Devazepide

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Basic information

CAS: 103420-77-5
Standard SMILES: CN1C(=O)[C@@H](NC(=O)c2cc3ccccc3[nH]2)N=C(c2ccccc2)c2ccccc21
InChIKey: NFHRQQKPEBFUJK-HSZRJFAPSA-N
Molecular formula: C25H20N4O2
Average molar mass: 408.5 g/mol
Monoisotopic mass: 408.15862589

Overview

Devazepide is an indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used for treatment of gastrointestinal disorders. It has a role as an antineoplastic agent, a gastrointestinal drug, an apoptosis inducer and a cholecystokinin antagonist. It is a 1,4-benzodiazepinone and an indolecarboxamide.

Names & identifiers

Preferred name: Devazepide
IUPAC: N-[(3S)-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]-1H-indole-2-carboxamide
English name: DEVAZEPIDE
Molecular formula: C25H20N4O2
Molecular weight: 408.45

Names & synonyms

DEVAZEPIDE103420-77-5MK-329DevazepidaDevazepidumMK 329L-364,718(S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)indole-2-carboxamideDTXSID2046092JE6P7QY7NHL 364718L-364718

Show more names

718evazepideEVAZEPIDE, PANOSMK-329(DevazepideBetaxolol Impurity 12(3S)-1-Methyl-3-[(1H-indol-2-yl)carbonylamino]-5-phenyl-1H-1,4-benzodiazepin-2(3H)-one

BRN 5156082L 364,7183(S)-(-)-1,3-Dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-(1,4)benzodiazepin-2-oneCHEBI:4460DTXCID0026092N-[(3S)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-1H-indole-2-carboxamide1H-Indole-2-carboxamide, N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-, (S)-MK329

Database identifiers

CAS: 103420-77-5
PubChem CID: 443375

Properties

Computed structural properties

XLogP: 4.2
Topological polar surface area: 77.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 31
Formal charge: 0
Complexity: 716

Physicochemical properties

Boiling point: 758.6 · 758.6±60.0 °C(Predicted)
Density: 1.31 · 1.31±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 5 mg/mL · DMSO: >5mg/mL
pka: 13.25 · 13.25±0.40(Predicted)
form: powder
color: white to off-white
InChI: 1S/C25H20N4O2/c1-29-21-14-8-6-12-18(21)22(16-9-3-2-4-10-16)27-23(25(29)31)28-24(30)20-15-17-11-5-7-13-19(17)26-20/h2-15,23,26H,1H3,(H,28,30)/t23-/m1/s1
InChIKey: NFHRQQKPEBFUJK-HSZRJFAPSA-N
SMILES: CN1C(=O)[C@@H](NC(=O)c2cc3ccccc3[nH]2)N=C(c4ccccc4)c5ccccc15
FDA UNII: 6 P7QY7NH · JE6P7QY7NH
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Safety data

wgk: 3
rtecs: NL5994460
ridadr: UN 2811 6.1 / PGI
risk_code: 28
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+
safety_code: 28-36/37-45
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard statements: H300
Hazard Classifications: Acute Tox. 1 Oral
Precautionary statements: P264-P301+P310

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.

Applications · 3 items

UsesAntagonist (cholecystokinin).

UsesDevazepide has been used as a cholecystokinin receptor 1 (CCK1R) antagonist in human embryonic kidney 293T cells and in human pancreatic slices.

General DescriptionDevazepide is derived from asperlicin by chemical modification and has the benzodiazepine backbone.

Additional notes · 1 item

DefinitionChEBI: An indolecarboxamide obtained by formal condensation of the carboxy group of indole-2-carboxylic acid with the exocyclic amino group of (3S)-3-amino-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one. A cholecystokinin antagonist used f r treatment of gastrointestinal disorders.

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