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: RefChem:929978, omeprazole, 73590-58-6, Losec, Antra (+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 swallowed
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)
Constituent Elements
Isomers8 compounds with formula C₁₇H₁₉N₃O₃S
6-methoxy-2-[(S)-(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole
CID 9568614 · 345.4 g/mol
5-(dimethylamino)-N-(3,4-dimethyl-1,2-oxazol-5-yl)naphthalene-1-sulfonamide
CID 122272 · 345.4 g/mol
6-methoxy-2-[(R)-(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-benzimidazole
CID 9579578 · 345.4 g/mol
N-(1,3-dimethyl-2-oxobenzimidazol-5-yl)-2,4-dimethylbenzenesulfonamide
CID 1253361 · 345.4 g/mol
1-ethyl-6-piperazin-1-ylsulfonylbenzo[cd]indol-2-one
CID 741724 · 345.4 g/mol
N,1,3,6-tetramethyl-2-oxo-N-phenylbenzimidazole-5-sulfonamide
CID 5300967 · 345.4 g/mol
N-(3,4-dimethylphenyl)-1,3-dimethyl-2-oxobenzimidazole-5-sulfonamide
CID 2990488 · 345.4 g/mol
2-[(6-ethoxy-1,3-benzothiazol-2-yl)diazenyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
CID 135439904 · 345.4 g/mol