Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H21N |
Molecular Weight | 287.3981 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC(CC1)=C2C3=C(C=CC=C3)C=CC4=C2C=CC=C4
InChI
InChIKey=JJCFRYNCJDLXIK-UHFFFAOYSA-N
InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
Molecular Formula | C21H21N |
Molecular Weight | 287.3981 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdfhttps://www.drugs.com/dosage/cyproheptadine.htmlCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7650688 | http://www.empr.com/cyproheptadine/drug/23/ | http://reference.medscape.com/drug/cyproheptadine-343389
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/087056s045lbl.pdfhttps://www.drugs.com/dosage/cyproheptadine.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7650688 | http://www.empr.com/cyproheptadine/drug/23/ | http://reference.medscape.com/drug/cyproheptadine-343389
Glutodine (Cyproheptadine), sold under the brand name Periactin or Peritol, is a first-generation antihistamine with additional antiserotonergic, anticholinergic and local anesthetic properties. Glutodine is a white to slightly yellowish crystalline solid, which is soluble in water, freely soluble in methanol, sparingly soluble in ethanol, soluble in chloroform, and practically insoluble in ether. Cyproheptadine is used to treat allergic reactions (specifically hay fever), Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods, uncomplicated allergic skin manifestations of urticaria and angioedema amelioration of allergic reactions to blood or plasma, Cold urticaria, and Dermatographism. Cyproheptadine is used off-label to treat Spasticity Associated With Spinal Cord, Migraine Headache Prophylaxis, Decreased Appetite Secondary to Chronic Disease, Drug-Induced Sexual Dysfunction, Serotonin Syndrome.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3943 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
2.7 nM [Ki] | ||
Target ID: CHEMBL2093870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
6.5 nM [Ki] | ||
Target ID: CHEMBL322 |
8.8 null [pKi] | ||
Target ID: CHEMBL1907609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6261070 |
19.0 nM [Ki] | ||
Target ID: CHEMBL3943 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7650688 |
0.537 nM [Ki] | ||
Target ID: CHEMBL322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11229772 |
1.6 nM [Ki] | ||
Target ID: CHEMBL3006 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11266163 |
11.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | CYPROHEPTADINE HYDROCHLORIDE Approved UseCyproheptadine hydrochloride is indicated for the treatment of Perennial and seasonal allergic rhinitis; Vasomotor rhinitis; Allergic conjunctivitis due to inhalant allergens and foods; Mild, uncomplicated allergic skin manifestations of urticaria and angioedema; Amelioration of allergic reactions to blood or plasma; Cold urticaria; Dermatographism; As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date3.16224012E11 |
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Primary | PERIACTIN Approved UseIndications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date-2.59113599E11 |
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Primary | PERIACTIN Approved UseIndications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date-2.59113599E11 |
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Primary | PERIACTIN Approved UseIndications and Usage. Perennial and seasonal allergic rhinitis, Vasomotor rhinitis, Allergic conjunctivitis due to inhalant allergens and foods. Mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Amelioration of allergic reactions to blood or plasma, Cold urticaria, Dermatographism. As therapy for anaphylactic reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled. Launch Date-2.59113599E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.25 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
CYPROHEPTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40.82 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
CYPROHEPTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.21 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21432861 |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: COBAMAMIDE |
CYPROHEPTADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended Dose: 0.227 mg/kg, 3 times / day Route: digestive tract route Route: multiple Dose: 0.227 mg/kg, 3 times / day Sources: |
unhealthy, 17.6 month n = 39 Health Status: unhealthy Condition: feeding intolerance or vomiting Age Group: 17.6 month Sex: M+F Population Size: 39 Sources: |
Other AEs: Sleepiness, Constipation... Other AEs: Sleepiness (4 patients) Sources: Constipation (3 patients) Abnormal behaviour NOS (2 patients) |
22.5 mg single, oral |
healthy, 4 n = 1 Health Status: healthy Age Group: 4 Population Size: 1 Sources: |
Other AEs: Disorientation, Abnormal behaviour... |
6 mg multiple, digestive tract route (median) Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 n = 80 Health Status: unhealthy Condition: refractory upper gastrointestinal symptoms Age Group: 9.8 Sex: M+F Population Size: 80 Sources: |
Other AEs: Somnolence, Irritability... Other AEs: Somnolence (16%) Sources: Irritability (6%) Increased appetite (5%) Abdominal pain (2.5%) |
32 mg multiple, oral Recommended |
unhealthy, <40 n = 20 Health Status: unhealthy Condition: endocrine disorders Age Group: <40 Population Size: 20 Sources: |
Other AEs: Weight gain, Drowsiness... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abnormal behaviour NOS | 2 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended Dose: 0.227 mg/kg, 3 times / day Route: digestive tract route Route: multiple Dose: 0.227 mg/kg, 3 times / day Sources: |
unhealthy, 17.6 month n = 39 Health Status: unhealthy Condition: feeding intolerance or vomiting Age Group: 17.6 month Sex: M+F Population Size: 39 Sources: |
Constipation | 3 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended Dose: 0.227 mg/kg, 3 times / day Route: digestive tract route Route: multiple Dose: 0.227 mg/kg, 3 times / day Sources: |
unhealthy, 17.6 month n = 39 Health Status: unhealthy Condition: feeding intolerance or vomiting Age Group: 17.6 month Sex: M+F Population Size: 39 Sources: |
Sleepiness | 4 patients | 0.227 mg/kg 3 times / day multiple, digestive tract route (median) Recommended Dose: 0.227 mg/kg, 3 times / day Route: digestive tract route Route: multiple Dose: 0.227 mg/kg, 3 times / day Sources: |
unhealthy, 17.6 month n = 39 Health Status: unhealthy Condition: feeding intolerance or vomiting Age Group: 17.6 month Sex: M+F Population Size: 39 Sources: |
Abnormal behaviour | 22.5 mg single, oral |
healthy, 4 n = 1 Health Status: healthy Age Group: 4 Population Size: 1 Sources: |
|
Disorientation | 22.5 mg single, oral |
healthy, 4 n = 1 Health Status: healthy Age Group: 4 Population Size: 1 Sources: |
|
Somnolence | 16% | 6 mg multiple, digestive tract route (median) Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 n = 80 Health Status: unhealthy Condition: refractory upper gastrointestinal symptoms Age Group: 9.8 Sex: M+F Population Size: 80 Sources: |
Abdominal pain | 2.5% | 6 mg multiple, digestive tract route (median) Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 n = 80 Health Status: unhealthy Condition: refractory upper gastrointestinal symptoms Age Group: 9.8 Sex: M+F Population Size: 80 Sources: |
Increased appetite | 5% | 6 mg multiple, digestive tract route (median) Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 n = 80 Health Status: unhealthy Condition: refractory upper gastrointestinal symptoms Age Group: 9.8 Sex: M+F Population Size: 80 Sources: |
Irritability | 6% | 6 mg multiple, digestive tract route (median) Recommended Dose: 6 mg Route: digestive tract route Route: multiple Dose: 6 mg Sources: |
unhealthy, 9.8 n = 80 Health Status: unhealthy Condition: refractory upper gastrointestinal symptoms Age Group: 9.8 Sex: M+F Population Size: 80 Sources: |
Drowsiness | 32 mg multiple, oral Recommended |
unhealthy, <40 n = 20 Health Status: unhealthy Condition: endocrine disorders Age Group: <40 Population Size: 20 Sources: |
|
Weight gain | 19 patients | 32 mg multiple, oral Recommended |
unhealthy, <40 n = 20 Health Status: unhealthy Condition: endocrine disorders Age Group: <40 Population Size: 20 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1.0 |
yes | |||
Page: 1.0 |
yes | |||
Page: 5.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 543.0 |
likely | |||
Page: 543.0 |
yes | |||
Page: 543.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Cyproheptadine use in hepatocellular carcinoma. | 2017 |
|
Polypharmacological in Silico Bioactivity Profiling and Experimental Validation Uncovers Sedative-Hypnotic Effects of Approved and Experimental Drugs in Rat. | 2017 Jun 16 |
|
Cyproheptadine: A Potentially Effective Treatment for Functional Gastrointestinal Disorders in Children. | 2017 Mar 1 |
|
A short history of the 5-HT(2C) receptor: from the choroid plexus to depression, obesity and addiction treatment. | 2017 May |
|
Reconsideration of the diagnosis and treatment of childhood migraine: A practical review of clinical experiences. | 2017 May |
Sample Use Guides
The total daily dose for adults should not exceed 0.5 mg/kg/day. The therapeutic range is 4 to 20 mg a day, with the majority of patients requiring 12 to 16 mg a day. An occasional patient may require as much as 32 mg a day for adequate relief. It is suggested that dosage be initiated with 4 mg (1 tablet) three times a day and adjusted according to the size and response of the patient.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25886177
The IC50 of cyproheptadine, determined as the concentration of the drug that inhibited cell growth by 50% after 24 h of treatment, was found to be 44.4, 44.7, and 118.1 uM in HepG2 cells, Huh-7 cells, and normal human hepatocytes, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:14:09 UTC 2023
by
admin
on
Thu Jul 06 22:14:09 UTC 2023
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Record UNII |
2YHB6175DO
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
R06AX02
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LIVERTOX |
NBK548422
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NCI_THESAURUS |
C29578
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WHO-VATC |
QR06AX02
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3013
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100000083988
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765
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CYPROHEPTADINE
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204-928-9
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |