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Updating {{drugbox}} (no changed fields - updated 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)
 
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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| verifiedrevid = 447569820
| verifiedrevid = 447569820
| IUPAC_name = (10R)-10-[(2-methyl-1''H''-imidazol-1-yl)methyl]-5,6,9,10<br>-tetrahydro-4''H''-pyrido(3,2,1-jk)carbazol-11-one
| IUPAC_name = (10''R'')-10-[(2-Methyl-1''H''-imidazol-1-yl)methyl]-5,6,9,10-tetrahydro-4''H''-pyrido(3,2,1-''jk'')carbazol-11-one
| image = Cilansetron.svg
| image = Cilansetron.svg


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<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 2297
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 120635-74-7
| CAS_number = 120635-74-7
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| ATC_suffix = AE03
| ATC_suffix = AE03
| PubChem = 6918107
| PubChem = 6918107
| ChEMBL = 2103778
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03495
| KEGG = D03495
| synonyms = Calmactin; KC 9946


<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=21 | N=3 | O=1
| C=20 | H=21 | N=3 | O=1
| molecular_weight = 319.4 g/mol
| smiles = O=C3c2c1cccc5c1n(c2CC[C@@H]3Cn4ccnc4C)CCC5
| smiles = O=C3c2c1cccc5c1n(c2CC[C@@H]3Cn4ccnc4C)CCC5
| InChI = 1/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1
| InChIKey = NCNFDKWULDWJDS-OAHLLOKOBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1
| StdInChI = 1S/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1
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}}
}}


'''Cilansetron''' is an experimental drug that is a [[5-HT3 antagonist|5-HT<sub>3</sub> antagonist]] under [[drug development|development]] by [[Solvay (company)|Solvay Pharmaceuticals]].<ref name="pmid15757394">{{cite journal | vauthors = Chey WD, Cash BD | title = Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea | journal = Expert Opinion on Investigational Drugs | volume = 14 | issue = 2 | pages = 185–93 | date = February 2005 | pmid = 15757394 | doi = 10.1517/13543784.14.2.185 | s2cid = 8606399 }}</ref><ref name="pmid16389408">{{cite journal | vauthors = Olden KW, Crowell MD | title = Cilansetron | journal = Drugs of Today | location = Barcelona, Spain | volume = 41 | issue = 10 | pages = 661–6 | date = October 2005 | pmid = 16389408 | doi = 10.1358/dot.2005.41.10.920427 }}</ref><ref name="pmid19072430">{{cite journal | vauthors = Stacher G | title = Cilansetron in the treatment of diarrhea-predominant irritable bowel syndrome? | journal = Expert Review of Gastroenterology & Hepatology | volume = 1 | issue = 1 | pages = 15–27 | date = October 2007 | pmid = 19072430 | doi = 10.1586/17474124.1.1.15 | s2cid = 24301639 }}</ref>
'''Cilansetron''' is a drug that is a [[5HT-3 antagonist]] currently under trial phase in the EU and US it is manufactured by [[Solvay (company)|Solvay Pharmaceuticals INC]].


[[5HT-3 receptor]]s are responsible for causing many things from nausea to excess [[Defecation|bowel movements]]. It is thought in conditions like [[irritable bowel syndrome]] (IBS) the receptors have become faulty or oversensitive. 5HT-3 antagonists work by blocking the nervous and chemical signals from reaching these receptors.
[[5-HT3 receptor|5-HT<sub>3</sub> receptors]] are responsible for causing many things from nausea to excess [[Defecation|bowel movements]]. In conditions such as [[irritable bowel syndrome]] (IBS), the receptors have become faulty or oversensitive. 5-HT<sub>3</sub> antagonists work by blocking the nervous and chemical signals from reaching these receptors.


Studies have shown that the drug can greatly improve quality of life in men and women with diahorrea predominant IBS ([http://www.drugdevelopment-technology.com/projects/cilanserton/ 1]) Cilansetron is the first 5HT antagonist specifically designed for IBS that is effective in men as well as women.([http://www.drugdevelopment-technology.com/projects/cilanserton/ 1])
Studies have shown that the drug can improve quality of life in men and women with diarrhea-predominant IBS.<ref name=cilanserton>[http://www.drugdevelopment-technology.com/projects/cilanserton/ General info on Cilansetron]</ref> Cilansetron is the first 5-HT antagonist specifically designed for IBS that is effective in men as well as women.<ref name=cilanserton/>


In 2005, Solvay received response from the U.S. Food and Drug Administration that cilansertron is not approvable without additional clinical trials;<ref>{{cite news | url = http://www.pharmatimes.com/news/solvays_cilansetron_not_approvable_998463 | title = Solvay's cilansetron "not approvable" | date = April 4, 2005 | publisher = PharmaTimes | access-date = August 14, 2019}}</ref><ref>{{cite web | url = https://www.drugs.com/history/calmactin.html | title = Calmactin Approval Status | access-date = August 14, 2019 | publisher = [[Drugs.com]] }}</ref> further development has been discontinued.<ref>{{cite web | url = https://adisinsight.springer.com/drugs/800005297 | title = Cilansetron | access-date = August 14, 2019}}</ref>
Solvay has had considerable difficulty with the medicines regulators in the UK, EU and USA with regards to licensing the drug. This could possibly be due to the problems discovered after licensing with the drug [[Alosetron|Lotronex]]. At time of writing; Solvay had recently withdrawn its application to the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) but was continuing its talks with the MHRA in the UK and EU regulators. ([http://www.solvaypress.com/pressreleases/0,,36423-2-0,00.htm#contact 2])

It is not currently known what sort of timeframe the public are looking at to be able to obtain the drug. This matter is not helped by the lack of information about cilansetron and its trials in the public domain. The regulators have also stated this in their responses.{{Citation needed|date=October 2007}}

There is no information about future trials currently available.

Some people have tried the Anti-emetic [[ondansetron]] HCl (Zofran) as a substitute for the time being, results are mixed but noted effect has been shown in some males and females ([http://www.blackwell-synergy.com/doi/abs/10.1046/j.1365-2036.1996.30172000.x 3])
However; due to its license in the UK it is usually only prescribable at consultant level. Since the licensing of a generic version it is more likely an NHS prescription will be accepted as the branded version is very expensive (Official NHS pricing.) In the USA and Canada: availability often depends on insurance and the doctors personal opinion on off-label prescribing.


==References==
==References==
{{reflist}}
# http://www.drugdevelopment-technology.com/projects/cilanserton (General info on Cilansetron.)
# http://www.solvaypress.com/pressreleases/0,,36423-2-0,00.htm#contact (Sovay press relaase 19 November 2005.)
# http://www.blackwell-synergy.com/doi/abs/10.1046/j.1365-2036.1996.30172000.x (Clinical trial for 5-HT3 antagonists use in Diarrhoea-predominant IBS)</small>


{{Drugs for functional gastrointestinal disorders}}
{{Drugs for functional gastrointestinal disorders}}
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[[Category:Imidazoles]]
[[Category:Imidazoles]]
[[Category:Ketones]]
[[Category:Ketones]]
[[Category:Nitrogen heterocycles]]
[[Category:Drugs developed by AbbVie]]
[[Category:Abandoned drugs]]
[[Category:Heterocyclic compounds with 4 rings]]

Latest revision as of 19:25, 20 December 2023

Cilansetron
Clinical data
Other namesCalmactin; KC 9946
Pregnancy
category
  • C
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Unlicensed
Pharmacokinetic data
Bioavailability87%
MetabolismHepatic
Elimination half-life1.6 - 1.9 hours
ExcretionRenal
Identifiers
  • (10R)-10-[(2-Methyl-1H-imidazol-1-yl)methyl]-5,6,9,10-tetrahydro-4H-pyrido(3,2,1-jk)carbazol-11-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H21N3O
Molar mass319.408 g·mol−1
3D model (JSmol)
  • O=C3c2c1cccc5c1n(c2CC[C@@H]3Cn4ccnc4C)CCC5
  • InChI=1S/C20H21N3O/c1-13-21-9-11-22(13)12-15-7-8-17-18(20(15)24)16-6-2-4-14-5-3-10-23(17)19(14)16/h2,4,6,9,11,15H,3,5,7-8,10,12H2,1H3/t15-/m1/s1 checkY
  • Key:NCNFDKWULDWJDS-OAHLLOKOSA-N checkY
  (verify)

Cilansetron is an experimental drug that is a 5-HT3 antagonist under development by Solvay Pharmaceuticals.[1][2][3]

5-HT3 receptors are responsible for causing many things from nausea to excess bowel movements. In conditions such as irritable bowel syndrome (IBS), the receptors have become faulty or oversensitive. 5-HT3 antagonists work by blocking the nervous and chemical signals from reaching these receptors.

Studies have shown that the drug can improve quality of life in men and women with diarrhea-predominant IBS.[4] Cilansetron is the first 5-HT antagonist specifically designed for IBS that is effective in men as well as women.[4]

In 2005, Solvay received response from the U.S. Food and Drug Administration that cilansertron is not approvable without additional clinical trials;[5][6] further development has been discontinued.[7]

References

[edit]
  1. ^ Chey WD, Cash BD (February 2005). "Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea". Expert Opinion on Investigational Drugs. 14 (2): 185–93. doi:10.1517/13543784.14.2.185. PMID 15757394. S2CID 8606399.
  2. ^ Olden KW, Crowell MD (October 2005). "Cilansetron". Drugs of Today. 41 (10). Barcelona, Spain: 661–6. doi:10.1358/dot.2005.41.10.920427. PMID 16389408.
  3. ^ Stacher G (October 2007). "Cilansetron in the treatment of diarrhea-predominant irritable bowel syndrome?". Expert Review of Gastroenterology & Hepatology. 1 (1): 15–27. doi:10.1586/17474124.1.1.15. PMID 19072430. S2CID 24301639.
  4. ^ a b General info on Cilansetron
  5. ^ "Solvay's cilansetron "not approvable"". PharmaTimes. April 4, 2005. Retrieved August 14, 2019.
  6. ^ "Calmactin Approval Status". Drugs.com. Retrieved August 14, 2019.
  7. ^ "Cilansetron". Retrieved August 14, 2019.
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