Mosapride citrate

Modify Date: 2024-01-04 06:54:36

Mosapride citrate Structure
Mosapride citrate structure
 Common Name Mosapride citrate
CAS Number 112885-42-4 Molecular Weight 614.016
Density N/A Boiling Point 549.2ºC at 760mmHg
Molecular Formula C27H33ClFN3O10 Melting Point N/A
MSDS N/A Flash Point 286ºC

 Use of Mosapride citrate


Mosapride citrate is a gastroprokinetic agent that acts as a selective 5HT4 agonist.Target: 5HT4 Mosapride is a gastroprokinetic agent that acts as a selective 5HT4 agonist. The major active metabolite of mosapride, known as M1, additionally acts as a 5HT3 antagonist, which accelerates gastric emptying throughout the whole of the gastrointestinal tract in humans, and is used for the treatment of gastritis, gastro-oesophageal reflux disease, functional dyspepsia and irritable bowel syndrome. It is recommended to be taken on an empty stomach (i.e. at least one hour before food or two hours after food).In addition to its prokinetic properties, mosapride also exerts anti-inflammatory effects on the gastrointestinal tract which may contribute to some of its therapeutic effects. Mosapride also promotes neurogenesis in the gastrointestinal tract which may prove useful in certain bowel disorders. The neurogenesis is due to mosapride's effect on the 5-HT4 receptor where it acts as an agonist.Its common side effects include dry mouth, abdominal pain, dizziness, headache, insomnia, malaise, nausea, diarrhoea and sometimes constipation. Unlike some other prokinetic agents, mosapride has little effect on potassium channels, no effect on hERG transfected cells, and no effect on cardiovascular function that could be detected in tests on humans. Due to the pharmacokinetics of mosapride, it would take 1,000 - 3,000 times the therapeutic dose to elicit cardiovascular effects.

 Names

Name Mosapride citrate
Synonym More Synonyms

 Mosapride citrate Biological Activity

Description Mosapride citrate is a gastroprokinetic agent that acts as a selective 5HT4 agonist.Target: 5HT4 Mosapride is a gastroprokinetic agent that acts as a selective 5HT4 agonist. The major active metabolite of mosapride, known as M1, additionally acts as a 5HT3 antagonist, which accelerates gastric emptying throughout the whole of the gastrointestinal tract in humans, and is used for the treatment of gastritis, gastro-oesophageal reflux disease, functional dyspepsia and irritable bowel syndrome. It is recommended to be taken on an empty stomach (i.e. at least one hour before food or two hours after food).In addition to its prokinetic properties, mosapride also exerts anti-inflammatory effects on the gastrointestinal tract which may contribute to some of its therapeutic effects. Mosapride also promotes neurogenesis in the gastrointestinal tract which may prove useful in certain bowel disorders. The neurogenesis is due to mosapride's effect on the 5-HT4 receptor where it acts as an agonist.Its common side effects include dry mouth, abdominal pain, dizziness, headache, insomnia, malaise, nausea, diarrhoea and sometimes constipation. Unlike some other prokinetic agents, mosapride has little effect on potassium channels, no effect on hERG transfected cells, and no effect on cardiovascular function that could be detected in tests on humans. Due to the pharmacokinetics of mosapride, it would take 1,000 - 3,000 times the therapeutic dose to elicit cardiovascular effects.
Related Catalog
References

[1]. Tack J, et al. Systematic review: cardiovascular safety profile of 5-HT(4) agonists developed for gastrointestinal disorders. Aliment Pharmacol Ther. 2012 Apr;35(7):745-67.

[2]. Curran MP, et al. Mosapride in gastrointestinal disorders. Drugs. 2008;68(7):981-91.

[3]. Odaka T, et al. Serotonin 5- HT4 receptor agonist (mosapride citrate). Nihon Rinsho. 2006 Aug;64(8):1491-4.

 Chemical & Physical Properties

Boiling Point 549.2ºC at 760mmHg
Molecular Formula C27H33ClFN3O10
Molecular Weight 614.016
Flash Point 286ºC
Exact Mass 613.183838
PSA 212.44000
LogP 2.93620
Vapour Pressure 4.11E-12mmHg at 25°C
Storage condition Desiccate at RT

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CU9316000
CAS REGISTRY NUMBER :
112885-42-4
LAST UPDATED :
199603
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C21-H25-Cl-F-N3-O3.C6-H8-O7
MOLECULAR WEIGHT :
614.08

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Liver - other changes
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
914 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>400 mg/kg
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3343,1993 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
27 gm/kg/13W-I
TOXIC EFFECTS :
Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3351,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9100 mg/kg/26W-I
TOXIC EFFECTS :
Gastrointestinal - changes in structure or function of salivary glands Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - lipids including transport
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3397,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
18200 mg/kg/13W-I
TOXIC EFFECTS :
Liver - changes in liver weight Endocrine - changes in spleen weight Blood - changes in platelet count
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3379,1993 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
99 gm/kg
SEX/DURATION :
male 13 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male Reproductive - Maternal Effects - other effects
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3411,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
330 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3423,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7800 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3447,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7800 mg/kg
SEX/DURATION :
female 17-21 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral Reproductive - Effects on Newborn - delayed effects
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3447,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6500 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3469,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3200 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - sex ratio
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 21,3469,1993

 Safety Information

Hazard Codes Xi

 Synthetic Route

Mosapride structure

Mosapride

CAS#:112885-41-3

~86%

Mosapride citrate Structure

Mosapride citrate

CAS#:112885-42-4

Literature: Richter Gedeon Vegyeszeti Gyar RT. Patent: WO2003/106440 A2, 2003 ; Location in patent: Page 10 ;
N/A structure

N/A

CAS#:636582-76-8

~83%

Mosapride citrate Structure

Mosapride citrate

CAS#:112885-42-4

Literature: Richter Gedeon Vegyeszeti Gyar RT. Patent: WO2003/106440 A2, 2003 ; Location in patent: Page 10 ;
Mosapride structure

Mosapride

CAS#:112885-41-3

Citric Acid structure

Citric Acid

CAS#:77-92-9

~96%

Mosapride citrate Structure

Mosapride citrate

CAS#:112885-42-4

Literature: RANBAXY LABORATORIES LIMITED; HASHMI, Mohd Salman; MADHRA, Mukesh Kumar; IF2 Patent: WO2011/107903 A1, 2011 ; Location in patent: Page/Page column 11 ;

 Synonyms

4-Amino-5-chloro-2-ethoxy-N-{[4-(4-fluorobenzyl)morpholin-2-yl]methyl}benzamide 2-hydroxypropane-1,2,3-tricarboxylate (1:1)
(±)-4-Amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamide Citrate
4-amino-5-chloro-2-ethoxy-N-{[4-(4-fluorobenzyl)morpholin-2-yl]methyl}benzamide 2-hydroxypropane-1,2,3-tricarboxylate (salt)
Benzamide (4-amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]-2-morpholinyl]methyl]
4-Amino-5-chloro-2-ethoxy-N-{[4-(4-fluorobenzyl)-2-morpholinyl]methyl}benzamide 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
Benzamide, 4-amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]-2-morpholinyl]methyl]-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1) (salt)
UNII:MF497J489P
4-amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl]benzamide,2-hydroxypropane-1,2,3-tricarboxylic acid
MFCD00874415
Mosapride Citrate
Mosapride (citrate)
Mosapride Impurity 2
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