Identification

Name
Busulfan
Accession Number
DB01008
Description

Busulfan is a bifunctional alkylating agent, having a selective immunosuppressive effect on bone marrow. It is not a structural analog of the nitrogen mustards. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic), but although symptomatic relief is provided, no permanent remission is brought about. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), busulfan is listed as a known carcinogen.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 246.302
Monoisotopic: 246.02317956
Chemical Formula
C6H14O6S2
Synonyms
  • 1,4-Bis(methanesulfonoxy)butane
  • 1,4-Butanediol dimethanesulfonate
  • 1,4-Dimesyloxybutane
  • 1,4-Dimethanesulfonoxybutane
  • Busulfan
  • Busulfano
  • Busulfanum
  • Busulphan
  • Tetramethylene bis(methanesulfonate)
External IDs
  • NCI-C01592
  • NSC-750

Pharmacology

Indication

For use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous (myeloid, myelocytic, granulocytic) leukemia (FDA has designated busulfan as an orphan drug for this use). It is also used as a component of pretransplant conditioning regimens in patients undergoing bone marrow transplantation for acute myeloid leukemia and nonmalignant diseases.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Busulfan is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn leads to a miscoding of DNA. Alkylating agents are cell cycle-nonspecific and work by three different mechanisms, all of which achieve the same end result - disruption of DNA function and cell death. Overexpression of MGST2, a glutathione s-transferase, is thought to confer resistance to busulfan. The role of MGST2 in the metabolism of busulfan is unknown however.

Mechanism of action

Busulfan is an alkylating agent that contains 2 labile methanesulfonate groups attached to opposite ends of a 4-carbon alkyl chain. Once busulfan is hydrolyzed, the methanesulfonate groups are released and carbonium ions are produced. These carbonium ions alkylate DNA, which results in the interference of DNA replication and RNA transcription, ultimately leading to the disruption of nucleic acid function. Specifically, its mechanism of action through alkylation produces guanine-adenine intrastrand crosslinks. These crosslinks occur through a SN2 reaction guanine N7 nucleophilically attacks the carbon adjacent to the mesylate leaving group. This kind of damage cannot be repaired by cellular machinery and thus the cell undergoes apoptosis.

TargetActionsOrganism
ADNA
cross-linking/alkylation
Humans
Absorption

Completely absorbed from the gastrointestinal tract. Busulfan is a small, highly lipophilic molecule that crosses the blood-brain-barrier. The absolute bioavailability, if a single 2 mg IV bolus injection is given to adult patients, is 80% ± 20%. In children (1.5 - 6 years old), the absolute bioavailability was 68% ± 31%. When a single oral dose is given to patients, the area under the curve (AUC) was 130 ng•hr/mL. The peak plasma concentration when given orally is 30 ng/mL (after dose normalization to 2 mg). It takes 0.9 hours to reach peak plasma concentration after dose normalization to 4 mg.

Volume of distribution
Not Available
Protein binding

32% bound to plasma proteins and 47% bound to red blood cells.

Metabolism

Busulfan is extensively metabolizes in the hepatic. Busulfan is predominantly metabolized by conjugation with glutathione, both spontaneously and by glutathione S-transferase (GST) catalysis. GSTA1 is the primary GST isoform that facilitates the the metabolism of busulfan. Other GST isoforms that are also involved are GSTM1 and GSTP1. At least 12 metabolites have been identified among which tetrahydrothiophene, tetrahydrothiophene 12-oxide, sulfolane, and 3-hydroxysulfolane were identified. These metabolites do not have cytotoxic activity.

Route of elimination

Following administration of 14C- labeled busulfan to humans, approximately 30% of the radioactivity was excreted into the urine over 48 hours; negligible amounts were recovered in feces. Less than 2% of the administered dose is excreted in the urine unchanged within 24 hours. Elimination of busulfan is independent of renal function.

Half-life

2.6 hours

Clearance
  • 2.52 ml/min/kg [Following an infusion of dose of 0.8 mg/kg every six hours, for a total of 16 doses over four days]
Adverse Effects
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Toxicity

Signs of overdose include allergic reaction, unusual bleeding or bruising, sudden weakness or unusual fatigue, persistent cough, congestion, or shortness of breath; flank, stomach or joint pain; pronounced nausea, vomiting, diarrhea, dizziness, confusion, or darkening of the skin, chills, fever, collapse, and loss of consciousness.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Busulfan can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Busulfan can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Busulfan.
AcalabrutinibThe metabolism of Busulfan can be decreased when combined with Acalabrutinib.
AcenocoumarolThe risk or severity of bleeding can be increased when Acenocoumarol is combined with Busulfan.
AcetaminophenAcetaminophen may decrease the excretion rate of Busulfan which could result in a higher serum level.
AcetazolamideThe metabolism of Busulfan can be decreased when combined with Acetazolamide.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Busulfan.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Acetylsalicylic acid is combined with Busulfan.
AdalimumabThe metabolism of Busulfan can be increased when combined with Adalimumab.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Drink plenty of fluids.
  • Exercise caution with grapefruit products.
  • Exercise caution with St. John's Wort.
  • Take at the same time every day.

Products

Product Images
International/Other Brands
Bisulfex / Busilvex (Pierre Fabre) / Leucosulfan / Mablin / Mielucin / Misulban / Mitostan / Myeloleukon
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Busulfan for InjectionSolutionIntravenousSterimax Inc2017-10-04Not applicableCanada flag
Busulfan for InjectionSolutionIntravenousMarcan Pharmaceuticals IncNot applicableNot applicableCanada flag
Busulfan InjectionSolutionIntravenousApotex CorporationNot applicableNot applicableCanada flag
BusulfexInjection, powder, for solution60 mg/1IntravenousESP Pharma, Inc.2006-08-092007-07-26US flag
BusulfexInjection6 mg/1mLIntravenousOtsuka America Pharmaceutical, Inc.2015-02-132021-01-31US flag
BusulfexSolution60 mgIntravenousOtsuka Pharmaceutical Co., Ltd.1999-09-23Not applicableCanada flag
BusulfexInjection6 mg/1mLIntravenousOtsuka America Pharmaceutical, Inc.1999-02-04Not applicableUS flag
BusulfexInjection60 mg/10mLIntravenousESP Pharma, Inc.2007-05-14Not applicableUS flag
MyleranTablet2 mgOralAspen Pharmacare Canada Inc.1954-12-31Not applicableCanada flag
MyleranTablet, film coated2 mg/1OralAspen Global Inc.1985-03-21Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BusulfanInjection, solution6 mg/1mLIntravenousHospira, Inc.2019-02-28Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousAccord Healthcare, Inc2019-07-22Not applicableUS flag
BusulfanInjection, solution, concentrate6 mg/1mLIntravenousAthenex Pharmaceutical Division, Llc.2019-02-10Not applicableUS flag
BusulfanInjection, solution, concentrate6 mg/1mLIntravenousActavis Pharma, Inc.2018-01-042021-01-31US flag
BusulfanInjection6 mg/1mLIntravenousCELLTRION USA, INC.2019-12-01Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousMylan Institutional LLC2017-11-21Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousAMERICAN REGENT, INC.2017-04-01Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousPharmascience Inc.2017-05-19Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousFresenius Kabi USA, LLC2019-11-11Not applicableUS flag
BusulfanInjection6 mg/1mLIntravenousApotex Corp.2019-08-19Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
L01AB01 — Busulfan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic sulfonic acids and derivatives
Sub Class
Organosulfonic acids and derivatives
Direct Parent
Organosulfonic acid esters
Alternative Parents
Sulfonic acid esters / Sulfonyls / Methanesulfonates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Methanesulfonate / Organic oxide / Organic oxygen compound / Organooxygen compound / Organosulfonic acid ester / Organosulfur compound / Sulfonic acid ester / Sulfonyl
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
methanesulfonate ester (CHEBI:28901)

Chemical Identifiers

UNII
G1LN9045DK
CAS number
55-98-1
InChI Key
COVZYZSDYWQREU-UHFFFAOYSA-N
InChI
InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
IUPAC Name
4-(methanesulfonyloxy)butyl methanesulfonate
SMILES
CS(=O)(=O)OCCCCOS(C)(=O)=O

References

Synthesis Reference

Timmis, G.M.; U S . Patent 2,917,432; December 15, 1959; assigned to Burroughs Wellcome & Co., Inc.

US2917432
General References
  1. Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. [PubMed:16601191]
  2. Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. doi: 10.1002/em.20603. [PubMed:20577993]
  3. Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. [PubMed:1422285]
  4. Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. doi: 10.1016/j.bbmt.2008.12.489. Epub 2009 Feb 12. [PubMed:19361744]
  5. McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. doi: 10.1517/17425250903107764. [PubMed:19611402]
  6. Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM: Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. [PubMed:18690982]
  7. Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. [PubMed:18690856]
Human Metabolome Database
HMDB0015143
KEGG Drug
D00248
KEGG Compound
C06862
PubChem Compound
2478
PubChem Substance
46506234
ChemSpider
2384
BindingDB
50237623
RxNav
1828
ChEBI
28901
ChEMBL
CHEMBL820
ZINC
ZINC000001530572
PharmGKB
PA448691
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Busulfan
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (50.7 KB)
MSDS
Download (67.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentLeukemia, Lymphocytic / Malignant Lymphomas / Myelodysplastic Syndromes (MDS) / Myeloproliferative Disorders / Plasma Cell Myeloma1
4Not Yet RecruitingTreatmentChronic Leukemias / Juvenile Myelomonocytic Leukemia / Leukemia, Acute / Myelodysplastic Syndrome1
4Not Yet RecruitingTreatmentLeukemias1
4RecruitingTreatmentThalassemia Major (TM)2
3Active Not RecruitingTreatmentAcute Myeloid Leukemia (AML) / Chronic Chronic myelogenous leukemia / Myelodysplastic Syndrome / Myeloid Malignancy / Myeloproliferative Disorders1
3Active Not RecruitingTreatmentDisorder Related to Bone Marrow Transplantation / Leukemias / Transplantation Infection1
3Active Not RecruitingTreatmentEwing's Sarcoma (ES)1
3Active Not RecruitingTreatmentLeukemias1
3CompletedTreatmentAcute Myeloid Leukemia (AML)2
3CompletedTreatmentAcute Myeloid Leukemia (AML) / Leukemias / Myelodysplastic Syndrome1

Pharmacoeconomics

Manufacturers
  • Otsuka pharmaceutical co ltd
  • Glaxosmithkline
Packagers
  • GlaxoSmithKline Inc.
  • Otsuka America
  • PDL BioPharma Inc.
Dosage Forms
FormRouteStrength
Injection, solution, concentrateIntravenous6 mg/ml
Injection, solution, concentrateIntravenous60 mg/10ml
InjectionIntravenous6 mg/1mL
Injection, solutionIntravenous6 mg/1mL
Injection, solution, concentrateIntravenous6 mg/1mL
SolutionIntravenous
Injection
SolutionIntravenous60 mg
Injection, solution, concentrateIntravenous; Parenteral6 MG/ML
InjectionIntravenous60 mg/10mL
Injection, powder, for solutionIntravenous60 mg/1
TabletOral2 mg
Tablet, film coatedOral2 mg/1
Tablet2 mg
Tablet, film coatedOral2 mg
Tablet
Prices
Unit descriptionCostUnit
Busulfex 6 mg/ml vial115.08USD ml
Myleran 2 mg tablet4.55USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5430057No1995-07-042014-03-30US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)106-107Timmis, G.M.; U S . Patent 2,917,432; December 15, 1959; assigned to Burroughs Wellcome & Co., Inc.
water solubility6.9E+004 mg/LNot Available
logP-0.52HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility5.16 mg/mLALOGPS
logP-0.9ALOGPS
logP-0.76ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area86.74 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.57 m3·mol-1ChemAxon
Polarizability23.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9059
Blood Brain Barrier+0.9674
Caco-2 permeable-0.5956
P-glycoprotein substrateNon-substrate0.7556
P-glycoprotein inhibitor INon-inhibitor0.7224
P-glycoprotein inhibitor IINon-inhibitor0.9651
Renal organic cation transporterNon-inhibitor0.8617
CYP450 2C9 substrateNon-substrate0.8656
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8678
CYP450 2C9 inhibitorNon-inhibitor0.85
CYP450 2D6 inhibitorNon-inhibitor0.9159
CYP450 2C19 inhibitorNon-inhibitor0.7723
CYP450 3A4 inhibitorNon-inhibitor0.9855
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9069
Ames testAMES toxic0.9305
CarcinogenicityCarcinogens 0.7585
BiodegradationReady biodegradable0.5
Rat acute toxicity2.3207 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6005
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0390000000-19a6e15d2bf397b244b1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-1490000000-7895468c598e6a0480c8
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Cross-linking/alkylation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Morales-Ramirez P, Gonzalez-Beltran F: Different behavior of SCE-eliciting lesions induced by low and high doses of busulfan. Environ Mol Mutagen. 2007 Oct;48(8):706-14. [PubMed:17896789]
  4. Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. doi: 10.1002/em.20603. [PubMed:20577993]
  5. Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. [PubMed:1422285]
  6. Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. doi: 10.1016/j.bbmt.2008.12.489. Epub 2009 Feb 12. [PubMed:19361744]
  7. McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. doi: 10.1517/17425250903107764. [PubMed:19611402]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Michalets EL: Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112. [PubMed:9469685]
  2. Sweiss K, Quigley JG, Oh A, Lee J, Ye R, Rondelli D, Patel P: A novel drug interaction between busulfan and blinatumomab. J Oncol Pharm Pract. 2017 Jan 1:1078155217729745. doi: 10.1177/1078155217729745. [PubMed:28857712]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA2
Uniprot ID
P09210
Uniprot Name
Glutathione S-transferase A2
Molecular Weight
25663.675 Da
References
  1. Vassord C, Lapoumeroulie C, Koumaravelou K, Srivastava A, Krishnamoorthy R: Endothelial cells do not express GSTA1: potential relevance to busulfan-mediated endothelial damage during haematopoietic stem cell transplantation. Eur J Haematol. 2008 Apr;80(4):299-302. doi: 10.1111/j.1600-0609.2008.01031.x. Epub 2008 Jan 14. [PubMed:18194479]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA1
Uniprot ID
P08263
Uniprot Name
Glutathione S-transferase A1
Molecular Weight
25630.785 Da
References
  1. Kusama M, Kubota T, Matsukura Y, Matsuno K, Ogawa S, Kanda Y, Iga T: Influence of glutathione S-transferase A1 polymorphism on the pharmacokinetics of busulfan. Clin Chim Acta. 2006 Jun;368(1-2):93-8. Epub 2006 Jan 31. [PubMed:16448639]
  2. Elhasid R, Krivoy N, Rowe JM, Sprecher E, Adler L, Elkin H, Efrati E: Influence of glutathione S-transferase A1, P1, M1, T1 polymorphisms on oral busulfan pharmacokinetics in children with congenital hemoglobinopathies undergoing hematopoietic stem cell transplantation. Pediatr Blood Cancer. 2010 Dec 1;55(6):1172-9. doi: 10.1002/pbc.22739. [PubMed:20672371]
  3. Vassord C, Lapoumeroulie C, Koumaravelou K, Srivastava A, Krishnamoorthy R: Endothelial cells do not express GSTA1: potential relevance to busulfan-mediated endothelial damage during haematopoietic stem cell transplantation. Eur J Haematol. 2008 Apr;80(4):299-302. doi: 10.1111/j.1600-0609.2008.01031.x. Epub 2008 Jan 14. [PubMed:18194479]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM1
Uniprot ID
P09488
Uniprot Name
Glutathione S-transferase Mu 1
Molecular Weight
25711.555 Da
References
  1. Czerwinski M, Gibbs JP, Slattery JT: Busulfan conjugation by glutathione S-transferases alpha, mu, and pi. Drug Metab Dispos. 1996 Sep;24(9):1015-9. [PubMed:8886613]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Czerwinski M, Gibbs JP, Slattery JT: Busulfan conjugation by glutathione S-transferases alpha, mu, and pi. Drug Metab Dispos. 1996 Sep;24(9):1015-9. [PubMed:8886613]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Leukotriene-c4 synthase activity
Specific Function
Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name
MGST2
Uniprot ID
Q99735
Uniprot Name
Microsomal glutathione S-transferase 2
Molecular Weight
16620.4 Da
References
  1. Harkey MA, Czerwinski M, Slattery J, Kiem HP: Overexpression of glutathione-S-transferase, MGSTII, confers resistance to busulfan and melphalan. Cancer Invest. 2005;23(1):19-25. [PubMed:15779864]

Drug created on June 13, 2005 07:24 / Updated on September 17, 2020 23:28

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