Details of the Drug

General Information of Drug (ID: DMCT3I8)

• Drug Name: Ifosfamide
• Synonyms: Cyfos; Holoxan; Ifex; Ifosfamid; Ifosfamida; Ifosfamidum; Ifosphamide; Ifsofamide; Iphosphamid; Iphosphamide; Isoendoxan; Isofosfamide; Isophosphamide; Isosfamide; Mitoxana; Naxamide; Ifosfamide Sterile; Iso Endoxan; A 4942; ASTA Z 4942; Holoxan 1000; MJF 9325; Z 4942; Z4942; I-Phosphamide; IFEX (TN); Ifex (TN); Ifosfamida [INN-Spanish]; Ifosfamidum [INN-Latin]; Iphosphamid(e); Iso-Endoxan; MJF-9325; Mitoxana (TN); NPFAPI-04; Z-4942; Mitoxana, Ifex, Ifosfamide; Ifosfamide (JAN/USP/INN); Ifosfamide [USAN:INN:BAN:JAN]; N,N-Bis(beta-chloroethyl)-amino-N',O-propylene-phosphoric acid ester diamide; N,3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide; N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylen ephosphoric acid diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylene phosphoric acid ester diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid diamide; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide; N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid; N-(2-Chloraethyl)-N'-(2-chloraethyl)-N',O-propylen-phosphorsaureester-diamid [German]; N-(2-Chloroethyl)-N-(3-(2-chloroethyl)-2-oxido-1,3,2-oxazaphosphinan-2-yl)amine; (+-)-Ifosfamid; (+-)-Ifosphamide; (+-)-Tetrahydro-N,3-bis(2-chloroethyl)-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; (D,L)-Ifosfamide; (R,S)-Ifosphamide; (R,S)-N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; 1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide; 1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide; 2,3-(N,N(sup 1)-Bis(2-chloroethyl)diamido)-1,3,2-oxazaphosphoridinoxyd; 2,3-N,N(sup 1)-Bis(2-chloroethyl)diamido-1,3,2-oxazaphosphoridinoxyd; 2H-1,3,2-Oxazaphosphorin-2-amine, N,3-bis(2-chloroethyl)tetrahydro-, 2-oxide; 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide; 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-, 2-oxide (8CI); 2H-1,3,2-Oxazaphosphorine, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide; 3,} 2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)perhydro-2H-1,3,2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2H-1,3,2-oxazaphosphorine oxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]perhydro-2H-1,3,2-oxazaphosphorineoxide; 3-(2-Chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide

Indication

Disease Entry	ICD 11	Status	REF
Adult central nervous system germ cell tumor	N.A.	Approved	[1]
Adult teratoma	N.A.	Approved	[1]
Advanced cancer	2A00-2F9Z	Approved	[1]
Extragonadal germ cell cancer	N.A.	Approved	[1]
Extragonadal germ cell tumor	N.A.	Approved	[1]
Kidney neoplasm	N.A.	Approved	[1]
Solid tumour/cancer	2A00-2F9Z	Approved	[2]
Testicular germ cell tumor	N.A.	Approved	[1]
Extragonadal nonseminomatous germ cell tumor	N.A.	Investigative	[1]
Extragonadal seminoma	N.A.	Investigative	[1]
Neuroblastoma	2D11.2	Investigative	[1]
Retinoblastoma	2D02.2	Investigative	[1]

• Therapeutic Class: Anticancer Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 261.079
  Logarithm of the Partition Coefficient (xlogp); 0.9
  Rotatable Bond Count (rotbonds); 5
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 4
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
  Bioavailability: 92% of drug becomes completely available to its intended biological destination(s) [4]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 1.1 mL/min/kg [5]
  Elimination: 10% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 7 - 15 hours [5]
  Metabolism: The drug is metabolized via the hepatic []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 113.5897 micromolar/kg/day [6]
  Unbound Fraction: The unbound fraction of drug in plasma is 1% [5]
  Vd: The volume of distribution (Vd) of drug is 0.64 L/kg []
  Water Solubility: The ability of drug to dissolve in water is measured as 100 mg/mL [3]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Arterial disorder	Not Available	ELN	OTFSO7PG	[7]
Drug tolerance	Not Available	ADRA2A	OTZFGOTP	[7]
Metabolic disorder	Not Available	AMD1	OTKAGZY3	[7]
Metabolic disorder	Not Available	ODC1	OTNDAGRR	[7]

• Chemical Identifiers:
  Formula: C7H15Cl2N2O2P
  IUPAC Name: N,3-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
  Canonical SMILES: C1CN(P(=O)(OC1)NCCCl)CCCl
  InChI: InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
  InChIKey: HOMGKSMUEGBAAB-UHFFFAOYSA-N
• Cross-matching ID:
  PubChem CID: 3690
  ChEBI ID: CHEBI:5864
  CAS Number: 3778-73-2
  DrugBank ID: DB01181
  TTD ID: D02TLO
  INTEDE ID: DR0855
  ACDINA ID: D01151
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human Deoxyribonucleic acid (hDNA)	TTUTN1I	NOUNIPROTAC	Modulator	[8]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[9]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[10]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[11]
Cytochrome P450 2A6 (CYP2A6)	DEJVYAZ	CP2A6_HUMAN	Substrate	[12]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[13]
Cytochrome P450 2B6 (CYP2B6)	DEPKLMQ	CP2B6_HUMAN	Substrate	[14]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[13]
Cytochrome P450 3A7 (CYP3A7)	DERD86B	CP3A7_HUMAN	Substrate	[15]
Prostaglandin G/H synthase 1 (COX-1)	DE073H6	PGH1_HUMAN	Substrate	[9]
Cytochrome P450 2C18 (CYP2C18)	DEZMWRE	CP2CI_HUMAN	Substrate	[11]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
(Lyso)-N-acylphosphatidylethanolamine lipase (ABHD4)	OTQK3M9X	ABHD4_HUMAN	Gene/Protein Processing	[16]
14-3-3 protein sigma (SFN)	OTLJCZ1U	1433S_HUMAN	Gene/Protein Processing	[16]
5'-AMP-activated protein kinase subunit beta-1 (PRKAB1)	OT1OG4QZ	AAKB1_HUMAN	Gene/Protein Processing	[16]
5'-AMP-activated protein kinase subunit beta-2 (PRKAB2)	OTLVN68B	AAKB2_HUMAN	Gene/Protein Processing	[16]
ABC-type oligopeptide transporter ABCB9 (ABCB9)	OTSOBOL5	ABCB9_HUMAN	Gene/Protein Processing	[16]
Adenylate kinase 4, mitochondrial (AK4)	OTA0T02Q	KAD4_HUMAN	Gene/Protein Processing	[16]
Agrin (AGRN)	OTWJENAZ	AGRIN_HUMAN	Gene/Protein Processing	[16]
Aldo-keto reductase family 1 member C2 (AKR1C2)	OTQ2XMO3	AK1C2_HUMAN	Gene/Protein Processing	[16]
Alpha-2A adrenergic receptor (ADRA2A)	OTZFGOTP	ADA2A_HUMAN	Drug Response	[7]
ALS2 C-terminal-like protein (ALS2CL)	OT8RY7TZ	AL2CL_HUMAN	Gene/Protein Processing	[16]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Ifosfamide

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
LEE011	DMMX75K	Moderate	Decreased metabolism of Ifosfamide caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[17]

Coadministration of a Drug Treating the Disease Different from Ifosfamide (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Decreased renal excretion of Ifosfamide caused by Remdesivir mediated nephrotoxicity.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[18]
Arn-509	DMT81LZ	Moderate	Increased metabolism of Ifosfamide caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[19]
Inotersen	DMJ93CT	Major	Increased risk of nephrotoxicity by the combination of Ifosfamide and Inotersen.	Amyloidosis [5D00]	[19]
Roflumilast	DMPGHY8	Moderate	Additive immunosuppressive effects by the combination of Ifosfamide and Roflumilast.	Asthma [CA23]	[19]
Dalfopristin	DM4LTKV	Moderate	Decreased metabolism of Ifosfamide caused by Dalfopristin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[20]
Sparfloxacin	DMB4HCT	Minor	Decreased absorption of Ifosfamide due to intestinal mucosa variation caused by Sparfloxacin.	Bacterial infection [1A00-1C4Z]	[21]
ABT-492	DMJFD2I	Minor	Decreased absorption of Ifosfamide due to intestinal mucosa variation caused by ABT-492.	Bacterial infection [1A00-1C4Z]	[21]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Ifosfamide caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[19]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Ifosfamide and Iodipamide.	Cholelithiasis [DC11]	[22]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Ifosfamide caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[23]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Ifosfamide caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[24]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Ifosfamide caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[25]
Rufinamide	DMWE60C	Moderate	Increased metabolism of Ifosfamide caused by Rufinamide mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[19]
Fosamprenavir	DM4W9B3	Moderate	Decreased metabolism of Ifosfamide caused by Fosamprenavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[26]
Darunavir	DMN3GCH	Moderate	Decreased metabolism of Ifosfamide caused by Darunavir mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[27]
Teriflunomide	DMQ2FKJ	Major	Additive myelosuppressive effects by the combination of Ifosfamide and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[28]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Ifosfamide and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[18]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Ifosfamide caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[29]
Denosumab	DMNI0KO	Moderate	Additive myelosuppressive effects by the combination of Ifosfamide and Denosumab.	Low bone mass disorder [FB83]	[30]
Ceritinib	DMB920Z	Moderate	Decreased metabolism of Ifosfamide caused by Ceritinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[19]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Ifosfamide caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[31]
Tecfidera	DM2OVDT	Moderate	Additive immunosuppressive effects by the combination of Ifosfamide and Tecfidera.	Multiple sclerosis [8A40]	[32]
Siponimod	DM2R86O	Major	Additive immunosuppressive effects by the combination of Ifosfamide and Siponimod.	Multiple sclerosis [8A40]	[18]
Fingolimod	DM5JVAN	Major	Additive immunosuppressive effects by the combination of Ifosfamide and Fingolimod.	Multiple sclerosis [8A40]	[33]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Ifosfamide and Ocrelizumab.	Multiple sclerosis [8A40]	[34]
Ozanimod	DMT6AM2	Major	Additive immunosuppressive effects by the combination of Ifosfamide and Ozanimod.	Multiple sclerosis [8A40]	[19]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive myelosuppressive effects by the combination of Ifosfamide and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[35]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Ifosfamide caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[36]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Ifosfamide caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[37]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Ifosfamide caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[38]
Temsirolimus	DMS104F	Moderate	Increased plasma concentrations of Ifosfamide and Temsirolimus due to competitive inhibition of the same metabolic pathway.	Renal cell carcinoma [2C90]	[39]
Canakinumab	DM8HLO5	Moderate	Additive immunosuppressive effects by the combination of Ifosfamide and Canakinumab.	Rheumatoid arthritis [FA20]	[40]
Rilonacept	DMGLUQS	Moderate	Additive immunosuppressive effects by the combination of Ifosfamide and Rilonacept.	Rheumatoid arthritis [FA20]	[40]
Golimumab	DMHZV7X	Major	Additive immunosuppressive effects by the combination of Ifosfamide and Golimumab.	Rheumatoid arthritis [FA20]	[41]
Anthrax vaccine	DM9GSWY	Moderate	Antagonize the effect of Ifosfamide when combined with Anthrax vaccine.	Sepsis [1G40-1G41]	[42]
Pitolisant	DM8RFNJ	Moderate	Increased metabolism of Ifosfamide caused by Pitolisant mediated induction of CYP450 enzyme.	Somnolence [MG42]	[19]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Ifosfamide caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[43]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Ifosfamide and Plazomicin.	Urinary tract infection [GC08]	[18]
Valganciclovir	DMS2IUH	Moderate	Increased risk of nephrotoxicity by the combination of Ifosfamide and Valganciclovir.	Virus infection [1A24-1D9Z]	[18]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Water	E00035	962	Solvent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ifosfamide 3gm/vial injectable	3gm/vial	Injectable	Injection
Ifosfamide 1gm/vial injectable	1gm/vial	Injectable	Injection

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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