Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21N5O2.C7H6O2 |
Molecular Weight | 461.513 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC=CC=C1.CN2C(=O)C=C(N3CCC[C@@H](N)C3)N(CC4=C(C=CC=C4)C#N)C2=O
InChI
InChIKey=KEJICOXJTRHYAK-XFULWGLBSA-N
InChI=1S/C18H21N5O2.C7H6O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19;8-7(9)6-4-2-1-3-5-6/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3;1-5H,(H,8,9)/t15-;/m1./s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.takeda.com/news/2013/20130924_5997.html;
http://www.ncbi.nlm.nih.gov/pubmed/22651127; http://www.ncbi.nlm.nih.gov/pubmed/17441705
Curator's Comment: description was created based on several sources, including
https://www.takeda.com/news/2013/20130924_5997.html;
http://www.ncbi.nlm.nih.gov/pubmed/22651127; http://www.ncbi.nlm.nih.gov/pubmed/17441705
Alogliptin (trade name Nesina in the US and Vipidia in Europe) is an orally administered anti-diabetic drug in the DPP-4 inhibitor class, discovered by Takeda Pharmaceutical Company's wholly owned subsidiary, Takeda San Diego, Inc. (former Syrrx) which was acquired by Takeda in 2005. Alogliptin does not decrease the risk of heart attack and stroke. Like other members of the gliptin class, it causes little or no weight gain, exhibits relatively little risk of causing hypoglycemia, and exhibits relatively modest glucose-lowering activity. Alogliptin and other gliptins are commonly used in combination with metformin in patients whose diabetes cannot adequately be controlled with metformin alone.
CNS Activity
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002178/WC500152200.pdf
Curator's Comment: Alogliptin is unlikely to have untoward pharmacologic activity in the central nervous system (CNS). Although alogliptin inhibited naloxone binding at nonselective opioid receptors in vitro in the rat cerebral cortex, it did not show any binding affinity for human receptors typically associated with abuse potential (human recombinant opiate receptors).
Originator
Sources: http://www.ncbi.nlm.nih.gov/pubmed/17441705
Curator's Comment: Alogliptin was discovered by Takeda’s wholly owned subsidiary, Takeda San Diego, Inc. # Takeda San Diego, Inc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P27487 Gene ID: 1803.0 Gene Symbol: DPP4 Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | NESINA Approved UseIndicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Limitation of Use: Not for treatment of type 1 diabetes or diabetic ketoacidosis. Launch Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
165 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25936384/ |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] ALOGLIPTIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
154.83 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg 1 times / day multiple, oral dose: 25 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
335.36 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
75.38 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg 1 times / day multiple, oral dose: 12.5 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
114.08 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg single, oral dose: 25 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
246 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg single, oral dose: 50 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
55.28 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg single, oral dose: 12.5 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1511 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25936384/ |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] ALOGLIPTIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1174.76 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg single, oral dose: 25 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
1625.58 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg 1 times / day multiple, oral dose: 25 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
2488.48 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg single, oral dose: 50 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
3389.21 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg 1 times / day multiple, oral dose: 50 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
601.65 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg single, oral dose: 12.5 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
842.17 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg 1 times / day multiple, oral dose: 12.5 mg route of administration: oral experiment type: multiple co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
1674.87999999999 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg single, oral dose: 25 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
3306.68 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg single, oral dose: 50 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
895.28 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg single, oral dose: 12.5 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25936384/ |
25 mg 1 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] ALOGLIPTIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
21 h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ALOGLIPTIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
20.67 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
12.5 mg single, oral dose: 12.5 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
19.45 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
25 mg single, oral dose: 25 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
17 h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01391663 |
50 mg single, oral dose: 50 mg route of administration: oral experiment type: single co-administered: |
ALOGLIPTIN plasma | Homo sapiens population: healthy age: Adults sex: food status: |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] ALOGLIPTIN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg single, oral Highest studied dose |
healthy, 26.6 years (range: 18-55 years) n = 5 Health Status: healthy Age Group: 26.6 years (range: 18-55 years) Sex: M Population Size: 5 Sources: |
|
400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
unhealthy, 55.6 years (range: 18 - 75 years) n = 16 Health Status: unhealthy Condition: type 2 diabetes Age Group: 55.6 years (range: 18 - 75 years) Sex: M+F Population Size: 16 Sources: |
Other AEs: Headache, Dizziness... Other AEs: Headache (6 patients) Sources: Dizziness (4 patients) Constipation (3 patients) |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Disc. AE: Acute myocardial infarction, Angina unstable... AEs leading to discontinuation/dose reduction: Acute myocardial infarction (8 patients) Sources: Page: p. 48Angina unstable (2 patients) Myocardial infarction (12 patients) Abdominal pain (2 patients) Diarrhea (1 patient) Nausea (3 patients) Edema peripheral (4 patients) Blood creatinine increased (6 patients) Creatinine renal clearance abnormal (3 patients) Creatinine renal clearance decreased (22 patients) Lipase increased (10 patients) Hyperglycemia (3 patients) Dizziness (4 patients) Headache (2 patients) Renal impairment (13 patients) Rash (2 patients) Rash pruritic (3 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Constipation | 3 patients | 400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
unhealthy, 55.6 years (range: 18 - 75 years) n = 16 Health Status: unhealthy Condition: type 2 diabetes Age Group: 55.6 years (range: 18 - 75 years) Sex: M+F Population Size: 16 Sources: |
Dizziness | 4 patients | 400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
unhealthy, 55.6 years (range: 18 - 75 years) n = 16 Health Status: unhealthy Condition: type 2 diabetes Age Group: 55.6 years (range: 18 - 75 years) Sex: M+F Population Size: 16 Sources: |
Headache | 6 patients | 400 mg 1 times / day steady, oral Highest studied dose Dose: 400 mg, 1 times / day Route: oral Route: steady Dose: 400 mg, 1 times / day Sources: |
unhealthy, 55.6 years (range: 18 - 75 years) n = 16 Health Status: unhealthy Condition: type 2 diabetes Age Group: 55.6 years (range: 18 - 75 years) Sex: M+F Population Size: 16 Sources: |
Diarrhea | 1 patient Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Lipase increased | 10 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Myocardial infarction | 12 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Renal impairment | 13 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Abdominal pain | 2 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Angina unstable | 2 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Headache | 2 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Rash | 2 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Creatinine renal clearance decreased | 22 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Creatinine renal clearance abnormal | 3 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Hyperglycemia | 3 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Nausea | 3 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Rash pruritic | 3 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Dizziness | 4 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Edema peripheral | 4 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Blood creatinine increased | 6 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Acute myocardial infarction | 8 patients Disc. AE |
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: Page: p. 48 |
unhealthy, adult n = 6626 Health Status: unhealthy Age Group: adult Population Size: 6626 Sources: Page: p. 48 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022271Orig1s000ClinPharmR.pdf#page=166 Page: 166151.0 |
inconclusive | no (co-administration study) Comment: cyclosporin does not have significant impact on plasma PK of SYR-322 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022271Orig1s000ClinPharmR.pdf#page=166 Page: 166151.0 |
||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022271Orig1s000ClinPharmR.pdf#page=164 Page: 164.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022271Orig1s000ClinPharmR.pdf#page=164 Page: 164.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/022271Orig1s000PharmR.pdf#page=109 Page: 109.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Alogliptin, a potent and selective dipeptidyl peptidase-IV inhibitor for the treatment of type 2 diabetes. | 2008 Apr |
|
Efficacy and safety of the dipeptidyl peptidase-4 inhibitor alogliptin in patients with type 2 diabetes inadequately controlled by glyburide monotherapy. | 2009 Feb |
|
The dipeptidyl peptidase-4 inhibitor alogliptin in combination with pioglitazone improves glycemic control, lipid profiles, and increases pancreatic insulin content in ob/ob mice. | 2009 Jan 14 |
|
A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease. | 2009 Jul 20 |
|
Combining a dipeptidyl peptidase-4 inhibitor, alogliptin, with pioglitazone improves glycaemic control, lipid profiles and beta-cell function in db/db mice. | 2009 Jun |
|
DPP4 inhibitors: from sitagliptin monotherapy to the new alogliptin-pioglitazone combination therapy. | 2009 Mar |
|
Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes. | 2009 Mar 1 |
|
Chronic administration of voglibose, an alpha-glucosidase inhibitor, increases active glucagon-like peptide-1 levels by increasing its secretion and decreasing dipeptidyl peptidase-4 activity in ob/ob mice. | 2009 May |
|
The efficacy and safety of saxagliptin when added to metformin therapy in patients with inadequately controlled type 2 diabetes with metformin alone. | 2009 Sep |
|
Differential chemistry (structure), mechanism of action, and pharmacology of GLP-1 receptor agonists and DPP-4 inhibitors. | 2009 Sep-Oct |
|
Effects of sitagliptin treatment on dysmetabolism, inflammation, and oxidative stress in an animal model of type 2 diabetes (ZDF rat). | 2010 |
|
Type 2 diabetes: postprandial hyperglycemia and increased cardiovascular risk. | 2010 Mar 24 |
|
Treatment of elderly patients with type 2 diabetes mellitus: a systematic review of the benefits and risks of dipeptidyl peptidase-4 inhibitors. | 2010 Oct |
|
Comparative clinical pharmacokinetics of dipeptidyl peptidase-4 inhibitors. | 2012 Aug 1 |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C98086
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DBSALT000007
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EEN99869SC
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850649-62-6
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1368000
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UU-165
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100000124472
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CHEMBL376359
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m1572
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16088021
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C75186
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DTXSID20582095
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SUB32165
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72324
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD