Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H26N2O4 |
Molecular Weight | 334.41 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1
InChI
InChIKey=DGMKFQYCZXERLX-UHFFFAOYSA-N
InChI=1S/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2862828Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2299627 | https://www.ncbi.nlm.nih.gov/pubmed/2741440 | https://www.drugs.com/international/proglumide.html | https://goo.gl/d51Yn7 | https://www.ncbi.nlm.nih.gov/pubmed/3651819 | https://www.ncbi.nlm.nih.gov/pubmed/2994583
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2862828
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2299627 | https://www.ncbi.nlm.nih.gov/pubmed/2741440 | https://www.drugs.com/international/proglumide.html | https://goo.gl/d51Yn7 | https://www.ncbi.nlm.nih.gov/pubmed/3651819 | https://www.ncbi.nlm.nih.gov/pubmed/2994583
Proglumide is a drug that inhibits gastrointestinal motility and reduces gastric secretions. It acts as a cholecystokinin antagonist, which blocks both the CCKA and CCKB subtypes. It was used mainly in the treatment of stomach ulcers, although it has now been largely replaced by newer drugs for this application. An interesting side effect of proglumide is that it enhances the analgesia produced by opioid drugs, and can prevent or even reverse the development of tolerance to opioid drugs. This can make it a useful adjuvant treatment to use alongside opioid drugs in the treatment of chronic pain conditions such as cancer, where opioid analgesics may be required for long periods and development of tolerance reduces clinical efficacy of these drugs.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2299627 |
250.0 µM [IC50] | ||
Target ID: CHEMBL298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2299627 |
900.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Proglumide Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The effects of an essential fatty acid compound and a cholecystokinin-8 antagonist on iron deficiency induced anorexia and learning deficits. | 2004 Apr |
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Suppression of food intake by GI fatty acid infusions: roles of celiac vagal afferents and cholecystokinin. | 2004 Aug |
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Effects of juice from Morinda citrifolia (Noni) on gastric emptying in male rats. | 2004 Dec 31 |
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Differential contribution of cholecystokinin receptors to stress-induced modulation of seizure and nociception thresholds in mice. | 2004 Jun |
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[New aspects of pharmaco-therapy for acute pancreatitis]. | 2004 Nov |
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Involvement of cholecystokinin in the opioid tolerance induced by dipyrone (metamizol) microinjections into the periaqueductal gray matter of rats. | 2004 Nov |
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Effect of lipopolysaccharide on expression and characterization of cholecystokinin receptors in rat pulmonary interstitial macrophages. | 2004 Oct |
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Pharmacological study of IQM-97,423, a potent and selective CCK1 receptor antagonist with protective effect in experimental acute pancreatitis. | 2004 Oct |
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Use of a hepta-Tyr antibiotic modified silica stationary phase for the enantiomeric resolution of D,L-loxiglumide by electrochromatography and nano-liquid chromatography. | 2004 Oct 8 |
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Cholecystokinin-induced satiety is mediated through interdependent cooperation of CCK-A and 5-HT3 receptors. | 2004 Sep 30 |
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Proopiomelanocortin neurons in nucleus tractus solitarius are activated by visceral afferents: regulation by cholecystokinin and opioids. | 2005 Apr 6 |
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Effect of cholecystokinin octapeptide on diacylglycerol-PKC signaling pathway in rat pulmonary interstitial macrophages stimulated by lipopolysaccharide. | 2005 Dec |
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Cholecystokinin inhibits evoked inhibitory postsynaptic currents in the rat nucleus accumbens indirectly through gamma-aminobutyric acid and gamma-aminobutyric acid type B receptors. | 2005 Feb 1 |
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Cholecystokinin octapeptide improves cardiac function by activating cholecystokinin octapeptide receptor in endotoxic shock rats. | 2005 Jun 14 |
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Proglumide attenuates experimental colitis in rats. | 2005 Mar |
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Long-term effects of proglumide on resection of cardiac adenocarcinoma. | 2005 May 7 |
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Role of cholecystokinin in appetite control and body weight regulation. | 2005 Nov |
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The combined effects of proglumide and fluorouracil on the growth of murine Colon 38 cancer cells in vitro. | 2005 Nov-Dec |
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Selective CCK-A but not CCK-B receptor antagonists inhibit HT-29 cell proliferation: synergism with pharmacological levels of melatonin. | 2005 Oct |
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Cholecystokinin octapeptide increases spontaneous glutamatergic synaptic transmission to neurons of the nucleus tractus solitarius centralis. | 2005 Oct |
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Mechanisms of oleoylethanolamide-induced changes in feeding behavior and motor activity. | 2005 Sep |
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Cholecystokinin1 receptors mediate the increase in Fos-like immunoreactivity in the rat myenteric plexus following intestinal oleate infusion. | 2005 Sep 15 |
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CCK1 antagonists: are they ready for clinical use? | 2006 |
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Anthranilic acid based CCK1 receptor antagonists and CCK-8 have a common step in their "receptor desmodynamic processes". | 2006 Apr 20 |
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Activation of neural cholecystokinin-1 receptors induces relaxation of the isolated rat duodenum which is reduced by nitric oxide synthase inhibitors. | 2006 Feb |
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Estrogen and CCK1 receptor modification of mu-opioid receptor binding in the cortex of female rats. | 2006 Feb 16 |
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Effects of amylin on feeding of goldfish: interactions with CCK. | 2006 Jan 15 |
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[Effects of gastrin receptor antagonist and cyclooxygenase-2 inhibitor on proliferation and apoptosis of gastric cancer cell]. | 2006 Jan 24 |
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Effects of the cholecystokinin A receptor antagonist loxiglumide on the proliferation and cell cycle time of pancreatic acinar cells in rats. | 2006 Mar |
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[Receptor mechanisms underlying the modulation of lipopolysaccharide-induced nuclear factor-kappaB expression in vascular endothelial cells by cholecystokinin octapeptide]. | 2006 Mar |
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Naloxone, not proglumide or MK-801, alters effects of morphine preexposure on morphine-induced taste aversions. | 2006 May |
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Involvement of cholecystokinin in peripheral nociceptive sensitization during diabetes in rats as revealed by the formalin response. | 2006 May |
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Caerulein-induced acute pancreatitis in mice that constitutively overexpress Reg/PAP genes. | 2006 May 15 |
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Cholecystokinin hyperresponsiveness in functional dyspepsia. | 2006 May 7 |
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Gastrin induces leukocyte-endothelial cell interactions in vivo and contributes to the inflammation caused by Helicobacter pylori. | 2006 Nov |
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The biochemical and neuroendocrine bases of the hyperalgesic nocebo effect. | 2006 Nov 15 |
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Characterisation of a transgenic mouse expressing R122H human cationic trypsinogen. | 2006 Oct 27 |
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Cholecystokinin-8s excites identified rat pancreatic-projecting vagal motoneurons. | 2007 Aug |
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Vagally mediated, nonparacrine effects of cholecystokinin-8s on rat pancreatic exocrine secretion. | 2007 Aug |
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Estrogen receptor alpha-induced cholecystokinin type A receptor expression in the female mouse pituitary. | 2007 Dec |
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Mechanism of the induction of brain c-Fos-positive neurons by lipid absorption. | 2007 Jan |
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The inhibitory effect of proglumide on meal-induced insulin sensitization in rats. | 2007 Jul |
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Activation of spinal cholecystokinin and neurokinin-1 receptors is associated with the attenuation of intrathecal morphine analgesia following electroacupuncture stimulation in rats. | 2007 Jun |
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Enterostatin (APGPR) enhances memory consolidation in mice. | 2007 Mar |
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Peripheral participation of cholecystokinin in the morphine-induced peripheral antinociceptive effect in non-diabetic and diabetic rats. | 2007 Mar |
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The use of animal models to study bacterial translocation during acute pancreatitis. | 2007 May |
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Effect of intravenous infusion of proglumide on ruminal motility in conscious sheep (Ovis aries). | 2007 Nov |
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Gastric antisecretory drugs induce leukocyte-endothelial cell interactions through gastrin release and activation of CCK-2 receptors. | 2007 Oct |
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Interaction of apolipoprotein AIV with cholecystokinin on the control of food intake. | 2007 Oct |
|
The effect of luminal ghrelin on pancreatic enzyme secretion in the rat. | 2007 Oct 4 |
Patents
Sample Use Guides
PO 400 mg 2-4 times/day, up to 800 mg 3 times/day. IV/IM 400-800 mg/day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2994583
The cell lines SW 403, Ls 174 T and Lovo (provided by the Institute for Immunbiology, Freiburg) were cultured in Dulbecco's or RPMI medium, with 10% fetal calf serum and antibiotics. The effects of proglumide (Milid, Opfermann, Bergisch-Gladbach) were estimated by cell count (Neubauer) and measurement of incorporation of [3H]thymidine (Amersham-Buchler, Braunschweig). Cells were counted after trypsinization (0.03%, 37 ~ C, 30rain in Hank's EDTA, Gibco) at the second and eighth day of culture. After cell harvesting, [3H]thymidine incorporation was estimated by beta counting equipment. Six-well plates containing 4 x 104 cells were used in each cellcounting experiment; 96-well plates were used for each [3H]thymidine-incorporation experiment. Medium was changed every second day and cell viability was proved by eosin staining. Gastrin and CEA concentrations were estimated by radioimmunoassay (Travenol, M/inchen; Abbott, Wiesbaden) in cell-culture medium. For synchronization the cells were incubated for 48 h in Dulbecco's or RPMI medium without fetal calf serum (37 ~ C). The cells were then cooled to 4 ~ C for 24 h and fetal calf serum (10%) and thymidine (2 nmol) were added. About 70%-75% cells survived this procedure, as has been shown by eosin staining. After 24 h the cells were incubated with various concentrations of gastrin, pentagastrin or proglumide.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
A02BX06
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NCI_THESAURUS |
C28197
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FDA ORPHAN DRUG |
762120
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FDA ORPHAN DRUG |
743020
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FDA ORPHAN DRUG |
756620
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WHO-VATC |
QA02BX06
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NCI_THESAURUS |
C29701
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EPL8W5565D
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757841
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32058
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4922
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25727-74-6
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2281
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PROGLUMIDE
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8730
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DTXSID7023516
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CHEMBL316561
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2161
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m9161
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229-567-4
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D011377
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DB13431
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24485-90-3
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6620-60-6
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SUB10078MIG
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100000081122
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ACTIVE MOIETY