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Isophosphamide

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Name

Isophosphamide

EINECS 223-237-3
CAS No. 3778-73-2 Density 1.33 g/cm3
Solubility Melting Point 48 °C
Formula C7H15Cl2N2O2P Boiling Point 336.1 °C at 760 mmHg
Molecular Weight 261.11 Flash Point 157.1 °C
Transport Information Appearance Crystalline Solid
Safety 26-45 Risk Codes 25-36
Molecular Structure Molecular Structure of 3778-73-2 (Isophosphamide) Hazard Symbols ToxicT
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;

 

Isophosphamide Chemical Properties

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

Isophosphamide Uses

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

Isophosphamide 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.

Isophosphamide 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.

Isophosphamide Safety Profile

Hazard Codes: ToxicT
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, NOx, and POx.

Isophosphamide 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.

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