Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C3H6N2O2 |
Molecular Weight | 102.0919 |
Optical Activity | ( + ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H]1CONC1=O
InChI
InChIKey=DYDCUQKUCUHJBH-UWTATZPHSA-N
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
Molecular Formula | C3H6N2O2 |
Molecular Weight | 102.0919 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2Curator's Comment: description was created based on several sources, including ISBN-13: 978-0199337149
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e1e08327-4b90-463e-bb2a-22438cabcef2
Curator's Comment: description was created based on several sources, including ISBN-13: 978-0199337149
Cycloserine was discovered simultaneously in 1954 by Eli Lilly and Merck. The drug was approved for the treatment of active pulmonary and extrapulmonary tuberculosis and marketed under the name Seromycin (among the others). Cycloserine suppresses the synthesis of bacterial wall by inhibitin two enzymes: alanine racemase and d-alanine ligase.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992 |
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Target ID: CHEMBL2030 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4919992 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | SEROMYCIN Approved UseSeromycin is indicated in the treatment of active pulmonary and extrapulmonary tuberculosis (including renal disease) when the causative organisms are susceptible to this drug and when treatment with the primary medications (streptomycin, isoniazid, rifampin, and ethambutol) has proved inadequate. Launch Date1964 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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42.92 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
D-CYCLOSERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
643.29 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
D-CYCLOSERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.27 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25869627 |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
D-CYCLOSERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg single, oral Recommended Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: Page: p.7 |
healthy, 4.2 n = 12 Health Status: healthy Age Group: 4.2 Sex: M+F Population Size: 12 Sources: Page: p.7 |
|
250 mg 2 times / day multiple, oral Recommended Dose: 250 mg, 2 times / day Route: oral Route: multiple Dose: 250 mg, 2 times / day Sources: Page: p.7 |
healthy, 4.2 n = 12 Health Status: healthy Age Group: 4.2 Sex: M+F Population Size: 12 Sources: Page: p.7 |
|
50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Other AEs: Anorexia, Dizziness... Other AEs: Anorexia (below serious, 4 patients) Sources: Dizziness (below serious, 4 patients) Restlessness (below serious, 7 patients) Sore throat (below serious, 6 patients) Urticaria (below serious, 5 patients) |
50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Autism Spectrum Disorders Population Size: 34 Sources: |
Other AEs: Headache, Vomiting... Other AEs: Headache (below serious, 9 patients) Sources: Vomiting (below serious, 6 patients) Irritability (below serious, 16 patients) Feeling sad (below serious, 5 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anorexia | below serious, 4 patients | 50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Dizziness | below serious, 4 patients | 50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Urticaria | below serious, 5 patients | 50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Sore throat | below serious, 6 patients | 50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Restlessness | below serious, 7 patients | 50 mg 1 times / week multiple, oral Dose: 50 mg, 1 times / week Route: oral Route: multiple Dose: 50 mg, 1 times / week Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Nicotine dependence Population Size: 30 Sources: |
Irritability | below serious, 16 patients | 50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Autism Spectrum Disorders Population Size: 34 Sources: |
Feeling sad | below serious, 5 patients | 50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Autism Spectrum Disorders Population Size: 34 Sources: |
Vomiting | below serious, 6 patients | 50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Autism Spectrum Disorders Population Size: 34 Sources: |
Headache | below serious, 9 patients | 50 mg single, oral Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Autism Spectrum Disorders Population Size: 34 Sources: |
PubMed
Title | Date | PubMed |
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Cycloserine: antituberculous activity in vitro and in the experimental animal. | 1956 Apr |
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Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs? | 1992 Dec |
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Role of specific aminotransferases in de novo glutamate synthesis and redox shuttling in the retina. | 2001 Dec 1 |
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Involvement of cholinergic and glutamatergic functions in working memory impairment induced by interleukin-1beta in rats. | 2001 Nov 2 |
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Effects of N-methyl-D-aspartate agonists and antagonists in rats discriminating amphetamine. | 2001 Sep |
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RS 67333 and D-cycloserine accelerate learning acquisition in the rat. | 2001 Sep |
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Determination of cycloserine in human plasma by high-performance liquid chromatography with fluorescence detection, using derivatization with p-benzoquinone. | 2001 Sep 15 |
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[Effect of glutoxim in the combination with antitubercular agents of the second choice on the growth of drug resistant Mycobacteria tuberculosis in the cultured murine lung tissue]. | 2002 |
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Direct calcium binding results in activation of brain serine racemase. | 2002 Aug 2 |
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Pilot-controlled trial of D-cycloserine for the treatment of post-traumatic stress disorder. | 2002 Dec |
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Homer 1a gene expression modulation by antipsychotic drugs: involvement of the glutamate metabotropic system and effects of D-cycloserine. | 2002 Dec |
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Ceramide signaling in fenretinide-induced endothelial cell apoptosis. | 2002 Dec 20 |
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A case series of D-cycloserine added to donepezil in the treatment of Alzheimer's disease. | 2002 Fall |
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D-Cycloserine added to risperidone in patients with primary negative symptoms of schizophrenia. | 2002 Jul 1 |
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A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. | 2002 Mar |
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Placebo-controlled trial of D-cycloserine added to conventional neuroleptics, olanzapine, or risperidone in schizophrenia. | 2002 Mar |
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Facilitation of conditioned fear extinction by systemic administration or intra-amygdala infusions of D-cycloserine as assessed with fear-potentiated startle in rats. | 2002 Mar 15 |
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[Pharmacological support of exposure therapy in anxiety disorders. Animal experiment studies]. | 2002 May |
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Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997. | 2002 Nov |
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Molecular epidemiology of tuberculosis in a sentinel surveillance population. | 2002 Nov |
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Structural studies of Salmonella typhimurium ArnB (PmrH) aminotransferase: a 4-amino-4-deoxy-L-arabinose lipopolysaccharide-modifying enzyme. | 2002 Nov |
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Effects of D-cycloserine on extinction of conditioned freezing. | 2003 Apr |
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Subunit interaction of monomeric alanine racemases from four Shigella species in catalytic reaction. | 2003 Apr 25 |
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Multidrug-resistant tuberculosis in HIV-negative patients, Buenos Aires, Argentina. | 2003 Aug |
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D-cycloserine-Naloxone interactions in opioid-dependent humans under a novel-response naloxone discrimination procedure. | 2003 Aug |
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Substrate reduction intervention by L-cycloserine in twitcher mice (globoid cell leukodystrophy) on a B6;CAST/Ei background. | 2003 Aug 14 |
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In vitro activity of C-8-methoxy fluoroquinolones against mycobacteria when combined with anti-tuberculosis agents. | 2003 Dec |
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N(2)-substituted D,L-cycloserine derivatives: synthesis and evaluation as alanine racemase inhibitors. | 2003 Feb |
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Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice. | 2003 Jan |
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Effects of antibiotics that inhibit the bacterial peptidoglycan synthesis pathway on moss chloroplast division. | 2003 Jul |
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D-cycloserine for the treatment of ataxia in spinocerebellar degeneration. | 2003 Jun 15 |
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A side reaction of alanine racemase: transamination of cycloserine. | 2003 May 20 |
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D-cycloserine facilitates synaptic plasticity but impairs glutamatergic neurotransmission in rat hippocampal slices. | 2003 Nov |
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Comparative roles of levofloxacin and ofloxacin in the treatment of multidrug-resistant tuberculosis: preliminary results of a retrospective study from Hong Kong. | 2003 Oct |
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Genome-wide transcriptional profiling of the response of Staphylococcus aureus to cell-wall-active antibiotics reveals a cell-wall-stress stimulon. | 2003 Oct |
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Pharmacokinetics and relative bioavailability of clofazimine in relation to food, orange juice and antacid. | 2004 |
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Pharmacy data for tuberculosis surveillance and assessment of patient management. | 2004 Aug |
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New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method. | 2004 Jan |
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Responsiveness to brightness change in male and female rats following treatment with the partial agonist of the N-methyl-D-aspartate receptor, D-cycloserine. | 2004 Jul 9 |
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Surveillance of Mycobacterium tuberculosis susceptibility to second-line drugs in Hong Kong, 1995-2002, after the implementation of DOTS-plus. | 2004 Jun |
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Psychiatric issues in the management of patients with multidrug-resistant tuberculosis. | 2004 Jun |
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D-cycloserine and the facilitation of extinction of conditioned fear: consequences for reinstatement. | 2004 Jun |
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Surprises and omissions in toxicology. | 2004 Mar |
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Self-administered, standardized regimens for multidrug-resistant tuberculosis in South Korea. | 2004 Mar |
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Model structures of the N-methyl-D-aspartate receptor subunit NR1 explain the molecular recognition of agonist and antagonist ligands. | 2004 Mar |
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Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein. | 2004 May |
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Cognitive enhancers as adjuncts to psychotherapy: use of D-cycloserine in phobic individuals to facilitate extinction of fear. | 2004 Nov |
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A pilot study of D-cycloserine in subjects with autistic disorder. | 2004 Nov |
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Multidrug resistant miliary tuberculosis and Pott's disease in an immunocompetent patient. | 2004 Oct |
|
Cell-surface alterations in class IIa bacteriocin-resistant Listeria monocytogenes strains. | 2004 Sep |
Patents
Sample Use Guides
The usual dosage is 500 mg to 1 g daily in divided doses monitored by blood levels. The initial adult dosage most frequently given is 250 mg twice daily at 12–hour intervals for the first 2 weeks. A daily dosage of 1 g should not be exceeded.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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on
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on
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Record UNII |
95IK5KI84Z
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QJ04AB01
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WHO-ATC |
J04AB01
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LIVERTOX |
NBK547876
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NCI_THESAURUS |
C280
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WHO-ESSENTIAL MEDICINES LIST |
6.2.4
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D003523
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577
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95IK5KI84Z
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Cycloserine
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154851
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3218
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76029
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m4019
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CYCLOSERINE
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PRIMARY | Description: A white or pale yellow, crystalline, powder.Solubility: Freely soluble in water; slightly soluble in methanol R and propylene glycol R; very slightly soluble in ethanol (~750 g/l)TS; practically insoluble in dichloromethane R.Category: Antibacterial drug; antituberculosis drug.Storage: Cycloserine should be kept in a tightly closed container.Additional information: Cycloserine is slightly hygroscopic and degrades upon exposure to a humid atmosphere, decompositionbeing faster at higher temperatures. | ||
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C47466
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DTXSID8022870
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DB00260
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23503
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CHEMBL771
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SUB06863MIG
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1158005
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40009
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75929
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759
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200-688-4
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6234
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95IK5KI84Z
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3007
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CYCLOSERINE
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100000083776
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68-41-7
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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