ID: ALA1200470

Max Phase: Approved

First Approval: 2005

Molecular Formula: C17H18N3NaO3S

Molecular Weight: 345.42

Molecule Type: Small molecule

Representations

Synonyms (3): Esomeprazole (as sodium) | Esomeprazole sodium | H199/18 SODIUM
Synonyms from Alternative Forms(3):

Trade Names(2): Esomeprazole sodium | Nexium iv

Canonical SMILES:  COc1ccc2[n-]c([S@@+]([O-])Cc3ncc(C)c(OC)c3C)nc2c1.[Na+]

Standard InChI:  InChI=1S/C17H18N3O3S.Na/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;/h5-8H,9H2,1-4H3;/q-1;+1/t24-;/m0./s1

Standard InChI Key:  RYXPMWYHEBGTRV-JIDHJSLPSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: Yes

Properties

Molecular Weight: 345.42

Molecular Weight (Monoisotopic): 345.1147

AlogP: 2.90

#Rotatable Bonds: 5

Polar Surface Area: 83.09

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.68

CX Basic pKa: 4.77

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.69

References

1. Unpublished dataset, 

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Bi Y, Might M, Vankayalapati H, Kuberan B..  (2017)  Repurposing of Proton Pump Inhibitors as first identified small molecule inhibitors of endo-β-N-acetylglucosaminidase (ENGase) for the treatment of NGLY1 deficiency, a rare genetic disease.,  27  (13): [PMID:28512024] [10.1016/j.bmcl.2017.05.010]

4. Unpublished dataset, 

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names