Ifosfamide

Identification

Name

Ifosfamide

Accession Number

DB01181

Description

Ifosfamide is a chemotherapeutic agent chemically related to the nitrogen mustards and a synthetic analog of cyclophosphamide. It is active as an alkylating agent and an immunosuppressive agent.

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Ifosfamide (DB01181)

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Weight

Average: 261.086
Monoisotopic: 260.02481966

Chemical Formula

C₇H₁₅Cl₂N₂O₂P

Synonyms

• 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
• Ifosfamida
• Ifosfamide
• Ifosfamidum
• Iphosphamide
• Isofosfamide
• Isophosphamide
• Isosfamide

External IDs

• Z4942

Pharmacology

Indication

Used as a component of various chemotherapeutic regimens as third-line therapy for recurrent or refractory germ cell testicular cancer. Also used as a component of various chemotherapeutic regimens for the treatment of cervical cancer, as well as in conjunction with surgery and/or radiation therapy in the treatment of various soft tissue sarcomas. Other indications include treatment of osteosarcoma, bladder cancer, ovarian cancer. small cell lung cancer, and non-Hodgkin's lymphoma.

Associated Conditions

• Cancer, Bladder
• Cervical Cancers
• Ewing's Sarcoma
• Head and Neck Carcinoma
• Lymphoma, Hodgkins
• Malignant Neoplasm of Pancreas
• Non-Hodgkin's Lymphoma (NHL)
• Ovarian Cancer
• Sarcoma, Osteogenic
• Small Cell Lung Cancer (SCLC)
• Soft Tissue Sarcoma (STS)
• Testicular Germ Cell Cancer
• Advanced thymic carcinoma

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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Pharmacodynamics

Ifosfamide requires activation by microsomal liver enzymes to active metabolites in order to exert its cytotoxic effects. Activation occurs by hydroxylation at the ring carbon atom 4 to form the unstable intermediate 4-hydroxyifosfamide. This metabolite than rapidly degrades to the stable urinary metabolite 4-ketoifosfamide. The stable urinary metabolite, 4-carboxyifosfamide, is formed upon opening of the ring. These urinary metabolites have not been found to be cytotoxic. N, N-bis (2-chloroethyl)-phosphoric acid diamide (ifosphoramide) and acrolein are also found. The major urinary metabolites, dechloroethyl ifosfamide and dechloroethyl cyclophosphamide, are formed upon enzymatic oxidation of the chloroethyl side chains and subsequent dealkylation. It is the alkylated metabolites of ifosfamide that have been shown to interact with DNA. Ifosfamide is cycle-phase nonspecific.

Mechanism of action

The exact mechanism of ifosfamide has not been determined, but appears to be similar to other alkylating agents. Ifosfamide requires biotransformation in the liver by mixed-function oxidases (cytochrome P450 system) before it becomes active. After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily through the alkylation of DNA, done by attaching the N-7 position of guanine to its reactive electrophilic groups. The formation of inter and intra strand cross-links in the DNA results in cell death.

Target	Actions	Organism
ADNA	other/unknown	Humans
UNuclear receptor subfamily 1 group I member 2	Not Available	Humans

Absorption

Not Available

Volume of distribution

Ifosfamide volume of distribution (Vd) approximates the total body water volume, suggesting that distribution takes place with minimal tissue binding. Following intravenous administration of 1.5 g/m2 over 0.5 hour once daily for 5 days to 15 patients with neoplastic disease, the median Vd of ifosfamide was 0.64 L/kg on Day 1 and 0.72 L/kg on Day 5. When given to pediatric patients, the volume of distribution was 21±1.6 L/m^2.

Protein binding

Ifosfamide shows little plasma protein binding.

Metabolism

Primarily hepatic. Ifosfamide is metabolized through two metabolic pathways: ring oxidation ("activation") to form the active metabolite, 4-hydroxy-ifosfamide and side-chain oxidation to form the inactive metabolites, 3-dechloro-ethylifosfamide or 2-dechloroethylifosfamide with liberation of the toxic metabolite, chloroacetaldehyde. Small quantities (nmol/mL) of ifosfamide mustard and 4-hydroxyifosfamide are detectable in human plasma. Metabolism of ifosfamide is required for the generation of the biologically active species and while metabolism is extensive, it is also quite variable among patients.

Hover over products below to view reaction partners

• Ifosfamide
  • 3-Dechloroethylifosfamide
  • Dechloroethylifosfamide
  • Chloroacetaldehyde
  • 4-Hydroxyifosfamide
    • 4-Thioifosfamide
    • aldoifosfamide
      • Isophosphamide mustard
        • Ifosforamide Aziridinium
      • Acrolein
        • Acrylic Acid
      • Carboxylifosfamide
      • Alcoifosfamide
    • 4-Ketoifosfamide

Route of elimination

Ifosfamide is extensively metabolized in humans and the metabolic pathways appear to be saturated at high doses. After administration of doses of 5 g/m2 of 14C-labeled ifosfamide, from 70% to 86% of the dosed radioactivity was recovered in the urine, with about 61% of the dose excreted as parent compound. At doses of 1.6–2.4 g/m2 only 12% to 18% of the dose was excreted in the urine as unchanged drug within 72 hours.

Half-life

7-15 hours. The elimination half-life increase appeared to be related to the increase in ifosfamide volume of distribution with age.

Clearance

• 2.4±0.33 L/h/m^2 [pediatric patients]

Adverse Effects

Learn about our commercial Adverse Effects data.

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Toxicity

LD₅₀ (mouse) = 390-1005 mg/kg, LD₅₀ (rat) = 150-190 mg/kg. Side effects include nausea, vomiting and myelosuppression. Toxic effects include central nervous system toxicity (confusion, hallucinations) and urotoxic effects (cystitis, blood in urine).

Affected organisms

• Humans and other mammals

Pathways

Pathway	Category
Ifosfamide Metabolism Pathway	Drug metabolism
Ifosfamide Action Pathway	Drug action

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Ifosfamide which could result in a higher serum level.
Abametapir	The serum concentration of Ifosfamide can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Ifosfamide can be increased when combined with Abatacept.
Abciximab	The risk or severity of bleeding can be increased when Ifosfamide is combined with Abciximab.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Ifosfamide.
Abiraterone	The metabolism of Ifosfamide can be decreased when combined with Abiraterone.
Acalabrutinib	The metabolism of Ifosfamide can be increased when combined with Acalabrutinib.
Acarbose	Acarbose may decrease the excretion rate of Ifosfamide which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Ifosfamide which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Ifosfamide which could result in a higher serum level.

Additional Data Available

Extended Description
Extended Description
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Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

• Avoid alcohol. Ingesting alcohol may worsen nausea and vomiting caused by ifosfamide.
• Exercise caution with grapefruit products. Grapefruit inhibits the CYP3A4 metabolism of ifosfamide to its active metabolite, therefore reducing its efficacy.
• Exercise caution with St. John's Wort. Close monitoring is warranted as this herb induces the CYP3A4 metabolism of ifosfamide to its alkylating active metabolites, including, chloroacetaldehyde, a nephrotoxic and neurotoxic metabolite.

Products

International/Other Brands

Celofos (Celon) / Cuantil (Teva) / Holoxan (Baxter) / Mitoxana (Baxter)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Ifex	Injection, powder, for solution	1 g/20mL	Intravenous	Baxter Healthcare Corporation	1988-12-30	Not applicable
Ifex	Injection, powder, for solution	3 g/60mL	Intravenous	E.R. Squibb & Sons, L.L.C.	2009-06-01	2012-03-31
Ifex	Powder, for solution	1 g	Intravenous	Baxter Laboratories	2001-03-20	Not applicable
Ifex	Injection, powder, for solution	1 g/20mL	Intravenous	E.R. Squibb & Sons, L.L.C.	2009-06-01	2012-01-31
Ifex	Powder, for solution	3 g	Intravenous	Baxter Laboratories	2001-01-25	Not applicable
Ifex	Injection, powder, for solution	3 g/60mL	Intravenous	Baxter Healthcare Corporation	1988-12-30	Not applicable
Ifex Pws 1gm/vial	Powder, for solution		Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1989-12-31	2001-04-09
Ifex Pws 2g/vial	Powder, for solution		Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1989-12-31	1997-08-14
Ifex Pws 3gm/vial	Powder, for solution		Intravenous	Bristol Labs Division Of Bristol Myers Squibb	1989-12-31	2002-07-11
Ifosfamide	Injection, powder, for solution	3 g/60mL	Intravenous	Baxter Healthcare Corporation	1988-12-30	Not applicable

Additional Data Available

Application Number
Application Number
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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
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A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Ifosfamide	Injection, solution	1 g/20mL	Intravenous	Teva Parenteral Medicines, Inc.	2007-07-26	Not applicable
Ifosfamide	Injection, solution	50 mg/1mL	Intravenous	Fresenius Kabi USA, LLC	2009-09-30	2012-07-31
Ifosfamide	Injection, solution	50 mg/1mL	Intravenous	Mylan Institutional	2012-11-27	2017-12-31
Ifosfamide	Injection	50 mg/1mL	Intravenous	Bedford Pharmaceuticals	2010-08-31	2010-09-01
Ifosfamide	Injection, powder, lyophilized, for solution	1 g/1	Intravenous	Fresenius Kabi USA, LLC	2003-01-28	Not applicable
Ifosfamide	Injection, solution	50 mg/1mL	Intravenous	Pfizer Laboratories Div Pfizer Inc.	2012-11-27	2017-12-31
Ifosfamide	Injection, solution	50 mg/1mL	Intravenous	Mylan Institutional	2012-11-27	2017-12-31
Ifosfamide	Injection	50 mg/1mL	Intravenous	Hikma Pharmaceuticals USA Inc.	2017-06-10	Not applicable
Ifosfamide	Injection	50 mg/1mL	Intravenous	Bedford Pharmaceuticals	2010-08-31	2010-09-01
Ifosfamide	Injection, solution	3 g/60mL	Intravenous	Teva Parenteral Medicines, Inc.	2007-07-26	Not applicable

Additional Data Available

Application Number
Application Number
Available for Purchase
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
Available for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
IFEX and MESNEX	Ifosfamide (1 g/20mL) + Mesna (100 mg/1mL)	Kit	Intravenous	E.R. Squibb & Sons, L.L.C.	2009-06-01	2010-06-30
IFEX and MESNEX	Ifosfamide (1 g/20mL) + Mesna (100 mg/1mL)	Kit	Intravenous	E.R. Squibb & Sons, L.L.C.	2009-06-01	2010-06-30
IFEX and MESNEX	Ifosfamide (3 g/60mL) + Mesna (100 mg/1mL)	Kit	Intravenous	E.R. Squibb & Sons, L.L.C.	2009-06-01	2010-03-31
Ifosfamide and Mesna	Ifosfamide (3 g/60mL) + Mesna (100 mg/1mL)	Kit	Intravenous	Teva Parenteral Medicines, Inc.	2012-09-26	2012-09-26
Ifosfamide and Mesna	Ifosfamide (1 g/20mL) + Mesna (100 mg/1mL)	Kit	Intravenous	Teva Parenteral Medicines, Inc.	2012-09-26	2012-09-26
Ifosfamide and Mesna	Ifosfamide (1 g/20mL) + Mesna (100 mg/1mL)	Kit	Intravenous	Teva Parenteral Medicines, Inc.	2002-05-01	2011-07-31

Categories

ATC Codes

L01AA06 — Ifosfamide

• L01AA — Nitrogen mustard analogues
• L01A — ALKYLATING AGENTS
• L01 — ANTINEOPLASTIC AGENTS
• L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Drug Categories

• Acids
• Acids, Noncarboxylic
• Alkylating Activity
• Alkylating Drugs
• Anions
• Antineoplastic Agents
• Antineoplastic Agents, Alkylating
• Antineoplastic and Immunomodulating Agents
• Cardiotoxic antineoplastic agents
• Cytochrome P-450 CYP2A6 Substrates
• Cytochrome P-450 CYP2A6 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2B6 Substrates
• Cytochrome P-450 CYP2B6 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2C18 Substrates
• Cytochrome P-450 CYP2C18 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C19 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2C8 Inducers
• Cytochrome P-450 CYP2C8 Inducers (strength unknown)
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP2E1 Substrates
• Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• Electrolytes
• Hydrocarbons, Halogenated
• Immunosuppressive Agents
• Ions
• Methemoglobinemia Associated Agents
• Mustard Compounds
• Myelosuppressive Agents
• Narrow Therapeutic Index Drugs
• Nitrogen Mustard Analogues
• Nitrogen Mustard Compounds
• Noxae
• Organophosphorus Compounds
• Oxazines
• Phosphoramide Mustards
• Phosphoramides
• Phosphoric Acids
• Phosphorus Acids
• Phosphorus Compounds
• Toxic Actions

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazaphosphinanes

Sub Class

Isofamides

Direct Parent

Isofamides

Alternative Parents

Phosphoric monoester diamides / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Alkyl chlorides

Substituents

Aliphatic heteromonocyclic compound / Alkyl chloride / Alkyl halide / Azacycle / Hydrocarbon derivative / Isofamide / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic phosphoric acid amide

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:5864)

Chemical Identifiers

UNII

UM20QQM95Y

CAS number

3778-73-2

InChI Key

HOMGKSMUEGBAAB-UHFFFAOYSA-N

InChI

InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)

IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one

SMILES

ClCCNP1(=O)OCCCN1CCCl

References

Synthesis Reference

U.S. Patent 3,732,340.

US3732340

General References

1. Furlanut M, Franceschi L: Pharmacology of ifosfamide. Oncology. 2003;65 Suppl 2:2-6. [PubMed:14586139]
2. Fleming RA: An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy. 1997 Sep-Oct;17(5 Pt 2):146S-154S. [PubMed:9322882]
3. Wagner T: Ifosfamide clinical pharmacokinetics. Clin Pharmacokinet. 1994 Jun;26(6):439-56. [PubMed:8070218]
4. Allen LM, Creaven PJ, Nelson RL: Studies on the human pharmacokinetics of isophosphamide (NSC-109724). Cancer Treat Rep. 1976 Apr;60(4):451-8. [PubMed:1277221]
5. Brade WP, Herdrich K, Varini M: Ifosfamide--pharmacology, safety and therapeutic potential. Cancer Treat Rev. 1985 Mar;12(1):1-47. [PubMed:3896483]
6. Zalupski M, Baker LH: Ifosfamide. J Natl Cancer Inst. 1988 Jun 15;80(8):556-66. [PubMed:3286879]
7. Willits I, Price L, Parry A, Tilby MJ, Ford D, Cholerton S, Pearson AD, Boddy AV: Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. [PubMed:15827549]
8. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183]
9. Schoenike SE, Dana WJ: Ifosfamide and mesna. Clin Pharm. 1990 Mar;9(3):179-91. [PubMed:2107997]
10. Dechant KL, Brogden RN, Pilkington T, Faulds D: Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Drugs. 1991 Sep;42(3):428-67. [PubMed:1720382]

External Links

Human Metabolome Database

HMDB0015312

KEGG Drug

D00343

KEGG Compound

C07047

PubChem Compound

3690

PubChem Substance

46508335

ChemSpider

3562

BindingDB

189358

RxNav

5657

ChEBI

5864

ChEMBL

CHEMBL1024

Therapeutic Targets Database

DAP000537

PharmGKB

PA449964

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Ifosfamide

AHFS Codes

• 10:00.00 — Antineoplastic Agents

MSDS

Download (293 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Adult Acute Lymphocytic Leukemia	3
4	Completed	Treatment	Burkitt's Lymphoma / Large Cell Anaplastic Lymphoma / Lymphoma, Lymphoblastic / Mediastinal Neoplasms	1
4	Completed	Treatment	Soft Tissue Sarcoma (STS)	1
4	Recruiting	Treatment	Peripheral T Cell Lymphoma (PTCL) / Peripheral T-Cell Lymphoma (PTCL)	1
4	Unknown Status	Treatment	Acute Lymphoblastic Leukaemias (ALL) / Non-Hodgkin's Lymphoma (NHL)	1
4	Unknown Status	Treatment	ALK-negative Anaplastic Large Cell Lymphoma / Angioimmunoblastic T Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Enteropathy Associated T Cell Lymphoma / Enteropathy-Associated T-Cell Lymphoma / Hepatosplenic T Cell Lymphoma / Hepatosplenic T-Cell Lymphoma / Peripherial T Cell Lymphoma,Not Otherwise Specified / Subcutaneous Panniculitis Like T Cell Lymphoma	1
4	Unknown Status	Treatment	Intracranial Germ Cell Tumors	1
3	Active Not Recruiting	Treatment	Acute Lymphoblastic Leukaemias (ALL)	1
3	Active Not Recruiting	Treatment	Adult T Acute Lymphoblastic Leukemia / Ann Arbor Stage II Adult Lymphoblastic Lymphoma / Ann Arbor Stage II Childhood Lymphoblastic Lymphoma / Ann Arbor Stage III Adult Lymphoblastic Lymphoma / Ann Arbor Stage III Childhood Lymphoblastic Lymphoma / Ann Arbor Stage IV Adult Lymphoblastic Lymphoma / Ann Arbor Stage IV Childhood Lymphoblastic Lymphoma / Childhood T Acute Lymphoblastic Leukemia	1
3	Active Not Recruiting	Treatment	Ewing's Sarcoma	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• APP Pharmaceuticals
• Baxter International Inc.
• Bristol-Myers Squibb Co.
• Teva Pharmaceutical Industries Ltd.

Dosage Forms

Form	Route	Strength
Injection, powder, for solution		500 mg
Injection, powder, for solution	Intravenous	200 mg
Injection, powder, for solution	Intravenous	500 mg
Injection, powder, for solution	Parenteral	1 G
Injection, solution	Intravenous	1 G/25ML
Injection, solution	Intravenous	2 G/50ML
Injection, solution, concentrate	Intravenous	1 g
Injection, solution, concentrate	Intravenous	500 mg
Powder, for solution	Intravenous	2 G
Injection, solution	Intravenous	0.5 g
Injection, powder, for solution		1 g
Injection, solution	Intravenous	1 g
Injection, powder, for solution		2 g
Injection, solution	Intravenous	2 g
Injection	Intravenous	1 GM
Injection, powder, for solution	Intravenous	2 g
Injection, powder, for solution	Intravenous	1 g/20mL
Injection, powder, for solution	Intravenous	3 g/60mL
Powder, for solution	Intravenous	1 g
Powder, for solution	Intravenous	3 g
Kit	Intravenous
Powder, for solution	Intravenous
Injection, solution, concentrate	Intravenous	1 g/25mL
Solution	Intravenous	1000 mg
Injection, powder, lyophilized, for solution	Intravenous	1000 mg
Solution	Parenteral	2 g
Powder, for suspension	Oral	1 g
Injection, powder, lyophilized, for solution	Intravenous	1 g
Injection, powder, for solution	Intravenous	1 g
Injection, powder, lyophilized, for solution	Parenteral	2 g
Injection	Intravenous	50 mg/1mL
Injection, powder, lyophilized, for solution	Intravenous	1 g/1
Injection, solution	Intravenous	1 g/20mL
Injection, solution	Intravenous	3 g/60mL
Injection, solution	Intravenous	50 mg/1mL
Injection, powder, lyophilized, for solution	Intravenous	2 g

Prices

Unit description	Cost	Unit
Ifex-mesnex kit	2709.98USD	kit
Ifosfamide-mesna kit	787.5USD	kit
Ifex 3 gm vial	489.13USD	vial
Ifex 1 gm vial	163.04USD	vial
Ifosfamide 3 gm vial	114.0USD	vial
Ifosfamide 1 gm vial	56.4USD	vial

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
Unlock Additional Data
US5252341	No	1993-10-12	2011-07-16

Additional Data Available

Filed On
Filed On
Available for Purchase
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	39-41 °C	U.S. Patent 3,732,340.
water solubility	3780 mg/L	Not Available
logP	0.86	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	15.0 mg/mL	ALOGPS
logP	0.57	ALOGPS
logP	0.097	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	0.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å2	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.48 m3·mol-1	ChemAxon
Polarizability	23.94 Å3	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9807
Blood Brain Barrier	+	0.9736
Caco-2 permeable	-	0.5411
P-glycoprotein substrate	Non-substrate	0.7098
P-glycoprotein inhibitor I	Non-inhibitor	0.6204
P-glycoprotein inhibitor II	Non-inhibitor	0.9617
Renal organic cation transporter	Non-inhibitor	0.8135
CYP450 2C9 substrate	Non-substrate	0.7674
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.5922
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8835
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9723
Ames test	AMES toxic	0.9108
Carcinogenicity	Non-carcinogens	0.8903
Biodegradation	Not ready biodegradable	0.7807
Rat acute toxicity	3.2294 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.8985
hERG inhibition (predictor II)	Non-inhibitor	0.8224

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0490000000-17ba12fd0e00df2723dc
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-d4e1a660175509162e8c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-c26cb9c6b0b1cafbc7c2
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0gx3-6960000000-e4f4eadda4e355e7dd84
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0f6x-8900000000-10d5b2623785719eb1e7
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-9500000000-d06de43b506b64b21f31
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-9300000000-698d7a6ed4f1837ad721
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-084cc16ffb95bd0ef960
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-03di-0090000000-1ae1b6f01a6e1a37e34c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0gx3-6960000000-ad40c4b969e8d0286677
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0f6x-8900000000-137610f53c637d8d5b79
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-9500000000-6b78178980477a0f7c08
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-9200000000-e6f6b95f30fc4c9fde8a
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0490000000-661cabcd304902a3d4b5
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0290000000-4c400c6848932e5bc304
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-1390000000-cb6bb34e3efac3f15b24
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0udi-3910000000-2729bcf5701a78198ad5
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable

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Drug created on June 13, 2005 07:24 / Updated on January 25, 2021 22:38