Ifosfamide | CAS#3778-73-2 | MedKoo Biosciences

MedKoo Cat#: 100460 | Name: Ifosfamide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ifosfamide is a synthetic analogue of the nitrogen mustard cyclophosphamide with antineoplastic activity. Ifosfamide alkylates and forms DNA crosslinks, thereby preventing DNA strand separation and DNA replication. This agent is a prodrug that must be activated through hydroxylation by hepatic microsomal enzymes. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

Ifosfamide

CAS#3778-73-2

Theoretical Analysis

MedKoo Cat#: 100460

Name: Ifosfamide

CAS#: 3778-73-2

Chemical Formula: C7H15Cl2N2O2P

Exact Mass: 260.0248

Molecular Weight: 261.08

Elemental Analysis: C, 32.20; H, 5.79; Cl, 27.16; N, 10.73; O, 12.26; P, 11.86

Price and Availability

Size	Price	Availability
100mg	USD 300.00	2 Weeks
250mg	USD 550.00	2 Weeks
1g	USD 950.00	2 Weeks

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Synonym

Ifomide; Iphosphamid; iphosphamide; Isoendoxan; IsoEndoxan; isophosphamide; Naxamide; US brand names: Cyfos; Ifex; Ifosfamidum.

IUPAC/Chemical Name

3-(2-chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide

InChi Key

HOMGKSMUEGBAAB-UHFFFAOYSA-N

InChi Code

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

SMILES Code

ClCCNP1(OCCCN1CCCl)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

DRUG DESCRIPTION IFEXÂ® (ifosfamide for injection) single-dose vials for constitution and administration by intravenous infusion each contain 1 gram or 3 grams of sterile ifosfamide. Ifosfamide is a chemotherapeutic agent chemically related to the nitrogen mustards and a synthetic analog of cyclophosphamide. Ifosfamide is 3-(2-chloroethyl)-2-[(2-chloroethyl) amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide. The molecular formula is C7H15Cl2N2O2P and its molecular weight is 261.1. CLINICAL PHARMACOLOGY Ifosfamide has been shown to require metabolic activation by microsomal liver enzymes to produce biologically active metabolites. Activation occurs by hydroxylation at the ring carbon atom 4 to form the unstable intermediate 4-hydroxyifosfamide. This metabolite rapidly degrades to the stable urinary metabolite 4-ketoifosfamide. Opening of the ring results in formation of the stable urinary metabolite, 4-carboxyifosfamide. These urinary metabolites have not been found to be cytotoxic. N, N-bis (2-chloroethyl)-phosphoric acid diamide (ifosphoramide) and acrolein are also found. Enzymatic oxidation of the chloroethyl side chains and subsequent dealkylation produces the major urinary metabolites, dechloroethyl ifosfamide and dechloroethyl cyclophosphamide. The alkylated metabolites of ifosfamide have been shown to interact with DNA. In vitro incubation of DNA with activated ifosfamide has produced phosphotriesters. The treatment of intact cell nuclei may also result in the formation of DNA-DNA cross-links. DNA repair most likely occurs in G-1 and G-2 stage cells.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ifosfamide is an alkylating chemotherapeutic agent with activity against a wide range of tumors.

In vitro activity:

An incubation of activated human peripheral blood lymphocytes (PBL) with 4-hydroxyifosfamide, the activated form of ifosfamide (4-OH-IF), resulted in a depletion of the intracellular GSH levels and a significant inhibition of the proliferative capacity in a dose-dependent manner. Reference: Blood. 1995 Apr 15;85(8):2124-31. https://pubmed.ncbi.nlm.nih.gov/7718883/

In vivo activity:

Treatment with high doses of ifosfamide caused small placentas, fewer viable fetuses, greater post-implantation losses and more resorbed fetuses. Reduced progesterone and increased prolactin levels also were found. Immunohistochemical staining, the TUNEL technique and histological studies showed increased apoptotic cells and many histological changes in the placenta, and in fetal brain, liver and kidney tissues. Ifosfamide treatment increased apoptosis and caused hypoplasia of placental basal and labyrinth zones, which resulted in pathological changes in developing fetal tissue. Reference: Biotech Histochem. 2016 Jul;91(5):357-68. https://pubmed.ncbi.nlm.nih.gov/27124550/

	Solvent	mg/mL	mM
Solubility
	DMF	50.0	191.51
	DMSO	44.0	168.53
	Ethanol	51.0	195.34
	PBS (pH 7.2)	10.0	38.30
	Water	52.0	199.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 261.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Multhoff G, Meier T, Botzler C, Wiesnet M, Allenbacher A, Wilmanns W, Issels RD. Differential effects of ifosfamide on the capacity of cytotoxic T lymphocytes and natural killer cells to lyse their target cells correlate with intracellular glutathione levels. Blood. 1995 Apr 15;85(8):2124-31. PMID: 7718883. 2. Han HY, Choi MS, Yoon S, Ko JW, Kim SK, Kim TW. Investigation of Ifosfamide Toxicity Induces Common Upstream Regulator in Liver and Kidney. Int J Mol Sci. 2021 Nov 11;22(22):12201. doi: 10.3390/ijms222212201. PMID: 34830083; PMCID: PMC8617928. 3. Helal M. Prenatal effects of transplacental exposure to ifosfamide in rats. Biotech Histochem. 2016 Jul;91(5):357-68. doi: 10.1080/10520295.2016.1176253. Epub 2016 Apr 28. PMID: 27124550.

In vitro protocol:

In vivo protocol:

1. Han HY, Choi MS, Yoon S, Ko JW, Kim SK, Kim TW. Investigation of Ifosfamide Toxicity Induces Common Upstream Regulator in Liver and Kidney. Int J Mol Sci. 2021 Nov 11;22(22):12201. doi: 10.3390/ijms222212201. PMID: 34830083; PMCID: PMC8617928. 2. Helal M. Prenatal effects of transplacental exposure to ifosfamide in rats. Biotech Histochem. 2016 Jul;91(5):357-68. doi: 10.1080/10520295.2016.1176253. Epub 2016 Apr 28. PMID: 27124550.