metoclopramide   

GtoPdb Ligand ID: 241

Synonyms: metaclopromide | methochlopramide | metochlopramide | metoclopramide hydrochloride | Reglan®
metoclopramide is an approved drug (FDA (1979))
Compound class: Synthetic organic
Comment: Metoclopramide is a promarily dopamine receptor antagonist, but it also exhibits mixed 5-HT3 receptor antagonist/5-HT4 receptor agonist activity.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 67.59
Molecular weight 299.14
XLogP 1.85
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
Isomeric SMILES CCN(CCNC(=O)c1cc(Cl)c(cc1OC)N)CC
InChI InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)
InChI Key TTWJBBZEZQICBI-UHFFFAOYSA-N
References
1. Brady CA, Stanford IM, Ali I, Lin L, Williams JM, Dubin AE, Hope AG, Barnes NM. (2001)
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
Neuropharmacology, 41 (2): 282-4. [PMID:11489465]
2. Claeysen S, Sebben M, Journot L, Bockaert J, Dumuis A. (1996)
Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor.
FEBS Lett., 398 (1): 19-25. [PMID:8946946]
3. Hope AG, Peters JA, Brown AM, Lambert JJ, Blackburn TP. (1996)
Characterization of a human 5-hydroxytryptamine3 receptor type A (h5-HT3R-AS) subunit stably expressed in HEK 293 cells.
Br. J. Pharmacol., 118 (5): 1237-45. [PMID:8818349]
4. Matsui A, Matsuo H, Takanaga H, Sasaki S, Maeda M, Sawada Y. (1998)
Prediction of catalepsies induced by amiodarone, aprindine and procaine: similarity in conformation of diethylaminoethyl side chain.
J. Pharmacol. Exp. Ther., 287 (2): 725-32. [PMID:9808703]