Clovoxamine

Clovoxamine
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 1-(4-chlorophenyl)-5-methoxypentan-1-one O-2-aminoethyl oxime;
CAS Number	54739-21-8 ;
PubChem CID	6335903;
ChemSpider	4891461 ;
UNII	7I22J7RY2A;
ChEMBL	CHEMBL2105603 ;
Chemical and physical data
Formula	C14H21ClN2O2
Molar mass	284.78 g/mol
3D model (JSmol)	Interactive image;
	SMILES COCCCCC(=NOCCN)C1=CC=C(C=C1)Cl;
	InChI InChI=1S/C14H21ClN2O2/c1-18-10-3-2-4-14(17-19-11-9-16)12-5-7-13(15)8-6-12/h5-8H,2-4,9-11,16H2,1H3/b17-14+ ; Key:XXPVSQRPGBUFKM-SAPNQHFASA-N ;
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Clovoxamine (INN) (developmental code name DU-23811) is a drug that was discovered in the 1970s and was subsequently investigated as an antidepressant and anxiolytic agent but was never marketed.^[1]^[2]^[3] It acts as a serotonin-norepinephrine reuptake inhibitor (SNRI), with little affinity for the muscarinic acetylcholine, histamine, adrenergic, and serotonin receptors.^[4]^[5] The compound is structurally related to fluvoxamine.

References

↑ Freeman; Wakelin, J. S.; Calanca, A.; Hole, G. (1982). "Initial clinical evaluation of a new nontricyclic antidepressant: clovoxamine". Advances in Biochemical Psychopharmacology. 32: 69–75. PMID 7046368.
↑ Jesinger; Gostick, N. (1989). "Anxiety neurosis in general practice. A double-blind comparative study of diazepam and clovoxamine, a novel inhibitor of noradrenaline and serotonin reuptake". International clinical psychopharmacology. 4 (4): 301–311. doi:10.1097/00004850-198910000-00005. PMID 2691573.
↑ Hurst; Jones, D. R.; Wright, J. H.; Jarboe, C. H. (1983). "Clovoxamine kinetics in an early clinical trial". Clinical Pharmacology and Therapeutics. 34 (2): 266–271. doi:10.1038/clpt.1983.164. PMID 6872422.
↑ Saletu; Grünberger, J.; Rajna, P.; Karobath, M. (1980). "Clovoxamine and fluvoxamine-2 biogenic amine re-uptake inhibiting antidepressants: quantitative EEG, psychometric and pharmacokinetic studies in man". Journal of neural transmission. 49 (1–2): 63–86. doi:10.1007/BF01249190. PMID 6777458.
↑ Bradford; Tulp, M. T.; Schipper, J. (1987). "Biochemical effects in rats after acute and long-term treatment with clovoxamine". Archives Internationales de Pharmacodynamie et de Thérapie. 287 (2): 188–202. PMID 2820327.

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[pmid7046368-1] Freeman; Wakelin, J. S.; Calanca, A.; Hole, G. (1982). "Initial clinical evaluation of a new nontricyclic antidepressant: clovoxamine". Advances in Biochemical Psychopharmacology. 32: 69–75. PMID 7046368.

[pmid2691573-2] Jesinger; Gostick, N. (1989). "Anxiety neurosis in general practice. A double-blind comparative study of diazepam and clovoxamine, a novel inhibitor of noradrenaline and serotonin reuptake". International clinical psychopharmacology. 4 (4): 301–311. doi:10.1097/00004850-198910000-00005. PMID 2691573.

[pmid6872422-3] Hurst; Jones, D. R.; Wright, J. H.; Jarboe, C. H. (1983). "Clovoxamine kinetics in an early clinical trial". Clinical Pharmacology and Therapeutics. 34 (2): 266–271. doi:10.1038/clpt.1983.164. PMID 6872422.

[pmid6777458-4] Saletu; Grünberger, J.; Rajna, P.; Karobath, M. (1980). "Clovoxamine and fluvoxamine-2 biogenic amine re-uptake inhibiting antidepressants: quantitative EEG, psychometric and pharmacokinetic studies in man". Journal of neural transmission. 49 (1–2): 63–86. doi:10.1007/BF01249190. PMID 6777458.

[pmid2820327-5] Bradford; Tulp, M. T.; Schipper, J. (1987). "Biochemical effects in rats after acute and long-term treatment with clovoxamine". Archives Internationales de Pharmacodynamie et de Thérapie. 287 (2): 188–202. PMID 2820327.

Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione) Piperoxan Prazosin Quinazosin Quinidine Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, brexpiprazole, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, gepirone, ipsapirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 1-(4-chlorophenyl)-5-methoxypentan-1-one O-2-aminoethyl oxime
CAS Number	54739-21-8^Y
PubChem CID	6335903
ChemSpider	4891461^N
UNII	7I22J7RY2A
ChEMBL	CHEMBL2105603^N
Chemical and physical data
Formula	C₁₄H₂₁ClN₂O₂
Molar mass	284.78 g/mol
3D model (JSmol)	Interactive image
SMILES COCCCCC(=NOCCN)C1=CC=C(C=C1)Cl
InChI InChI=1S/C14H21ClN2O2/c1-18-10-3-2-4-14(17-19-11-9-16)12-5-7-13(15)8-6-12/h5-8H,2-4,9-11,16H2,1H3/b17-14+^N Key:XXPVSQRPGBUFKM-SAPNQHFASA-N^N
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