Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H14O6S2 |
Molecular Weight | 246.302 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)OCCCCOS(C)(=O)=O
InChI
InChIKey=COVZYZSDYWQREU-UHFFFAOYSA-N
InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
Molecular Formula | C6H14O6S2 |
Molecular Weight | 246.302 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01008
https://en.wikipedia.org/wiki/Busulfan
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB01008
https://en.wikipedia.org/wiki/Busulfan
Busulfan is a bifunctional alkylating agent, having a selective immunosuppressive effect on bone marrow. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic). Most common adverse reactions (incidence greater than 60%) were: myelosuppression, nausea, stomatitis, vomiting, anorexia, diarrhea, insomnia, fever, hypomagnesemia, abdominal pain, anxiety, headache, hyperglycemia and hypokalemia. Itraconazole and acetaminophen can decrease busulfan clearance. Phenytoin increases hepatic clearance of busulfan.
CNS Activity
Sources: http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Busulfan_monograph_1June2014.pdf
Curator's Comment: Busulfan is a small, highly lipophilic molecule that easily crosses the blood brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | MYLERAN Approved UseBUSULFEX is indicated for use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous leukemia. BUSULFEX is an alkylating drug indicated for: •Use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous leukemia (CML) (1) Launch Date1954 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1222 ng/mL |
0.8 mg/kg 4 times / day steady-state, intravenous dose: 0.8 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
BUSULFAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1167 μM × min |
0.8 mg/kg 4 times / day steady-state, intravenous dose: 0.8 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
BUSULFAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.35 h |
0.8 mg/kg 4 times / day steady-state, intravenous dose: 0.8 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
BUSULFAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
67.6% |
0.8 mg/kg 4 times / day steady-state, intravenous dose: 0.8 mg/kg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
BUSULFAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg/m2 4 times / day multiple, intravenous MTD Dose: 40 mg/m2, 4 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 4 times / day Sources: |
unhealthy, 1.2–17.2 Health Status: unhealthy Age Group: 1.2–17.2 Sex: M+F Sources: |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: |
4 mg/kg 4 times / day multiple, oral Overdose Dose: 4 mg/kg, 4 times / day Route: oral Route: multiple Dose: 4 mg/kg, 4 times / day Sources: |
unhealthy, 14 |
Disc. AE: Seizures... AEs leading to discontinuation/dose reduction: Seizures Sources: |
18 mg/kg single, oral Overdose Dose: 18 mg/kg Route: oral Route: single Dose: 18 mg/kg Sources: |
unhealthy, 48 |
|
0.8 mg/kg 4 times / day multiple, intravenous Recommended Dose: 0.8 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 0.8 mg/kg, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Myelosuppression, Seizures... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Sources: Seizures Venoocclusive disease Fetal damage |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hepatotoxicity | Disc. AE | 40 mg/m2 4 times / day multiple, intravenous MTD Dose: 40 mg/m2, 4 times / day Route: intravenous Route: multiple Dose: 40 mg/m2, 4 times / day Sources: |
unhealthy, 1.2–17.2 Health Status: unhealthy Age Group: 1.2–17.2 Sex: M+F Sources: |
Seizures | Disc. AE | 4 mg/kg 4 times / day multiple, oral Overdose Dose: 4 mg/kg, 4 times / day Route: oral Route: multiple Dose: 4 mg/kg, 4 times / day Sources: |
unhealthy, 14 |
Fetal damage | Disc. AE | 0.8 mg/kg 4 times / day multiple, intravenous Recommended Dose: 0.8 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 0.8 mg/kg, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Seizures | Disc. AE | 0.8 mg/kg 4 times / day multiple, intravenous Recommended Dose: 0.8 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 0.8 mg/kg, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Venoocclusive disease | Disc. AE | 0.8 mg/kg 4 times / day multiple, intravenous Recommended Dose: 0.8 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 0.8 mg/kg, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Myelosuppression | severe Disc. AE |
0.8 mg/kg 4 times / day multiple, intravenous Recommended Dose: 0.8 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 0.8 mg/kg, 4 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >1000 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
Page: (PMDA) 18, (PMDA_I100_2) 14 |
no [IC50 >812 uM] | |||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
A phase I/II study of multiple-dose intravenous busulfan as myeloablation prior to stem cell transplantation. | 2000 Nov |
|
Individualizing high-dose oral busulfan: prospective dose adjustment in a pediatric population undergoing allogeneic stem cell transplantation for advanced hematologic malignancies. | 2000 Sep |
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Detection of minimal residual disease in a patient having acute myelogenous leukemia with t(16;21)(p11;q22) treated by allogeneic bone marrow transplantation. | 2001 |
|
Secondary failure of platelet recovery after hematopoietic stem cell transplantation. | 2001 |
|
Oral busulfan pharmacokinetics and engraftment in children with Hurler syndrome and other inherited metabolic storage diseases undergoing hematopoietic cell transplantation. | 2001 Apr |
|
Immunotherapy by non-myeloablative allogeneic stem cell transplantation in multiple myeloma: results of a pilot study as salvage therapy after autologous transplantation. | 2001 Apr |
|
Four year follow-up of a case of fucosidosis treated with unrelated donor bone marrow transplantation. | 2001 Apr |
|
Bone marrow transplantation for T-B- severe combined immunodeficiency disease in Athabascan-speaking native Americans. | 2001 Apr |
|
Unrelated donor cord blood transplantation in adults with chronic myelogenous leukemia: results in nine patients from a single institution. | 2001 Apr |
|
Results of an outpatient-based stem cell allotransplant program using nonmyeloablative conditioning regimens. | 2001 Apr |
|
Stability of busulfan in frozen plasma and whole blood samples. | 2001 Apr |
|
[Complications after high dose therapy and autologous stem cell transplantation. Retrospective study of an unselected patient sample]. | 2001 Apr 15 |
|
Dose-reduced conditioning and allogeneic hematopoietic stem cell transplantation from unrelated donors in 42 patients. | 2001 Aug |
|
The pharmacodynamic effect of busulfan in the P39 myeloid cell line in vitro. | 2001 Aug |
|
Developing a pediatric outpatient transplantation program. The Children's Memorial Hospital experience. | 2001 Aug 1 |
|
Comparison of total body irradiation vs busulfan in combination with cyclophosphamide as conditioning for unrelated stem cell transplantation in CML patients. | 2001 Feb |
|
The predictive value of vascular risk factors and gender for the development of thrombotic complications in essential thrombocythemia. | 2001 Feb |
|
Idiopathic pneumonia syndrome following myeloablative chemotherapy and autologous transplantation. | 2001 Feb |
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Fatal upper and lower gastrointestinal cytomegalovirus disease following autologous peripheral blood stem cell transplantation. | 2001 Feb |
|
Results of intensive chemotherapy followed by hematopoietic stem-cell rescue in 22 patients with refractory or recurrent primary CNS lymphoma or intraocular lymphoma. | 2001 Feb 1 |
|
Mouse carotid artery ligation induces platelet-leukocyte-dependent luminal fibrin, required for neointima development. | 2001 Feb 2 |
|
Bone marrow transplantation in a case of severe, type II congenital dyserythropoietic anaemia (CDA II). | 2001 Jan |
|
The biology and treatment of chronic myelogenous leukemia. | 2001 Jan |
|
Successful unrelated bone marrow transplantation for Shwachman-Diamond syndrome. | 2001 Jan |
|
Evaluation of the Murex CMV DNA Hybrid Capture assay (version 2.0) for early diagnosis of cytomegalovirus infection in recipients of an allogeneic stem cell transplant. | 2001 Jul |
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Successful HLA-identical bone marrow transplantation in a patient with PNP deficiency using busulfan and fludarabine for conditioning. | 2001 Jul |
|
Therapeutic activity of 7-[(2-trimethylsilyl)ethyl)]-20 (S)-camptothecin against central nervous system tumor-derived xenografts in athymic mice. | 2001 Jul |
|
No disadvantage in outcome of using matched unrelated donors as compared with matched sibling donors for bone marrow transplantation in children with acute lymphoblastic leukemia in second remission. | 2001 Jul 15 |
|
Costimulation blockade, busulfan, and bone marrow promote titratable macrochimerism, induce transplantation tolerance, and correct genetic hemoglobinopathies with minimal myelosuppression. | 2001 Jul 15 |
|
Arsenic trioxide in the management of acute promyelocytic leukaemia. | 2001 Jul-Aug |
|
Congenital sideroblastic anaemia successfully treated using allogeneic stem cell transplantation. | 2001 Jun |
|
Allogeneic bone marrow transplantation for chronic myeloid leukemia: a retrospective study of busulfan-cytoxan versus total body irradiation-cytoxan as preparative regimen in Koreans. | 2001 Jun |
|
A single institutional experience with 43 pregnancies in essential thrombocythemia. | 2001 Mar |
|
Efficacy of high-dose therapy and autologous hematopoietic stem cell transplantation for non-Hodgkin's lymphoma in adults 60 years of age and older. | 2001 Mar |
|
Accidental busulfan overdose: enhanced drug clearance with hemodialysis in a child with Wiskott-Aldrich syndrome. | 2001 Mar |
|
Pharmacokinetics of liposomal busulphan in man. | 2001 Mar |
|
Low-intensity conditioning is sufficient to ensure engraftment in matched unrelated bone marrow transplantation. | 2001 Mar |
|
Prognostic impact of bone marrow erythropoietic precursor cells and myelofibrosis at diagnosis of Ph1+ chronic myelogenous leukaemia--a multicentre study on 495 patients. | 2001 Mar |
|
Glutathione S-transferase activity influences busulfan pharmacokinetics in patients with beta thalassemia major undergoing bone marrow transplantation. | 2001 Mar |
|
Total body irradiation before allogeneic bone marrow transplantation: is more dose better? | 2001 Mar 15 |
|
Synthesis and in vitro cytotoxicity of novel long chain busulphan analogues. | 2001 Mar 26 |
|
Marked reduction in the incidence of hepatic veno-occlusive disease after allogeneic hematopoietic stem cell transplantation with CD34(+) positive selection. | 2001 May |
|
High-dose melphalan with G-CSF-stimulated whole blood rescue followed by stem cell harvesting and busulphan/cyclophosphamide with autologous stem cell transplantation in multiple myeloma. | 2001 May |
|
O6-Benzylguanine potentiates BCNU but not busulfan toxicity in hematopoietic stem cells. | 2001 May |
|
Bizarre epithelial atypia of the sinonasal tract after chemotherapy. | 2001 May |
|
Considerations in the selection of an appropriate conditioning regimen for the treatment of rheumatoid arthritis by autologous peripheral blood stem cell transplantation. | 2001 Oct |
|
Early full donor myeloid chimerism after reduced-intensity stem cell transplantation using a combination of fludarabine and busulfan. | 2001 Oct |
|
Monitoring of busulfan area under the curve: estimation by a single measurement. | 2001 Oct |
|
[Hematopoietic stem cell transplantation with busulfanthiotepa-cyclophosphamide conditioning for pediatric patients with high-risk acute lymphoblastic leukemia]. | 2001 Sep |
|
Non-myeloablative conditioning regimen of fludarabine, busulfan, anti-thymocyte globulin, and methylprednisolone for allogeneic peripheral blood hematopoietic cell transplantation. | 2001 Sep |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Oral administration: adult dose range for remission induction is 4 to 8 mg, total dose, daily. Dosing on a weight basis is the same for both pediatric patients and adults, approximately 60 mcg/kg of body weight or 1.8 mg/m2 of body surface, daily.
http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=bf456fc7-3a79-47f7-8acc-600b5e2f0dc2
0.8 mg per kg intravenously six hours for four consecutive days for a total of 16 doses
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11480566
P39 myeloid cells were incubated with busulfan in concentrations ranging from 10 to 100 microg/ml for 2, 4 or 8 h, then washed and cultured in busulfan-free medium for 72 h.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:50:41 GMT 2025
by
admin
on
Mon Mar 31 17:50:41 GMT 2025
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Record UNII |
G1LN9045DK
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
BUSULFAN FRESENIUS KABI (AUTHORIZED: HEMATOPOIETIC STEM CELL TRANSPLANTATION)
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FDA ORPHAN DRUG |
140700
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FDA ORPHAN DRUG |
394513
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NDF-RT |
N0000000236
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FDA ORPHAN DRUG |
160402
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FDA ORPHAN DRUG |
81694
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LIVERTOX |
NBK548886
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FDA ORPHAN DRUG |
161602
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NDF-RT |
N0000175558
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EU-Orphan Drug |
EU/3/00/011
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WHO-VATC |
QL01AB01
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FDA ORPHAN DRUG |
105897
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EMA ASSESSMENT REPORTS |
BUSILVEX (AUTHORIZED: HEMATOPOIETIC STEM CELL TRANSPLANTATION)
Created by
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FDA ORPHAN DRUG |
83094
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WHO-ATC |
L01AB01
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IARC | Busulfan | ||
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NCI_THESAURUS |
C222
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Code System | Code | Type | Description | ||
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D002066
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PRIMARY | |||
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SUB05993MIG
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PRIMARY | |||
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busulfan
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PRIMARY | |||
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BUSULFAN
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PRIMARY | |||
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1828
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PRIMARY | RxNorm | ||
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DB01008
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PRIMARY | |||
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BUSULFAN
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PRIMARY | Description: A white, crystalline powder. Solubility: Very slightly soluble in water; sparingly soluble in acetone R; slightly soluble in ethanol (~750 g/l) TS. Category: Cytotoxic drug. Storage: Busulfan should be kept in a well-closed container, protected from light. Additional information: CAUTION: Busulfan must be handled with care, avoiding contact with the skin and inhalation of airborne particles. Definition: Busulfan contains not less than 98.5% and not more than 100.5% of C6H14O6S2, calculated with reference to the dried substance. | ||
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55-98-1
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PRIMARY | |||
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100000085245
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7136
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438
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2478
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C321
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7605
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G1LN9045DK
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Busulfan
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G1LN9045DK
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28901
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m2778
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PRIMARY | Merck Index | ||
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750
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PRIMARY | |||
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200-250-2
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564
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DTXSID3020910
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CHEMBL820
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BINDER->LIGAND |
BINDING
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.63.pdf
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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