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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
Effects of short term treatment with pentagastrin, proglumide, tamoxifen given separately or together with 5-fluorouracil on the growth in the murine transplantable Colon 38 cancer.
2001
Effect of three nonpeptide cholecystokinin antagonists on human isolated gallbladder.
2001 Dec
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
Eradication of Helicobacter pylori restores the inhibitory effect of cholecystokinin on gastric motility in duodenal ulcer patients.
2001 Mar
Inhibition of the preferential binding of actin to the N-terminal hydratase domain of the 78-kDa gastrin-binding protein by non-steroidal anti-inflammatory drugs and gastrin receptor antagonists.
2001 May 1
CCK1 central receptor antagonist prevented the intestinal stress symptoms in sheep.
2002
Modulation of cholestasis-induced antinociception by CCK receptor agonists and antagonists.
2002 Apr
Inhibitory effect of loxiglumide (CR 1505), a cholecystokinin receptor antagonist, on N-nitrosobis(2-oxopropyl) amine-induced biliary carcinogenesis in Syrian hamsters.
2002 Mar
Cholecystokinin reduces ethanol consumption in golden hamsters.
2003 Apr
Enterostatin inhibition of dietary fat intake is dependent on CCK-A receptors.
2003 Aug
Effect of cholecystokinin1 receptor antagonist loxiglumide (CR1505) on basal pancreatic exocrine secretion in conscious rats.
2003 Jan
Effect of Dai-kenchu-to (Da-Jian-Zhong-Tang) on the delayed intestinal propulsion induced by chlorpromazine in mice.
2003 May
Sensitive SPE-HPLC method to determine a novel angiotensin-AT1 antagonist in biological samples.
2004 Apr 16
Effects of juice from Morinda citrifolia (Noni) on gastric emptying in male rats.
2004 Dec 31
Anxiogenic effect of cholecystokinin in the dorsal periaqueductal gray.
2004 Jan
Involvement of capsaicin-sensitive afferent nerves and cholecystokinin 2/gastrin receptors in gastroprotection and adaptation of gastric mucosa to Helicobacter pylori-lipopolysaccharide.
2004 Jul
Expression of cannabinoid CB1 receptors by vagal afferent neurons is inhibited by cholecystokinin.
2004 Mar 17
Effect of lipopolysaccharide on expression and characterization of cholecystokinin receptors in rat pulmonary interstitial macrophages.
2004 Oct
Proopiomelanocortin neurons in nucleus tractus solitarius are activated by visceral afferents: regulation by cholecystokinin and opioids.
2005 Apr 6
Cholecystokinin octapeptide improves cardiac function by activating cholecystokinin octapeptide receptor in endotoxic shock rats.
2005 Jun 14
Role of cholecystokinin in appetite control and body weight regulation.
2005 Nov
The combined effects of proglumide and fluorouracil on the growth of murine Colon 38 cancer cells in vitro.
2005 Nov-Dec
Cholecystokinin octapeptide increases spontaneous glutamatergic synaptic transmission to neurons of the nucleus tractus solitarius centralis.
2005 Oct
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
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 the cholecystokinin A receptor antagonist loxiglumide on the proliferation and cell cycle time of pancreatic acinar cells in rats.
2006 Mar
Caerulein-induced acute pancreatitis in mice that constitutively overexpress Reg/PAP genes.
2006 May 15
Estrogen receptor alpha-induced cholecystokinin type A receptor expression in the female mouse pituitary.
2007 Dec
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 GMT 2023
Edited
by admin
on Sat Dec 16 17:59:01 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
FDA ORPHAN DRUG 762120
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
FDA ORPHAN DRUG 743020
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
FDA ORPHAN DRUG 756620
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
WHO-VATC QA02BX06
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
NCI_THESAURUS C29701
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
Code System Code Type Description
FDA UNII
EPL8W5565D
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
NSC
757841
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
CHEBI
32058
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
PUBCHEM
4922
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
NCI_THESAURUS
C81916
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
CAS
25727-74-6
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
SUPERSEDED
DRUG CENTRAL
2281
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
WIKIPEDIA
PROGLUMIDE
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
RXCUI
8730
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7023516
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL316561
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
INN
2161
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
MERCK INDEX
m9161
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
229-567-4
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
MESH
D011377
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
DRUG BANK
DB13431
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
CAS
24485-90-3
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
SUPERSEDED
CAS
6620-60-6
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
EVMPD
SUB10078MIG
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
SMS_ID
100000081122
Created by admin on Sat Dec 16 17:59:01 GMT 2023 , Edited by admin on Sat Dec 16 17:59:01 GMT 2023
PRIMARY
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