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Chemistry

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Also known as: Isophosphamide, 3778-73-2, Iphosphamide, Isofosfamide, Ifex, Ifosfamid

Molecular Formula

C₇H₁₅Cl₂N₂O₂P

Molecular Weight

261.08 g/mol

InChI Key

HOMGKSMUEGBAAB-UHFFFAOYSA-N

FDA UNII

UM20QQM95Y

Positional isomer of CYCLOPHOSPHAMIDE which is active as an alkylating agent and an immunosuppressive agent.

Ifosfamide is an Alkylating Drug. The mechanism of action of ifosfamide is as an Alkylating Activity.

1 2D Structure

Ifosfamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,3-bis(2-chloroethyl)-2-oxo-1,3,25-oxazaphosphinan-2-amine

2.1.2 InChI

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

2.1.3 InChI Key

HOMGKSMUEGBAAB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(P(=O)(OC1)NCCCl)CCCl

2.2 Other Identifiers

2.2.1 UNII

UM20QQM95Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Asta Z 4942

2. Holoxan

3. Iphosphamide

4. Iso Endoxan

5. Iso-endoxan

6. Isofosfamide

7. Isophosphamide

8. Nsc 109,724

9. Nsc 109724

10. Nsc-109,724

11. Nsc-109724

12. Nsc109,724

13. Nsc109724

2.3.2 Depositor-Supplied Synonyms

1. Isophosphamide

2. 3778-73-2

3. Iphosphamide

4. Isofosfamide

5. Ifex

6. Ifosfamid

7. Mitoxana

8. Iphosphamid

9. Isoendoxan

10. Naxamide

11. I-phosphamide

12. Holoxan

13. Cyfos

14. Ifsofamide

15. Holoxan 1000

16. Asta Z 4942

17. Mjf 9325

18. Ifosfamida

19. Ifosfamidum

20. Mjf-9325

21. Isosfamide

22. Nsc-109724

23. Nci-c01638

24. Z4942

25. Z-4942

26. Ifomide

27. Nsc 109724

28. A 4942

29. Z 4942

30. 2h-1,3,2-oxazaphosphorin-2-amine, N,3-bis(2-chloroethyl)tetrahydro-, 2-oxide

31. 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2h-1,3,2-oxazaphosphorine 2-oxide

32. Nsc109724

33. N,3-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide

34. N-(2-chloroethyl)-n'-(2-chloroethyl)-n',o-propylenephosphoric Acid Diamide

35. Um20qqm95y

36. N,3-bis(2-chloroethyl)tetrahydro-2h-1,3,2-oxazaphosphorin-2-amine 2-oxide

37. 3-(2-chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide

38. Chebi:5864

39. Ifosphamide

40. 1,3,2-oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide

41. 2h-1,3,2-oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide

42. 3-(2-chloroethyl)-2-(2-chloroethylamino)tetrahydro-2h-1,3,2-oxaazaphosphorin 2-oxide

43. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2h-1,3,2-oxazaphosphorineoxide

44. N-(2-chloroethyl)-n'-(2-chloroethyl)-n',o-propylene Phosphoric Acid Ester Diamide

45. Ncgc00016639-01

46. Cas-3778-73-2

47. Dsstox_cid_760

48. Ifosfamide Sterile

49. Dsstox_rid_75775

50. Dsstox_gsid_20760

51. Ifosfamidum [inn-latin]

52. Ifosfamida [inn-spanish]

53. (r)-ifosfamide

54. (s)-ifosfamide

55. (r)-3-(2-chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide

56. Ccris 352

57. Hsdb 7023

58. Sr-05000002022

59. Einecs 223-237-3

60. Ifex (tn)

61. Unii-um20qqm95y

62. Brn 0611835

63. Ifosfamide (jan/usp/inn)

64. N,3-bis(2-chloroethyl)-2-oxo-1,3,2?^{5}-oxazaphosphinan-2-amine

65. Ifosfamid A

66. 3-(2-chloroethyl)-2-((2-chloroethyl)amino)perhydro-2h-1,3,2-oxazaphosphorineoxide

67. Ifosfamide In Bulk

68. 2,3-(n,n(sup 1)-bis(2-chloroethyl)diamido)-1,3,2-oxazaphosphoridinoxyd

69. Isophosphamide,(s)

70. N,n-bis(beta-chloroethyl)-amino-n',o-propylene-phosphoric Acid Ester Diamide

71. N-(2-chloroethyl)-n'-(2-chloroethyl)-n',o-propylenephosphoric Acid Ester Diamide

72. Mfcd00057374

73. 3-(2-chloroethyl)-2-((2-chloroethyl)amino)perhydro-2h-1,3,2-oxazaphosphorine Oxide

74. N-(2-chloraethyl)-n'-(2-chloraethyl)-n',o-propylen-phosphorsaureester-diamid [german]

75. Ifosfamide - Bio-x

76. Ifosfamide [usan:usp:inn:ban:jan]

77. Starbld0001221

78. Ifosfamide, >=98%

79. Ifosfamide [mi]

80. Isocyclophosphamide

81. Ifosfamide [inn]

82. Ifosfamide [jan]

83. Prestwick0_000833

84. Prestwick1_000833

85. Prestwick2_000833

86. Prestwick3_000833

87. Ifosfamide [hsdb]

88. Ifosfamide [usan]

89. Intermediate Of Ifosfamide

90. Ifosfamide [vandf]

91. N-(2-chloraethyl)-n'-(2-chloraethyl)-n',o-propylen-phosphorsaureester-diamid

92. Ifosfamide [mart.]

93. Schembl4885

94. Chembl1024

95. Ifosfamide [usp-rs]

96. Ifosfamide [who-dd]

97. Bspbio_000785

98. Isophosphamide [iarc]

99. Mls002154021

100. Ifex (tn) (bristol Meyers)

101. Spbio_002706

102. Bpbio1_000865

103. Gtpl7201

104. Dtxsid7020760

105. Ifosfamide [ep Impurity]

106. Ifosfamide [orange Book]

107. Ifosfamide [ep Monograph]

108. (s)-3-(2-chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide

109. Bdbm189358

110. Hms1570h07

111. Hms2090m12

112. Hms2093n07

113. Hms2097h07

114. Hms2232o10

115. Hms3374b08

116. Hms3654b15

117. Hms3714h07

118. Ifosfamide [usp Monograph]

119. Pharmakon1600-01505480

120. {3-(2-chloroethyl)-2-[(2-

121. Bcp06596

122. Wln: T6npotj Am2g Bo B2g

123. Tox21_110539

124. Tox21_201815

125. Tox21_302775

126. Bbl028071

127. N,3-bis(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine

128. N,3-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine

129. Nsc759154

130. S1302

131. Stl058690

132. Akos005711213

133. N,3-bis(2-chloroethyl)tetrahydro-2h-1,3,2-oxazaphosphorin-2-amine-2-oxide

134. Tox21_110539_1

135. Ab02316

136. Ac-2113

137. Ccg-213464

138. Cs-1424

139. Db01181

140. Nsc-759154

141. N-(2-chloroethyl)-n-(3-(2-chloroethyl)-2-oxido-1,3,2-oxazaphosphinan-2-yl)amine

142. Ifosfamide, Analytical Reference Material

143. Ncgc00179435-01

144. Ncgc00179435-02

145. Ncgc00179435-03

146. Ncgc00179435-06

147. Ncgc00179435-07

148. Ncgc00256413-01

149. Ncgc00259364-01

150. As-10978

151. Bi166243

152. Hy-17419

153. Nci60_000233

154. Smr001233348

155. Sbi-0206804.p001

156. Db-049196

157. Ab00513932

158. Ft-0603650

159. Ft-0670282

160. I0713

161. Sw197177-4

162. C07047

163. D00343

164. Ab00513932-06

165. Ab00513932-07

166. Ab00513932-08

167. Ab00513932_09

168. Ab00513932_10

169. 778i732

170. A823873

171. Q418560

172. Q-101874

173. Sr-05000002022-1

174. Sr-05000002022-3

175. Sr-05000002022-5

176. Brd-a67097164-001-11-2

177. Ifosfamide, British Pharmacopoeia (bp) Reference Standard

178. Ifosfamide, European Pharmacopoeia (ep) Reference Standard

179. Ifosfamide, United States Pharmacopeia (usp) Reference Standard

180. 2,n(sup 1)-bis(2-chloroethyl)diamido-1,3,2-oxazaphosphoridinoxy-

181. 2,n(sup 1)-bis(2-chloroethyl)diamido-1,3,2-oxazaphosphoridinoxyd

182. N,3-bis(2-chloroethyl)-2-oxo-1,3,2$l;{5}-oxazaphosphinan-2-amine

183. {3-(2-chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2h-1,3,} 2-oxazaphosphorine Oxide

184. 1,2-oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide

185. 2h-1,2-oxazaphosphorin-2-amine, N,3-bis(2-chloroethyl)tetrahydro-, 2-oxide

186. 2h-1,2-oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide

187. 3-(2-chloroethyl)-2-(2-chloroethylamino)tetrahydro-2h-1,3,2-oxazaphosphorin-2-one

188. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one

189. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one

190. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2h-1,2-oxazaphosphorine Oxide

191. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2h-1,2-oxazaphosphorineoxide

192. 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2h-1,2-oxazaphosphorine 2-oxide

193. N,3-bis(2-chloroethyl)tetrahydro-2h-1,3,2-oxazaphosphinan-2-amine 2-oxide #

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₇H₁₅Cl₂N₂O₂P
Molecular Weight	261.08 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	260.0248201 g/mol
Monoisotopic Mass	260.0248201 g/mol
Topological Polar Surface Area	41.6 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	218
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Ifex
PubMed Health	Ifosfamide (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	IFEX (ifosfamide for injection, USP) 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 mustard...
Active Ingredient	Ifosfamide
Dosage Form	Injectable
Route	Injection
Strength	1gm/vial; 3gm/vial
Market Status	Prescription
Company	Baxter Hlthcare

2 of 4
Drug Name	Ifosfamide
PubMed Health	Ifosfamide (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Ifosfamide injection sterile, single-dose vials for administration by intravenous infusion each contains 1 gram or 3 grams of ifosfamide, USP. The 1-gram vial also contains 69.0 mg monobasic sodium phosphate monohydrate, USP, 21.3 mg dibasic sodium p...
Active Ingredient	Ifosfamide
Dosage Form	Injectable
Route	Injection
Strength	1gm/20ml (50mg/ml); 3gm/60ml(50mg/ml); 1gm/vial; 3gm/vial; 1gm/20ml(50mg/ml); 3gm/60ml (50mg/ml)
Market Status	Prescription
Company	Teva Pharms Usa; Fresenius Kabi Usa; Onco Therapies; Eurohlth Intl

3 of 4
Drug Name	Ifex
PubMed Health	Ifosfamide (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	IFEX (ifosfamide for injection, USP) 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 mustard...
Active Ingredient	Ifosfamide
Dosage Form	Injectable
Route	Injection
Strength	1gm/vial; 3gm/vial
Market Status	Prescription
Company	Baxter Hlthcare

4 of 4
Drug Name	Ifosfamide
PubMed Health	Ifosfamide (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	Ifosfamide injection sterile, single-dose vials for administration by intravenous infusion each contains 1 gram or 3 grams of ifosfamide, USP. The 1-gram vial also contains 69.0 mg monobasic sodium phosphate monohydrate, USP, 21.3 mg dibasic sodium p...
Active Ingredient	Ifosfamide
Dosage Form	Injectable
Route	Injection
Strength	1gm/20ml (50mg/ml); 3gm/60ml(50mg/ml); 1gm/vial; 3gm/vial; 1gm/20ml(50mg/ml); 3gm/60ml (50mg/ml)
Market Status	Prescription
Company	Teva Pharms Usa; Fresenius Kabi Usa; Onco Therapies; Eurohlth Intl

4.2 Therapeutic Uses

Ifosfamide currently is approved for use in combination with other drugs for germ cell testicular cancer & is widely used to treat pediatric & adult sarcomas. Clinical trials also have shown ifosfamide to be active against carcinomas of the cervix & lung & against lymphomas. It is a common component of high-dose chemotherapy regimens with bone marrow or stem cell rescue; in these regimens, in total doses of 12-14 g/sq m, it may cause severe neurological toxicity, including coma & death. This toxicity is thought to result form a metabolite, chloracetaldehyde. In addition to hemorrhagic cystitis, ifosfamide causes nausea, vomiting, anorexia, leukopenia, nephrotoxicity, & CNS disturbances (especially somnolence & confusion).

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1396

Ifosfamide is indicated, in combination with other antineoplastic agents and a prophylactic agent against hemorrhagic cystitis (such as mesna), for treatment of germ cell testicular tumors. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1677

Ifosfamide is indicated as reasonable medical therapy for treatment of head and neck carcinoma. (Evidence rating: IIID) /NOT included in US product labeling/

Ifosfamide is used for treatment of soft-tissue sarcomas, Ewing's sarcoma, and Hodgkin's and non-Hodgkin's lymphomas. /NOT included in US product labeling/

For more Therapeutic Uses (Complete) data for IFOSFAMIDE (9 total), please visit the HSDB record page.

4.3 Drug Warning

It is a common component of high-dose chemotherapy regimens with bone marrow or stem cell rescue; in these regimens, in total doses of 12-14 g/sq m, it may cause severe neurological toxicity, including coma & death. This toxicity is thought to result form a metabolite, chloracetaldehyde. In addition to hemorrhagic cystitis, ifosfamide causes nausea, vomiting, anorexia, leukopenia, nephrotoxicity, & CNS disturbances (especially somnolence & confusion).

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1396

Ifosfamide is distributed into breast milk. Breast feeding is not recommended during chemotherapy because of the risks to the infant (adverse effects, mutagenicity, carcinogenicity).

The bone marrow depressant effects of ifosfamide may result in an increased incidence of microbial infection, delayed healing, and gingival bleeding. Dental work, whenever possible, should be completed prior to initiation of therapy or deferred until blood counts have returned to normal. Patients should be instructed in proper oral hygiene during treatment, including caution in use of regular toothbrushes, dental floss, and toothpicks.

Many side effects of antineoplastic therapy are unavoidable and represent the medication's pharmacologic action. Some of these (for example, leukopenia and thrombocytopenia) are actually used as parameters to aid in individual dosage titration.

For more Drug Warnings (Complete) data for IFOSFAMIDE (20 total), please visit the HSDB record page.

4.4 Drug 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.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Alkylating

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

IFOSFAMIDE

5.3.2 FDA UNII

UM20QQM95Y

5.3.3 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.4 ATC Code

L01AA06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01A - Alkylating agents

L01AA - Nitrogen mustard analogues

L01AA06 - Ifosfamide

5.5 Absorption, Distribution and Excretion

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 1.62.4 g/m2 only 12% to 18% of the dose was excreted in the urine as unchanged drug within 72 hours.

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 211.6 L/m^2.

Clearance

2.40.33 L/h/m^2 [pediatric patients]

Renal excretion & t1/2 are dose & schedule dependent. 60-80% recovered as unchanged drug or metabolite in urine within 72 hr after admin.

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 90-13

The distribution of ifosfamide (IF) and its metabolites 2-dechloroethylifosfamide (2DCE), 3-dechloroethylifosfamide (3DCE), 4-hydroxyifosfamide (4OHIF) and ifosforamide mustard (IFM) between plasma and erythrocytes was examined in vitro and in vivo. In vitro distribution was investigated by incubating blood with various concentrations of IF and its metabolites. In vivo distribution of IF, 2DCE, 3DCE and 4OHIF was determined in 7 patients receiving 9 g/m(2)/72 h intravenous continuous IF infusion. In vitro distribution equilibrium between erythrocytes and plasma was obtained quickly after drug addition. Mean (+/-sem) in vitro and in vivo erythrocyte (e)-plasma (p) partition coefficients (P(e/p)) were 0.75+/-0.01 and 0.81+/-0.03, 0.62+/-0.09 and 0.73+/-0.05, 0.76+/-0.10 and 0.93+/-0.05 and 1.38+/-0.04 and 0.98+/-0.09 for IF, 2DCE, 3DCE and 4OHIF, respectively. These ratios were independent of concentration and unaltered with time. The ratios of the area under the erythrocyte and plasma concentration--time curves (AUC(e/p)) were 0.96+/-0.03, 0.87+/-0.07, 0.98+/-0.06 and 1.34+/-0.39, respectively. A time- and concentration-dependent distribution--equilibrium phenomenon was observed with the relative hydrophilic IFM. It is concluded that IF and metabolites rapidly reach distribution equilibrium between erythrocytes and plasma; the process is slower for IFM. Drug distribution to the erythrocyte fraction ranged from about 38% for 2DCE to 58% for 4OHIF, and was stable over a wide range of clinically relevant concentrations. A strong parallelism in the erythrocyte and plasma concentration profiles was observed for all compounds. Thus, pharmacokinetic assessment using only plasma sampling yields direct and accurate insights into the whole blood kinetics of IF and metabolites and may be used for pharmacokinetic-pharmacodynamic studies.

PMID:11745912 Kerbusch T, et al; Biopharm Drug Dispos 22 (3): 99-108 (2001)

... To assess the feasibility of a sparse sampling approach for the determination of the population pharmacokinetics of ifosfamide, 2- and 3-dechloroethyl-ifosfamide and 4-hydroxy-ifosfamide in children treated with single-agent ifosfamide against various malignant tumours. ... Pharmacokinetic assessment followed by model fitting. Patients: The analysis included 32 patients aged between 1 and 18 years receiving a total of 45 courses of ifosfamide 1.2, 2 or 3 g/m2 in 1 or 3 hours on 1, 2 or 3 days. ... A total of 133 blood samples (median of 3 per patient) were collected. Plasma concentrations of ifosfamide and its dechloroethylated metabolites were determined by gas chromatography. Plasma concentrations of 4-hydroxy-ifosfamide were measured by high-performance liquid chromatography. The models were fitted to the data using a nonlinear mixed effects model as implemented in the NONMEM program. A cross-validation was performed. ... Population values (mean +/- standard error) for the initial clearance and volume of distribution of ifosfamide were estimated at 2.36 +/- 0.33 L/h/m2 and 20.6 +/- 1.6 L/m2 with an interindividual variability of 43 and 32%, respectively. The enzyme induction constant was estimated at 0.0493 +/- 0.0104 L/h2/m2. The ratio of the fraction of ifosfamide metabolised to each metabolite to the volume of distribution of that metabolite, and the elimination rate constant, of 2- and 3-dechloroethyl-ifosfamide and 4-hydroxy-ifosfamide were 0.0976 +/- 0.0556, 0.0328 +/- 0.0102 and 0.0230 +/- 0.0083 m2/L and 3.64 +/- 2.04, 0.445 +/- 0.174 and 7.67 +/- 2.87 h(-1), respectively. Interindividual variability of the first parameter was 23, 34 and 53%, respectively. Cross-validation indicated no bias and minor imprecision (12.5 +/- 5.1%) for 4-hydroxy-ifosfamide only. ... We have developed and validated a model to estimate ifosfamide and metabolite concentrations in a paediatric population by using sparse sampling.

PMID:11523727 Kerbusch T, et al; Clin Pharmacokinet 40 (8): 615-625 (2001)

... The population pharmacokinetics and pharmacodynamics of the cytostatic agent ifosfamide and its main metabolites 2- and 3-dechloroethylifosfamide and 4-hydroxyifosfamide were assessed in patients with soft tissue sarcoma. ... Twenty patients received 9 or 12 g/m2 ifosfamide administered as a 72-h continuous intravenous infusion. The population pharmacokinetic model was built in a sequential manner, starting with a covariate-free model and progressing to a covariate model with the aid of generalised additive modelling. ... The addition of the covariates weight, body surface area, albumin, serum creatinine, serum urea, alkaline phosphatase and lactate dehydrogenase improved the prediction errors of the model. Typical pretreatment (mean +/- SEM) initial clearance of ifosfamide was 3.03 +/- 0.18 l/h with a volume of distribution of 44.0 +/- 1.8 l. Autoinduction, dependent on ifosfamide levels, was characterised by an induction half-life of 11.5 +/- 1.0 h with 50% maximum induction at 33.0 +/- 3.6 microM ifosfamide. Significant pharmacokinetic-pharmacodynamic relationships (P = 0.019) were observed between the exposure to 2- and 3-dechloroethylifosfamide and orientational disorder, a neurotoxic side-effect. No pharmacokinetic-pharmacodynamic relationships between exposure to 4-hydroxyifosfamide and haematological toxicities could be observed in this population.

PMID:11699611 Kerbusch T, et al; Eur J Clin Pharmacol 57 (6-7): 467-477 (2001)

For more Absorption, Distribution and Excretion (Complete) data for IFOSFAMIDE (6 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

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.

Like cyclophosphamide, ifosfamide is activated in the liver by hydroxylation. However, the activation of ifosfamide proceeds more slowly, with greater production of dechlorinated metabolites & chloroacetaldehyde. These differences in metabolism likely account for the higher doses of ifosfamide required for equitoxic effects & the possible difference in antitumor spectrum of the two agents.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1391

Like cyclophosphamide, isophosphamide requires metabolism by microsomal enzymes to act as a cytotoxic agent. It is rapidly metabolized in many species, including rodents and dogs; the urinary metabolites indicate that a series of reactions take place analogous to those in the metabolism of cyclophosphamide. Acrolein is produced during its oxidative degradation, and one product of the reaction is the ring-opened carboxy derivative. Dogs also rapidly metabolize isophosphamide, and the carboxy derivative and 4-keto isophosphamide have been identified in the urine.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V26 243 (1981)

The aim of this study was to develop a population pharmacokinetic model that could describe the pharmacokinetics of ifosfamide. 2- and 3-dechloroethylifosfamide and 4-hydroxyifosfamide, and calculate their plasma exposure and urinary excretion. A group of 14 patients with small-cell lung cancer received a 1-h intravenous infusion of 2.0 or 3.0 g/m2 ifosfamide over 1 or 2 days in combination with 175 mg/m2 paclitaxel and carboplatin at AUC 6. The concentration-time profiles of ifosfamide were described by an ifosfamide concentration-dependent development of autoinduction of ifosfamide clearance. Metabolite compartments were linked to the ifosfamide compartment enabling description of the concentration-time profiles of 2- and 3-dechloroethylifosfamide and 4-hydroxyifosfamide. The Bayesian estimates of the pharmacokinetic parameters were used to calculate the systemic exposure to ifosfamide and its metabolites for the four ifosfamide schedules. Fractionation of the dose over 2 days resulted increased metabolite formation, especially of 2-dechloroethylifosfamide, probably due to increased autoinduction. Renal recovery was only minor with 6.6% of the administered dose excreted unchanged and 9.8% as dechloroethylated metabolites. In conclusion, ifosfamide pharmacokinetics were described with an ifosfamide concentration-dependent development of autoinduction and allowed estimation of the population pharmacokinetics of the metabolites of ifosfamide. Fractionation of the dose resulted in increased exposure to 2-dechloroethylifosfamide, probably due to increased autoinduction.

PMID:11488525 Kerbusch T, et al; Cancer Chemother Pharmacol 48 (1): 53-61 (2001)

The anticancer drug ifosfamide is a prodrug requiring activation through 4-hydroxyifosfamide to ifosforamide mustard, to exert cytotoxicity. Deactivation of ifosfamide leads to 2- and 3-dechloroethylifosfamide and the release of potentially neurotoxic chloracetaldehyde. The aim of this study was to quantify and to compare the pharmacokinetics of ifosfamide, 2- and 3-dechloroethylifosfamide, 4-hydroxyifosfamide, and ifosforamide mustard in short (1-4 h), medium (24-72 h), and long infusion durations (96-240 h) of ifosfamide. An integrated population pharmacokinetic model was used to describe the autoinducible pharmacokinetics of ifosfamide and its four metabolites in 56 patients. The rate by which autoinduction of the metabolism of ifosfamide developed was found to be significantly dependent on the infusion schedule. The rate was 52% lower with long infusion durations compared with short infusion durations. This difference was, however, comparable with its interindividual variability (22%) and was, therefore, considered to be of minor clinical importance. Autoinduction caused a less than proportional increase in the area under the ifosfamide plasma concentration-time curve (AUC) and more than proportional increase in metabolite exposure with increasing ifosfamide dose. During long infusion durations dose-corrected exposures (AUC/D) were significantly decreased for ifosfamide and increased for 3-dechloroethylifosfamide compared with short infusion durations. No differences in dose-normalized exposure to ifosfamide and metabolites were observed between short and medium infusion durations. This study demonstrates that the duration of ifosfamide infusion influences the exposure to the parent and its metabolite 3-dechloroethylifosfamide. The observed dose and infusion duration dependence should be taken into account when modeling ifosfamide metabolism.

PMID:11408362 Kerbusch T, et al; Drug Metab Dispos 29 (7): 967-975 (2001)

Ifosfamide is a known human metabolite of L-trofosfamide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

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

The elimination half-life associated with doses of 2.5 g/sq m is 6-8 hr, whereas the elimination half-life associated with doses of 3.5-5 g/sq m is 14-16 hr.

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 91-22

5.8 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.

Mechanism of action: metabolites cause alkylation of DNA. /from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 90-12

Ifosfamide, a structural analog of cyclophosphamide, belongs to the oxazaphosphorine class of antitumor alkylating agents which must be activated by the mixed function oxidase system of the liver. The 4-hydroxy oxazaphosphorines are a reactive species capable of interacting with nucleic acids & cellular materials to cause cell damage & death. The 4-hydroxy metabolite spontaneously liberates acrolein in many sites throughout the body & it is this substance that is responsible for oxazaphosphorine urotoxicity. Both ifosfamide & cyclophosphamide produce cystitis characterized by tissue edema & ulceration followed by sloughing of mucosal epithelial cells, necrosis of smooth muscle fibers & arteries, & culminating in focal hemorrhage. The selective urotoxicity of oxazaphosphorine occurs because the bladder contains a very low concn of thiol cmpds (glutathione, cysteine) which, by virtue of their nucleophilic sulfhydryl groups, are able to react & neutralize many reactive chemicals. Because the metabolic activation of ifosfamide proceeds more slowly than that of cyclophosphamide, doses of ifosfamide are 3-4 times higher than those of cyclophosphamide. This explains the higher incidence of urotoxicity associated with ifosfamide.

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 91-21

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