(2S)-4-Diisopropylamino-2,2-diphenyl-butyramide

ID: ALA8821

Chembl Id: CHEMBL8821

Cas Number: 74464-84-9

PubChem CID: 156295

Max Phase: Preclinical

Molecular Formula: C21H29N3O

Molecular Weight: 339.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: disopiramide | 74464-84-9|Disopyramide, (S)-|4HB8OU08NH|S-(+)-disopyramide|D-DISOPYRAMIDE|(S)-DISOPYRAMIDE|DISOPYRAMIDE, D-|(+)-DISOPYRAMIDE|UNII-4HB8OU08NH|CHEMBL8821|SCHEMBL41811|(+)-(S)-DISOPYRAMIDE|(S)-(+)-DISOPYRAMIDE|DTXSID301043597|2-Pyridineacetamide, alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-, (S)-|NS00116086|(2S)-4-(dipropan-2-ylamino)-2-phenyl-2-(pyridin-2-yl)butanamide|2-PYRIDINEACETAMIDE, .ALPHA.-(2-(BIS(1-METHYLETHYL)AMINO)ETHYL)-.ALPHA.-PHENYL-, (.ALPHA.S)-|2-PYRIDINEAShow More⌵

Canonical SMILES:  CC(C)N(CC[C@](C(N)=O)(c1ccccc1)c1ccccn1)C(C)C

Standard InChI:  InChI=1S/C21H29N3O/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)/t21-/m0/s1

Standard InChI Key:  UVTNFZQICZKOEM-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA8821

   (S)-DISOPYRAMIDE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 339.48

Molecular Weight (Monoisotopic): 339.2311

AlogP: 3.36

#Rotatable Bonds: 8

Polar Surface Area: 59.22

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.42

CX LogP: 3.47

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.80

Np Likeness Score: -0.74

References

1. Burke TR, Nelson WL, Mangion M, Hite GJ, Mokler CM, Ruenitz PC..  (1980)  Resolution, absolute configuration, and antiarrhythmic properties of the enantiomers of disopyramide, 4-(diisopropylamino)-2-(2-pyridyl)-2-phenylbutyramide.,  23  (9): [PMID:7411548] [10.1021/jm00183a015]

2. Nelson WL, Sneed CK, Giacomini KM, Giacomini JC, Stauss J, Blaschke TF, Cox BM..  (1981)  Synthesis and anticholinergic properties of the enantiomers of 4-(isopropylamino)-2-(2-pyridyl)-2-phenylbutyramide, the mono-N-dealkylated metabolite of disopyramide.,  24  (5): [PMID:7241519] [10.1021/jm00137a024]

3. Moda TL, Montanari CA, Andricopulo AD..  (2007)  Hologram QSAR model for the prediction of human oral bioavailability.,  15  (24): [PMID:17870541] [10.1016/j.bmc.2007.08.060]

4. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

5. Alimuddin M, Grant D, Bulloch D, Lee N, Peacock M, Dahl R..  (2008)  Determination of log D via automated microfluidic liquid-liquid extraction.,  51  (16): [PMID:18666772] [10.1021/jm8005228]

6. Garrido A, Lepailleur A, Mignani SM, Dallemagne P, Rochais C..  (2020)  hERG toxicity assessment: Useful guidelines for drug design.,  195  [PMID:32283295] [10.1016/j.ejmech.2020.112290]

Source

Source(1):

• Scientific Literature