BUSULFAN

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

HIDE SMILES / InChI

Molecular Formula	C6H14O6S2
Molecular Weight	246.302
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278	Crosslinking Agent 81

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic myeloid leukemia 25	Palliative		Approved 8,429	MYLERAN

C_max

Value	Dose	Co-administered	Analyte	Population
1222 ng/mL	0.8 mg/kg 4 times / day steady-state, intravenous		BUSULFAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1167 μM × min	0.8 mg/kg 4 times / day steady-state, intravenous		BUSULFAN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.35 h	0.8 mg/kg 4 times / day steady-state, intravenous		BUSULFAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
67.6%	0.8 mg/kg 4 times / day steady-state, intravenous		BUSULFAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
40 mg/m2 4 times / day multiple, intravenous MTD	unhealthy, 1.2–17.2 n = 6	Disc. AE: Hepatotoxicity...
4 mg/kg 4 times / day multiple, oral Overdose	unhealthy, 14 n = 1	Disc. AE: Seizures...
18 mg/kg single, oral Overdose	unhealthy, 48 n = 1
0.8 mg/kg 4 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Myelosuppression, Seizures...

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AEs

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AE	Significance	Dose	Population
Hepatotoxicity	Disc. AE	40 mg/m2 4 times / day multiple, intravenous MTD	unhealthy, 1.2–17.2 n = 6
Seizures	Disc. AE	4 mg/kg 4 times / day multiple, oral Overdose	unhealthy, 14 n = 1
Fetal damage	Disc. AE	0.8 mg/kg 4 times / day multiple, intravenous Recommended	unhealthy
Seizures	Disc. AE	0.8 mg/kg 4 times / day multiple, intravenous Recommended	unhealthy
Venoocclusive disease	Disc. AE	0.8 mg/kg 4 times / day multiple, intravenous Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C19 1,478 CYP2E1 882 BSEP 402 OATP1B1 788 OATP1B3 706 MRP2 383 MRP3 157 MRP4 204

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3,277	no [IC50 >10 uM]
CYP2C19 1,553	inhibitor 3,277	no [IC50 >10 uM]
CYP2C9 1,819	inhibitor 3,277	no [IC50 >10 uM]
CYP2D6 1,891	inhibitor 3,277	no [IC50 >10 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,737	substrate 3,367	likely

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28901	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28901
ChemicalBook	CB2105891	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2105891
ChemicalBook	CB72673681	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB72673681
MolPort	MolPort-001-783-406	https://www.molport.com/shop/molecule-link/MolPort-001-783-406
Selleck Chemicals	Busulfan(Busulfex)	http://www.selleckchem.com/products/Busulfan(Busulfex).html

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PubMed

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Title	Date	PubMed
Endocardial fibrosis following busulfan treatment.	1975 Feb 3	1054099
Determination of tetrahydrothiophene formation as a probe of in vitro busulfan metabolism by human glutathione S-transferase A1-1: use of a highly sensitive gas chromatographic-mass spectrometric method.	1999 Jun 25	10437668
Thiotepa, busulfan and cyclophosphamide as a preparative regimen for allogeneic transplantation for advanced chronic myelogenous leukemia.	1999 May	10373061
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	11340253
Four year follow-up of a case of fucosidosis treated with unrelated donor bone marrow transplantation.	2001 Apr	11360116

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Patents

Sample Use Guides

In Vivo Use Guide

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

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
Record UNII	G1LN9045DK
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

BUSULFAN

Official Name

English

BUSULFANUM [WHO-IP LATIN]

Common Name

English

BUSULFAN [MI]

Common Name

English

BUSULFAN [JAN]

Common Name

English

BUSULFAN [EMA EPAR]

Common Name

English

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Classification Tree

Code System

Code

STEM CELL TRANSPLANTATION

EMA ASSESSMENT REPORTS

BUSULFAN FRESENIUS KABI (AUTHORIZED: HEMATOPOIETIC STEM CELL TRANSPLANTATION)

Designated/Withdrawn

FDA ORPHAN DRUG

140700

Designated

FDA ORPHAN DRUG

394513

Physiochemical Activity

NDF-RT

N0000000236

Designated

FDA ORPHAN DRUG

160402

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Code System

Code

Type

Description

MESH

D002066

PRIMARY

EVMPD

SUB05993MIG

PRIMARY

ALANWOOD

busulfan

PRIMARY

WIKIPEDIA

BUSULFAN

PRIMARY

RXCUI

1828

PRIMARY

RxNorm

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

32 % (average)

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Related Record

Type

Details


					G1LN9045DK

BUSULFAN

ACTIVE MOIETY

Comments:

http://apps.who.int/phint/pdf/b/Jb.6.1.63.pdf

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	0.64 Liters/Kilogram (average)

Biological Half-life	PHARMACOKINETIC	[2 to 3] hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator