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6620-60-6

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6620-60-6 Usage

Description

Proglumide (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.Proglumide is a nonpeptide and orally active cholecystokinin (CCK)-A/B receptors antagonist. Proglumide selective blocks CCK’s effects in the central nervous system (CNS). Proglumide has ability to inhibit gastric secretion and to protect the gastroduodenal mucosa. Proglumide also has antiepileptic and antioxidant activities.

Chemical Properties

White Solid

Uses

Anticholinergic.

Brand name

Nulsa (Wallace).

Side effects

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.Proglumide has also been shown to act as a δ-opioid agonist, which may contribute to its analgesic effects.

Safety Profile

Moderately toxic by severalroutes. An experimental teratogen. When heated todecomposition it emits toxic fumes of NOx.

Enzyme inhibitor

This anticholinergic agent (FWfree-acid = 334.42 g/mol; CAS 6620-60-6), also known as DL-4-benzamido-N,N-dipropylglutaramic acid and 4- (benzoylamino)-5-(dipropylamino)-5-oxopentanoic acid, is a cholecystokinin receptor antagonist. Proglumide A also exerts an inhibitory effect on gastric secretion and reduces gastrointestinal motility. It finds use clinically as a therapy for gastrointestinal ulcers. Target(s): cholecystokinin receptor; gastrin receptor.

Check Digit Verification of cas no

The CAS Registry Mumber 6620-60-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,2 and 0 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6620-60:
(6*6)+(5*6)+(4*2)+(3*0)+(2*6)+(1*0)=86
86 % 10 = 6
So 6620-60-6 is a valid CAS Registry Number.
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)

6620-60-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name proglumide

1.2 Other means of identification

Product number -
Other names N-benzoyl-N',N'-dipropyl-RS-isoglutamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6620-60-6 SDS

6620-60-6Synthetic route

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

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

proglumide
6620-60-6

proglumide

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1h;95%
N-benzoyl-DL-glutamic acid-anhydride
91569-94-7

N-benzoyl-DL-glutamic acid-anhydride

di-n-propylamine
142-84-7

di-n-propylamine

A

proglumide
6620-60-6

proglumide

B

proglumide
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

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

proglumide
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

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

proglumide
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
di-n-propylamine
142-84-7

di-n-propylamine

proglumide
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

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

proglumide
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
desmethyl anethole trithione
18274-81-2

desmethyl anethole trithione

proglumide
6620-60-6

proglumide

C27H30N2O4S3

C27H30N2O4S3

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

methanol

proglumide
6620-60-6

proglumide

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

D

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

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;
propan-1-ol
71-23-8

propan-1-ol

proglumide
6620-60-6

proglumide

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

D

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

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;
octanol
111-87-5

octanol

proglumide
6620-60-6

proglumide

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

D

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

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;
n-heptan1ol
111-70-6

n-heptan1ol

proglumide
6620-60-6

proglumide

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

D

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

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

Conditions
ConditionsYield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;
proglumide
6620-60-6

proglumide

butan-1-ol
71-36-3

butan-1-ol

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

Conditions
ConditionsYield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction;
proglumide
6620-60-6

proglumide

hexan-1-ol
111-27-3

hexan-1-ol

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

C

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

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

D

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

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

Conditions
ConditionsYield
With Candida cylindracea In hexane at 30℃; for 33h; Enzymatic reaction; Title compound not separated from byproducts;
proglumide
6620-60-6

proglumide

A

5-dipropylamino-4(S)-benzamido-5-oxo-pentanoic acid
32999-84-1

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

B

5-dipropylamino-4(R)-benzamido-5-oxo-pentanoic acid
32999-90-9

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

Conditions
ConditionsYield
With MCCD-HPS packed column In hydrogenchloride; acetonitrile pH=8.6;
With (R)-1-phenyl-ethyl-amine In ethanol Solvent; Heating;A n/a
B 98 g
With ammonium formate In methanol at 20℃; pH=3.6; Reagent/catalyst; Solvent; Resolution of racemate;

6620-60-6Relevant articles and documents

Generation of Oxyphosphonium Ions by Photoredox/Cobaloxime Catalysis for Scalable Amide and Peptide Synthesis in Batch and Continuous-Flow

Chen, Xiangyang,Houk, Kendall N.,Mo, Jia-Nan,Su, Junqi,Umanzor, Alexander,Zhang, Zheng,Zhao, Jiannan

, (2022/01/06)

Phosphine-mediated deoxygenative nucleophilic substitutions, such as the Mitsunobu reaction, are of great importance in organic synthesis. However, the conventional protocols require stoichiometric oxidants to trigger the formation of the oxyphosphonium i

New glutamic and aspartic derivatives with potent CCK-antagonistic activity

Makovec,Chiste,Bani,et al.

, p. 9 - 20 (2007/10/02)

New derivatives of aspartic and glutamic acid were synthesized and evaluated in vitro and in vivo for anti-CCK activity on the guinea pig gallbladder. The anti-CCK activity of some 4-benzamido-glutaramic acid derivatives was a hundred times greater than that of proglutamide, the model compound, and they have been selected for further studies.

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