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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
Structure of GLUFOSFAMIDE

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
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

CNS Active
4002
Curator's Comment: Ifosfamide crosses the blood-brain barrier and may cause encephalopathy.

Originator

Approval Year

1987
121
Targets

Targets

Primary TargetPharmacologyConditionPotency
Crosslinking Agent
83
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
IFEX

Approved Use

Ifosfamide injection, used in combination with certain other approved antineoplastic agents, is indicated for third line chemotherapy of germ cell testicular cancer. It should be used in combination with a prophylactic agent for hemorrhagic cystitis, such as mesna.

Launch Date

1988
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
346 μM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/9528844
3 g/m² single, intravenous
dose: 3 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
200 μM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, oral
dose: 1.5 g/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
203 μM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, intravenous
dose: 1.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2197 mM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/9528844
3 g/m² single, intravenous
dose: 3 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1360 μM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, oral
dose: 1.5 g/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1520 μM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, intravenous
dose: 1.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7.54 mM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8339288
3 g/m² 1 times / day multiple, intravenous
dose: 3 g/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.33 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/9528844
3 g/m² single, intravenous
dose: 3 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, oral
dose: 1.5 g/m²
route of administration: Oral
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5.6 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/1795004
1.5 g/m² single, intravenous
dose: 1.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.12 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8339288
3 g/m² 1 times / day multiple, intravenous
dose: 3 g/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
IFOSFAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
unknown
 IFOSFAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
18 g/m2 1 times / day multiple, intravenous
MTD
Dose: 18 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 18 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
DLT: Neutropenia, Infection...
Dose limiting toxicities:
Neutropenia (grade 4, 83.3%)
Infection (severe, 33.3%)
Thrombocytopenia (grade 4, 66.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
2.25 g/m2 1 times / day multiple, intravenous
MTD
Dose: 2.25 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.25 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
DLT: Neutropenia, Febrile neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 66.7%)
Febrile neutropenia (grade 5, 33.3%)
Thrombocytopenia (grade 4, 66.7%)
Anemia (grade 4, 66.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
1.2 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 1.2 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 g/m2, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
Disc. AE: Nephrotoxicity, Renal failure...
AEs leading to
discontinuation/dose reduction:
Nephrotoxicity (severe)
Renal failure (severe)
Cystitis hemorrhagic (severe)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Thrombocytopenia grade 4, 66.7%
DLT
18 g/m2 1 times / day multiple, intravenous
MTD
Dose: 18 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 18 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
Neutropenia grade 4, 83.3%
DLT
18 g/m2 1 times / day multiple, intravenous
MTD
Dose: 18 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 18 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
Infection severe, 33.3%
DLT
18 g/m2 1 times / day multiple, intravenous
MTD
Dose: 18 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 18 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10572607
Anemia grade 4, 66.7%
DLT
2.25 g/m2 1 times / day multiple, intravenous
MTD
Dose: 2.25 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.25 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
Neutropenia grade 4, 66.7%
DLT
2.25 g/m2 1 times / day multiple, intravenous
MTD
Dose: 2.25 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.25 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
Thrombocytopenia grade 4, 66.7%
DLT
2.25 g/m2 1 times / day multiple, intravenous
MTD
Dose: 2.25 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.25 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
Febrile neutropenia grade 5, 33.3%
DLT, Disc. AE
2.25 g/m2 1 times / day multiple, intravenous
MTD
Dose: 2.25 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.25 g/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
unhealthy, 45
Health Status: unhealthy
Age Group: 45
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/11840607
Cystitis hemorrhagic severe
Disc. AE
1.2 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 1.2 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 g/m2, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
Nephrotoxicity severe
Disc. AE
1.2 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 1.2 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 g/m2, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
Renal failure severe
Disc. AE
1.2 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 1.2 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 g/m2, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019763s017lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inducer
1087
substrate
1193

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
776

CYP3A5
446

CYP2B1
12

CYP2C19
1119

CYP2A6
626

CYP2C8
810

UGT
219

alcohol dehydrogenase
7

ALDH1
3

P-gp
2052

OCT2
434

OAT1
395

OAT3
391

MRP1
113
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
2633
 yes
PXR
51
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OAT1
395
 no
OAT3
391
 no
P-gp
2052
 no
CYP2C9
1193
 poor
ALDH1
3
 yes
Aldoifosfamide
3
CYP2A6
626
 yes
CYP2B1
12
 yes
CYP2C19
1119
 yes
CYP2C8
810
 yes
CYP3A5
446
 yes
MRP1
113
 yes
OCT2
434
 yes
UGT
219
 yes
4-HYDROXYIFOSFAMIDE
3
alcohol dehydrogenase
7
 yes
4-HYDROXYIFOSFAMIDE
3
CYP2B6
776
 yes
no (co-administration study)
Comment: Coadministration of ifosfamide with ketoconazole or rifampin did not produce changes inthe pharmacokinetics of the parent or metabolites that may result in an increased benefit of ifosfamidetherapy. (https://pubmed.ncbi.nlm.nih.gov/11503007/)
Page: 28.0
CYP3A4
1946
 yes
no (co-administration study)
Comment: Coadministration of ifosfamide with ketoconazole or rifampin did not produce changes inthe pharmacokinetics of the parent or metabolites that may result in an increased benefit of ifosfamidetherapy. (https://pubmed.ncbi.nlm.nih.gov/11503007/)
Page: 28.0
PubMed

PubMed

TitleDatePubMed
Taurine attenuates fanconi syndrome induced by ifosfamide without compromising its antitumor activity.
1998
Intratumoral injection of encapsulated cells producing an oxazaphosphorine activating cytochrome P450 for targeted chemotherapy.
1998
Anticancer drug sensitivity and expression of multidrug resistance markers in early passage human sarcomas.
1999 Aug
L-Histidinol attenuates Fanconi syndrome induced by ifosfamide in rats.
1999 Jul-Aug
Methylene blue in the treatment and prevention of ifosfamide-induced encephalopathy: report of 12 cases and a review of the literature.
2000 Jan
Manic episode in an ifosfamide-treated patient.
2000 Jan-Feb
Subacute central nervous system degeneration in a child: an unusual manifestation of ifosfamide intoxication.
2000 Jul
Two episodes of ifosfamide-related neurotoxicity in the same patient following different schedules and doses of the drug. A case report.
2000 Nov-Dec
Thymic malignancies.
2001
Modified dorsalis pedis flap for coverage of a pretibial pressure sore after hip rotationplasty.
2001 Apr
Local hyperthermia, radiation, and chemotherapy in recurrent breast cancer is feasible and effective except for inflammatory disease.
2001 Apr 1
Phase II study of a high-dose ifosfamide-based chemotherapy regimen with growth factor rescue in recurrent aggressive NHL. High response rates and limited toxicity, but limited impact on long-term survival.
2001 Feb
Chemotherapy agents in transitional cell carcinoma: the old and the new.
2001 Feb
Absence of major peripheral neuropathy in a phase II trial of ifosfamide with vinorelbine in patients with ovarian cancer previously treated with platinum and paclitaxel.
2001 Feb
Selective use of whole-lung irradiation for patients with Ewing sarcoma family tumors and pulmonary metastases at the time of diagnosis.
2001 Feb
Adult Gaucher disease in association with primary malignant bone tumors.
2001 Feb 1
[Prostatic angiosarcoma: report of a new case].
2001 Jan
Recurrent germinoma in the optic nerve: report of two cases.
2001 Jan
A randomized trial of amifostine as a cytoprotective agent in patients receiving chemotherapy for small cell lung cancer.
2001 Jan 5
Necrotic, rather than apoptotic, cell death caused by cytochrome P450-activated ifosfamide.
2001 Mar
Gemcitabine for the treatment of non-small-cell lung cancer.
2001 Mar
Ifosfamide and mitoxantrone in the treatment of recurrent and/or metastatic squamous cell carcinoma of the head and neck.
2001 Mar
Intrasellar rhabdomyosarcoma: case report.
2001 Mar
[A case of primary malignant hemangiopericytoma of the lung with marked response to combination chemotherapy with cisplatin, ifosfamide and gemcitabine].
2001 Mar
Phase I trial of ifosfamide and 24-h infusional paclitaxel in pelvic malignancies: a Gynecologic Oncology Group study.
2001 Mar
Metastatic osteosarcoma to the liver after treatment for synovial sarcoma: a case report.
2001 Mar
Adjuvant chemotherapy for adult soft tissue sarcomas of the extremities and girdles: results of the Italian randomized cooperative trial.
2001 Mar 1
Localized Ewing tumor of bone: final results of the cooperative Ewing's Sarcoma Study CESS 86.
2001 Mar 15
Patents

Patents

04929607
3
20110251159
6
6197760
3
8507464
4
JP2002511777A
420
JP2003529540A
50
JP2006528196A
42
JP2007507506A
3
JP2008510829A
14
JP2008519861A
32
JP2009513567A
66
JP2011522802A
31
JP2011524416A
146
JP4787165B2
104
JPS63230697A
3

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
Created
by admin
on Mon Mar 31 18:04:09 GMT 2025
Edited
by admin
on Mon Mar 31 18:04:09 GMT 2025
Record UNII
1W5N8SZD9A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
D19575
Preferred Name English
GLUFOSFAMIDE
HSDB   INN   MART.   MI   WHO-DD  
INN  
Official Name English
D-19575
Code English
GLUCOSYLIFOSFAMIDE MUSTARD
Common Name English
GLUFOSFAMIDE [HSDB]
Common Name English
GLUFOSFAMIDE [MI]
Common Name English
GLUFOSFAMIDE [MART.]
Common Name English
glufosfamide [INN]
Common Name English
.BETA.-D-GLUCOPYRANOSE, 1-(N,N'-BIS(2-CHLOROETHYL))PHOSPHORODIAMIDATE
Common Name English
Glufosfamide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
EU-Orphan Drug EU/3/11/851
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
FDA ORPHAN DRUG 221606
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
Code System Code Type Description
MERCK INDEX
m5774
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C1612
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
DRUG BANK
DB06177
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
HSDB
7024
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL2107143
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
FDA UNII
1W5N8SZD9A
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
EVMPD
SUB07941MIG
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
SMS_ID
100000084228
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID001031222
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
WIKIPEDIA
Glufosfamide
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
INN
7590
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
CAS
132682-98-5
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
PUBCHEM
123628
Created by admin on Mon Mar 31 18:04:09 GMT 2025 , Edited by admin on Mon Mar 31 18:04:09 GMT 2025
PRIMARY
Related Record Type Details
Structure of 4-HYDROXYIFOSFAMIDE
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
Structure of 4-HYDROXYIFOSFAMIDE
ACTIVE MOIETY
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