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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
Structure of PROGLUMIDE

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)

HIDE SMILES / InChI

Molecular Formula C18H26N2O4
Molecular Weight 334.41
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
250.0 µM [IC50]
900.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Proglumide

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Opioidergic effects of nonopioid analgesics on the central nervous system.
2002 Dec
Role of CCK(A) receptors in postprandial lower esophageal sphincter function in morbidly obese subjects.
2002 Nov
Involvement of cholecystokinin receptor in the inhibition of gastrointestinal motility by estradiol in ovariectomized rats.
2002 Oct
Effect of cholecystokinin-A receptor blockade on postprandial insulinaemia and gastric emptying in humans.
2002 Oct
Cholecystokinin reduces ethanol consumption in golden hamsters.
2003 Apr
Pharmacological effects of oxytocin on gastric emptying and intestinal transit of a non-nutritive liquid meal in female rats.
2003 Apr
[Effects of cholecystokinin-octapeptide on the tension of pulmonary artery in rabbits with endotoxic shock].
2003 Apr 25
Enterostatin inhibition of dietary fat intake is dependent on CCK-A receptors.
2003 Aug
CCK-1 receptor blockade for treatment of biliary colic: a pilot study.
2003 Aug 1
Involvement of local cholecystokinin in the tolerance induced by morphine microinjections into the periaqueductal gray of rats.
2003 Mar
Role of leptin in the control of feeding of goldfish Carassius auratus: interactions with cholecystokinin, neuropeptide Y and orexin A, and modulation by fasting.
2003 May 16
The cholecystokinin antagonist proglumide enhances the analgesic effect of dihydrocodeine.
2003 May-Jun
Circulating ethanol does not stimulate pancreatic secretion in conscious rats.
2003 Nov
Differential mechanism and site of action of CCK on the pancreatic secretion and growth in rats.
2003 Oct
The effects of an essential fatty acid compound and a cholecystokinin-8 antagonist on iron deficiency induced anorexia and learning deficits.
2004 Apr
Analysis of strain difference in behavior to Cholecystokinin (CCK) receptor mediated drugs in PVG hooded and Sprague-Dawley rats using elevated plus-maze test apparatus.
2004 Apr 1
Glycine-extended gastrin induces matrix metalloproteinase-1- and -3-mediated invasion of human colon cancer cells through type I collagen gel and Matrigel.
2004 Aug 10
Effects of juice from Morinda citrifolia (Noni) on gastric emptying in male rats.
2004 Dec 31
Differential contribution of cholecystokinin receptors to stress-induced modulation of seizure and nociception thresholds in mice.
2004 Jun
Long-term bile diversion enhances basal and duodenal oleate-stimulated pancreatic exocrine secretion in dogs.
2004 Jun
[New aspects of pharmaco-therapy for acute pancreatitis].
2004 Nov
Involvement of cholecystokinin in the opioid tolerance induced by dipyrone (metamizol) microinjections into the periaqueductal gray matter of rats.
2004 Nov
Effect of lipopolysaccharide on expression and characterization of cholecystokinin receptors in rat pulmonary interstitial macrophages.
2004 Oct
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
Cholecystokinin-induced satiety is mediated through interdependent cooperation of CCK-A and 5-HT3 receptors.
2004 Sep 30
Proopiomelanocortin neurons in nucleus tractus solitarius are activated by visceral afferents: regulation by cholecystokinin and opioids.
2005 Apr 6
Effect of cholecystokinin octapeptide on diacylglycerol-PKC signaling pathway in rat pulmonary interstitial macrophages stimulated by lipopolysaccharide.
2005 Dec
Cholecystokinin octapeptide improves cardiac function by activating cholecystokinin octapeptide receptor in endotoxic shock rats.
2005 Jun 14
Proglumide attenuates experimental colitis in rats.
2005 Mar
Long-term effects of proglumide on resection of cardiac adenocarcinoma.
2005 May 7
Role of cholecystokinin in appetite control and body weight regulation.
2005 Nov
Selective CCK-A but not CCK-B receptor antagonists inhibit HT-29 cell proliferation: synergism with pharmacological levels of melatonin.
2005 Oct
Mechanisms of oleoylethanolamide-induced changes in feeding behavior and motor activity.
2005 Sep
Cholecystokinin1 receptors mediate the increase in Fos-like immunoreactivity in the rat myenteric plexus following intestinal oleate infusion.
2005 Sep 15
CCK1 antagonists: are they ready for clinical use?
2006
Effects of amylin on feeding of goldfish: interactions with CCK.
2006 Jan 15
[Effects of gastrin receptor antagonist and cyclooxygenase-2 inhibitor on proliferation and apoptosis of gastric cancer cell].
2006 Jan 24
Naloxone, not proglumide or MK-801, alters effects of morphine preexposure on morphine-induced taste aversions.
2006 May
Caerulein-induced acute pancreatitis in mice that constitutively overexpress Reg/PAP genes.
2006 May 15
Cholecystokinin hyperresponsiveness in functional dyspepsia.
2006 May 7
Characterisation of a transgenic mouse expressing R122H human cationic trypsinogen.
2006 Oct 27
Cholecystokinin-8s excites identified rat pancreatic-projecting vagal motoneurons.
2007 Aug
Estrogen receptor alpha-induced cholecystokinin type A receptor expression in the female mouse pituitary.
2007 Dec
Mechanism of the induction of brain c-Fos-positive neurons by lipid absorption.
2007 Jan
The inhibitory effect of proglumide on meal-induced insulin sensitization in rats.
2007 Jul
Activation of spinal cholecystokinin and neurokinin-1 receptors is associated with the attenuation of intrathecal morphine analgesia following electroacupuncture stimulation in rats.
2007 Jun
Enterostatin (APGPR) enhances memory consolidation in mice.
2007 Mar
The use of animal models to study bacterial translocation during acute pancreatitis.
2007 May
Gastric antisecretory drugs induce leukocyte-endothelial cell interactions through gastrin release and activation of CCK-2 receptors.
2007 Oct
Interaction of apolipoprotein AIV with cholecystokinin on the control of food intake.
2007 Oct
Patents

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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:59:01 UTC 2023
Edited
by admin
on Sat Dec 16 17:59:01 UTC 2023
Record UNII
EPL8W5565D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROGLUMIDE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
PROGLUMIDE [MI]
Common Name English
CR-242
Code English
ULCUTIN
Brand Name English
PROGLUMIDE [JAN]
Common Name English
Proglumide [WHO-DD]
Common Name English
MILID
Brand Name English
XYLAMIDE
Brand Name English
GASTROTOPIC
Brand Name English
BINOSIDE
Brand Name English
MIDELID
Brand Name English
(±)-4-BENZAMIDO-N,N-DIPROPYLGLUTARAMIC ACID
Systematic Name English
PROGLUMIDE [MART.]
Common Name English
proglumide [INN]
Common Name English
W-5219
Code English
PROMID
Brand Name English
4-(BENZOYLAMINO)-5-(DIPROPYLAMINO)-5-OXOPENTANOIC ACID
Systematic Name English
XYDE
Brand Name English
PENTANOIC ACID, 4-(BENZOYLAMINO)-5-(DIPROPYLAMINO)-5-OXO-, (±)-
Common Name English
NULSA
Brand Name English
DL-PROGLUMIDE
Common Name English
PROGLUMIDE [USAN]
Common Name English
NSC-757841
Code English
GLUTARAMIC ACID, 4-BENZAMIDO-N,N-DIPROPYL-, DL-
Common Name English
Classification Tree Code System Code
WHO-ATC A02BX06
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
FDA ORPHAN DRUG 762120
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
FDA ORPHAN DRUG 743020
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
FDA ORPHAN DRUG 756620
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
WHO-VATC QA02BX06
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
NCI_THESAURUS C29701
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
Code System Code Type Description
FDA UNII
EPL8W5565D
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
NSC
757841
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
CHEBI
32058
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
PUBCHEM
4922
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
NCI_THESAURUS
C81916
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
CAS
25727-74-6
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
SUPERSEDED
DRUG CENTRAL
2281
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
WIKIPEDIA
PROGLUMIDE
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
RXCUI
8730
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7023516
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL316561
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
INN
2161
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
MERCK INDEX
m9161
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
229-567-4
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
MESH
D011377
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
DRUG BANK
DB13431
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
CAS
24485-90-3
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
SUPERSEDED
CAS
6620-60-6
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
EVMPD
SUB10078MIG
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
SMS_ID
100000081122
Created by admin on Sat Dec 16 17:59:01 UTC 2023 , Edited by admin on Sat Dec 16 17:59:01 UTC 2023
PRIMARY
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