Flerobuterol

Flerobuterol
Clinical data
Other names	CRL-40827
Drug class	β-Adrenergic receptor agonist
Identifiers
	IUPAC name 2-(tert-butylamino)-1-(2-fluorophenyl)ethanol;
CAS Number	82101-10-8;
PubChem CID	71254;
ChemSpider	64385;
UNII	F05RR5M463;
ChEMBL	ChEMBL2106772;
CompTox Dashboard (EPA)	DTXSID80868640 ;
Chemical and physical data
Formula	C12H18FNO
Molar mass	211.280 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)NCC(C1=CC=CC=C1F)O;
	InChI InChI=1S/C12H18FNO/c1-12(2,3)14-8-11(15)9-6-4-5-7-10(9)13/h4-7,11,14-15H,8H2,1-3H3; Key:XTJMTDZHCLBKFU-UHFFFAOYSA-N;

Flerobuterol (INNTooltip International Nonproprietary Name; developmental code name CRL-40827) is a selective β-adrenergic receptor agonist related to salbutamol which was under development for the treatment of major depressive disorder but was never marketed.^[1]^[2]^[3] It is an agonist of the β₁-, β₂-, and β₃-adrenergic receptors.^[2]^[4] The drug was under development in France by Cephalon and Lafon and reached phase 2 clinical trials prior to its development being discontinued.^[1] It was first described in the scientific literature by 1988^[3] and its development was terminated in 2007.^[1]

References

^ ^a ^b ^c "Flerobuterol". AdisInsight. Springer Nature Switzerland AG. 26 October 2011. Retrieved 27 September 2024.
^ ^a ^b Bosker FJ, Westerink BH, Cremers TI, Gerrits M, van der Hart MG, Kuipers SD, et al. (2004). "Future antidepressants: what is in the pipeline and what is missing?". CNS Drugs. 18 (11): 705–732. doi:10.2165/00023210-200418110-00002. PMID 15330686.
^ ^a ^b Chariot J, De La Tour J, Vaille C, Rozé C (January 1988). "Effects of CRL 40827 and salbutamol on exocrine pancreatic secretion in rats". European Journal of Pharmacology. 146 (1): 17–25. doi:10.1016/0014-2999(88)90482-7. PMID 2895009.
^ Zini R, Morin D, Martin P, Puech AJ, Tillement JP (October 1991). "Interactions of flerobuterol, an antidepressant drug candidate, with beta adrenoceptors in the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 259 (1): 414–422. PMID 1681091.

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[AdisInsight-1] "Flerobuterol". AdisInsight. Springer Nature Switzerland AG. 26 October 2011. Retrieved 27 September 2024.

[BoskerWesterinkCremers2004-2] Bosker FJ, Westerink BH, Cremers TI, Gerrits M, van der Hart MG, Kuipers SD, et al. (2004). "Future antidepressants: what is in the pipeline and what is missing?". CNS Drugs. 18 (11): 705–732. doi:10.2165/00023210-200418110-00002. PMID 15330686.

[ChariotDeLaTourVaille1988-3] Chariot J, De La Tour J, Vaille C, Rozé C (January 1988). "Effects of CRL 40827 and salbutamol on exocrine pancreatic secretion in rats". European Journal of Pharmacology. 146 (1): 17–25. doi:10.1016/0014-2999(88)90482-7. PMID 2895009.

[ZiniMorinMartin1991-4] Zini R, Morin D, Martin P, Puech AJ, Tillement JP (October 1991). "Interactions of flerobuterol, an antidepressant drug candidate, with beta adrenoceptors in the rat brain". The Journal of Pharmacology and Experimental Therapeutics. 259 (1): 414–422. PMID 1681091.

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Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine