Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H30Cl2N10.2C2H4O2 |
| Molecular Weight | 625.551 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)=O.CC(O)=O.ClC1=CC=C(NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC2=CC=C(Cl)C=C2)C=C1
InChI
InChIKey=WDRFFJWBUDTUCA-UHFFFAOYSA-N
InChI=1S/C22H30Cl2N10.2C2H4O2/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18;2*1-2(3)4/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34);2*1H3,(H,3,4)
DescriptionCurator's Comment: Description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf
http://www.drugbank.ca/drugs/DB00878
http://www.wikidoc.org/index.php/Chlorhexidine_gluconate
Curator's Comment: Description was created based on several sources, including:
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019028s022lbl.pdf
http://www.drugbank.ca/drugs/DB00878
http://www.wikidoc.org/index.php/Chlorhexidine_gluconate
Chlorhexidine is a broad-spectrum biocide effective against Gram-positive bacteria, Gram-negative bacteria and fungi. It is used primarily as its salts (e.g., the dihydrochloride, diacetate, and digluconate). Chlorhexidine inactivates microorganisms with a broader spectrum than other antimicrobials (e.g. antibiotics) and has a quicker kill rate than other antimicrobials (e.g. povidone-iodine). It has both bacteriostatic (inhibits bacterial growth) and bactericidal (kills bacteria) mechanisms of action, depending on its concentration. Chlorhexidine kills by disrupting the cell membrane. The most common side effects associated with chlorhexidine gluconate oral rinses are: 1) an increase in staining of teeth and other oral surfaces; 2) an increase in calculus formation; and 3) an alteration in taste perception; 4) toothache; 5) upper respiratory tract infection; and 6) headache.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: bacterial cell wall |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | HIBICLENS Approved UseUse for the preparation of the patient's skin prior to surgery. Helps to reduce bacteria that potentially can cause skin infection. Launch Date1976 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2007 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9869352 |
2.5 mg single, dental dose: 2.5 mg route of administration: Dental experiment type: SINGLE co-administered: |
CHLORHEXIDINE inflammatory exudate | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.206 μg/g |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORHEXIDINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
187083.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9869352 |
2.5 mg single, dental dose: 2.5 mg route of administration: Dental experiment type: SINGLE co-administered: |
CHLORHEXIDINE inflammatory exudate | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
148287.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869 |
0.2 % single, dental dose: 0.2 % route of administration: Dental experiment type: SINGLE co-administered: |
CHLORHEXIDINE saliva | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
180892.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26271869 |
0.2 % 1 times / day multiple, dental dose: 0.2 % route of administration: Dental experiment type: MULTIPLE co-administered: |
CHLORHEXIDINE saliva | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4269593 |
CHLORHEXIDINE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
||
73% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4269593/ |
CHLORHEXIDINE saliva | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2 % 1 times / day single, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: single Dose: 2 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-64 years n = 36 Health Status: healthy Age Group: 18-64 years Sex: M+F Population Size: 36 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
Other AEs: Redness... Other AEs: Redness (grade 2) Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-79 years n = 204 Health Status: healthy Age Group: 18-79 years Sex: M+F Population Size: 204 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
Disc. AE: Papule, Erythema... AEs leading to discontinuation/dose reduction: Papule Sources: Page: nda/2005/21669s000_MedR.pdf - p.83Erythema (grade 2) Edema (grade 1) |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 22-60 years n = 23 Health Status: healthy Age Group: 22-60 years Sex: M+F Population Size: 23 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
Disc. AE: Burning sensation, Petechial rash... AEs leading to discontinuation/dose reduction: Burning sensation (grade 1) Sources: Page: nda/2005/21669s000_MedR.pdf - p.83Petechial rash (grade 1) Scab |
1.5 oz 1 times / day single, oral (mean) Studied dose Dose: 1.5 oz, 1 times / day Route: oral Route: single Dose: 1.5 oz, 1 times / day Sources: |
healthy, child n = 1 Health Status: healthy Age Group: child Population Size: 1 Sources: |
Other AEs: Distress epigastric, Nausea... Other AEs: Distress epigastric Sources: Nausea Alcohol intoxication |
2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
Other AEs: Toothache, Upper respiratory tract infection... Other AEs: Toothache (50.7%) Sources: Upper respiratory tract infection (28.4%) Headache (27.1%) Sinusitis (13.8%) Influenza-like symptoms (7.6%) Back pain (6.7%) Tooth disorder (6.2%) Bronchitis (6.2%) Abscess (5.8%) Pain (4.9%) Allergy (4%) Myalgia (4%) Gum hyperplasia (3.6%) Pharyngitis (3.6%) Arthralgia (3.1%) Dysmenorrhea (3.1%) Dyspepsia (3.1%) Rhinitis (2.7%) Coughing (2.7%) Arthrosis (2.7%) Hypertension (2.2%) Stomatitis ulcerative (2.2%) Tendinitis (2.2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Redness | grade 2 | 2 % 1 times / day single, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: single Dose: 2 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-64 years n = 36 Health Status: healthy Age Group: 18-64 years Sex: M+F Population Size: 36 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Papule | Disc. AE | 3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-79 years n = 204 Health Status: healthy Age Group: 18-79 years Sex: M+F Population Size: 204 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Edema | grade 1 Disc. AE |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-79 years n = 204 Health Status: healthy Age Group: 18-79 years Sex: M+F Population Size: 204 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Erythema | grade 2 Disc. AE |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 18-79 years n = 204 Health Status: healthy Age Group: 18-79 years Sex: M+F Population Size: 204 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Scab | Disc. AE | 3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 22-60 years n = 23 Health Status: healthy Age Group: 22-60 years Sex: M+F Population Size: 23 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Burning sensation | grade 1 Disc. AE |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 22-60 years n = 23 Health Status: healthy Age Group: 22-60 years Sex: M+F Population Size: 23 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Petechial rash | grade 1 Disc. AE |
3 % 1 times / day multiple, topical (mean) Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
healthy, 22-60 years n = 23 Health Status: healthy Age Group: 22-60 years Sex: M+F Population Size: 23 Sources: Page: nda/2005/21669s000_MedR.pdf - p.83 |
| Alcohol intoxication | 1.5 oz 1 times / day single, oral (mean) Studied dose Dose: 1.5 oz, 1 times / day Route: oral Route: single Dose: 1.5 oz, 1 times / day Sources: |
healthy, child n = 1 Health Status: healthy Age Group: child Population Size: 1 Sources: |
|
| Distress epigastric | 1.5 oz 1 times / day single, oral (mean) Studied dose Dose: 1.5 oz, 1 times / day Route: oral Route: single Dose: 1.5 oz, 1 times / day Sources: |
healthy, child n = 1 Health Status: healthy Age Group: child Population Size: 1 Sources: |
|
| Nausea | 1.5 oz 1 times / day single, oral (mean) Studied dose Dose: 1.5 oz, 1 times / day Route: oral Route: single Dose: 1.5 oz, 1 times / day Sources: |
healthy, child n = 1 Health Status: healthy Age Group: child Population Size: 1 Sources: |
|
| Sinusitis | 13.8% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Hypertension | 2.2% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Stomatitis ulcerative | 2.2% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Tendinitis | 2.2% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Arthrosis | 2.7% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Coughing | 2.7% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Rhinitis | 2.7% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Headache | 27.1% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Upper respiratory tract infection | 28.4% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Arthralgia | 3.1% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Dysmenorrhea | 3.1% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Dyspepsia | 3.1% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Gum hyperplasia | 3.6% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Pharyngitis | 3.6% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Allergy | 4% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Myalgia | 4% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Pain | 4.9% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Abscess | 5.8% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Toothache | 50.7% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Bronchitis | 6.2% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Tooth disorder | 6.2% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Back pain | 6.7% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
| Influenza-like symptoms | 7.6% | 2.5 mg 3 times / month multiple, subgingival Recommended Dose: 2.5 mg, 3 times / month Route: subgingival Route: multiple Dose: 2.5 mg, 3 times / month Sources: |
unhealthy, mean age 47 years n = 225 Health Status: unhealthy Condition: periodontitis Age Group: mean age 47 years Sex: M+F Population Size: 225 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Disturbances of taste from oral disinfectants (author's transl)]. | 1978 Oct |
|
| Some toxic effects of lead, other metals and antibacterial agents on the nervous system--animal experiment models. | 1984 |
|
| [Anaphylactic shock with ventricular fibrillation induced by chlorhexidine]. | 1992 Mar |
|
| The activity of candidate virucidal agents, low pH and genital secretions against HIV-1 in vitro. | 1995 Jul-Aug |
|
| 6-month use of 0.2% delmopinol hydrochloride in comparison with 0.2% chlorhexidine digluconate and placebo. (I). Effect on plaque formation and gingivitis. | 1998 Sep |
|
| Developing a dynamic pharmacophore model for HIV-1 integrase. | 2000 Jun 1 |
|
| Chlorhexidine and taste. Influence of mouthwashes concentration and of rinsing time. | 2000 May |
|
| Effects of a chlorhexidine gluconate-containing mouthwash on the vitality and antimicrobial susceptibility of in vitro oral bacterial ecosystems. | 2003 Aug |
|
| Chlorhexidine induces DNA damage in rat peripheral leukocytes and oral mucosal cells. | 2004 Oct |
|
| Chemoenzymatic synthesis and antimicrobial and haemolytic activities of amphiphilic bis(phenylacetylarginine) derivatives. | 2006 Oct |
|
| [Ultrastructure study of pathogen of acanthamoeba keratitis]. | 2008 Nov |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
| Food components with anticaries activity. | 2012 Apr |
|
| Cytotoxicity and genotoxicity of chlorhexidine on macrophages in vitro. | 2014 Apr |
Patents
Sample Use Guides
Recommended use is twice daily oral rinsing for 30 seconds, morning and evening after tooth brushing. Usual dosage is 15 ml (1 tablespoon) of undiluted Chlorhexidine gluconate oral rinse. Prophylaxis intervals - no longer than six months.
Route of Administration:
Topical
In Vitro Use Guide
Curator's Comment: Chlorhexidine caused significant decreases in both total anaerobe and total aerobe/facultative anaerobe counts (P < 0.05), together with lesser decreases in gram-negative anaerobes.
Minimum bactericidal concentrations are different for different bacterial strains (3.9-83.3 mg/l).
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EPA PESTICIDE CODE |
45502
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SUB20822
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ACTIVE MOIETY
SUBSTANCE RECORD
