metoclopramide

Modify Date: 2024-01-02 19:35:16

metoclopramide Structure
metoclopramide structure
 Common Name metoclopramide
CAS Number 364-62-5 Molecular Weight 299.80
Density 1.2±0.1 g/cm3 Boiling Point 454.8±55.0 °C at 760 mmHg
Molecular Formula C14H22ClN3O2 Melting Point 146-148°C
MSDS Chinese USA Flash Point 228.9±31.5 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of metoclopramide


Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.IC50 Value:Target: D2 ReceptorMetoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. In various countries, metoclopramide is the antiemetic drug of choice in pregnant women. Findings provide reassurance regarding the safety of metoclopramide for the fetus when the drug is given to women to relieve nausea and vomiting during pregnancy. Evidence also supports its use for gastroparesis (poor stomach emptying) and gastroesophageal reflux disease. It appears to bind to dopamine D2 receptors where it is a receptor antagonist, and is also a mixed 5-HT3 receptor antagonist/ 5-HT4 receptor agonist.

 Names

Name metoclopramide
Synonym More Synonyms

 metoclopramide Biological Activity

Description Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic.IC50 Value:Target: D2 ReceptorMetoclopramide is a dopamine receptor antagonist which has been used for treatment of a variety of gastrointestinal symptoms over the last thirty years. In various countries, metoclopramide is the antiemetic drug of choice in pregnant women. Findings provide reassurance regarding the safety of metoclopramide for the fetus when the drug is given to women to relieve nausea and vomiting during pregnancy. Evidence also supports its use for gastroparesis (poor stomach emptying) and gastroesophageal reflux disease. It appears to bind to dopamine D2 receptors where it is a receptor antagonist, and is also a mixed 5-HT3 receptor antagonist/ 5-HT4 receptor agonist.
Related Catalog
References

[1]. Navari RM, Nagy CK, Gray SE. The use of olanzapine versus metoclopramide for the treatment of breakthrough chemotherapy-induced nausea and vomiting in patients receiving highly emetogenic chemotherapy. Support Care Cancer. 2013 Jan 12.

[2]. Gutiérrez-Hermosillo H, Díaz de León-González E, Beltrán Santiago D et al. Metoclopramide as a risk factor for postprandial hyperglycemia in type 2 diabetes. Nutr Hosp. 2012 Jul-Aug;27(4):1267-71.

[3]. Ilan Matok, Sc.Pharm., Rafael Gorodischer, et al. The Safety of Metoclopramide Use in the First Trimester of Pregnancy. N Engl J Med 2009; 360:2528-2535.

[4]. DN Bateman, C Kahn, K Mashiter, DS Davies. Pharmacokinetic and concentration-effect studies with intravenous metoclopramide. British Journal of Clinical Pharmacology.1978,6(5): 401-407

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 454.8±55.0 °C at 760 mmHg
Melting Point 146-148°C
Molecular Formula C14H22ClN3O2
Molecular Weight 299.80
Flash Point 228.9±31.5 °C
PSA 67.59000
LogP 3.10
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.545

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BZ3300000
CHEMICAL NAME :
n-Anisamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-
CAS REGISTRY NUMBER :
364-62-5
LAST UPDATED :
199801
DATA ITEMS CITED :
21
MOLECULAR FORMULA :
C14-H22-Cl-N3-O2
MOLECULAR WEIGHT :
299.84
WISWESSER LINE NOTATION :
2N2&2MVR DZ CG FO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
632 mg/kg/59D-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - toxic psychosis Behavioral - excitement
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
3600 ug/kg/6D-I
TOXIC EFFECTS :
Behavioral - tremor Gastrointestinal - changes in structure or function of salivary glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
900 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - diplopia Behavioral - muscle contraction or spasticity
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
111 mg/kg/37W-I
TOXIC EFFECTS :
Peripheral Nerve and Sensation - fasciculations
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
2 mg/kg/1D-C
TOXIC EFFECTS :
Behavioral - excitement
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
2400 ug/kg
TOXIC EFFECTS :
Vascular - BP elevation not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
14 ug/kg
TOXIC EFFECTS :
Vascular - BP elevation not characterized in autonomic section Biochemical - Neurotransmitters or modulators (putative) - catecholamine levels in sympathetic nerves
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
750 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
114 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
340 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
270 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
96 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
190 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
33 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 mg/kg/30D-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in ovarian weight Related to Chronic Data - changes in uterine weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
34 mg/kg
SEX/DURATION :
male 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - impotence
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1155 mg/kg
SEX/DURATION :
female 33 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Human Leukocyte
DOSE/DURATION :
100 nmol/L
REFERENCE :
CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 12,1613,1991 *** REVIEWS *** TOXICOLOGY REVIEW AJHPA9 American Journal of Hospital Pharmacy. (American Soc. of Hospital Pharmacists, 4630 Montgomery Ave., Bethesda, MD 20814) V.15- 1958- Volume(issue)/page/year: 38,829,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5297 No. of Facilities: 20 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 821 (estimated) No. of Female Employees: 456 (estimated)

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H362
Precautionary Statements P263
Hazard Codes Xn
Risk Phrases 22-64
Safety Phrases 36/37
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2924299090

 Synthetic Route

4-Amino-5-Chloro-2-Methoxybenzoic Acid structure

4-Amino-5-Chlor...

CAS#:7206-70-4

2-aminoethyldiethylamine structure

2-aminoethyldie...

CAS#:100-36-7

1-methanesulfonyloxy-1,2,3-benzotriazole structure

1-methanesulfon...

CAS#:54769-22-1

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: US4242507 A1, ;
4-Amino-5-Chloro-2-Methoxybenzoic Acid structure

4-Amino-5-Chlor...

CAS#:7206-70-4

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Journal of Medicinal Chemistry, , vol. 36, # 21 p. 3166 - 3170
N/A structure

N/A

CAS#:89881-28-7

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Zhichkin, Paul E.; Peterson, Lisa H.; Beer, Catherine M.; Rennells, W. Martin Journal of Organic Chemistry, 2008 , vol. 73, # 22 p. 8954 - 8959
carbon monoxide structure

carbon monoxide

CAS#:201230-82-2

2-Chloro-4-iodo-5-methoxyaniline structure

2-Chloro-4-iodo...

CAS#:1285695-15-9

2-aminoethyldiethylamine structure

2-aminoethyldie...

CAS#:100-36-7

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels Journal of the American Chemical Society, 2011 , vol. 133, # 15 p. 6061 - 6071
Methyl 4-amino-2-methoxybenzoate structure

Methyl 4-amino-...

CAS#:27492-84-8

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Archiv der Pharmazie, , vol. 313, # 4 p. 297 - 300
6-Chloro-m-anisidine structure

6-Chloro-m-anisidine

CAS#:2401-24-3

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Journal of the American Chemical Society, , vol. 133, # 15 p. 6061 - 6071
4-amino-5-chloro-2-methoxybenzoic (ethyl carbonic) anhydride structure

4-amino-5-chlor...

CAS#:150007-96-8

2-aminoethyldiethylamine structure

2-aminoethyldie...

CAS#:100-36-7

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Journal of Medicinal Chemistry, , vol. 36, # 21 p. 3166 - 3170
Methyl 4-acetamido-2-methoxybenzoate structure

Methyl 4-acetam...

CAS#:4093-29-2

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Archiv der Pharmazie, , vol. 313, # 4 p. 297 - 300
Methyl 4-acetamido-5-chloro-2-methoxybenzoate structure

Methyl 4-acetam...

CAS#:4093-31-6

2-aminoethyldiethylamine structure

2-aminoethyldie...

CAS#:100-36-7

~%

metoclopramide Structure

metoclopramide

CAS#:364-62-5

Literature: Archiv der Pharmazie, , vol. 313, # 4 p. 297 - 300

 Customs

HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

Pramin
Imperan
MAXOLON
Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-
Benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-
Reglan
Maxeran
EINECS 206-662-9
Plasil
metoclopramide
Benzenecarboximidic acid, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-
Eucil
Primperan
metoclopramidum [INN_la]
4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzenecarboximidic acid
4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,Methoxychloroprocainamide
4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide
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Related Compounds: More...
Metoclopramide-d3
1216522-89-2
MetoclopraMide HCI
54143-57-6
metoclopramide hcl
7232-21-5
metoclopramide sulfone
139339-72-3
metoclopramide sulfide
102670-58-6
metoclopramide N-oxide
171367-22-9
N-Acetylmetoclopramide
5608-13-9
N-deethyl-Metoclopramide
27260-19-1
Metoclopramide-d3 N-Oxide
1246816-54-5
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
2-Chloro-5-butylbenzonitrile
1237117-29-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
6-fluoro-4-hydroxy-N-(5-isopropyl-1,3,4-thiadiazol-2-yl)quinoline-3-carboxamide
951993-68-3
5-(Dimethyl-1,3-thiazol-5-yl)-1,3,4-oxadiazole-2-thiol
941133-94-4
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
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