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CAS No.: | 6620-60-6 |
---|---|
Name: | Proglumide |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C18H26N2O4 |
Molecular Weight: | 334.415 |
Synonyms: | Milid;Milide;Nulsa;Proglumide;Promid;Promide (parasympatholytic);Ulcutin;W 5219;Xyde;Xylamide;Xylamide(gastroprotective agent);Glutaramicacid, 4-benzamido-N,N-dipropyl-, DL- (8CI);Pentanoic acid,4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (?à)-;Binoside;CR 242;DL-4-Benzamido-N,N-dipropylglutaramicacid;DL-Proglumide;Gastrotopic;Midelid;Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (±)-; |
EINECS: | 229-567-4 |
Density: | 1.136 g/cm3 |
Melting Point: | 148-150°C |
Boiling Point: | 589.8 °C at 760 mmHg |
Flash Point: | 310.5 °C |
Appearance: | White solid |
PSA: | 86.71000 |
LogP: | 2.68930 |
proglumide
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1h; | 95% |
N-benzoyl-DL-glutamic acid-anhydride
di-n-propylamine
A
proglumide
B
proglumide
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 3h; | A n/a B 16.2% |
proglumide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 1.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 2.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme |
proglumide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane 2.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 3.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 3.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 4.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane 2.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 3.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 3.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 4.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme |
proglumide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; trichlorophosphate / dichloromethane / 2 h / -30 °C 2.1: potassium fluoride; 18-crown-6 ether / tetrahydrofuran / 0.17 h / 60 °C / Inert atmosphere; Sealed tube 2.2: 1.5 h / 60 °C / Inert atmosphere; Sealed tube 3.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; Inert atmosphere; | 75% |
methanol
proglumide
A
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
B
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
Conditions | Yield |
---|---|
With Candida cylindraceae In hexane at 35℃; Product distribution; Further Variations:; Reaction partners; Reagents; Temperatures; Solvents; Enzymatic reaction; |
propan-1-ol
proglumide
A
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
B
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
Conditions | Yield |
---|---|
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts; |
octanol
proglumide
A
5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
B
5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
Conditions | Yield |
---|---|
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts; |
The Proglumide, with the CAS registry number 6620-60-6 and EINECS registry number 229-567-4, has the systematic name of N2-benzoyl-N,N-dipropyl-α-glutamine. And the molecular formula of this chemical is C18H26N2O4. And its classification codes are: Anti-ulcer agents; Anticholinergic; Drug/herapeutic Agent; Gastrointestinal Agents; Reproductive Effect.
The Proglumide is a drug that exerts an inhibitory effect on gastric secretion and reduces gastrointestinal motility. It is used clinically in the drug therapy of gastrointestinal ulcers. What's more, it also acts as a δ-opioid agonist, which may contribute to its analgesic effects. And it also works as a placebo effect amplifier for pain conditions.
The physical properties of Proglumide are as following: (1)ACD/LogP: 2.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): -0.3; (5)ACD/BCF (pH 5.5): 4.58; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 52.56; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 66.92 Å2; (13)Index of Refraction: 1.534; (14)Molar Refractivity: 91.47 cm3; (15)Molar Volume: 294.2 cm3; (16)Polarizability: 36.26×10-24cm3; (17)Surface Tension: 46.4 dyne/cm; (18)Density: 1.136 g/cm3; (19)Flash Point: 310.5 °C; (20)Enthalpy of Vaporization: 92.57 kJ/mol; (21)Boiling Point: 589.8 °C at 760 mmHg; (22)Vapour Pressure: 9.33E-15 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NC(C(=O)N(CCC)CCC)CCC(=O)O)c1ccccc1
(2)InChI: InChI=1/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)
(3)InChIKey: DGMKFQYCZXERLX-UHFFFAOYAW
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1480mg/kg (1480mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978. | |
mouse | LD50 | intravenous | 2250mg/kg (2250mg/kg) | Minerva Medica. Vol. 58, Pg. 3653, 1967. | |
mouse | LD50 | oral | 2250mg/kg (2250mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 10, Pg. 892, 1968. | |
mouse | LD50 | subcutaneous | > 5190mg/kg (5190mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE ENDOCRINE: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 203, 1971. |
rat | LD50 | intraperitoneal | 1420mg/kg (1420mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978. | |
rat | LD50 | oral | 20gm/kg (20000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 20, Pg. 447, 1978. | |
rat | LD50 | subcutaneous | > 5190mg/kg (5190mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) ENDOCRINE: OTHER CHANGES SKIN AND APPENDAGES (SKIN): CORROSIVE: AFTER TOPICAL EXPOSURE | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 203, 1971. |