|
|
Substance Name: Cyclophosphamide [USP:INN]
RN: 50-18-0
UNII: 6UXW23996M
InChIKey: CMSMOCZEIVJLDB-UHFFFAOYSA-N
Note
- Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the LIVER to form the active ALDOPHOSPHAMIDE. It has been used in the treatment of LYMPHOMA and LEUKEMIA. Its side effect, ALOPECIA, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer.
Molecular Formula
- C7-H15-Cl2-N2-O2-P
Molecular Weight
- 261.0875
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Agricultural Chemical
- Alkylating Agents
- Antineoplastic Agents
- Antineoplastic Agents, Alkylating
- Antirheumatic Agents
- Drug / Therapeutic Agent
- Experimental Pesticide
- Human Data
- Immunologic Factors
- Immunosuppressive Agents
- Mutagens
- Mutation Data
- Myeloablative Agonists
- Noxae
- Reproductive Effect
- Tumor Data
- Unspecified / Unclassified Pesticide
Superlist Classification Codes
- Known to be a Carcinogen
- Overall Carcinogenic Evaluation: Group 1
- Reportable Quantity (RQ) = 10 lb
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
Names and Synonyms
Results Name
- Cyclophosphamide [USP:INN]
Name of Substance
- Cyclophosphamide
- Cyclophosphamide (anhydrous)
- Cyclophosphamide [USP:INN]
MeSH Heading
- Cyclophosphamide
Synonyms
- (+-)-Cyclophosphamide
- (RS)-Cyclophosphamide
- 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin
- 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide
- 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide
- 4-27-00-09750 (Beilstein Handbook Reference)
- 4-Hydroxy-cyclophosphan-mamophosphatide
- AI3-26198
- ASTA B518
- B 518
- Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester
- BRN 0011744
- CB 4564
- CCRIS 188
- Ciclofosfamida
- Ciclofosfamida [INN-Spanish]
- Ciclophosphamide
- Ciclophosphamide [INN]
- Clafen
- Claphene
- Cyclophosphamid
- Cyclophosphamide
- Cyclophosphamidum
- Cyclophosphamidum [INN-Latin]
- Cyclophosphan
- Cyclophosphane
- Cyclophosphanum
- Cyclophosphoramide
- Cyclostin
- Cyklofosfamid
- Cyklofosfamid [Czech]
- Cytophosphan
- Cytophosphane
- Cytoxan
- D,L-Cyclophosphamide
- EINECS 200-015-4
- Endoxan
- Endoxan R
- Endoxan-asta
- Endoxana
- Endoxanal
- Genoxal
- HSDB 3047
- Lyophilized cytoxan
- N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide
- N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
- N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester diamide
- N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide
- N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid
- N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid [German]
- N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide
- NCI-C04900
- Neosar
- NSC 26271
- NSC-26271
- Occupation, cyclophosphamide exposure
- Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester
- Procytox
- RCRA waste number U058
- Sendoxan
- SK 20501
- UNII-6UXW23996M
- Zyklophosphamid
- Zyklophosphamid [German]
Systematic Names
- 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide
- 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide
- Cyclophosphamide
Superlist Names
- 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide
- Cyclophosphamide (anhydrous form)
- Cyclophosphamide (anhydrous)
- RCRA waste no. U058
Registry Numbers
CAS Registry Number
- 50-18-0
FDA UNII
- 6UXW23996M
Other Registry Numbers
- 60007-95-6
- 75526-90-8
Related Registry Number
- 6055-19-2 (monohydrate)
System Generated Number
- 0000050180
Structure Descriptors
InChI
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)InChIKey
CMSMOCZEIVJLDB-UHFFFAOYSA-NSmiles
ClCCN(CCCl)Toxicity
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) | American Journal of Diseases of Children. Vol. 140, Pg. 1094, 1986. | |
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) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES CARDIAC: 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) | BEHAVIORAL: MUSCLE WEAKNESS SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ATAXIA | 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: ATAXIA BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Experientia. Vol. 37, Pg. 401, 1981. |
human | TDLo | oral | 20mg/kg (20mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES GASTROINTESTINAL: OTHER CHANGES SKIN AND APPENDAGES (SKIN): HAIR: OTHER | 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: OTHER CHANGES LIVER: LIVER FUNCTION TESTS IMPAIRED LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | American Journal of Gastroenterology. Vol. 95, Pg. 845, 2000. |
monkey | LDLo | intravenous | 45mg/kg (45mg/kg) | Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 191, 1965. | |
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 | intraperitoneal | 420mg/kg (420mg/kg) | Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 263, 1986. | |
mouse | LD50 | intraperitoneal | 420mg/kg (420mg/kg) | BEHAVIORAL: ATAXIA | Archivum Immunologiae et Therapiae Experimentalis. Vol. 34, Pg. 263, 1986. |
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) | Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 431, 1982. | |
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. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 51.5 | deg C | EXP | |
log P (octanol-water) | 0.63 | (none) | EXP | |
Water Solubility | 4.00E+04 | mg/L | 20 | EXP |
Vapor Pressure | 4.45E-05 | mm Hg | 25 | EST |
Henry's Law Constant | 1.40E-11 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 7.03E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.