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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

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
Loxiglumide, a CCK-A receptor antagonist, stimulates calorie intake and hunger feelings in humans.
2001 Apr
Synthesis, molecular modeling and QSAR studies in chiral 2,3-disubstituted-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indoles as potential modulators of opioid antinociception.
2001 Jun
Puerperal blockade of cholecystokinin (CCK1) receptors disrupts maternal behavior in lactating rats.
2002 Feb-Apr
Effects of cholecystokinin octapeptide on rat cardiac function and the receptor mechanism.
2002 Jun 25
Inhibitory effect of loxiglumide (CR 1505), a cholecystokinin receptor antagonist, on N-nitrosobis(2-oxopropyl) amine-induced biliary carcinogenesis in Syrian hamsters.
2002 Mar
Involvement of local cholecystokinin in the tolerance induced by morphine microinjections into the periaqueductal gray of rats.
2003 Mar
Sensitive SPE-HPLC method to determine a novel angiotensin-AT1 antagonist in biological samples.
2004 Apr 16
Cholecystokinin octapeptide increases free intracellular calcium of guinea pig cardiomyocytes through activation of Ca2+ channel and tyrosine kinase.
2004 Feb 25
[New aspects of pharmaco-therapy for acute pancreatitis].
2004 Nov
Cholecystokinin-induced satiety is mediated through interdependent cooperation of CCK-A and 5-HT3 receptors.
2004 Sep 30
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
The combined effects of proglumide and fluorouracil on the growth of murine Colon 38 cancer cells in vitro.
2005 Nov-Dec
Selective CCK-A but not CCK-B receptor antagonists inhibit HT-29 cell proliferation: synergism with pharmacological levels of melatonin.
2005 Oct
Cholecystokinin octapeptide increases spontaneous glutamatergic synaptic transmission to neurons of the nucleus tractus solitarius centralis.
2005 Oct
Mechanisms of oleoylethanolamide-induced changes in feeding behavior and motor activity.
2005 Sep
CCK1 antagonists: are they ready for clinical use?
2006
Anthranilic acid based CCK1 receptor antagonists and CCK-8 have a common step in their "receptor desmodynamic processes".
2006 Apr 20
Estrogen and CCK1 receptor modification of mu-opioid receptor binding in the cortex of female rats.
2006 Feb 16
[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
Cholecystokinin hyperresponsiveness in functional dyspepsia.
2006 May 7
Gastrin induces leukocyte-endothelial cell interactions in vivo and contributes to the inflammation caused by Helicobacter pylori.
2006 Nov
The biochemical and neuroendocrine bases of the hyperalgesic nocebo effect.
2006 Nov 15
Characterisation of a transgenic mouse expressing R122H human cationic trypsinogen.
2006 Oct 27
Vagally mediated, nonparacrine effects of cholecystokinin-8s on rat pancreatic exocrine secretion.
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
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
Peripheral participation of cholecystokinin in the morphine-induced peripheral antinociceptive effect in non-diabetic and diabetic rats.
2007 Mar
The use of animal models to study bacterial translocation during acute pancreatitis.
2007 May
Effect of intravenous infusion of proglumide on ruminal motility in conscious sheep (Ovis aries).
2007 Nov
The effect of luminal ghrelin on pancreatic enzyme secretion in the rat.
2007 Oct 4
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.
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 Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
NCI_THESAURUS C28197
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
FDA ORPHAN DRUG 762120
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
FDA ORPHAN DRUG 743020
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
FDA ORPHAN DRUG 756620
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
WHO-VATC QA02BX06
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
NCI_THESAURUS C29701
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
Code System Code Type Description
FDA UNII
EPL8W5565D
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
NSC
757841
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY
CHEBI
32058
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
PUBCHEM
4922
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY
NCI_THESAURUS
C81916
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY
CAS
25727-74-6
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
SUPERSEDED
DRUG CENTRAL
2281
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
WIKIPEDIA
PROGLUMIDE
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY
RXCUI
8730
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7023516
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL316561
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
INN
2161
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
MERCK INDEX
M9161
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
229-567-4
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
MESH
D011377
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
DRUG BANK
DB13431
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
CAS
24485-90-3
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
SUPERSEDED
CAS
6620-60-6
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
EVMPD
SUB10078MIG
Created by admin on Thu Jul 06 23:17:56 UTC 2023 , Edited by admin on Thu Jul 06 23:17:56 UTC 2023
PRIMARY
SMS_ID
100000081122
Created by admin on Thu Jul 06 23:17:57 UTC 2023 , Edited by admin on Thu Jul 06 23:17:57 UTC 2023
PRIMARY