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| CAS No.: | 50-18-0 |
|---|---|
| Name: | Cyclophosphamide |
| Molecular Structure: | |
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|
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| Formula: | C7H15Cl2N2O2P |
| Molecular Weight: | 261.088 |
| Synonyms: | 2H-1,3,2-Oxazaphosphorine,2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide (6CI,8CI);(RS)-Cyclophosphamide;2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin 2-oxide;Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester;CB 4564;CY;Clafen;Claphene;Cycloblastin;Cyclophosphamid;Cyclophosphan;Cyclophosphane;Cyclostin;Cytophosphan;Cytoxan;Endoxan;Endoxan R;Endoxan-Asta;Endoxana;Endoxanal;Endoxane;Enduxan;Genoxal;Mitoxan;N,N-Bis(b-chloroethyl)-N',O-trimethylenephosphoricacid ester diamide;Neosar;Neosar (antineoplastic);Procytox;Revimmune;SK 20501;Semdoxan;Sendoxan;Senduxan;Zyklophosphamid; |
| EINECS: | 200-015-4 |
| Density: | 1.33 g/cm3 |
| Melting Point: | 41-45 °C |
| Boiling Point: | 336.1 °C at 760 mmHg |
| Flash Point: | 157.1 °C |
| Solubility: | Soluble. 1-5 g/100 mL at 23 ºC |
| Appearance: | white crystalline powder |
| Safety: | 22-24/25 |
| Transport Information: | UN 1851 |
| PSA: | 51.38000 |
| LogP: | 2.21280 |
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| Conditions | Yield |
|---|---|
| With ammonia at 120℃; under 3040.2 Torr; for 2h; Molecular sieve; | 92.3% |
| With ammonia; triethylamine at 20℃; under 375.038 Torr; for 2.3h; | 90.6% |
| Conditions | Yield |
|---|---|
| Stage #1: bis-(2-chloroethyl)amine hydrochloride With 4-methyl-morpholine; trichlorophosphate In neat (no solvent) at 4 - 20℃; for 5h; Green chemistry; Stage #2: propan-1-ol-3-amine In neat (no solvent) at 4 - 20℃; for 18h; Reagent/catalyst; Green chemistry; | 77.6% |
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In ethyl acetate under 2068.6 - 2327.2 Torr; for 72h; Ambient temperature; Yield given; | A n/a B 22% |
| With hydrogen; palladium on activated charcoal In ethyl acetate under 2068.6 - 2327.2 Torr; for 72h; Ambient temperature; Yields of byproduct given; | A n/a B 22% |
A
- 50-18-0
cyclophosphamide
B
- 10199-13-0
2-chloro-1,3,5-trimethyl-2-oxo-2λ5-[1,3,5,2]triazaphosphinane-4,6-dione
| Conditions | Yield |
|---|---|
| With sulfuryl dichloride In dichloromethane at 0℃; for 1h; | A 10.9% B n/a |
- 127-88-8
N,N-di(2-chloroethyl)amidophosphoric acid dichloride
- 156-87-6
propan-1-ol-3-amine
- 50-18-0
cyclophosphamide
| Conditions | Yield |
|---|---|
| With 1,4-dioxane; triethylamine | |
| With triethylamine In ethyl acetate | |
| With triethylamine In tetrachloromethane at 0℃; for 10h; | |
| With triethanolamine In dichloromethane |
- 195966-75-7
(2-Oxo-2λ5-[1,3,2]oxazaphosphinan-2-yl)-bis-(2-trimethylsilanyloxy-ethyl)-amine
- 50-18-0
cyclophosphamide
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 76.3 percent / CH2Cl2 / 24 h / Ambient temperature 2: 10.9 percent / SO2Cl2 / CH2Cl2 / 1 h / 0 °C View Scheme |
| Conditions | Yield |
|---|---|
| With triethylamine In methanol; dichloromethane |
- 58028-71-0
2(R)--3-<(R)-α-methylbenzyl>-1,3,2-oxazaphosphorinane 2-oxide
A
- 50-18-0
cyclophosphamide
| Conditions | Yield |
|---|---|
| With ammonium sulfate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; trifluoroacetic acid |
- 50-18-0
cyclophosphamide
| Conditions | Yield |
|---|---|
| With bromine; potassium carbonate In dichloromethane for 2h; | 100% |
- 50-18-0
cyclophosphamide
| Conditions | Yield |
|---|---|
| With sodium hypochlorite In chloroform for 18h; | 87% |
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Consensus Reports
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 182.(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) ; Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 , 1981,p. 165.(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 Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 , 1981,p. 165.(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) ; IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 , 1975,p. 135.(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) ; Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 , 1975,p. 135.(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 Studies (ipr); Clear Evidence: mouse, rat RRCRBU Recent Results in Cancer Research. 52 (1975),1. . EPA Genetic Toxicology Program.
Specification
The Cyclophosphoramide with CAS registry number of 50-18-0 is also called 2H-1,3,2-Oxazaphosphorin-2-amine,N,N-bis(2-chloroethyl)tetrahydro-,2-oxide. The IUPAC name is N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide. Its EINECS registry number is 200-015-4. In addition, the formula is C7H15Cl2N2O2P and the molecular weight is 261.085961. What's more, it is stable and incompatible with oxidizing agents. But it is sensitive to light.
Physical properties about this chemical are: (1)ACD/LogP: 0.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.23; (4)ACD/LogD (pH 7.4): 0.23; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 31.69; (8)ACD/KOC (pH 7.4): 31.76; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 42.59 Å2; (13)Index of Refraction: 1.505; (14)Molar Refractivity: 58.09 cm3; (15)Molar Volume: 195.6 cm3; (16)Polarizability: 23.03 ×10-24cm3; (17)Surface Tension: 44.3 dyne/cm; (18)Density: 1.33 g/cm3; (19)Flash Point: 157.1 °C; (20)Enthalpy of Vaporization: 57.92 kJ/mol; (21)Boiling Point: 336.1 °C at 760 mmHg ; (22)Vapour Pressure: 0.000115 mmHg at 25°C.
Uses of Cyclophosphoramide: it can treat many diseases such as malignant lymphoma, multiple myeloma, lymphocytic leukemia, cervical cancer, prostate cancer, colon cancer, bronchial cancer, solid tumors, rheumatoid arthritis and autoimmune diseases. In addition, it can be used to get 3-chlorocyclophosphamide. This reaction will need reagent aq.sodium hypochlorite and solvent CHCl3. The reaction time is 18 hours and the yield is about 87%.
When you are using this chemical, please be cautious about it as the following:
You should avoid contact with skin and eyes and should not breathe dust.
You can still convert the following datas into molecular structure:
(1)SMILES: O=P1(OCCCN1)N(CCCl)CCCl
(2)InChI: InChI=1/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
(3)InChIKey: CMSMOCZEIVJLDB-UHFFFAOYAB
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | intraperitoneal | 50mg/kg (50mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| child | TDLo | oral | 2500ug/kg (2.5mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | American Journal of Diseases of Children. Vol. 140, Pg. 1094, 1986. |
| 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 | 11mg/kg (11mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965. |
| domestic animals - goat/sheep | LD50 | intravenous | 45100ug/kg (45.1mg/kg) | CARDIAC: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES LIVER: OTHER CHANGES | Dongbei Nongxueyuan Xuebao. Journal of Northeast Agricultural College. Vol. 34, Pg. 56, 1980. |
| guinea pig | LDLo | intraperitoneal | 200mg/kg (200mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ATAXIA BEHAVIORAL: MUSCLE WEAKNESS | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| hamster | LD10 | parenteral | 110mg/kg (110mg/kg) | Journal of Surgical Oncology. Vol. 15, Pg. 355, 1980. | |
| hamster | LD50 | intraperitoneal | 429mg/kg (429mg/kg) | Cancer Letters Vol. 2, Pg. 267, 1977. | |
| hamster | LD50 | oral | 763mg/kg (763mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA | Experientia. Vol. 37, Pg. 401, 1981. |
| human | TDLo | oral | 20mg/kg (20mg/kg) | GASTROINTESTINAL: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Arthritis and Rheumatism. Vol. 12, Pg. 663, 1969. |
| man | LDLo | multiple routes | 45mg/kg/26W-I (45mg/kg) | BLOOD: OTHER CHANGES | American Journal of the Medical Sciences. Vol. 254, Pg. 48, 1967. |
| man | TDLo | oral | 56mg/kg/26D-I (56mg/kg) | BLOOD: AGRANULOCYTOSIS | American Journal of Medicine. Vol. 81, Pg. 1059, 1986. |
| man | TDLo | oral | 56mg/kg/4W-I (56mg/kg) | LIVER: OTHER CHANGES | Southern Medical Journal. Vol. 78, Pg. 222, 1985. |
| man | TDLo | oral | 579mg/kg/2Y-I (579mg/kg) | LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: LIVER FUNCTION TESTS IMPAIRED LIVER: OTHER CHANGES | American Journal of Gastroenterology. Vol. 95, Pg. 845, 2000. |
| monkey | LDLo | intravenous | 45mg/kg (45mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965. |
| mouse | LD50 | intraperitoneal | 110mg/kg (110mg/kg) | Farmakologiya i Toksikologiya Vol. 41, Pg. 90, 1978. | |
| mouse | LD50 | intravenous | 140mg/kg (140mg/kg) | "Radiation-Induced Cancer, Proceedings of a Symposium, Athens, 1969," Lanham, MD, Bernan-UNIPUB, 1969Vol. -, Pg. 97, 1969. | |
| mouse | LD50 | oral | 137mg/kg (137mg/kg) | Russian Pharmacology and Toxicology Vol. 36, Pg. 240, 1973. | |
| mouse | LD50 | parenteral | 315mg/kg (315mg/kg) | Transplantation. Vol. 13, Pg. 316, 1972. | |
| mouse | LD50 | subcutaneous | 200mg/kg (200mg/kg) | Advances in the Study of Birth Defects. Vol. 2, Pg. 95, 1979. | |
| mouse | LD50 | unreported | 480mg/kg (480mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 157S, 1968. | |
| mouse | LDLo | intratracheal | 200mg/kg (200mg/kg) | Toxicology Letters. Vol. 30, Pg. 63, 1986. | |
| 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. |
| rabbit | LDLo | intravenous | 300mg/kg (300mg/kg) | Journal of Toxicological Sciences. Vol. 34, Pg. 308, 1999. | |
| rat | LD50 | intracrebral | > 400ug/kg (0.4mg/kg) | Journal of Pharmacy and Pharmacology. Vol. 18, Pg. 760, 1966. | |
| rat | LD50 | intraperitoneal | 40mg/kg (40mg/kg) | Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962. | |
| rat | LD50 | intravenous | 148mg/kg (148mg/kg) | BLOOD: NORMOCYTIC ANEMIA | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| rat | LD50 | oral | 100mg/kg (100mg/kg) | Drugs in Japan Vol. -, Pg. 516, 1995. | |
| rat | LD50 | subcutaneous | 144mg/kg (144mg/kg) | BLOOD: NORMOCYTIC ANEMIA | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. |
| rat | LD50 | unreported | 190mg/kg (190mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64(4), Pg. 157S, 1968. | |
| women | LDLo | oral | 16mg/kg/4D-I (16mg/kg) | BLOOD: OTHER CHANGES | American Journal of the Medical Sciences. Vol. 254, Pg. 48, 1967. |
| women | TDLo | intravenous | 13500ug/kg (13.5mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE | Annals of Internal Medicine. Vol. 116, Pg. 92, 1992. |
| women | TDLo | intravenous | 60mg/kg/9W-I (60mg/kg) | Archives of Internal Medicine. Vol. 145, Pg. 548, 1985. | |
| women | TDLo | oral | 45mg/kg (45mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Arthritis and Rheumatism. Vol. 15, Pg. 530, 1972. |