Omeprazole
C₁₇H₁₉N₃O₃S·345.416 g/mol·Pharmaceutical·CID 4594
Drug
The first proton pump inhibitor (PPI), irreversibly blocking gastric H⁺/K⁺-ATPase to reduce stomach acid production by up to 99%. Revolutionized treatment of peptic ulcers and GERD. One of the most prescribed drugs worldwide.
IUPAC: 6-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole
Also known as: 73590-58-6, Losec, Antra, Omeprazon, Audazol (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
345.400g/mol
Exact Mass
345.114713Da
Monoisotopic Mass
345.114713Da
XLogP
2.2
Polar Surface Area
96.3Ų
Complexity
453
Formal Charge
0
H-Bond Donors
1
H-Bond Acceptors
6
Rotatable Bonds
5
Heavy Atoms
24
Stereo Centers
0
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 345.4 g/mol
MW ≤ 500
✓ 2.2
LogP ≤ 5
✓ 1
H-bond donors ≤ 5
✓ 6
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
GHS Hazard Classification
Warning
Hazards
H302Harmful if swallowedH312Harmful in contact with skinH315Causes skin irritationH317May cause an allergic skin reactionH319Causes serious eye irritationH332Harmful if inhaledH335May cause respiratory irritationH412Harmful to aquatic life with long lasting effects
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C17H19N3O3S/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,(H,19,20)