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50-18-0

50-18-0 structure
50-18-0 structure
  • Name: Cyclophosphamide
  • Chemical Name: cyclophosphamide
  • CAS Number: 50-18-0
  • Molecular Formula: C7H15Cl2N2O2P
  • Molecular Weight: 261.086
  • Catalog: Biochemical Inhibitor Immune inhibitor
  • Create Date: 2018-03-07 08:00:00
  • Modify Date: 2024-01-02 18:41:33
  • Cyclophosphamide is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities.
Name cyclophosphamide
Synonyms ASTA
N,N-Bis(b-chloroethyl)-N',O-propylenephosphoric Acid Ester Diamide
cycloblastin
cyclophosphane
2H-1,3,2-Oxazaphosphorine, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide
2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide
N,N-bis(2-chloroéthyl)-1,3,2-oxazaphosphinan-2-amine-2-oxyde
2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide
Mitoxan
cytophosphan
B 518
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide
EINECS 200-015-4
N,N-Bis(b-chloroethyl)-N',O-trimethylenephosphoric Acid Ester Diamide
CB 4564
2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Clafen
Cytoxan
Endoxana
N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
Endoxan
UNII:6UXW23996M
Enduxan
2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Neosar
Genoxal
Cyclophosphamide
2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazophosphorine 2-Oxide
2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide
2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide (9CI)
(RS)-Cyclophosphamide
Ciclophosphamide
(±)-Cyclophosphamide
2-(bis(2-Chloroethyl)-amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide
Description Cyclophosphamide is a synthetic alkylating agent chemically related to the nitrogen mustards with antineoplastic and immunosuppressive activities.
Related Catalog
Target

DNA Alkylator[1]

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.
Density 1.3±0.1 g/cm3
Boiling Point 336.1±52.0 °C at 760 mmHg
Melting Point 41-45ºC
Molecular Formula C7H15Cl2N2O2P
Molecular Weight 261.086
Flash Point 157.1±30.7 °C
Exact Mass 260.024811
PSA 51.38000
LogP 0.23
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.506
Stability Stable, but light sensitive. Incompatible with oxidizing agents.
Water Solubility Soluble. 1-5 g/100 mL at 23 ºC
Name: Cyclophosphamide monohydrate 97% Material Safety Data Sheet
Synonym: N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide monohydrate; 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide monohydrate; Cancer research tool
CAS: 50-18-0
Section 1 - Chemical Product MSDS Name:Cyclophosphamide monohydrate 97% Material Safety Data Sheet
Synonym:N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide monohydrate; 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide monohydrate; Cancer research tool
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
50-18-0 Cyclophosphamide monohydrate 97 unlisted
Hazard Symbols: T
Risk Phrases: 25 41 45 46 48/23/24/25 61
Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed. Risk of serious damage to eyes. May cause cancer. May cause heritable genetic damage. Toxic : danger of serious damage to health by prolonged exposure through inhalation, contact with skin and if swallowed. May cause harm to the unborn child.
Potential Health Effects
Eye:
Causes severe eye irritation and possible injury.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. Poison by ingestion.
May cause nausea and vomiting.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
May cause nausea and possible vomiting.
Chronic:
May cause cancer in humans. May cause reproductive and fetal effects.
Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.
Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.
Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions. Provide ventilation.
Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Do not get in eyes, on skin, or on clothing. Take precautionary measures against static discharges. Do not breathe dust. Use only with adequate ventilation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Keep under an argon blanket.
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 50-18-0: CAS# 6055-19-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to almost white
Odor: odorless
pH: 4 - 6 (2% aq soln)
Vapor Pressure: 0.000033 HPa @ 20 deg C
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 49 - 53 deg C
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 90 deg C
Solubility in water: 40 g/l water
Specific Gravity/Density:
Molecular Formula: C7H15Cl2N2O2P.H2O
Molecular Weight: 279.09
Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Exothermic decomposition at 90C (Method VDI 2263).
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, phosphine, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported.
Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 50-18-0: RP5950000 CAS# 6055-19-2: RP6157750 LD50/LC50:
CAS# 50-18-0: Oral, mouse: LD50 = 137 mg/kg; Oral, rat: LD50 = 100 mg/kg.
CAS# 6055-19-2: Oral, mouse: LD50 = 350 mg/kg; Oral, rat: LD50 = 94 mg/kg.
Primary irritative effect to the eyes: Corrosive, rabbit, OECD 405.
Carcinogenicity:
Cyclophosphamide (anhydrous form) - California: carcinogen, initial date 2/27/87 NTP: Known carcinogen IARC: Group 1 carcinogen Cyclophosphamide monohydrate - California: carcinogen, initial date 2/27/87 IARC: Group 1 carcinogen Other:
See actual entry in RTECS for complete information.
Section 12 - ECOLOGICAL INFORMATION
Other No information available.
Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III
USA RQ: CAS# 50-18-0: 10 lb final RQ; 4.54 kg final RQ
Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 45 May cause cancer.
R 46 May cause heritable genetic damage.
R 61 May cause harm to the unborn child.
R 25 Toxic if swallowed.
R 41 Risk of serious damage to eyes.
R 48/23/24/25 Toxic : danger of serious damage to
health by prolonged exposure through inhalation,
contact with skin and if swallowed.
Safety Phrases:
S 53 Avoid exposure - obtain special instructions
before use.
S 15 Keep away from heat.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 50-18-0: No information available.
CAS# 6055-19-2: 3
Canada
CAS# 50-18-0 is listed on Canada's DSL List.
CAS# 50-18-0 is not listed on Canada's Ingredient Disclosure List.
CAS# 6055-19-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 50-18-0 is not listed on the TSCA inventory.
It is for research and development use only.
CAS# 6055-19-2 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A
Safety Phrases S22-S24/25
RIDADR UN 1851
Packaging Group III
Hazard Class 6.1(b)
HS Code 2924299090
127-88-8 structure

127-88-8

156-87-6 structure

156-87-6

~%

50-18-0 structure

50-18-0

Literature: Angewandte Chemie, , vol. 70, p. 539,543
195966-75-7 structure

195966-75-7

~%

50-18-0 structure

50-18-0

Literature: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, , vol. 52, # 8 p. 943 - 946
821-48-7 structure

821-48-7

156-87-6 structure

156-87-6

~78%

50-18-0 structure

50-18-0

Literature: US2014/66654 A1, ; Paragraph 0039; 0040; 0041; 0042 ;
78336-01-3 structure

78336-01-3

~0%

50-18-0 structure

50-18-0

78336-02-4 structure

78336-02-4

Literature: Journal of Medicinal Chemistry, , vol. 24, # 12 p. 1404 - 1408
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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