Tamibarotene

Tamibarotene
Names

Preferred IUPAC name 4-[(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid
Identifiers
CAS Number	94497-51-5
3D model (JSmol)	Interactive image
Beilstein Reference	3564473
ChEBI	CHEBI:32181
ChEMBL	ChEMBL25202
ChemSpider	97231
DrugBank	DB04942
IUPHAR/BPS	2648
KEGG	D01418
PubChem CID	108143
UNII	08V52GZ3H9^Y
CompTox Dashboard (EPA)	DTXSID5046853
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)
SMILES O=C(O)c1ccc(cc1)C(=O)Nc2ccc3c(c2)C(CCC3(C)C)(C)C
Properties
Chemical formula	C₂₂H₂₅NO₃
Molar mass	351.446 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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) .^[1] It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA.^[2] Tamibarotene has been tested in many other cancer types, including Acute Myeloid Leukemia where it shows no benefit,^[3] and lung cancer, where it accelerated the cancer growth and increased mortality.^[4]

It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma and Crohn's disease.^[2]^[5] 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.^[6]

Synthesis

Reaction of the diol (1) with hydrogen chloride affords the corresponding dichloro derivative (2). Aluminum chloride mediated Friedel–Crafts alkylation of acetanilide with the dichloride affords the tetralin (3). Basic hydrolysis leads to the primary amine (4). Acylation of the primary amino group with the half acid chloride half ester from terephthalic acid (5) leads to the amide (6). Basic hydrolysis of the ester grouping then affords (7).^[7]

References

^ "Tamibarotene: AM 80, retinobenzoic acid, Tamibaro". Drugs in R&D. 5 (6): 359–62. 2004. doi:10.2165/00126839-200405060-00010. PMID 15563242. S2CID 34546131.
^ ^a ^b Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs of Today. 43 (8): 563–568. doi:10.1358/dot.2007.43.8.1072615. PMID 17925887.
^ "Syros Provides Update on SELECT-AML-1 Phase 2 Clinical Trial :: Syros Pharmaceuticals, Inc. (SYRS)". Syros Pharmaceuticals, Inc. 2024-08-12. Retrieved 2024-08-15.
^ Arrieta, Oscar; Levitt, Daniel J.; Pendergrass, Kelly B.; Gladkov, Oleg; Bondarenko, Igor; Jain, Minish Mahendra; Wieland, Scott (2015-05-20). "Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer". Journal of Clinical Oncology. 33 (15_suppl): e19034–e19034. doi:10.1200/jco.2015.33.15_suppl.e19034. ISSN 0732-183X.
^ Fukasawa, H; Nakagomi, M; Yamagata, N; Katsuki, H; Kawahara, K; Kitaoka, K; Miki, T; Shudo, K (2012). "Tamibarotene: a candidate retinoid drug for Alzheimer's disease" (PDF). Biological & Pharmaceutical Bulletin. 35 (8): 1206–1212. doi:10.1248/bpb.b12-00314. PMID 22863914.
^ Arrieta, Oscar; Levitt, Daniel J.; Pendergrass, Kelly B.; Gladkov, Oleg; Bondarenko, Igor; Jain, Minish Mahendra; Wieland, Scott (2015-05-20). "Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer". Journal of Clinical Oncology. 33 (15_suppl): e19034–e19034. doi:10.1200/jco.2015.33.15_suppl.e19034. ISSN 0732-183X.
^ Y. Hamada, I. Yamada, M. Uenaka, T. Sakata, U.S. patent 5,214,202 (1993).

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ Vinorelbine^#)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib^‡ Duvelisib Idelalisib Inavolisib Umbralisib^‡) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Eflornithine Elesclomol^§ Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Carotenoids
Carotenes (C₄₀)	α-Carotene β-Carotene γ-Carotene δ-Carotene ε-Carotene ζ-Carotene Lycopene Neurosporene Phytoene Phytofluene Torulene Lycopersene
Xanthophylls (C₄₀)	Antheraxanthin Astaxanthin Canthaxanthin Citranaxanthin Cryptoxanthin Diadinoxanthin Diatoxanthin Dinoxanthin Echinenone Flavoxanthin Fucoxanthin Lutein Neoxanthin Rhodoxanthin Rubixanthin Violaxanthin Zeaxanthin Zeinoxanthin
Apocarotenoids (C_<40)	Abscisic acid Apocarotenal Bixin Crocetin Food orange 7 Ionones Peridinin
Vitamin A retinoids (C₂₀)	Retinal Retinoic acid Retinol
Retinoid drugs	Acitretin Alitretinoin Bexarotene Etretinate Fenretinide Isotretinoin Tazarotene Temarotene Tretinoin Zuretinol acetate

v t e Retinoid receptor modulators
RARTooltip Retinoic acid receptor	Agonists: 9CDHRA 9-cis-Retinoic acid (alitretinoin) AC-261066 AC-55649 Acitretin Adapalene all-trans-Retinoic acid (tretinoin) AM-580 BMS-493 BMS-753 BMS-961 CD-1530 CD-2314 CD-437 Ch-55 EC 23 Etretinate Fenretinide Isotretinoin Palovarotene Retinoic acid Retinol (vitamin A) Tamibarotene Tazarotene Tazarotenic acid Trifarotene TTNPB Antagonists: BMS-195614 BMS-493 CD-2665 ER-50891 LE-135 MM-11253 Retinoic acid metabolism inhibitors: Liarozole
RXRTooltip Retinoid X receptor	Agonists: 9CDHRA 9-cis-Retinoic acid (alitretinoin) all-trans-Retinoic acid (tretinoin) Bexarotene CD 3254 Docosahexaenoic acid Fluorobexarotene Isotretinoin LG-100268 LG-101506 LG-100754 Retinoic acid Retinol (vitamin A) SR-11237 Antagonists: HX-531 HX-630 LG-100754 PA-452 UVI-3003 HX-603 LE135 (RAR beta selective) LE-540 CD3254 PA-451 PA-452 Rhein HX-711 6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid
See also Receptor/signaling modulators

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