Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H12N2O5S |
| Molecular Weight | 308.31 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)NC1=CC=C(C=C1OC2=CC=CC=C2)[N+]([O-])=O
InChI
InChIKey=HYWYRSMBCFDLJT-UHFFFAOYSA-N
InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
DescriptionSources: https://www.drugbank.ca/drugs/DB04743Curator's Comment: description was created based on several sources, including
http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf
Sources: https://www.drugbank.ca/drugs/DB04743
Curator's Comment: description was created based on several sources, including
http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf
Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the second line treatment of acute pain and primary dysmenorrhoea. Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15656909
Curator's Comment: Known to be CNS active in rat. Human data not available.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL221 |
17.4 µM [IC50] | ||
Target ID: CHEMBL230 |
0.6 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Nimesulide Approved UseTreatment of acute pain.
Primary dysmenorrhoea. |
|||
| Primary | Nimesulide Approved UseTreatment of acute pain.
Primary dysmenorrhoea. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.58 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7506196/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5099 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27284972/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
75 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2227079/ |
100 mg single, rectal dose: 100 mg route of administration: Rectal experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
12.06 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22451531/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
65.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9832296/ |
10 mg single, topical dose: 10 mg route of administration: Topical experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.36 mg/L |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.3 mg/L |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.8 mg/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.85 mg/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.17 mg/L |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.37 mg/L |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.94 mg/L |
200 mg 2 times / day multiple, rectal dose: 200 mg route of administration: Rectal experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
49000 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27284972/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
113 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22451531/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9832296/ |
10 mg single, topical dose: 10 mg route of administration: Topical experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
12.3 mg × h/L |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
22.57 mg × h/L |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
54.09 mg × h/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
81.97 mg × h/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
43 mg × h/L |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
66.13 mg × h/L |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
24.36 mg × h/L |
200 mg 2 times / day multiple, rectal dose: 200 mg route of administration: Rectal experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7506196/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27284972/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2227079/ |
100 mg single, rectal dose: 100 mg route of administration: Rectal experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
4.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22451531/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9832296/ |
10 mg single, topical dose: 10 mg route of administration: Topical experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.44 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.63 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.73 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.95 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.75 h |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.81 h |
100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.76 h |
200 mg 2 times / day multiple, rectal dose: 200 mg route of administration: Rectal experiment type: MULTIPLE co-administered: |
NIMESULIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4% |
NIMESULIDE plasma | Homo sapiens |
||
1% |
NIMESULIDE serum | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg 1 times / day multiple, oral Higher than recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
40 mg/kg single, oral Overdose Dose: 40 mg/kg Route: oral Route: single Dose: 40 mg/kg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Hypotension, Hypothermia... AEs leading to discontinuation/dose reduction: Hypotension Sources: Hypothermia Hypoglycaemia |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Hypoglycaemia | Disc. AE | 40 mg/kg single, oral Overdose Dose: 40 mg/kg Route: oral Route: single Dose: 40 mg/kg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Hypotension | Disc. AE | 40 mg/kg single, oral Overdose Dose: 40 mg/kg Route: oral Route: single Dose: 40 mg/kg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Hypothermia | Disc. AE | 40 mg/kg single, oral Overdose Dose: 40 mg/kg Route: oral Route: single Dose: 40 mg/kg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Randomized pilot study of nimesulide treatment in Alzheimer's disease. | 2002-04-09 |
|
| The MDR phenotype is associated with the expression of COX-2 and iNOS in a human hepatocellular carcinoma cell line. | 2002-04 |
|
| Evaluation of a selective prostaglandin E receptor EP1 antagonist for potential properties in colon carcinogenesis. | 2002-03-26 |
|
| A countrywide post-marketing surveillance of nimesulide suspension. | 2002-03 |
|
| Evaluation of isolated case reports on hepatotoxicity. | 2002-02 |
|
| Increased expression of cyclooxygenase-2 protein during rat hepatocarcinogenesis caused by a choline-deficient, L-amino acid-defined diet and chemopreventive efficacy of a specific inhibitor, nimesulide. | 2002-02 |
|
| Efficacy of nimesulide in pain relief after day care surgery. | 2002-02 |
|
| The effect of nimesulide on the indomethacin- and ethanol-induced gastric ulcer in rats. | 2002-02 |
|
| Nimesulide, a preferential cyclooxygenase 2 inhibitor, suppresses peroxisome proliferator-activated receptor induction of cyclooxygenase 2 gene expression in human synovial fibroblasts: evidence for receptor antagonism. | 2002-02 |
|
| N-(3-Phenoxy-4-pyridinio)methanesulfonamidate. | 2002-02 |
|
| Nimesulide and acute renal failure caused by oxalate precipitation. | 2002-02 |
|
| Induction of the complement component C1qB in brain of transgenic mice with neuronal overexpression of human cyclooxygenase-2. | 2002-02 |
|
| Regulation of prostaglandin production in an immortalized human myometrial cell line by cytokines and non-steroidal anti-inflammatory drugs. | 2002-01-10 |
|
| Antipyretics in children. | 2002-01 |
|
| Possible ranitidine-induced cholestatic jaundice. | 2002-01 |
|
| Lichenoid photodermatitis associated with nimesulide. | 2001-12 |
|
| Cyclo-oxygenase-1/cyclo-oxygenase-2 non selective non-steroidal anti-inflammatory drugs: epidemiology of gastrointestinal events. | 2001-12 |
|
| The effect of alpha-melanocyte stimulating hormone on endotoxin-induced intestinal injury. | 2001-12 |
|
| Quantification of nimesulide in human plasma by high-performance liquid chromatography/tandem mass spectrometry. Application to bioequivalence studies. | 2001-12 |
|
| Hypoglycaemia and hypothermia due to nimesulide overdose. | 2001-12 |
|
| Effects of nimesulide and its metabolites or manufacturing intermediates on the viability and growth of the human hepatoma HepG2 cell line. | 2001-11-09 |
|
| Identification of dual cyclooxygenase-eicosanoid oxidoreductase inhibitors: NSAIDs that inhibit PG-LX reductase/LTB(4) dehydrogenase. | 2001-11-09 |
|
| COX-2 inhibitors compared and contrasted. | 2001-11 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001-11 |
|
| Fenamates stimulate BKCa channel osteoblast-like MG-63 cells activity in the human. | 2001-11 |
|
| Activation of cyclo-oxygenase-2 contributes to motor and cognitive dysfunction following diffuse traumatic brain injury in rats. | 2001-11 |
|
| Role of COX-2-derived metabolites in regulation of the renal hemodynamic response to norepinephrine. | 2001-11 |
|
| Inhibition of prostaglandin synthesis and its effect on uterine activity during established premature labor in sheep. | 2001-10-26 |
|
| The ever-emerging anti-inflammatories. Have there been any real advances? | 2001-10-12 |
|
| Lipopolysaccharide-mediated immobility in mice: reversal by cyclooxygenase enzyme inhibitors. | 2001-10 |
|
| Effects of a COX-2 preferential agent nimesulide on TNBS-induced acute inflammation in the gut. | 2001-10 |
|
| Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. | 2001-10 |
|
| Double-blind study comparing the long-term efficacy of the COX-2 inhibitor nimesulide and naproxen in patients with osteoarthritis. | 2001-10 |
|
| Pathogenetic role of cyclooxygenase-2 in hyperprostaglandin E syndrome/antenatal Bartter syndrome: therapeutic use of the cyclooxygenase-2 inhibitor nimesulide. | 2001-10 |
|
| The effects of cervical application of inhibitors of inducible nitric oxide synthase, cyclooxygenase-1, and cyclooxygenase-2 on delivery in rats. | 2001-10 |
|
| Evaluation of skin sensitization potential of melatonin and nimesulide by murine local lymph node assay. | 2001-10 |
|
| Uterine relaxant effects of cyclooxygenase-2 inhibitors in vitro. | 2001-10 |
|
| CaR-mediated COX-2 expression in primary cultured mTAL cells. | 2001-10 |
|
| Nimesulide-induced acute hepatitis. | 2001-09 |
|
| Tolerability to new COX-2 inhibitors in NSAID-sensitive patients with cutaneous reactions. | 2001-09 |
|
| Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation. | 2001-08-24 |
|
| Evaluation of efficacy and safety of nimesulide with betacyclodextrin vs nimesulide tablets in osteoarthritis. | 2001-08 |
|
| Corneal stimulation of MMP-1, -9 and uPA by platelet-activating factor is mediated by cyclooxygenase-2 metabolites. | 2001-08 |
|
| Tolerability of nimesulide and paracetamol in patients with NSAID-induced urticaria/angioedema. | 2001-08 |
|
| Effects of furocoumarins from Cachrys trifida on some macrophage functions. | 2001-08 |
|
| Fatal hepatoxicity secondary to nimesulide. | 2001-07 |
|
| NSAID antinociception measured in a chemical and a thermal assay in mice. | 2001 |
|
| Patient and physician satisfaction with rofecoxib in osteoarthritis: results of the EVA (experience with VIOXX in arthritis) survey. | 2001 |
|
| Risks and benefits of nonsteroidal anti-inflammatory drugs in children: a comparison with paracetamol. | 2001 |
|
| Adverse drug reactions related to the use of NSAIDs with a focus on nimesulide: results of spontaneous reporting from a Northern Italian area. | 2001 |
Sample Use Guides
The recommended dosage is 100 mg twice daily and the maximum duration of treatment are 15 days with the shortest duration of treatment recommended.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9820127
Nimesulide (1-100 microM) inhibited platelet aggregation induced by adrenaline (20-200 microM). It also inhibited thromboxane A2 formation by platelets at low concentration (IC50 = 1 microM). However, much lower concentrations of nimesulide (0.01-0.1 microM) potentiated the aggregatory response of subthreshold concentrations of adrenaline (0.2-2 microM).
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| Classification Tree | Code System | Code | ||
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WHO-ATC |
M02AA26
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WHO-VATC |
QM01AX17
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NCI_THESAURUS |
C1323
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WHO-ATC |
M01AX17
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WHO-VATC |
QM02AA26
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53694
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44445
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V4TKW1454M
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C012655
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51803-78-2
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1935
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257-431-4
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758412
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C29842
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DTXSID3037250
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NIMESULIDE
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100000091080
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SUB09294MIG
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DB04743
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7401
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m7903
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4885
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4495
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CHEMBL56367
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ACTIVE MOIETY