GLUFOSFAMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H21Cl2N2O7P
Molecular Weight	383.163
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC[C@H]1O[C@@H](OP(=O)(NCCCl)NCCCl)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=PSVUJBVBCOISSP-SPFKKGSWSA-N

InChI=1S/C10H21Cl2N2O7P/c11-1-3-13-22(19,14-4-2-12)21-10-9(18)8(17)7(16)6(5-15)20-10/h6-10,15-18H,1-5H2,(H2,13,14,19)/t6-,7-,8+,9-,10+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H21Cl2N2O7P
Molecular Weight	383.163
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Ifosfamide (IF) is a widely used antitumor prodrug. It is in the oxazaphosphorine class of alkylating agents, and it is effective against solid tumors. Ifosfamide mechanism of crosslinking DNA plays a major role in preventing cancer cells from proliferating. Ifosfamide is approved by FDA for the treatment of germ cell testicular cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Germ cell testicular cancer 3	Primary		Approved 8,583	IFEX

C_max

Value	Dose	Analyte	Population
346 μM	3 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens
200 μM	1.5 g/m² single, oral	IFOSFAMIDE plasma	Homo sapiens
203 μM	1.5 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
2197 mM × h	3 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens
1360 μM × h	1.5 g/m² single, oral	IFOSFAMIDE plasma	Homo sapiens
1520 μM × h	1.5 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens
7.54 mM × h	3 g/m² 1 times / day multiple, intravenous	IFOSFAMIDE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.33 h	3 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens
5 h	1.5 g/m² single, oral	IFOSFAMIDE plasma	Homo sapiens
5.6 h	1.5 g/m² single, intravenous	IFOSFAMIDE plasma	Homo sapiens
2.12 h	3 g/m² 1 times / day multiple, intravenous	IFOSFAMIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
100%	unknown		IFOSFAMIDE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
18 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45	DLT: Neutropenia, Infection...
2.25 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45	DLT: Neutropenia, Febrile neutropenia...
1.2 g/m2 1 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Nephrotoxicity, Renal failure...

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AEs

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AE	Significance	Dose	Population
Thrombocytopenia	grade 4, 66.7% DLT	18 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45
Neutropenia	grade 4, 83.3% DLT	18 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45
Infection	severe, 33.3% DLT	18 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45
Anemia	grade 4, 66.7% DLT	2.25 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45
Neutropenia	grade 4, 66.7% DLT	2.25 g/m2 1 times / day multiple, intravenous MTD	unhealthy, 45

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inducer 1,087	substrate 1,193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP3A5 446 CYP2B1 12 CYP2C19 1,119 CYP2A6 626 CYP2C8 810 UGT 219 alcohol dehydrogenase 7 ALDH1 3 P-gp 2,052 OCT2 434 OAT1 395 OAT3 391 MRP1 113

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2,633	inducer 1,966	yes
PXR 51	activator 342	yes

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Drug as victim

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Target	Modality	Activity	Metabolite
OAT1 395	substrate 4,014	no
OAT3 391	substrate 4,014	no
P-gp 2,052	substrate 4,014	no
CYP2C9 1,193	substrate 4,014	poor
ALDH1 3	substrate 4,014	yes	Aldoifosfamide 3

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PubMed

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Title	Date	PubMed
Taurine attenuates fanconi syndrome induced by ifosfamide without compromising its antitumor activity.	1998	10063969
Thymoquinone attenuates ifosfamide-induced Fanconi syndrome in rats and enhances its antitumor activity in mice.	1999 Nov 1	10619376
Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response.	1999 Nov-Dec	10774566
Preresectional chemotherapy in stage IIIA non-small-cell lung cancer: a 7-year assessment of a randomized controlled trial.	1999 Oct	10574676
Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature.	2000 Jan	10646879

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Patents

Sample Use Guides

In Vivo Use Guide

30-min infusion at a dose of 1.2 grams per m2 per day for 5 consecutive days

Route of Administration: Intravenous

In Vitro Use Guide

Human testicular germ cell tumour lines H 12.1 and 2102 EP were treated with ifosfamide at 50 mg kg-1 day-1.

Substance Class	Chemical
Record UNII	1W5N8SZD9A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

D19575

Preferred Name

English

GLUFOSFAMIDE

Official Name

English

D-19575

Code

English

GLUCOSYLIFOSFAMIDE MUSTARD

Common Name

English

GLUFOSFAMIDE [HSDB]

Common Name

English

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Classification Tree

Code System

Code

Mustard Agent

NCI_THESAURUS

C697

Positive

EU-Orphan Drug

EU/3/11/851

Designated

FDA ORPHAN DRUG

221606

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Code System

Code

Type

Description

MERCK INDEX

m5774

PRIMARY

Merck Index

NCI_THESAURUS

C1612

PRIMARY

DRUG BANK

DB06177

PRIMARY

HSDB

7024

PRIMARY

ChEMBL

CHEMBL2107143

PRIMARY

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Related Record

Type

Details


					ARX5AJ985I

4-HYDROXYIFOSFAMIDE

METABOLITE ACTIVE -> PRODRUG

Amount:

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Related Record

Type

Details


					ARX5AJ985I

4-HYDROXYIFOSFAMIDE

ACTIVE MOIETY

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator