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

MedKoo CAT#: 100460

CAS#: 3778-73-2

Description: 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

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Ifosfamide
CAS# 3778-73-2

Theoretical Analysis

MedKoo Cat#: 100460
Name: Ifosfamide
CAS#: 3778-73-2
Chemical Formula: C7H15Cl2N2O2P
Exact Mass: 260.02
Molecular Weight: 261.083
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 Quantity
100mg USD 300 2 Weeks
250mg USD 550 2 Weeks
1g USD 950 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 IFEX® (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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. 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

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.

Recalculate based on batch purity %
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: 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.
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.

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