| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-04-16 16:47:42 |
| Primary Accession Number |
DB00448 |
| Secondary Accession Number |
|
| Name |
Lansoprazole |
| Drug Type |
- Approved
- Investigational
- Small Molecule
|
| Description |
Lansoprazole is a proton pump inhibitor which prevents the stomach from producing acid. It is manufactured by TAP Pharmaceutical Products. Lansoprazole has been marketed for many years and is one of several PPI's available. |
| Synonyms |
- AG 1749
- lansoprazole
|
| Brand Names |
- Agopton
- Amarin
- Aprazol
- Bamalite
- Biuret
- Biuret Gr
- Biuret Reagent
- Biuret Reagent Solution
- Blason
- Compraz
- Dakar
- Ilsatec
- Ketian
- Lancid
- Lanproton
- Lansopep
- Lansoprazol [INN-Spanish]
- Lansoprazole [Usan:Ban:Inn]
- Lansoprazolum [INN-Latin]
- Lanston
- Lanz
- Lanzol-30
- Lanzopral
- Lanzor
- Lasoprol
- Limpidex
- Mesactol
- Monolitum
- Ogast
- Ogastro
- Opiren
- Prevacid
- Prevacid Iv
- Prevacid Solutab
- Prevpac
- Prezal
- Pro Ulco
- Promp
- Prosogan
- Suprecid
- Takepron
- Ulpax
- Zoprol
- Zoton
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole |
| Chemical Formula |
C16H14F3N3O2S |
| Chemical Structure |
 |
| CAS Registry Number |
103577-45-3 |
| InChI Identifier |
InChI=1/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/f/h21H |
| InChI Key |
MJIHNNLFOKEZEW-PKSOQXRJCC |
| KEGG Drug |
D00355  |
| KEGG Compound |
Not Available |
| PubChem Compound |
3883  |
| PubChem Substance |
196229  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA450180  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02165503  |
| RxList Link |
http://www.rxlist.com/cgi/generic/lansop.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Lansoprazole  |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
Not Available |
| Synthesis Reference |
A. Nohara, Y. Marki, U.S. Pat. 4,628,098 (1986) |
| Average Molecular Weight |
369.3610 |
| Monoisotopic Molecular Weight |
369.0759 |
| State |
Solid |
| Melting Point |
178-182 oC |
| Experimental Water Solubility |
0.97 mg/L
Source: PhysProp
|
| Predicted Water Solubility |
2.50e-01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
1.9
Source: PhysProp
|
| Predicted LogP |
2.84
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-3.17
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CC1=C(OCC(F)(F)F)C=CN=C1C[S@](=O)C1=NC2=CC=CC=C2N1 |
| Canonical SMILES |
CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 |
| Drug Category |
- Anti-Infective Agents
- Anti-Infectives
- Anti-Ulcer Agents
- Enzyme Inhibitors
- Proton-pump Inhibitors
|
| ATC Codes |
|
| AHFS Codes |
|
| Indication |
For treatment of Acid-reflux disorders (GERD), peptic Ulcer Disease, duodenal ulcers, esophagitis, and Zollinger-Ellison syndrome |
| Pharmacology |
Lansoprazole, an acid proton-pump inhibitor similar to omeprazole, is used as an untiulcer drug in the treatment and maintenance of healing of duodenal or gastric ulcers, erosive and reflux esophagitis, NSAID-induced ulcer, Zollinger-Ellison syndrome, and Barrett's esophagus. Lansoprozole is active against Helicobacter pylori. The plasma elimination half-life of lansoprazole does not reflect its duration of suppression of gastric acid secretion. Thus, the plasma elimination half-life is less than two hours, while the acid inhibitory effect lasts more than 24 hours. |
| Mechanism of Action |
Lansoprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but rather suppress gastric acid secretion by specific inhibition of the (H+,K+)-ATPase enzyme system at the secretory surface of the gastric parietal cell. Because this enzyme system is regarded as the acid (proton) pump within the parietal cell, Lansoprazole has been characterized as a gastric acid-pump inhibitor, in that it blocks the final step of acid production. This effect is dose-related and leads to inhibition of both basal and stimulated gastric acid secretion irrespective of the stimulus. |
| Absorption |
The absorption of lansoprazole is rapid, with mean Cmax occurring approximately 1.7 hours after oral dosing, and relatively complete with absolute bioavailability over 80%. |
| Toxicity |
Symptoms of overdose include abdominal pain, nausea and diarrhea. |
| Protein Binding |
97% |
| Biotransformation |
Hepatic. Two metabolites have been identified in measurable quantities in plasma (the hydroxylated sulfinyl and sulfone derivatives of lansoprazole). These metabolites have very little or no antisecretory activity. Lansoprazole is thought to be transformed into two active species which inhibit acid secretion by (H+,K+)-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation. |
| Half Life |
1.5 (± 1.0) hours |
| Dosage Forms |
| Form |
Route |
| Capsule, delayed release |
Oral |
| Tablet, delayed release |
Oral |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Show  |
| Drug Interactions |
| Drug |
Interaction |
| Atazanavir |
This gastric pH modifier decreases the levels/effects of atazanavir |
| Enoxacin |
The agent decreases the absorption of enoxacin |
| Indinavir |
Omeprazole decreases the absorption of indinavir |
| Itraconazole |
The proton pump inhibitor decreases the absorption of imidazole |
| Ketoconazole |
The proton pump inhibitor decreases the absorption of imidazole |
| Sucralfate |
Sucralfate decreases the effect of lansoprazole |
|
| Food Interactions |
- Avoid alcohol.
- Food reduces bioavailabilty, but this has very little clinical impact.
- Take 30-60 minutes before meals.
|
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Lansoprazole Pathway |
SMP00227  |
|
|
| General References |
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Phase 1 Metabolizing Enzymes |
- Cytochrome P450 2C19 (CYP2C19)
- Cytochrome P450 2C9 (CYP2C9)
|
| Targets |
- Potassium-transporting ATPase alpha chain 1
|
|
Drug Target 1
[top]
|
| Target 1 ID |
385 |
| Target 1 Name |
Potassium-transporting ATPase alpha chain 1 |
| Target 1 Synonyms |
- EC 3.6.3.10
- Gastric H(+)/K(+) ATPase subunit alpha
- Proton pump
|
| Target 1 Gene Name |
ATP4A |
| Target 1 Protein Sequence |
>Potassium-transporting ATPase alpha chain 1
GKAENYELYSVELGPGPGGDMAAKMSKKKKAGGGGGKRKEKLENMKKEMEINDHQLSVAE
LEQKYQTSATKGLSASLAAELLLRDGPNALRPPRGTPEYVKFARQLAGGLQCLMWVAAAI
CLIAFAIQASEGDLTTDDNLYLAIALIAVVVVTGCFGYYQEFKSTNIIASFKNLVPQQAT
VIRDGDKFQINADQLVVGDLVEMKGGDRVPADIRILAAQGCKVDNSSLTGESEPQTRSPE
CTHESPLETRNIAFFSTMCLEGTAQGLVVNTGDRTIIGRIASLASGVENEKTPIAIEIEH
FVDIIAGLAILFGATFFIVAMCIGYTFLRAMVFFMAIVVAYVPEGLLATVTVCLSLTAKR
LASKNCVVKNLEAVETLGSTSVICSDKTGTLTQNRMTVSHLWFDNHIHTADTTEDQSGQT
FDQSSETWRALCRVLTLCNRAAFKSGQDAVPVPKRIVIGDASETALLKFSELTLGNAMGY
RDRFPKVCEIPFNSTNKFQLSIHTLEDPRDPRHLLVMKGAPERVLERCSSILIKGQELPL
DEQWREAFQTAYLSLGGLGERVLGFCQLYLNEKDYPPGYAFDVEAMNFPSSGLCFAGLVS
MIDPPRATVPDAVLKCRTAGIRVIMVTGDHPITAKAIAASVGIISEGSETVEDIAARLRV
PVDQVNRKDARACVINGMQLKDMDPSELVEALRTHPEMVFARTSPQQKLVIVESCQRLGA
IVAVTGDGVNDSPALKKADIGVAMGIAGSDAAKNAADMILLDDNFASIVTGVEQGRLIFD
NLKKSIAYTLTKNIPELTPYLIYITVSVPLPLGCITILFIELCTDIFPSVSLAYEKAESD
IMHLRPRNPKRDRLVNEPLAAYSYFQIGAIQSFAGFTDYFTAMAQEGWFPLLCVGLRAQW
EDHHLQDLQDSYGQEWTFGQRLYQQYTCYTVFFISIEVCQIADVLIRKTRRLSAFQQGFF
RNKILVIAIVFQVCIGCFLCYCPGMPNIFNFMPIRFQWWLVPLPYGILIFVYDEIRKLGV
RCCPGSWWDQELYY
|
| Target 1 Number of Residues |
1051 |
| Target 1 Molecular Weight |
113961 |
| Target 1 Theoretical pI |
5.54 |
| Target 1 GO Classification |
|
Function
|
hydrolase activity
hydrolase activity, acting on acid anhydrides
hydrolase activity, acting on acid anhydrides, catalyzing transmembrane movement of substances
catalytic activity
binding
nucleotide binding
purine nucleotide binding
adenyl nucleotide binding
ATP binding
monovalent inorganic cation transporter activity
transporter activity
ion transporter activity
cation transporter activity
ATPase activity, coupled to transmembrane movement of ions, phosphorylative mechanism |
|
Process
|
metabolism
monovalent inorganic cation transport
physiological process
cellular physiological process
transport
ion transport
cation transport |
|
Component
|
intrinsic to membrane
integral to membrane
cell
membrane |
|
| Target 1 General Function |
Inorganic ion transport and metabolism |
| Target 1 Specific Function |
Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach |
| Target 1 Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Oxidative phosphorylation |
|
map00190  |
|
| Target 1 Reactions |
- ATP + H2O + H+in + K+out = ADP + phosphate + H+out + K+in
|
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 98-118
- 142-162
- 299-318
- 331-348
- 783-802
- 813-833
- 854-876
- 929-948
- 963-981
- 997-1017
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
561634  |
| Target 1 UniProtKB/Swiss-Prot ID |
P20648  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
ATP4A_HUMAN  |
| Target 1 PDB ID |
Not Available |
| Target 1 Cellular Location |
- Membrane
- multi-pass membrane protein
|
| Target 1 Gene Sequence |
>3108 bp
ATGGGGAAGGCCGAGAACTATGAGCTCTACTCGGTGGAGCTGGGTCCTGGCCCTGGCGGG
GACATGGCTGCCAAGATGAGCAAGAAGAAGAAGGCGGGTGGCGGGGGTGGCAAGAGGAAG
GAGAAGCTGGAGAACATGAAGAAGGAGATGGAGATTAACGACCACCAGCTGTCAGTGGCG
GAGCTGGAACAGAAATACCAGACCAGTGCCACCAAGGGCCTCTCTGCGAGCCTGGCTGCT
GAGCTGCTGCTGCGGGATGGGCCCAACGCACTGCGGCCACCACGGGGCACCCCAGAGTAC
GTCAAGTTCGCGAGGCAGCTGGCCGGGGGCCTGCAGTGCCTCATGTGGGTTGCCGCCGCC
ATCTGCCTCATCGCCTTTGCCATCCAGGCTAGTGAGGGGGACCTCACCACCGACGACAAT
CTGTACCTGGCAATCGCTCTCATTGCTGTGGTTGTCGTCACCGGCTGCTTTGGCTACTAC
CAGGAATTCAAGAGCACCAACATCATCGCCAGCTTTAAGAACCTTGTGCCACAGCAAGCC
ACTGTCATCCGCGATGGAGACAAATTCCAGATCAACGCTGACCAACTGGTGGTGGGCGAC
CTGGTGGAGATGAAAGGTGGGGACAGAGTGCCCGCCGACATCCGCATCCTGGCGGCCCAG
GGCTGCAAGGTGGACAACTCCTCGCTGACAGGGGAGTCTGAGCCACAGACCCGCTCACCC
GAGTGCACGCACGAGAGCCCTCTGGAGACCCGCAACATCGCCTTCTTCTCCACCATGTGC
CTTGAGGGCACCGCGCAGGGCCTGGTGGTGAACACGGGCGACCGCACCATCATTGGGCGC
ATCGCATCGCTGGCGTCGGGGGTGGAAAACGAGAAGACACCCATCGCTATCGAGATCGAG
CATTTTGTGGACATCATCGCGGGCCTGGCCATTCTCTTCGGTGCCACATTTTTTATTGTG
GCCATGTGCATTGGCTACACCTTCCTGCGGGCCATGGTCTTCTTCATGGCCATCGTGGTG
GCCTATGTGCCTGAGGGGCTGCTGGCCACTGTCACAGTCTGCCTGTCCCTGACAGCCAAG
CGCCTGGCCAGTAAGAACTGCGTGGTCAAGAACCTGGAGGCGGTGGAGACATTGGGCTCC
ACTTCGGTGATCTGCTCGGACAAGACAGGGACTCTCACTCAGAACCGCATGACTGTGTCC
CATCTTTGGTTTGACAACCACATCCACACAGCTGACACCACGGAAGACCAGTCAGGGCAG
ACGTTTGACCAGTCCTCGGAGACGTGGCGGGCGCTGTGCCGGGTGCTCACCCTGTGCAAC
CGCGCCGCCTTCAAGTCCGGCCAGGATGCAGTGCCTGTGCCCAAGCGCATCGTGATTGGA
GACGCATCGGAGACGGCGCTGCTCAAGTTCTCGGAGCTGACGCTGGGCAACGCCATGGGC
TACCGGGACCGCTTCCCAAAAGTCTGCGAGATACCCTTCAACTCCACCAACAAGTTCCAG
CTGTCCATACATACGCTGGAGGACCCGCGGGACCCGCGACACTTGCTGGTGATGAAGGGC
GCCCCCGAGCGCGTGCTGGAGCGCTGCAGCTCCATCCTTATCAAGGGCCAGGAGCTGCCG
CTGGACGAGCAGTGGCGCGAGGCCTTCCAGACCGCCTACCTCAGCCTGGGAGGCCTGGGC
GAACGCGTGCTCGGCTTCTGCCAGCTCTACCTGAATGAGAAGGACTACCCGCCTGGCTAT
GCCTTCGACGTAGAGGCCATGAACTTTCCATCTAGCGGCCTCTGCTTTGCGGGACTTGTA
TCCATGATTGACCCACCCCGGGCCACCGTCCCTGATGCTGTGCTCAAGTGTCGCACCGCA
GGCATCCGGGTGATCATGGTAACGGGTGACCACCCCATCACCGCCAAGGCCATTGCAGCC
AGTGTGGGCATCATCTCGGAAGGCAGCGAGACAGTGGAGGACATCGCTGCCCGCCTCCGT
GTGCCCGTAGACCAGGTTAATCGCAAGGATGCCCGTGCCTGTGTGATCAATGGCATGCAG
CTGAAGGACATGGACCCATCGGAACTGGTCGAGGCCCTGCGCACCCACCCCGAGATGGTG
TTTGCGCGCACCAGCCCCCAGCAGAAGCTGGTGATCGTGGAGAGCTGCCAGCGGCTGGGT
GCGATTGTGGCCGTCACGGGGGATGGTGTGAATGACTCCCCAGCTCTGAAGAAGGCAGAC
ATCGGAGTAGCCATGGGCATCGCTGGCTCAGATGCTGCCAAAAATGCAGCTGACATGATC
CTGCTGGATGACAACTTTGCCTCCATTGTGACAGGCGTGGAGCAGGGTCGACTGATCTTC
GACAACCTGAAGAAGTCTATTGCCTACACATTGACCAAGAACATCCCAGAGCTGACACCC
TACCTCATCTACATCACCGTCAGCGTGCCCCTGCCCCTCGGGTGCATCACCATCCTCTTC
ATCGAACTCTGCACTGACATTTTCCCATCTGTGTCCCTGGCATATGAAAAGGCCGAGAGT
GACATCATGCACCTGCGTCCACGCAACCCAAAGCGTGACAGATTGGTCAACGAGCCCCTG
GCTGCCTACTCCTACTTCCAGATTGGTGCCATTCAGTCCTTTGCTGGCTTCACTGACTAC
TTCACGGCAATGGCCCAGGAGGGCTGGTTCCCACTGCTGTGCGTGGGGCTGCGGGCGCAG
TGGGAGGACCACCACCTACAAGATCTGCAGGACAGCTACGGCCAGGAGTGGACATTCGGG
CAGCGCCTGTACCAGCAGTACACCTGCTACACCGTGTTCTTCATCAGCATTGAGGTGTGC
CAGATCGCCGATGTCCTCATCCGCAAGACGCGCCGTCTCTCTGCCTTCCAGCAAGGCTTC
TTCAGGAATAAGATCCTGGTGATCGCCATCGTGTTCCAGGTCTGCATCGGCTGCTTCCTG
TGCTACTGCCCCGGCATGCCCAACATCTTCAACTTCATGCCCATTCGGTTCCAGTGGTGG
CTGGTCCCCCTGCCCTACGGCATCCTCATCTTCGTCTATGATGAGATCCGGAAGCTTGGA
GTTCGCTGTTGCCCAGGGAGCTGGTGGGACCAGGAACTCTACTATTAG
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
ATP4A  |
| Target 1 GenAtlas ID |
ATP4A  |
| Target 1 HGNC ID |
HGNC:819  |
| Target 1 Chromosome Location |
19 |
| Target 1 Locus |
19q13.1 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- Maeda M, Oshiman K, Tamura S, Futai M: Human gastric (H+ + K+)-ATPase gene. Similarity to (Na+ + K+)-ATPase genes in exon/intron organization but difference in control region. J Biol Chem. 1990 Jun 5;265(16):9027-32. [PubMed
]
- Newman PR, Greeb J, Keeton TP, Reyes AA, Shull GE: Structure of the human gastric H,K-ATPase gene and comparison of the 5'-flanking sequences of the human and rat genes. DNA Cell Biol. 1990 Dec;9(10):749-62. [PubMed
]
- Sverdlov ED, Monastyrskaya GS, Broude NE, Ushkaryov YuA, Allikmets RL, Melkov AM, Smirnov YuV, Malyshev IV, Dulobova IE, Petrukhin KE, et al.: The family of human Na+,K+-ATPase genes. No less than five genes and/or pseudogenes related to the alpha-subunit. FEBS Lett. 1987 Jun 15;217(2):275-8. [PubMed
]
|
| Target 1 Drug References |
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed
]
|