Casopitant

Casopitant
Systematic (IUPAC) name

(2S,4S)-4-(4-Acetyl-1-piperazinyl)-N-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluoro-2-methylphenyl)-N-methyl-1-piperidinecarboxamide
Identifiers
CAS Number	414910-27-3
ATC code	A04AD13 (WHO)
PubChem	CID 23725089
ChemSpider	25069049
UNII	3B03KPM27L^Y
ChEMBL	CHEMBL2107320
Chemical data
Formula	C₃₀H₃₅F₇N₄O₂
Molar mass	616.26 g/mol
SMILES CC1=C(C=CC(=C1)F)[C@@H]2C[C@H](CCN2C(=O)N(C)[C@H](C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C(=O)C
InChI InChI=1S/C30H35F7N4O2/c1-18-13-24(31)5-6-26(18)27-17-25(40-11-9-39(10-12-40)20(3)42)7-8-41(27)28(43)38(4)19(2)21-14-22(29(32,33)34)16-23(15-21)30(35,36)37/h5-6,13-16,19,25,27H,7-12,17H2,1-4H3/t19-,25-,27+/m1/s1 Key:XGGTZCKQRWXCHW-JRLVAEJTSA-N
(verify)

Casopitant (trade names Rezonic (US), Zunrisa (EU)) is an neurokinin 1 (NK₁) receptor antagonist undergoing research for the treatment of chemotherapy-induced nausea and vomiting (CINV).^[1] It is currently under development by GlaxoSmithKline (GSK).

In July 2008, the company filed a marketing authorisation application with the European Medicines Agency. The application was withdrawn in September 2009 because GSK decided that further safety assessment was necessary.^[2]

References

↑ Lohr L (2008). "Chemotherapy-induced nausea and vomiting". Cancer J 14 (2): 85–93. doi:10.1097/PPO.0b013e31816a0f07. PMID 18391612.
↑ "GlaxoSmithKline withdraws its marketing authorisation application for Zunrisa" (PDF). London: EMEA. 13 October 2009. Retrieved 21 December 2009.

Antiemetics (A04)

5-HT3 Serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Metoclopramide Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron

5-HT Serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone

CB₁ Agonists (Cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)

D₂/D₃ Antagonists	Alizapride Bromopride Chlorpromazine Clebopride Domperidone Haloperidol Hydroxyzine Itopride Metoclopramide Metopimazine Prochlorperazine Thiethylperazine

H₁ antagonists (Antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclozine Promethazine

mACh antagonists (Anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine

NK₁ Antagonists	Aprepitant Casopitant Ezlopitant Fosaprepitant Maropitant Netupitant Rolapitant Vestipitant

Others	Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol Trimethobenzamide

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡

SNRIs	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine

NRIs	Atomoxetine Reboxetine Viloxazine

NDRIs	Amineptine^‡ Nomifensine^‡

SARIs	Etoperidone Nefazodone^‡ Trazodone

SMSs	Vilazodone Vortioxetine

Others	Agomelatine Amisulpride Amitriptyline/perphenazine Buprenorphine Bupropion Etryptamine^‡ Flupentixol/melitracen Esketamine Ketamine Indeloxazine Lurasidone Medifoxamine^‡ Metryptamine^‡ Olanzapine/fluoxetine Oxaflozane^‡ Quetiapine Tandospirone Teniloxazine Tianeptine Tranylcypromine/trifluoperazine

Tricyclic and tetracyclic antidepressants

TCAs	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine

TeCAs	Amoxapine Maprotiline Mianserin Mirtazapine Setiptiline

Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tranylcypromine Reversible: Caroxazone^‡

MAO_A-selective	Reversible: Bifemelane Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone

MAO_B-Selective	Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics (aripiprazole, lurasidone, olanzapine, quetiapine) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous

Ademetionine (SAMe) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Tryptophan

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

Anxiolytics (N05B)

5-HT_1A agonists	Buspirone Tandospirone

GABA_AR PAMs	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 Carbamates Chlormezanone^‡ Ethanol Etifoxine; Herbs: Kava Skullcap Valerian

α₂δ VDCC blockers	Gabapentin Gabapentin enacarbil Phenibut Pregabalin

Antidepressants	SSRIs SNRIs SARIs TCAs TeCAs MAOIs; Others: Agomelatine Bupropion Vilazodone Vortioxetine

Sympatholytics	Beta blockers Clonidine Guanfacine Prazosin

Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tenoten Tiagabine Tofisopam Validolum

Peptide receptor modulators

Adiponectin

AdipoR₁	Agonists: Peptide: Adiponectin ADP-355 ADP-399; Non-peptide: AdipoRon (–)-Arctigenin Arctiin Gramine Matairesinol Antagonists: Peptide: ADP-400

AdipoR₂	Agonists: Peptide: Adiponectin ADP-355 ADP-399; Non-peptide: AdipoRon Deoxyschizandrin Parthenolide Syringing Taxifoliol Antagonists: Peptide: ADP-400

Angiotensin

Agonists: Angiotensin II
Angiotensin III
Angiotensin IV
Saralasin

Antagonists: Abitesartan
Azilsartan
Azilsartan medoxomil
Candesartan
Elisartan
Embusartan
Eprosartan
EXP-3174
Fimasartan
Forasartan
Irbesartan
Losartan
Milfasartan
Olmesartan
Olmesartan medoxomil
PD123319
Pomisartan
Pratosartan
Ripisartan
Saprisartan
Sparsentan
Tasosartan
Telmisartan
Valsartan
Zolasartan

Bradykinin

Agonists: Bradykinin
Kallidin

Antagonists: FR-173657
Icatibant
LF22-0542

CGRP

Agonists: Amylin
CGRP
Pramlintide

Antagonists: BI 44370 TA
BMS-927711
CGRP (8-37)
MK-3207
Olcegepant
Rimegepant
SB-268262
Telcagepant
Ubrogepant

Cholecystokinin

CCK_A	Agonists: Cholecystokinin CCK-4 Antagonists: Amiglumide Asperlicin Devazepide Dexloxiglumide Lintitript Lorglumide Loxiglumide Pranazepide Proglumide Tarazepide Tomoglumide

CCK_B	Agonists: Cholecystokinin CCK-4 Gastrin Antagonists: CI-988 (PD-134,308) Itriglumide L-365,360 Netazepide Proglumide Spiroglumide

Unsorted	Antagonists: Nastorazepide

CRH

CRF₁	Agonists: Cortagine Corticorelin Corticotropin releasing hormone Sauvagine Stressin I Urocortin Antagonists: Antalarmin Astressin-B CP-154,526 Emicerfont Hypericin LWH-234 NBI-27914 Pexacerfont R-121,919 TS-041 Verucerfont

CRF₂	Agonists: Corticorelin Corticotropin releasing hormone Sauvagine Urocortin Antagonists: Astressin-B

Endothelin

Agonists: Endothelin 1
Endothelin 2
Endothelin 3
IRL-1620

Antagonists: A-192,621
ACT-132577
Ambrisentan
Atrasentan
Avosentan
Bosentan
BQ-123
BQ-788
Clazosentan
Darusentan
Edonentan
Enrasentan
Fandosentan
Feloprentan
Macitentan
Nebentan
Sitaxentan
Sparsentan
Tezosentan
Zibotentan

Galanin

GAL₁	Agonists: Galanin Galanin (1-15) Galanin-like peptide Galmic Galnon Antagonists: C7 Dithiepine-1,1,4,4-tetroxide Galantide (M15) M32 M35 M40 SCH-202596

GAL₂	Agonists: Galanin Galanin (1-15) Galanin (2-11) Galanin-like peptide Galmic Galnon J18 Antagonists: C7 Galantide (M15) M32 M35 M40 M871

GAL₃	Agonists: Galanin Galanin (1-15) Galmic Galnon Antagonists: C7 Galantide (M15) GalR3ant HT-2157 M32 M35 M40 SNAP-37889 SNAP-398299

Ghrelin/GHS

Agonists: Peptide: Alexamorelin
Cortistatin-14
Examorelin (hexarelin)
Ghrelin (lenomorelin)
GHRP-1
GHRP-3
GHRP-4
GHRP-5
GHRP-6
Ipamorelin
Pralmorelin (GHRP-2)
Relamorelin
Tabimorelin
Ulimorelin; Non-peptide: Adenosine
Anamorelin
Capromorelin
CP-464709
Ibutamoren (MK-677)
L-692,585
Macimorelin
SM-130,686; Unsorted: LY-426410
LY-444711

Antagonists: A-778,193
Cortistatin-8
(D-Lys^3)-GHRP-6
JMV2959
YIL-781

Agonists: Bovine somatotropin
Efpegsomatropin
Human placental lactogen
MOD-4023
Somapacitan
Somatotropin (growth hormone)
Somatrem
Somavaratan

Antagonists: G120K-hGH
Pegvisomant

GHRH

Agonists: Peptide: CJC-1295
Dumorelin
GHRH (somatorelin)
Modified GRF (1-29)
Rismorelin
Sermorelin
Tesamorelin

Antagonists: MZ-5-156

GLP

GLP-1	Agonists: Albiglutide Dulaglutide Efpeglenatide Exenatide GLP-1 Langlenatide Liraglutide Lixisenatide Oxyntomodulin Semaglutide Taspoglutide

GLP-2	Agonists: Elsiglutide GLP-2 Teduglutide

Glucagon

Agonists: Glucagon

Antagonists: L-168,049
LGD-6972

GnRH

Antagonists: Peptide: Abarelix
Acyline
Cetrorelix
Degarelix
Detirelix
Ganirelix
Iturelix
Ozarelix
Prazarelix
Ramorelix
Teverelix (antarelix); Non-peptide: ASP-1707
Elagolix
KLH-2109
Relugolix
Sufugolix

Gonadotropin

LH/CG	Agonists: Human chorionic gonadotropin Luteinizing hormone

FSH	Agonists: Follicle-stimulating hormone

Insulin

Antagonists: BMS-754807
S661
S961

Interleukin

IL-1	Agonists: Interleukin-1 α β Antagonists: IL-1RA (anakinra) Antibodies: Canakinumab

IL-6	Agonists: Interleukin-6 Antibodies: Clazakizumab Elsilimomab Olokizumab Sarilumab Siltuximab Sirukumab Tocilizumab

Kisspeptin

Agonists: Kisspeptin
Kisspeptin-10

Antagonists: Kisspeptin-234

Leptin

Agonists: Leptin

MCH

MCH₁	Agonists: Melanin concentrating hormone Antagonists: ATC-0065 ATC-0175 GW-803,430 NGD-4715 SNAP-7941 SNAP-94847

MCH₂	Agonists: Melanin concentrating hormone

Melanocortin

MC₁	Agonists: α-MSH β-MSH γ-MSH ACTH (corticotropin) Afamelanotide BMS-470,539 Bremelanotide HS-014 HS-024 Melanotan II Modimelanotide PL-8177 SHU-8914 SHU-9005 SHU-9119 SNAP-7941 Antagonists: ASIP

MC₂	Agonists: ACTH (corticotropin) Alsactide Codactide Giractide Norleusactide (pentacosactride) Seractide Tetracosactide (tetracosactrin, cosyntropin) Tosactide (octacosactrin) Tricosactide Tridecactide

MC₃	Agonists: α-MSH β-MSH γ-MSH ACTH (corticotropin) Afamelanotide Bremelanotide Melanotan II Modimelanotide PG-931 Antagonists: AGRP ASIP HS-014 ML-00253764 PG-106 SHU-8914 SHU-9005 SHU-9119

MC₄	Agonists: α-MSH β-MSH γ-MSH ACTH (corticotropin) Afamelanotide AZD2820 BIM-22493 Bremelanotide LY-2112688 Melanotan II MK-0493 Modimelanotide PF-00446687 PG-931 PL-6983 Ro 27-3225 Setmelanotide THIQ Antagonists: AGRP ASIP HS-014 HS-024 HS-131 JKC-363 MCL-0020 MCL-0042 MCL-0129 ML-00253764 MPB-10 SHU-8914 SHU-9005 SHU-9119 Unknown: Semax

MC₅	Agonists: α-MSH β-MSH γ-MSH ACTH (corticotropin) Afamelanotide Bremelanotide HS-014 HS-024 Melanotan II Modimelanotide SHU-8914 SHU-9005 SHU-9119 Antagonists: ASIP ML-00253764 Unknown: Semax

Unsorted	Agonists: Alsactide Codactide Giractide Norleusactide (pentacosactride) Seractide Tetracosactide (tetracosactrin, cosyntropin) Tosactide (octacosactrin) Tricosactide Tridecactide

Neuropeptide FF

Agonists: Neuropeptide AF
Neuropeptide FF
Neuropeptide SF (RFRP-1)
Neuropeptide VF (RFRP-3)

Antagonists: BIBP-3226
RF9

Neuropeptide S

Agonists: Neuropeptide S

Antagonists: ML-154
SHA-68

Neuropeptide Y

Y₁	Agonists: Neuropeptide Y Peptide YY Antagonists: BIBO-3304 BIBP-3226 BVD-10 GR-231,118 PD-160,170

Y₂	Agonists: 2-Thiouridine 5'-triphosphate Neuropeptide Y Neuropeptide Y (13-36) Peptide YY Peptide YY (3-36) Antagonists: BIIE-0246 JNJ-5207787 SF-11

Y₄	Agonists: GR-231,118 Neuropeptide Y Pancreatic polypeptide Peptide YY Antagonists: UR-AK49

Y₅	Agonists: BWX-46 Neuropeptide Y Peptide YY Antagonists: CGP-71683 FMS-586 L-152,804 Lu AA-33810 MK-0557 NTNCB Velneperit (S-2367)

Neurotensin

NTS₁	Agonists: Neurotensin Neuromedin N Antagonists: Meclinertant SR-142,948

NTS₂	Agonists: Neurotensin Antagonists: Levocabastine SR-142,948

Neurotrophin

See here instead.

Opioid

See here instead.

Orexin

OX₁	Agonists: Orexin-A Orexin-B Antagonists: ACT-335827 ACT-462206 Almorexant Filorexant Lemborexant SB-334,867 SB-408,124 SB-649,868 Suvorexant TCS-1102

OX₂	Agonists: Orexin-A Orexin-B SB-668,875 Antagonists: ACT-335827 ACT-462206 Almorexant EMPA Filorexant JNJ-10397049 MIN-202 (JNJ-42847922) Lemborexant MK-1064 SB-649,868 Suvorexant TCS-1102 TCS-OX2-29

Oxytocin

Agonists: Peptide: Aspartocin
Carbetocin
Cargutocin
Demoxytocin
Lipo-oxytocin-1
Merotocin
Nacartocin
Oxytocin
TGOT
Vasotocin (argiprestocin); Non-peptide: TC OT 39
WAY-267,464

Antagonists: Peptide: Atosiban
Tocinoic acid; Non-peptide: Barusiban
Epelsiban
Erlosiban
IX-01
L-368,899
L-371,257
L-372,662
Retosiban
SSR-126,768
WAY-162,720

Prolactin

Antagonists: Δ1–9-G129R-hPRL
Δ1–14-G129R-hPRL
G120K-hGH
G129R-hPRL

PTH

Agonists: Abaloparatide
PTH
PTHrP
Semparatide
Teriparatide

Somatomedin

IGF-1	Agonists: des(1-3)IGF-1 IGF-1 (somatomedin C) (mecasermin, mecasermin rinfabate) IGF-1 LR3 IGF-2 (somatomedin A) Insulin Antagonists: BMS-754807 Antibodies: AVE1642 Cixutumumab Dalotuzumab Figitumumab Ganitumab NVP-ADW742 NVP-AEW541 Robatumumab OSl-906 R1507

IGF-2	Agonists: IGF-2 (somatomedin A)

Somatostatin

Agonists: BIM-23052
CH-275
Cortistatin-14
Depreotide
Ilatreotide
L-803,087
L-817,818
Lanreotide
NNC 26-9100
Octreotide
Pasireotide
Pentetreotide
RC-160
Seglitide
Somatostatin (GHIH)
Somatostatin (1-28)
SRIF-14
SRIF-28
TT-232
Vapreotide

Antagonists: BIM-23056
Cyclosomatostatin
CYN-154806

Tachykinin

NK₁	Agonists: Substance P Antagonists: Aprepitant Befetupitant Burapitant Casopitant CI-1021 CP-96,345 CP-99,994 CP-122,721 Dapitant Ezlopitant Figopitant FK-888 Fosaprepitant Fosnetupitant GR-203,040 GW-597,599 HSP-117 L-733,060 L-741,671 L-743,310 L-758,298 Lanepitant LY-306,740 Maropitant Netupitant NKP-608 Nolpitantium besilate Orvepitant Rolapitant RP-67,580 SDZ NKT 343 Serlopitant Telmapitant Tradipitant Vestipitant Vofopitant

NK₂	Agonists: Neurokinin A Antagonists: GR-159,897 Ibodutant Nepadutant Saredutant

NK₃	Agonists: Neurokinin B Antagonists: Osanetant Talnetant

TRH

Agonists: Azetirelin
Fertirelin
Montirelin
Orotirelin
Posatirelin
Protirelin
Rovatirelin
Taltirelin
TRH/TRF

TSH

Agonists: TSH (thyrotropin)

Vasopressin

V_1A	Agonists: Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Atosiban Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LY-307174 PF-184563 Relcovaptan RG7314 SRX246 SRX251 TC OT 39 WAY-267,464 YM-218 YM-471 YM-35471

V_1B	Agonists: Desmopressin Felypressin Lypressin Ornipressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: ABT-436 Nelivaptan ORG-52186

V₂	Agonists: Desmopressin Felypressin Lypressin Ornipressin TC OT 39 Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Conivaptan JNJ-17079166 Lixivaptan Mozavaptan RWJ-351647 Satavaptan Tolvaptan YM-471 YM-35471

Unsorted	Antagonists: Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546

VIP

VIPR₁	Agonists: Peptide: LBT-3393 VIP

VIPR₂	Agonists: Peptide: LBT-3627 VIP

Unsorted

Isunakinra
Trofinetide

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Casopitant

See also

References