Isophosphamide

Base Information

• Chemical Name: Isophosphamide
• CAS No.: 3778-73-2
• Deprecated CAS: 36341-88-5,84711-20-6
• Molecular Formula: C7H15Cl2N2O2P
• Molecular Weight: 261.088
• Hs Code.: 29349990
• European Community (EC) Number: 223-237-3
• NSC Number: 759154,109724
• UNII: UM20QQM95Y
• DSSTox Substance ID: DTXSID7020760
• Nikkaji Number: J599.676G,J599.677E,J2.196B,J26.476H
• Wikipedia: Ifosfamide
• Wikidata: Q418560
• NCI Thesaurus Code: C564
• RXCUI: 5657
• Metabolomics Workbench ID: 43398
• ChEMBL ID: CHEMBL1024
• Mol file: 3778-73-2.mol

Synonyms:2H-1,3,2-Oxazaphosphorine,3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-, 2-oxide (8CI);3-(2-Chloroethyl)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorin2-oxide;A 4942;Asta Z 4942;Cyfos;Holoxan;Holoxan 1000;Ifex;Ifomide;Ifosfamid;Ifosfamide;MJF 9325;Mitoxana;NSC 109724;Naxamide;Z 4942;Ifosfamide;

Chemical Property of Isophosphamide

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Melting Point: 48 °C
• Boiling Point: 336.1 °C at 760 mmHg
• PKA: 1.44±0.20(Predicted)
• Flash Point: 157.1 °C
• PSA: 51.38000
• Density: 1.33 g/cm³
• LogP: 2.21280
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 260.0248201
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ifosfamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

Useful:

• Drug Classes: Antineoplastic Agents, Alkylating Agents
• Canonical SMILES: C1CN(P(=O)(OC1)NCCCl)CCCl
• Recent ClinicalTrials: A Study Evaluating the Efficacy, Safety, and Pharmacokinetics of Glofitamab in Combination With Rituximab Plus Ifosfamide, Carboplatin Etoposide Phosphate in Participants With Relapsed/Refractory Transplant or CAR-T Therapy Eligible Diffuse B-Cell Lymphoma
• Recent EU Clinical Trials: A PHASE I/II, OPEN-LABEL, SINGLE-ARM, TWO-PART TRIAL TO EVALUATE SAFETY, TOLERABILITY, PHARMACOKINETICS, AND ANTI-TUMOR ACTIVITY OF GLOFITAMAB IN COMBINATION WITH CHEMOIMMUNOTHERAPY IN PEDIATRIC AND YOUNG ADULT PARTICIPANTS WITH RELAPSED/REFRACTORY MATURE B-CELL NON-HODGKIN LYMPHOMA
• Recent NIPH Clinical Trials: Phase II study of VI / VPC / IE / VAC for patients with newly diagnosed high-risk rhabdomyosarcoma.
• Uses: 1.? Anti-cancer drugs; 2.? For the treatment of malignant lymphoma, lung cancer, breast cancer, esophageal cancer, bone and soft tissue sarcoma, non-small cell lung cancer, head and neck cancer, cervical cancer A cytostatic agent, related structurally to cyclophosphamide antibacterial Ifosphamide USP (Ifex)is used to treat germ cell testicular cancer; used in combination with mesna.
• Indications: Ifosfamide (Ifex) is an analogue of cyclophosphamide that requires metabolic activation to form 4-hydroxyifosfamide. In general, the metabolism, serum half-life, and excretion of ifosfamide are similar to those of cyclophosphamide. Ifosfamide is active against a broad spectrum of tumors, including germ cell cancers of the testis, lymphomas, sarcomas, and carcinomas of the lung, breast, and ovary. It is thought to be more active than cyclophosphamide in germ cell cancers and sarcomas. Ifosfamide is less myelosuppressive than cyclophosphamide but is more toxic to the bladder. It also may produce alopecia, nausea, vomiting, infertility, and second tumors, particularly acute leukemias. Neurological symptoms including confusion, somnolence, and hallucinations have also been reported. It is recommended that ifosfamide be coadministered with the thiol compound mesna (Mesnex) to avoid hemorrhagic cystitis.
• Therapeutic Function: Antineoplastic
• Clinical Use: Ifosamide currently is used as “third-line” therapy against testicular cancer, although it also has shown activity in a number of solid tumors and hematologic cancers.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhanced effect of coumarins. Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).

Technology Process of Isophosphamide

There total 15 articles about Isophosphamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

2-aziridino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin 2-oxide (29102-47-4) → ilfosfamide (3778-73-2,84711-20-6)

Guidance literature:

With hydrogenchloride; In chloroform;

Reference yield: 75.0%

→ ilfosfamide (3778-73-2,84711-20-6)

Guidance literature:

Reference yield: 28.0%

(2S)-2-<(chloroacetyl)amino>-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide (84681-45-8) → ilfosfamide (3778-73-2,84711-20-6)

Guidance literature:

With B₂F₆; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1021/jm00359a010

upstream raw materials:

3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (S)-2-oxide

3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide

(2S)-2-<(chloroacetyl)amino>-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide

3-(chloroethyl)-2-chlorooxaazaphosphorinane 2-oxide

Downstream raw materials:

N-(2-bromoethyl)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide

3-(2-chloroethyl)-N-<2-ethyl>tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide

3-(2-chloroethyl)-N-<2-(tosyloxy)ethyl>tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide

2-chloroethanal

Refernces

• 1、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.
• 2、 Neda,Sonnenburg,Schmutzler,Niemeyer,Kutscher,Engel,Kleemann. "A new method for the preparation of ifosfamide and cyclophosphamide". . p. 943 - 946. Retrieved 2007/10/03.