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Basic Information

Molecular Structure:
CAS No.:	3778-73-2
Name:	Isophosphamide
Article Data:	13

Formula:	C₇H₁₅Cl₂N₂O₂P
Molecular Weight:	261.088
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;
EINECS:	223-237-3
Density:	1.33 g/cm³
Melting Point:	48 °C
Boiling Point:	336.1 °C at 760 mmHg
Flash Point:	157.1 °C
Appearance:	Crystalline Solid
Hazard Symbols:	T
Risk Codes:	25-36
Safety:	26-45
PSA:	51.38000
LogP:	2.21280

Synthetic route

: 29102-47-4
2-aziridino-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin 2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
With hydrogenchloride In chloroform	78%

: 84681-45-8
(2S)-2-<(chloroacetyl)amino>-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
With B2F6 In tetrahydrofuran for 12h; Ambient temperature;	28%

: 2-{2-[3-(2-Chloro-ethyl)-2-oxo-2λ5-[1,3,2]oxazaphosphinan-2-ylamino]-ethoxy}-1,3,5-trimethyl-[1,3,5,2]triazaphosphinane-4,6-dione

A: 3778-73-2
ilfosfamide

B: 10199-13-0
2-chloro-1,3,5-trimethyl-2-oxo-2λ5-[1,3,5,2]triazaphosphinane-4,6-dione

Conditions

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 0℃; for 1h;	A 14.8% B n/a

: 72578-72-4
3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (S)-2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
With diborane In tetrahydrofuran

: 72578-71-3
3-chloroacetyl-2-(2-chloro-ethylamino)-[1,3,2]oxazaphosphinane (R)-2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
With diborane In tetrahydrofuran

: 81485-04-3
3-(chloroethyl)-2-chlorooxaazaphosphorinane 2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94.9 percent / Et3N / CH2Cl2 / 5 h / -15 °C 2: 86.5 percent / CH2Cl2 / 24 h / Ambient temperature 3: 14.8 percent / SO2Cl2 / CH2Cl2 / 1 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine / benzene / 15 h 2: 47 percent / H2 / 10percent Pd/C / ethanol / 96 h / Ambient temperature 3: 50 percent / tetrahydrofuran / 12 h / Ambient temperature 4: 28 percent / B2F6 / tetrahydrofuran / 12 h / Ambient temperature View Scheme

: 195966-73-5
[3-(2-Chloro-ethyl)-2-oxo-2λ5-[1,3,2]oxazaphosphinan-2-yl]-(2-trimethylsilanyloxy-ethyl)-amine

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86.5 percent / CH2Cl2 / 24 h / Ambient temperature 2: 14.8 percent / SO2Cl2 / CH2Cl2 / 1 h / 0 °C View Scheme

: 31190-87-1
3-(1-Ethylenimino)-1-propanol

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 41 percent / triethylamine, phosphoryl chloride / benzene / 4 h 2: triethylamine / benzene / 15 h 3: 47 percent / H2 / 10percent Pd/C / ethanol / 96 h / Ambient temperature 4: 50 percent / tetrahydrofuran / 12 h / Ambient temperature 5: 28 percent / B2F6 / tetrahydrofuran / 12 h / Ambient temperature View Scheme

: 83802-21-5
(+)-2-Dechloroethylifosfamide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / tetrahydrofuran / 12 h / Ambient temperature 2: 28 percent / B2F6 / tetrahydrofuran / 12 h / Ambient temperature View Scheme

: 84681-43-6
(1'R,2S)-2-<(1'-methylbenzyl)amino>-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide

: 3778-73-2
ilfosfamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 47 percent / H2 / 10percent Pd/C / ethanol / 96 h / Ambient temperature 2: 50 percent / tetrahydrofuran / 12 h / Ambient temperature 3: 28 percent / B2F6 / tetrahydrofuran / 12 h / Ambient temperature View Scheme

Raw Materials

Downstream Products

107-02-8

107-20-0

Total:184 Page 1 of 5 1 2 3 4 5 Next>>

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Chemistry

IUPAC Name: N,2-bis(2-chloroethyl)-1-oxo-6-oxa-2-aza-1λ5-phosphacyclohexan-1-amine
Molecular Formula:C₇H₁₅Cl₂N₂O₂P
Molecular Weight:261.11g/mol
EINECS: 223-237-3
Structure of Isophosphamide (CAS NO.3778-73-2):

Index of Refraction: 1.505
Molar Refractivity: 58.09 cm³
Molar Volume: 195.6 cm³
Polarizability: 23.03×10^-24cm³
Surface Tension: 44.3 dyne/cm
Density: 1.33 g/cm³
Flash Point: 157.1 °C
Enthalpy of Vaporization: 57.92 kJ/mol
Melting Point: 48°C
Boiling Point: 336.1 °C at 760 mmHg
Vapour Pressure: 0.000115 mmHg at 25°C
Product Categories: Anti-Cancer;Pharmaceutical material and intermeidates;Antibiotics;Intermediates & Fine Chemicals;Pharmaceuticals
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

Uses

Isophosphamide (3778-73-2) can be used as a cytostatic agent, related structurally to cyclophosphamide.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intraperitoneal	100mg/kg (100mg/kg)	BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
dog	LDLo	intraperitoneal	50mg/kg (50mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
dog	LDLo	intravenous	66mg/kg (66mg/kg)	LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: OTHER CHANGES BLOOD: HEMORRHAGE	National Technical Information Service. Vol. PB220-927,
guinea pig	LDLo	intraperitoneal	400mg/kg (400mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE WEAKNESS	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
human	TDLo	intravenous	130mg/kg/13D- (130mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Cancer Research. Vol. 32, Pg. 921, 1972.
human	TDLo	intravenous	1915mg/kg/2W- (1915mg/kg)	KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: "INFLAMMATION, NECROSIS, OR SCARRING OF BLADDER"	Lancet. Vol. 2, Pg. 657, 1980.
human	TDLo	intravenous	2298mg/kg/3D- (2298mg/kg)	KIDNEY, URETER, AND BLADDER: HEMATURIA BLOOD: LEUKOPENIA	European Journal of Cancer. Vol. 12, Pg. 195, 1976.
human	TDLo	intravenous	2873mg/kg/5D- (2873mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" KIDNEY, URETER, AND BLADDER: HEMATURIA	Cancer Research. Vol. 36, Pg. 2945, 1976.
human	TDLo	oral	100mg/kg (100mg/kg)	BLOOD: LEUKOPENIA BLOOD: THROMBOCYTOPENIA	Cancer Chemotherapy Reports, Part 3. Vol. 3, Pg. 33, 1972.
human	TDLo	oral	150mg/kg (150mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: PROTEINURIS SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Cancer Research. Vol. 32, Pg. 921, 1972.
mouse	LD50	intraperitoneal	397mg/kg (397mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1149, 1974.
mouse	LD50	intravenous	338mg/kg (338mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
mouse	LD50	oral	1005mg/kg (1005mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
mouse	LD50	subcutaneous	656mg/kg (656mg/kg)	SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rabbit	LDLo	intraperitoneal	200mg/kg (200mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat	LD50	intraperitoneal	140mg/kg (140mg/kg)		United States Patent Document. Vol. #3732340,
rat	LD50	intravenous	190mg/kg (190mg/kg)	BLOOD: NORMOCYTIC ANEMIA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat	LD50	oral	143mg/kg (143mg/kg)	BLOOD: NORMOCYTIC ANEMIA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat	LD50	subcutaneous	160mg/kg (160mg/kg)	BLOOD: NORMOCYTIC ANEMIA	Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982.
rat	LD50	unreported	325mg/kg (325mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1369, 1975.
women	TDLo	intravenous	218mg/kg (218mg/kg)	BRAIN AND COVERINGS: DEMYELINATION BRAIN AND COVERINGS: CHANGES IN SURFACE EEG	Journal of Toxicology, Clinical Toxicology. Vol. 27, Pg. 293, 1989.

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 , 1981,p. 237.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (ipr); Clear Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-32 ,1977. . EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes: Toxic T
Risk Statements: 25-36
R25 :Toxic if swallowed.
R36:Irritating to eyes.
Safety Statements: 26-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 3249
RTECS: RP6050000
HazardClass: 6.1(b)
PackingGroup: III
Suspected carcinogen with experimental carcinogenic and neoplastigenic data. A poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion and intravenous routes: nausea or vomiting; proteinuria, hematuria, inflammation, necrosis or scarring of the bladder, and other kidney, ureter, or bladder changes; changes in hair covering the skin; leukopenia (decreased white blood cell count), thrombocytopenia (decrease in the number of blood platelets); hallucinations, distorted perceptions; tumorigenic effects (active as an anti-cancer agent). Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic Cl⁻, NO_x, and PO_x.

Specification

Isophosphamide , its cas register number is 3778-73-2. It also can be called 2,3-(N,N(sup 1)-Bis(2-chloroethyl)diamido)-1,3,2-oxazaphosphoridinoxyd ; 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 ; ASTA Z 4942 ; Cyfos ; HSDB 7023 ; Holoxan ; I-Phosphamide ; Ifex ; Ifosfamid ; Ifosfamida ; Ifosfamide ; Ifosfamidum ; Ifsofamide ; Iphosphamid ;
Iphosphamide ; Isoendoxan ; Isofosfamide ; Mitoxana ; N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-
amine 2-oxide ; N,N-Bis(beta-chloroethyl)-amino-N',O-propylene-phosphoric 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'-(2-chloroethyl)-N',O-propylenephosphoric acid diamide ; N-(2-Chloroethyl)-N'-(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide ; Naxamide ; UNII-UM20QQM95Y .
Isophosphamide (CAS NO.3778-73-2) is a crystalline solid.