ifosfamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antineoplastic, alkylating agents, (beta-chloroethyl)amine derivatives 1421 3778-73-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ifosfamide
  • holoxan
  • ifomide
  • ifosfamid
  • ifosfomide
  • ifosphamide
  • iphosphamide
  • isoendoxan
  • isofosfamide
  • isophosphamide
  • mitoxana
  • naxamide
Positional isomer of CYCLOPHOSPHAMIDE which is active as an alkylating agent and an immunosuppressive agent.
  • Molecular weight: 261.08
  • Formula: C7H15Cl2N2O2P
  • CLOGP: 0.92
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 41.57
  • ALOGS: -1.24
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 10 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 113.59 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 92 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.62 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 30, 1988 FDA BAXTER HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 1264.60 68.79 289 1968 10593 2345235
Encephalopathy 906.33 68.79 189 2068 4372 2351456
Neutropenia 679.79 68.79 204 2053 21344 2334484
Off label use 581.69 68.79 249 2008 73349 2282479
Ovarian failure 570.53 68.79 84 2173 184 2355644
Mucosal inflammation 508.25 68.79 121 2136 5103 2350725
Bone marrow failure 498.05 68.79 121 2136 5565 2350263
Product use in unapproved indication 346.53 68.79 105 2152 11095 2344733
Acute myeloid leukaemia 343.73 68.79 78 2179 2632 2353196
Thrombocytopenia 325.67 68.79 114 2143 19017 2336811
Myelodysplastic syndrome 272.86 68.79 64 2193 2496 2353332
Haematotoxicity 245.66 68.79 51 2206 1116 2354712
Anaemia 240.06 68.79 108 2149 34684 2321144
Pyrexia 238.14 68.79 123 2134 53585 2302243
Neurotoxicity 230.86 68.79 54 2203 2076 2353752
Febrile bone marrow aplasia 207.03 68.79 42 2215 815 2355013
Malignant neoplasm progression 204.77 68.79 72 2185 12056 2343772
Pancytopenia 174.36 68.79 63 2194 11389 2344439
Vomiting 161.81 68.79 106 2151 71496 2284332
Disease progression 159.98 68.79 66 2191 17029 2338799
Confusional state 159.31 68.79 73 2184 24271 2331557
Nausea 144.15 68.79 118 2139 112071 2243757
Second primary malignancy 143.88 68.79 32 2225 974 2354854
Leukopenia 139.95 68.79 52 2205 10144 2345684
Platelet count decreased 130.96 68.79 56 2201 15757 2340071
Infection 127.09 68.79 57 2200 17972 2337856
Septic shock 127.00 68.79 44 2213 7010 2348818
Hypokalaemia 119.81 68.79 47 2210 10607 2345221
Acute kidney injury 105.82 68.79 58 2199 28064 2327764
Diarrhoea 96.72 68.79 83 2174 83481 2272347
White blood cell count decreased 95.60 68.79 47 2210 18161 2337667
Posterior reversible encephalopathy syndrome 92.63 68.79 27 2230 2453 2353375
Neutrophil count decreased 91.87 68.79 34 2223 6533 2349295
Ovarian disorder 90.02 68.79 17 2240 222 2355606
Aplasia 89.24 68.79 19 2238 468 2355360
Renal impairment 87.62 68.79 37 2220 10055 2345773
Toxic encephalopathy 84.63 68.79 20 2237 798 2355030
Sepsis 83.18 68.79 43 2214 18445 2337383
Abdominal pain 82.34 68.79 53 2204 34321 2321507
Haemophagocytic lymphohistiocytosis 78.93 68.79 21 2236 1362 2354466
Cystitis haemorrhagic 78.78 68.79 18 2239 618 2355210
Neutropenic sepsis 78.06 68.79 21 2236 1421 2354407

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 1502.50 72.97 392 2737 10708 1732944
Off label use 712.92 72.97 304 2825 38267 1705385
Neutropenia 652.90 72.97 233 2896 18027 1725625
Encephalopathy 576.19 72.97 153 2976 4299 1739353
Bone marrow failure 497.63 72.97 141 2988 5059 1738593
Thrombocytopenia 417.65 72.97 176 2953 21073 1722579
Myelodysplastic syndrome 358.97 72.97 99 3030 3190 1740462
Pancytopenia 326.47 72.97 124 3005 11233 1732419
Product use in unapproved indication 315.10 72.97 115 3014 9307 1734345
Acute myeloid leukaemia 279.17 72.97 80 3049 2961 1740691
Malignant neoplasm progression 263.02 72.97 113 3016 14045 1729607
Second primary malignancy 260.11 72.97 61 3068 998 1742654
Pyrexia 259.36 72.97 165 2964 46235 1697417
Sepsis 256.02 72.97 122 3007 19316 1724336
Mucosal inflammation 254.26 72.97 80 3049 4089 1739563
Leukopenia 244.81 72.97 93 3036 8387 1735265
Anaemia 213.55 72.97 124 3005 29333 1714319
Neurotoxicity 188.97 72.97 54 3075 1970 1741682
Acute kidney injury 179.13 72.97 118 3011 34826 1708826
Haematotoxicity 177.60 72.97 44 3085 914 1742738
Renal tubular disorder 161.24 72.97 40 3089 835 1742817
Stomatitis 158.35 72.97 60 3069 5344 1738308
Disease progression 149.99 72.97 82 3047 17181 1726471
Fanconi syndrome 140.43 72.97 30 3099 311 1743341
Pneumonia 138.78 72.97 113 3016 46069 1697583
Vomiting 128.35 72.97 100 3029 38215 1705437
Neutropenic sepsis 126.70 72.97 37 3092 1455 1742197
Febrile bone marrow aplasia 126.57 72.97 33 3096 845 1742807
Nervous system disorder 124.47 72.97 41 3088 2413 1741239
Septic shock 122.08 72.97 56 3073 8053 1735599
Drug ineffective 120.23 72.97 120 3009 63681 1679971
Cytopenia 119.73 72.97 32 3097 904 1742748
Aplasia 115.49 72.97 27 3102 433 1743219
Salivary gland cancer 105.29 72.97 19 3110 72 1743580
Cystitis haemorrhagic 100.67 72.97 26 3103 640 1743012
Device related infection 99.31 72.97 34 3095 2252 1741400
Metastases to lung 95.65 72.97 30 3099 1505 1742147
Lymphopenia 95.23 72.97 32 3097 2001 1741651
Tubulointerstitial nephritis 94.41 72.97 35 3094 2923 1740729
Confusional state 92.29 72.97 65 3064 21213 1722439
Nausea 91.99 72.97 94 3035 51102 1692550
Diffuse large B-cell lymphoma 91.45 72.97 27 3102 1102 1742550
Renal failure 91.14 72.97 63 3066 19954 1723698
Toxicity to various agents 84.46 72.97 70 3059 29071 1714581
Neoplasm progression 83.93 72.97 33 3096 3234 1740418
Neoplasm recurrence 81.51 72.97 20 3109 397 1743255
Diarrhoea 81.00 72.97 90 3039 53762 1689890
Treatment failure 80.93 72.97 35 3094 4366 1739286
White blood cell count decreased 80.88 72.97 50 3079 13099 1730553
Acute lymphocytic leukaemia 80.46 72.97 21 3108 539 1743113
Nephropathy toxic 80.08 72.97 27 3102 1705 1741947
Respiratory failure 78.84 72.97 51 3078 14454 1729198
Renal impairment 78.73 72.97 48 3081 12266 1731386
Osteosarcoma 78.44 72.97 14 3115 49 1743603
Multiple organ dysfunction syndrome 77.58 72.97 43 3086 9199 1734453
Metastases to muscle 73.13 72.97 12 3117 21 1743631

Pharmacologic Action:

SourceCodeDescription
ATC L01AA06 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ALKYLATING AGENTS
Nitrogen mustard analogues
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000477 Alkylating Agents
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35705 immunosuppressive agent
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018906 Antineoplastic Agents, Alkylating
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Testicular Germ Cell Tumor indication
Ewing's sarcoma off-label use 76909002 DOID:3369
Burkitt's lymphoma off-label use 118617000
Small cell carcinoma of lung off-label use 254632001 DOID:5409
Non-small cell lung cancer off-label use 254637007 DOID:3908
Malignant tumor of head and/or neck off-label use 255056009
Osteosarcoma of bone off-label use 307576001 DOID:3376
Soft or Connective Tissue Sarcoma off-label use
Progressive Diffuse Large B-Cell Lymphoma off-label use
Invasive Bladder Malignancy off-label use
Renal tubular acidosis contraindication 1776003 DOID:14219
Hyperbilirubinemia contraindication 14783006 DOID:2741
Dehydration contraindication 34095006
Fanconi syndrome contraindication 40488004 DOID:1062
Hypokalemia contraindication 43339004
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Kidney excision contraindication 108022006
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Impaired wound healing contraindication 271618001
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Coma contraindication 371632003
Impaired cognition contraindication 386806002
Breastfeeding (mother) contraindication 413712001
Polyneuropathies contraindication
CNS Toxicity contraindication
Cancer Chemotherapy Induced Hemorrhagic Cystitis contraindication
Severe Bone Marrow Depression contraindication
Bone Metastases contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.54 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

None

External reference:

IDSource
D007069 MESH_DESCRIPTOR_UI
4019476 VUID
N0000147596 NUI
C0020823 UMLSCUI
D00343 KEGG_DRUG
108757000 SNOMEDCT_US
44391 MMSL
5657 RXNORM
386904003 SNOMEDCT_US
4867 MMSL
d00257 MMSL
4019476 VANDF
002642 NDDF
CHEBI:5864 CHEBI
CHEMBL1024 ChEMBL_ID
UM20QQM95Y UNII
2865 INN_ID
DB01181 DRUGBANK_ID
3690 PUBCHEM_CID
7201 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Ifosfamide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9530 INJECTION 50 mg INTRAVENOUS ANDA 18 sections
Ifosfamide HUMAN PRESCRIPTION DRUG LABEL 1 0143-9531 INJECTION 50 mg INTRAVENOUS ANDA 18 sections
IFEX HUMAN PRESCRIPTION DRUG LABEL 1 0338-3991 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS NDA 19 sections
IFEX HUMAN PRESCRIPTION DRUG LABEL 1 0338-3993 INJECTION, POWDER, FOR SOLUTION 3 g INTRAVENOUS NDA 19 sections
Ifosfamide HUMAN PRESCRIPTION DRUG LABEL 1 0703-3427 INJECTION, SOLUTION 1 g INTRAVENOUS ANDA 18 sections
Ifosfamide HUMAN PRESCRIPTION DRUG LABEL 1 0703-3429 INJECTION, SOLUTION 3 g INTRAVENOUS ANDA 18 sections
IFOSFAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10019-925 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS NDA 19 sections
IFOSFAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10019-926 INJECTION, POWDER, FOR SOLUTION 3 g INTRAVENOUS NDA 19 sections
IFOSFAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10019-927 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS NDA 18 sections
IFOSFAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 10019-929 INJECTION, POWDER, FOR SOLUTION 3 g INTRAVENOUS NDA 18 sections
Ifosfamide HUMAN PRESCRIPTION DRUG LABEL 1 63323-142 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 18 sections