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Lorpiprazole
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name (5aR,8aS)-3-(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-5,5a,6,7,8,8a-hexahydrocyclopenta[3,4]pyrrolo[2,1-c][1,2,4]triazole;
CAS Number	108785-69-9;
PubChem CID	3045380;
ChemSpider	16736802;
UNII	0M14O7T47Q;
CompTox Dashboard (EPA)	DTXSID30883181 ;
Chemical and physical data
Formula	C21H26F3N5
Molar mass	405.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c1cc(ccc1)N5CCN(CCc4nnc2n4C[C@@H]3CCC[C@H]23)CC5;

Lorpiprazole (INN) (brand name Normarex) is a marketed anxiolytic drug of the phenylpiperazine group.^[1]^[2]^[3] It has been described as a serotonin antagonist and reuptake inhibitor (SARI) in the same group as trazodone, nefazodone, and etoperidone.^[3]

References

^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 742–. ISBN 978-1-4757-2085-3.
^ Negwer M, Scharnow HG (2001). Organic-Chemical Drugs and Their Synonyms. Vol. 1–6 (8th ed.). Weinheim: Wiley-VCH. ISBN 3-527-30247-6.
^ ^a ^b Fagiolini A, Comandini A, Catena Dell'Osso M, Kasper S (December 2012). "Rediscovering trazodone for the treatment of major depressive disorder". CNS Drugs. 26 (12): 1033–49. doi:10.1007/s40263-012-0010-5. PMC 3693429. PMID 23192413.

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 742–. ISBN 978-1-4757-2085-3.

[isbn3-527-30247-6-2] Negwer M, Scharnow HG (2001). Organic-Chemical Drugs and Their Synonyms. Vol. 1–6 (8th ed.). Weinheim: Wiley-VCH. ISBN 3-527-30247-6.

[FagioliniComandini2012-3] Fagiolini A, Comandini A, Catena Dell'Osso M, Kasper S (December 2012). "Rediscovering trazodone for the treatment of major depressive disorder". CNS Drugs. 26 (12): 1033–49. doi:10.1007/s40263-012-0010-5. PMC 3693429. PMID 23192413.

[1]

[2]

[3]

Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (5aR,8aS)-3-(2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-5,5a,6,7,8,8a-hexahydrocyclopenta[3,4]pyrrolo[2,1-c][1,2,4]triazole
CAS Number	108785-69-9
PubChem CID	3045380
ChemSpider	16736802
UNII	0M14O7T47Q
CompTox Dashboard (EPA)	DTXSID30883181
Chemical and physical data
Formula	C₂₁H₂₆F₃N₅
Molar mass	405.469 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1cc(ccc1)N5CCN(CCc4nnc2n4C[C@@H]3CCC[C@H]23)CC5

FAIR and interactive data graphics from a scientific knowledge graph

See also

References