issue=15_suppl |pages=e19034 |doi=10.1200/jco.2015.33.15_suppl.e19034 |issn=0732-183X}}

It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma and Crohn's disease.{{Cite journal |last=Fukasawa, H |last2=Nakagomi, M |last3=Yamagata, N |last4=Katsuki, H |last5=Kawahara, K |last6=Kitaoka, K |last7=Miki, T |last8=Shudo, K |date=2012 |title=Tamibarotene: a candidate retinoid drug for Alzheimer's disease |url=https://www.jstage.jst.go.jp/article/bpb/35/8/35_b12-00314/_pdf |format=PDF |journal=Biological & Pharmaceutical Bulletin |volume=35 |issue=8 |pages=1206–1212 |doi=10.1248/bpb.b12-00314 |pmid=22863914 |doi-access=free}} Tamibarotene shows a similar side effect profile to Tretinoin, but exhibits lower clearance, resulting in improved dosing regiments. Hyperlipidemia is a common finding from Tamibarotene dosing.{{Cite journal |last=Arrieta |first=Oscar |last2=Levitt |first2=Daniel J. |last3=Pendergrass |first3=Kelly B. |last4=Gladkov |first4=Oleg |last5=Bondarenko |first5=Igor |last6=Jain |first6=Minish Mahendra |last7=Wieland |first7=Scott |date=2015-05-20 |title=Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer. |url=https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034 |journal=Journal of Clinical Oncology |language=en |volume=33 |issue=15_suppl |pages=e19034 |doi=10.1200/jco.2015.33.15_suppl.e19034 |issn=0732-183X}}