Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H17Cl2NO2 |
| Molecular Weight | 314.207 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C3=CC(Cl)=CC(Cl)=C3
InChI
InChIKey=MNJNPLVXBISNSX-WDNDVIMCSA-N
InChI=1S/C15H17Cl2NO2/c1-18-12-2-3-13(18)8-14(7-12)20-15(19)9-4-10(16)6-11(17)5-9/h4-6,12-14H,2-3,7-8H2,1H3/t12-,13+,14+
| Molecular Formula | C15H17Cl2NO2 |
| Molecular Weight | 314.207 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Bemesetron, also known as MDL 72222, is a potent and highly selective antagonist of neuronal 5-hydroxytryptamine receptors, 5HT3. Bemesetron possesses antiemetic efficacy in comparison with a high-dose metoclopramide regimen (HDM) for chemotherapy-induced nausea and vomiting. But this application is not clinically used. Drug is used as scientific tool for the study 5HT3 receptor properties in the actions of drugs of abuse.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The chemical basis of pharmacology. | 2010-12-07 |
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| 5-HT3 receptor-dependent modulation of respiratory burst frequency, regularity, and episodicity in isolated adult turtle brainstems. | 2010-06-30 |
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| GABA(A) receptors mediate the attenuating effects of a 5-HT(3) receptor antagonist on methamphetamine-induced behavioral sensitization in mice. | 2010-04 |
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| Effects of serotonin on acid secretion in isolated rat stomach: the role of 5-HT3 receptors. | 2009-11-30 |
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| Effects of triterpenoids from Poria cocos Wolf on the serotonin type 3A receptor-mediated ion current in Xenopus oocytes. | 2009-08-01 |
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| Mechanisms of analgesic action of pulsed radiofrequency on adjuvant-induced pain in the rat: roles of descending adrenergic and serotonergic systems. | 2009-03 |
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| Long-term depression in the superior cervical ganglion of the rat. | 2008-10-09 |
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| A dual role of 5-hydroxytryptamine receptor 3 in serotonin induced ion transport in rat distal colon. | 2008-04-14 |
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| Dopamine neurotransmission is involved in the attenuating effects of 5-HT3 receptor antagonist MDL 72222 on acute methamphetamine-induced locomotor hyperactivity in mice. | 2008-01 |
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| Involvement of 5-HT receptors in the development and expression of methamphetamine-induced behavioral sensitization: 5-HT receptor channel and binding study. | 2006-11 |
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| Effects of repeated daily treatments with a 5-HT3 receptor antagonist on dopamine neurotransmission and functional activity of 5-HT3 receptors within the nucleus accumbens of Wistar rats. | 2006-06 |
|
| Effect of 5-HT3 receptor antagonist MDL 72222 on behaviors induced by ketamine in rats and mice. | 2006-05 |
|
| Rewarding properties of 1-benzylpiperazine, a new drug of abuse, in rats. | 2006-04 |
|
| Blockade of 5-HT(3) receptor with MDL7222 and Y25130 reduces hydrogen peroxide-induced neurotoxicity in cultured rat cortical cells. | 2005-12-05 |
|
| Antinociceptive effect of shakuyakukanzoto, a Kampo medicine, in diabetic mice. | 2005-12 |
|
| Blockade of 5-HT(3) receptor with MDL 72222 and Y 25130 reduces beta-amyloid protein (25--35)-induced neurotoxicity in cultured rat cortical neurons. | 2005-09-27 |
|
| Effects of quipazine and m-chlorophenylbiguanide (m-CPBG) on temporal differentiation: evidence for the involvement of 5-HT2A but not 5-HT3 receptors in interval timing behaviour. | 2005-09 |
|
| The serotonin type 3A receptor facilitates luteinizing hormone release and LHbeta promoter activity in immortalized pituitary gonadotropes. | 2005-06 |
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| Mechanisms of analgesic action of neurotropin on chronic pain in adjuvant-induced arthritic rat: roles of descending noradrenergic and serotonergic systems. | 2005-03 |
|
| Effects of quipazine and m-chlorophenylbiguanide (m-CPBG) on the discrimination of durations: evidence for the involvement of 5-HT2A but not 5-HT3 receptors. | 2005-02 |
|
| Evaluation of the anti-emetic potential of anti-migraine drugs to prevent resiniferatoxin-induced emesis in Suncus murinus (house musk shrew). | 2005-01-31 |
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| 5HT2 and 5HT3 receptors' contribution to modeling of post-serotonin respiratory pattern in cats. | 2004-09-24 |
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| Reduced 5-HT3 receptor binding and lower baseline plus maze anxiety in the alcohol-preferring inbred fawn-hooded rat. | 2004-02 |
|
| Roles for CCK1 and 5-HT3 receptors in the effects of CCK on presympathetic vasomotor neuronal discharge in the rat. | 2003-05 |
|
| 5-HT2 and 3 receptor antagonists suppress the response of rat type I slowly adapting mechanoreceptor: an in vitro study. | 2003-04-18 |
|
| Effects of ginsenoside Rg2 on the 5-HT3A receptor-mediated ion current in Xenopus oocytes. | 2003-02-28 |
|
| Conditional involvement of striatal serotonin3 receptors in the control of in vivo dopamine outflow in the rat striatum. | 2003-02 |
|
| Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats. | 2003-02 |
|
| Dual cooperative allosteric modulation of binding to ionotropic glycine receptors. | 2002-12 |
|
| Pharmacology of serotonin receptors modulating electrically-induced [3h]-norepinephrine release from isolated mammalian iris-ciliary bodies. | 2002-08 |
|
| 5-HT3 receptor antagonist MDL 72222 attenuates cocaine- and mazindol-, but not methylphenidate-induced neurochemical and behavioral effects in the rat. | 2002-02 |
|
| Effects of 5-HT2 and 5-HT3 receptors on the modulation of nociceptive transmission in rat spinal cord according to the formalin test. | 2001-07-13 |
|
| Serotonin and NO complementarily regulate generation of oscillatory activity in the olfactory CNS of a terrestrial mollusk. | 2001-06 |
Patents
Sample Use Guides
MDL 72,222 (Bemesetron) was given in 20 mg intravenous doses 30 minutes before chemotherapy, as well as 2, 6, and 12 hours after chemotherapy infusion
Route of Administration:
Intravenous
The properties of MDL 72222 (bemesetron) with potent and selective blocking actions at certain excitatory 5-hydroxytryptamine (5-HT) receptors on mammalian peripheral neurones, are described. On the rabbit isolated heart, MDL 72222 was a potent antagonist of responses mediated through the receptors for 5-HT present on the terminal sympathetic fibres. The threshold for antagonism was approximately 0.1 nM and the negative logarithm of the molar concentration of MDL 72222 which reduced the chronotropic response of the isolated rabbit heart to twice an ED50 of 5-HT to that of the ED50 was 9.27. MDL 72222 was also highly selective since responses to the nicotine receptor agonist, dimethylphenylpiperazinum iodine (DMPP), were inhibited only at concentrations more than 1000 times those necessary to inhibit 5-HT.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:40:38 GMT 2025
by
admin
on
Wed Apr 02 09:40:38 GMT 2025
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| Record UNII |
O98T3677PA
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| Record Status |
Validated (UNII)
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C94726
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C042253
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Bemesetron
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DTXSID8042632
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40796-97-2
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BB-8
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CHEMBL2107804
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100000086139
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SUB05692MIG
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6682
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C80766
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O98T3677PA
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TARGET -> INHIBITOR |
BINDING
IC50
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ACTIVE MOIETY |
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