Cyclophosphamide (hydrate)

Modify Date: 2024-01-02 10:42:58

Cyclophosphamide (hydrate) Structure
Cyclophosphamide (hydrate) structure
 Common Name Cyclophosphamide (hydrate)
CAS Number 6055-19-2 Molecular Weight 279.101
Density N/A Boiling Point 336.1ºC at 760 mmHg
Molecular Formula C7H17Cl2N2O3P Melting Point 49-51 °C(lit.)
MSDS Chinese USA Flash Point >230 °F
Symbol GHS06 GHS08
GHS06, GHS08		 Signal Word Danger

 Use of Cyclophosphamide (hydrate)


Cyclophosphamide hydrate is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities.

 Names

Name cyclophosphamide hydrate
Synonym More Synonyms

 Cyclophosphamide (hydrate) Biological Activity

Description Cyclophosphamide hydrate is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities.
Related Catalog
In Vitro Cyclophosphamide induces outer membrane blebbing, leads to DNA fragmentation, as revealed by TUNEL staining of free 3'-OH DNA ends, and induces cleavage of the caspase 3 and caspase 7 substrate PARP in 9L/P450 cells. Bcl-2 expression fully blocks the activation of both initiator caspases as well as the effector caspase 3 in cells treated with activated Cyclophosphamide. Bcl-2 inhibits the cytotoxic effects but not the cytostatic effects of activated Cyclophosphamide[1]. Cyclophosphamide inhibits the AChE reversibly with an IC50 of 511 μM[2]. Carbon tetrachloride does not affect the direct cytotoxicity of cyclophosphamide or 4-hydroxycyclophosphamide to cells in culture[3].
Kinase Assay 9L cells are treated with drug for the times indicated in each experiment. Floating and attached cells are collected, pooled, resuspended in lysis buffer (10 mM HEPES buffer, pH 7.4, containing 2 mM EDTA, 0.1% CHAPS detergent, 5 mM DTT, 350 ng/mL phenylmethylsulfonyl fluoride, 10 ng/mL pepstatin A, 10 ng/mL aprotinin, and 20 ng/mL leupeptin) and lysed by three freeze-thaw cycles (alternating between a dry ice isopropanol bath and a 37°C water bath). Lysates are spun in a bench top centrifuge at full speed for 15 min and the supernatant (cell extract) fraction transferred to a new tube. Cell extracts (20 μL) are assayed for caspase 9, caspase 8, and caspase 3 activity by incubation at 37°C for either 1 h (caspase 3) or 3 h (caspase 9 and caspase 8) in 500 μL of reaction buffer (10 mM HEPES, pH 7.4, 2 mM EDTA, 0.1% CHAPS, and 5 mM DTT) containing 50 μM caspase form-selective substrate: Ac-LETD-AFC for caspase 8; Ac-LEHD-AFC for caspase 9; and Ac-DEVD-AMC for caspase 3. Background activity is determined for each sample as follows. Cell extracts are preincubated for 15 min at room temperature, with or without caspase form-selective inhibitor: 1 μM z-LETD-FMK for caspase 8, 1 μM z-LEHD-FMK for caspase 9, and 5 μL of Casputin for caspase 3. Caspase activity measured in the absence of inhibitor is divided by the background caspase activity measured in the presence of inhibitor. A value of 1 is subtracted from each measured activity, such that a caspase activity of 0 corresponds to no increase in the specific caspase activity with drug treatment. Fluorescence of the caspase product (excitation at 395 nm and emission at 525 nm for AFC substrates, and excitation at 380 nm and emission at 460 nm for the AMC substrate) is measured using a Shimadzu model RF-1501 spectrofluorophotometer and the manufacturer's PC-1501 software package.
Cell Assay 9L/pBabe, 9L/Bax, and 9L/Bcl-2 cells are treated with 12, 24, or 50 μM MFA for 72 h. Cells remaining on the plates at 0, 24, 48, and 72 h are washed twice with cold PBS and then stained for 5 min with crystal violet [1.25 g of crystal violet dissolved in a solution containing 50 mL of 37% formaldehyde and 450 mL of methanol]. The stained cells are washed three times in tap water and the plates are allowed to dry. The stain is eluted from the cells with 70% ethanol and the absorbance is then read at 595 nm. The staining intensity of each drug-treated sample (A 595) is then graphed as a percentage of the staining intensity at the 0-h time point.
References

[1]. Schwartz PS, et al. Cyclophosphamide induces caspase 9-dependent apoptosis in 9L tumor cells. Mol Pharmacol. 2001 Dec;60(6):1268-1279.

[2]. al-Jafari AA, et al. Inhibition of human acetylcholinesterase by cyclophosphamide. Toxicology. 1995 Jan 19;96(1):1-6.

[3]. Harris RN, et al. Carbon tetrachloride-induced increase in the antitumor activity of cyclophosphamide in mice: a pharmacokineticstudy. Cancer Chemother Pharmacol. 1984;12(3):167-72.

 Chemical & Physical Properties

Boiling Point 336.1ºC at 760 mmHg
Melting Point 49-51 °C(lit.)
Molecular Formula C7H17Cl2N2O3P
Molecular Weight 279.101
Flash Point >230 °F
Exact Mass 278.035370
PSA 60.61000
LogP 2.14850
Storage condition 2-8°C
Water Solubility 40 g/L

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RP6157750
CHEMICAL NAME :
2H-1,3,2-Oxazaphosphorine, tetrahydro-2-(bis(2-chloroethyl)amino)-, 2-oxide, monohydrate
CAS REGISTRY NUMBER :
6055-19-2
LAST UPDATED :
199710
DATA ITEMS CITED :
36
MOLECULAR FORMULA :
C7-H15-Cl2-N2-O2-P.H2-O
MOLECULAR WEIGHT :
279.13

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
94 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Kidney, Ureter, Bladder - urine volume increased Blood - hemorrhage
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
121 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
350 mg/kg
TOXIC EFFECTS :
Behavioral - ataxia Kidney, Ureter, Bladder - urine volume increased Blood - hemorrhage
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
275 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
44 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
130 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
240 mg/kg/4W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - hematuria Blood - changes in leukocyte (WBC) count Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
480 mg/kg/8W-I
TOXIC EFFECTS :
Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
480 mg/kg/24D-C
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in leukocyte (WBC) count Immunological Including Allergic - decrease in humoral immune response
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
150 mg/kg/9W-I
TOXIC EFFECTS :
Blood - changes in leukocyte (WBC) count Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
150 mg/kg/4W-I
TOXIC EFFECTS :
Blood - changes in leukocyte (WBC) count Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Bird - domestic
DOSE/DURATION :
60 mg/kg/3D-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Blood - changes in leukocyte (WBC) count Immunological Including Allergic - decrease in humoral immune response
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
40 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow) Reproductive - Specific Developmental Abnormalities - hepatobiliary system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
321 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
88 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
27500 ug/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
27500 ug/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
27500 ug/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
100 mg/kg/5D (Continuous)
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 69,149,1980 *** REVIEWS *** IARC Cancer Review:Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 9,135,1975 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 9,135,1975 IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 26,165,1981 IARC Cancer Review:Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 26,165,1981

 Safety Information

Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H301-H350
Precautionary Statements P201-P301 + P310 + P330-P308 + P313
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R25;R36/37/38;R45;R46;R61
Safety Phrases S53-S45-S37/39-S26
RIDADR UN 3464 6.1/PG 3
WGK Germany 3
RTECS RP6157750
Packaging Group II
Hazard Class 6.1
HS Code 2924299090

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

CCRIS 7469 {Hydrate}
MFCD00149395
Cytoxan
N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide hydrate
2H-1,3,2-Oxazaphosphorine, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide, monohydrate
Cyclophosphamide Monohydrate
EINECS 200-015-4
UNII-8N3DW7272P
2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, hydrate (1:1)
CYCLOPHOSPHAMIDE HYDRATE
N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide hydrate (1:1)
Endoxon
N,N-bis(2-chloroethyl)-2-oxo-1,3,2λ<sup>5</sup>-oxazaphosphinan-2-amine,hydrate
Cyclophosphamide (hydrate)
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