Compound: proglumide
SMILES: O=C(NC(C(=O)N(CCC)CCC)CCC(=O)O)c1ccccc1
InChIKey: DGMKFQYCZXERLX-UHFFFAOYSA-N
Synonyms: proglumide, 6620-60-6, 4-benzamido-5-(dipropylamino)-5-oxopentanoic acid, Binoside, Xylamide, dl-proglumide, Milid, Nulsa, Gastrotopic, Midelid, Ulcutin, Proglumida, Xyde, Proglumidum, Promid, W-5219, 242 DL, CR-242, (+-)-4-Benzamido-N,N-dipropylglutaramic acid, W 5219, NSC-757841, EPL8W5565D, Glutaramic acid, 4-benzamido-N,N-dipropyl-, DL-, DTXSID7023516, 4-(benzoylamino)-5-(dipropylamino)-5-oxopentanoic acid, DTXCID003516, CHEBI:32058, Xilamide, RefChem:868577, A02BX06, (4RS)-4-Benzoylamino-N,N-dipropylglutaramic acid, 229-567-4, Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, MFCD00055071, Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (+-)-, DL-4-benzamido-N,N-dipropylglutaramic acid, CHEMBL316561, Milide, 4-(Benzoylamino)-5-(dipropylamino)-5-oxo-pentanoic Acid, Proglumidum [INN-Latin], Proglumida [INN-Spanish], Promide (parasympatholytic), CR 242, 24485-90-3, Xylamide (gastroprotective agent), SR-01000002970, EINECS 229-567-4, BRN 4151696, UNII-EPL8W5565D, 4-(N,N-dipropylcarbamoyl)-4-(phenylcarbonylamino)butanoic acid, racemic proglumide, (RS)-proglumide, Proglumide [USAN:INN:BAN:JAN], NCGC00016676-01, (+-)-proglumide, Prestwick_602, CAS-6620-60-6, Nulsa (TN), (+/-)-Proglumide, Spectrum_001332, PROGLUMIDE [MI], PROGLUMIDE [INN], PROGLUMIDE [JAN], Prestwick0_000240, Prestwick1_000240, Prestwick2_000240, Prestwick3_000240, Spectrum2_001406, Spectrum3_001444, Spectrum4_000425, Spectrum5_001591, PROGLUMIDE [USAN], PROGLUMIDE [MART.], (+/-)-4-Benzamido-N,N-dipropylglutaramic acid, PROGLUMIDE [WHO-DD], Lopac0_000832, SCHEMBL93339, BSPBio_000319, BSPBio_002907, GTPL893, KBioGR_000750, KBioSS_001812, MLS002154246, DivK1c_000684, SPECTRUM1501119, 4-benzamido-5-(dipropylamino)-5-oxo-pentanoic acid, SPBio_001452, SPBio_002240, 4-(Benzoylamino)-5-(dipropylamino)-5-oxovaleric acid, BPBio1_000351, orb1309933, Proglumide - Bio-X trade mark, Proglumide (JP17/USAN/INN), CHEBI:76266, HMS502C06, KBio1_000684, KBio2_001812, KBio2_004380, KBio2_006948, KBio3_002407, NINDS_000684, GLXC-06113, HMS1568P21, HMS1921F19, HMS2092D13, HMS2095P21, HMS2235B24, HMS3262H05, HMS3369D14, HMS3712P21, Pharmakon1600-01501119, HY-B1330, MSK10335, Tox21_110557, Tox21_500832, BDBM50014888, CCG-39024, NSC757841, SBB058173, AKOS015895810, Tox21_110557_1, AC-1274, CS-8029, DB13431, FP27175, KS-1212, LP00832, NSC 757841, SDCCGSBI-0050809.P004, 4-Benzamido-N,N-dipropylglutaramic acid, IDI1_000684, NCGC00015623-03, NCGC00015623-04, NCGC00015623-05, NCGC00015623-06, NCGC00015623-07, NCGC00015623-10, NCGC00015623-14, NCGC00094163-01, NCGC00094163-02, NCGC00094163-03, NCGC00094163-04, NCGC00261517-01, BP166197, DA-66886, SMR001233513, SBI-0050809.P003, N(2)-benzoyl-N,N-dipropyl-alpha-glutamine, N~2~-Benzoyl-N,N-dipropyl-alpha-glutamine, AB00052206, EU-0100832, M-001, NS00004778, ST51015098, 4-Benzoylamino-4-dipropylcarbamoyl-butyric acid, D01818, G12126, rac-N(2)-benzoyl-N,N-dipropyl-alpha-glutamine, AB00052206_08, 4-Benzoylamino-5-dipropylamino-5-oxopentanoic acid, N~2~-(phenylcarbonyl)-N,N-dipropyl-alpha-glutamine, Q7248362, SR-01000002970-2, SR-01000002970-4, SR-01000002970-7, BRD-A44863528-001-05-8, BRD-A44863528-001-08-2, BRD-A44863528-001-13-2, PENTANOIC ACID, 4-(BENZOYLAMINO)-5-(DIPROPYLAMINO)-5-OXO-, (+/-)-
Theoretical properties:
molecular_formula: C18H26N2O4
molecular_weight: 334.4 g/mol
exact_mass: 334.18925731 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 10
heavy_atom_count: 24
topological_polar_surface_area: 86.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Proglumide is a racemate composed of equal amounts of (R)- and (S)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs. It has a role as an opioid analgesic, a cholinergic antagonist, a drug metabolite, an anti-ulcer drug, a gastrointestinal drug, a delta-opioid receptor agonist, a cholecystokinin antagonist and a xenobiotic metabolite. It contains a (R)-proglumide and a (S)-proglumide.", "chebi": "A racemate composed of equal amounts of (<i>R</i>)- and (<i>S</i>)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs.", "chembl": "PROGLUMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Proglumide, sold under the brand name Milid, 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.\nAn 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.\nProglumide has also been shown to act as a \u03b4-opioid receptor (DOR) agonist, which may contribute to its analgesic effects. However, other studies show that proglumide has low affinity to the \u03bc-opioid receptor (MOR) and the \u03ba-opioid receptor (KOR) (13% of MOR and 17% of KOR occupancy at 100 \u03bcM), but no affinity to DOR. It is questionable whether this is clinically significant, since the concentration they used was very high, and the occupancies were low even at that point. \nProglumide also works as a placebo effect amplifier for pain conditions. When injected visibly to a subject, its analgesic effect is bigger than a similarly administered placebo. When injected secretly, it does not have any effect, whereas standard pain drugs have an effect, even if they are administered without the subject's awareness. The supposed mechanism is an enhancement of the neural pathways of expectation as a result of dopamine and endogenous opioids being suddenly released throughout numerous structures of the brain and spinal cord.\nThe ventral tegmental area is the structure believed to mediate proglumide's analgesic and euphoric effects, however dozens of areas with a wide range of physical and psychological functions are implicated in the mediation of the placebo effect (this accounts for proglumide's ability to produce physically measurable effects on vital signs such as heart rate, blood pressure, respiration rate, and tidal volume which cannot be accounted for by its clinically insignificant \u03b4-opioid affinity."}