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 Date-4.89715204E11 |
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 Co-administed with:: etoposide. i.v.(60 mg/kg; over 4 h on day4) Sources: Page: p.407cyclophosphamide. i.v.(120 mg/kg over 1h on days 3, and 2) |
unhealthy, 1.2–17.2 n = 6 Health Status: unhealthy Condition: Acute Myelogenous Leukemia|Myelodysplastic syndrome Age Group: 1.2–17.2 Sex: M+F Population Size: 6 Sources: Page: p.407 |
Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: Page: p.407 |
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: Page: p.127 |
unhealthy, 14 n = 1 Health Status: unhealthy Condition: Myelodysplastic syndrome Age Group: 14 Sex: F Population Size: 1 Sources: Page: p.127 |
Disc. AE: Seizures... AEs leading to discontinuation/dose reduction: Seizures Sources: Page: p.127 |
18 mg/kg single, oral Overdose Dose: 18 mg/kg Route: oral Route: single Dose: 18 mg/kg Sources: Page: p.126 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Myelodysplastic syndrome Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.126 |
|
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic myelogenous leukemia Sources: Page: p.1 |
Disc. AE: Myelosuppression, Seizures... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Sources: Page: p.1Seizures 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 Co-administed with:: etoposide. i.v.(60 mg/kg; over 4 h on day4) Sources: Page: p.407cyclophosphamide. i.v.(120 mg/kg over 1h on days 3, and 2) |
unhealthy, 1.2–17.2 n = 6 Health Status: unhealthy Condition: Acute Myelogenous Leukemia|Myelodysplastic syndrome Age Group: 1.2–17.2 Sex: M+F Population Size: 6 Sources: Page: p.407 |
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: Page: p.127 |
unhealthy, 14 n = 1 Health Status: unhealthy Condition: Myelodysplastic syndrome Age Group: 14 Sex: F Population Size: 1 Sources: Page: p.127 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic myelogenous leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic myelogenous leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic myelogenous leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Chronic myelogenous leukemia Sources: Page: p.1 |
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 new method for tolerance induction: busulfan administration followed by intravenous injection of neuraminidase-treated donor bone marrow. | 2001 |
|
[Hemorrhagic cystitis related to the high-dose conditioning therapy in a bone marrow recipient]. | 2001 |
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Oral busulfan pharmacokinetics and engraftment in children with Hurler syndrome and other inherited metabolic storage diseases undergoing hematopoietic cell transplantation. | 2001 Apr |
|
Thiotepa, busulfan, cyclophosphamide (TBC) and autologous hematopoietic transplantation: an intensive regimen for the treatment of multiple myeloma. | 2001 Apr |
|
Allogeneic stem cell transplantation reduces disease progression compared to autologous transplantation in patients with multiple myeloma. | 2001 Apr |
|
[Mantle cell lymphoma]. | 2001 Apr |
|
[Successful second transplant from one-locus HLA-mismatched unrelated donor for graft rejection following initial transplant from another unrelated donor in a patient with chronic myelogenous leukemia]. | 2001 Aug |
|
Griscelli syndrome: report of the first peripheral blood stem cell transplant and the role of mutations in the RAB27A gene as an indication for BMT. | 2001 Aug |
|
Immune reconstitution following allogeneic stem cell transplantation in recipients conditioned by low intensity vs myeloablative regimen. | 2001 Aug |
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The pharmacodynamic effect of busulfan in the P39 myeloid cell line in vitro. | 2001 Aug |
|
Sensitive and rapid quantification of busulfan in small plasma volumes by liquid chromatography-electrospray mass spectrometry. | 2001 Aug |
|
Changes in erythropoietin pharmacokinetics following busulfan-induced bone marrow ablation in sheep: evidence for bone marrow as a major erythropoietin elimination pathway. | 2001 Aug |
|
Thiotepa, busulfan, and cyclophosphamide as a preparative regimen for allogeneic transplantation for advanced myelodysplastic syndrome and acute myelogenous leukemia. | 2001 Aug |
|
Myeloablation and autologous peripheral blood stem cell rescue results in hematologic and clinical responses in patients with myeloid metaplasia with myelofibrosis. | 2001 Aug 1 |
|
Rhenium 188-labeled anti-CD66 (a, b, c, e) monoclonal antibody to intensify the conditioning regimen prior to stem cell transplantation for patients with high-risk acute myeloid leukemia or myelodysplastic syndrome: results of a phase I-II study. | 2001 Aug 1 |
|
Systemic fusariosis after a preparative regimen including thiotepa, VP-16 and busulfan used for blood stem cell transplantation in Hodgkin's disease. | 2001 Jan |
|
Autologous peripheral blood stem cell transplantation for patients with malignancies: the Tri-Service General Hospital experience. | 2001 Jul |
|
Lethal adenovirus infection in a patient who had undergone nonmyeloablative stem cell transplantation. | 2001 Jul |
|
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 |
|
High-dose melphalan with autologous hematopoietic stem cell transplantation for acute myeloid leukemia: results of a retrospective analysis of the Italian Pediatric Group for Bone Marrow Transplantation. | 2001 Jul |
|
Successful HLA-identical bone marrow transplantation in a patient with PNP deficiency using busulfan and fludarabine for conditioning. | 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 |
|
Busulfan levels are influenced by prior treatment and are associated with hepatic veno-occlusive disease and early mortality but not with delayed complications following marrow transplantation. | 2001 Jun |
|
A cautionary tale: how to delete mouse haemopoietic stem cells with busulphan. | 2001 Jun |
|
Congenital sideroblastic anaemia successfully treated using allogeneic stem cell transplantation. | 2001 Jun |
|
Estrogen receptor-alpha is required by the supporting somatic cells for spermatogenesis. | 2001 Jun 10 |
|
Bone marrow features improve prognostic efficiency in multivariate risk classification of chronic-phase Ph(1+) chronic myelogenous leukemia: a multicenter trial. | 2001 Jun 15 |
|
Overview of the treatment of infant central nervous system tumors: medulloblastoma as a model. | 2001 Jun-Jul |
|
Pharmacodynamics of high-dose chemotherapy. | 2001 Mar |
|
Cidofovir treatment of human polyomavirus-associated acute haemorrhagic cystitis. | 2001 Mar |
|
Hepatic venoocclusive disease: a major complication of hematopoietic stem cell transplantation in cancer patients. | 2001 Mar-Apr |
|
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 |
|
Hydroxyurea and periodicity in myeloproliferative disease. | 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 |
|
Standardized, unrelated donor cord blood transplantation in adults with hematologic malignancies. | 2001 Oct 15 |
|
[Hematopoietic stem cell transplantation with busulfanthiotepa-cyclophosphamide conditioning for pediatric patients with high-risk acute lymphoblastic leukemia]. | 2001 Sep |
|
Allogeneic bone marrow transplantation-mediated transfer of specific immunity against Toxocara canis associated with excessive IgE. | 2001 Sep |
|
Intravenous busulphan for conditioning before autologous or allogeneic human blood stem cell transplantation. | 2001 Sep |
|
Unexplained pulmonary hypertension in chronic myeloproliferative disorders. | 2001 Sep |
|
Neonatal bone marrow transplantation for severe combined immunodeficiency. | 2001 Sep |
|
Sexual differentiation of germ cell deficient gonads in the medaka, Oryzias latipes. | 2001 Sep 1 |
|
New method for thyroid transplantation across major histocompatibility complex barriers using allogeneic bone marrow transplantation. | 2001 Sep 27 |
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
Wed Jul 05 22:44:49 UTC 2023
by
admin
on
Wed Jul 05 22:44:49 UTC 2023
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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)
Created by
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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
Created by
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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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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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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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