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Proglumide
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Name

Proglumide

 EINECS 229-567-4
CAS No. 6620-60-6 Density 1.136 g/cm3
PSA 86.71000 LogP 2.68930
Solubility N/A Melting Point 148-150°C
Formula C18H26N2O4 Boiling Point 589.8 °C at 760 mmHg
Molecular Weight 334.415 Flash Point 310.5 °C
Transport Information N/A Appearance White solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 6620-60-6 (Proglumide) Hazard Symbols N/A
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-, (±)-;

 

Proglumide Synthetic route

benzyl 4-benzamido-5-(dipropylamino)-5-oxopentanoate

6620-60-6

proglumide

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1h;95%
91569-94-7

N-benzoyl-DL-glutamic acid-anhydride

142-84-7

di-n-propylamine

A

6620-60-6

proglumide

B

102743-01-1

proglumide

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 3h;A n/a
B 16.2%

benzyl 5-(dipropylamino)-4-isocyano-5-oxopentanoate

6620-60-6

proglumide

Conditions
ConditionsYield
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

5-(benzyloxy)-2-formamido-5-oxopentanoic acid

6620-60-6

proglumide

Conditions
ConditionsYield
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
142-84-7

di-n-propylamine

6620-60-6

proglumide

Conditions
ConditionsYield
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

benzyl 5-(dipropylamino)-4-formamido-5-oxopentanoate

6620-60-6

proglumide

Conditions
ConditionsYield
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
18274-81-2

desmethyl anethole trithione

6620-60-6

proglumide

C27H30N2O4S3

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; Inert atmosphere;75%
67-56-1

methanol

6620-60-6

proglumide

A

32999-84-1

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B

32999-90-9

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C

N-benzoyl-N',N'-dipropyl-S-isoglutamine methyl ester

D

N-benzoyl-N',N'-dipropyl-R-isoglutamine methyl ester

Conditions
ConditionsYield
With Candida cylindraceae In hexane at 35℃; Product distribution; Further Variations:; Reaction partners; Reagents; Temperatures; Solvents; Enzymatic reaction;
...Expand
71-23-8

propan-1-ol

6620-60-6

proglumide

A

32999-84-1

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B

32999-90-9

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C

N-benzoyl-N',N'-dipropyl-S-isoglutamine propyl ester

D

N-benzoyl-N',N'-dipropyl-R-isoglutamine propyl ester

Conditions
ConditionsYield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;
...Expand
111-87-5

octanol

6620-60-6

proglumide

A

32999-84-1

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid

B

32999-90-9

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid

C

N-benzoyl-N',N'-dipropyl-S-isoglutamine octyl ester

D

N-benzoyl-N',N'-dipropyl-R-isoglutamine octyl ester

Conditions
ConditionsYield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;
...Expand

Proglumide Specification

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.

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