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CAS 50-18-0 Cyclophosphamide molecular structure lightbox
CAS RN: 50-18-0

Cyclophosphamide

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50-18-0 / N,N-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine

cyclophosphamide | Cytoxan | Cyclophosphamid

Standard CAS: 50-18-0 Multi CAS: Yes
Basic Information Physical Properties Computed Properties Safety & Transport

Basic Information

CAS
50-18-0
Multi CAS
Yes
Molecular Formula
C7H15CL2N2O2P
Molecular Weight
261.080000
Exact Mass
260.024820
SMILES
C1CNP(=O)(OC1)N(CCCl)CCCl
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-N
Synonyms
cyclophosphamide Cytoxan Cyclophosphamid Cyclophosphane Clafen

Physical Properties

Melting Point
106 to 113 °F (NTP, 1992) 48-49 49.5-53 °C 41 - 45 °C 49.5 - 53 °C
Boiling Point
336 °C
Density
1.48 g/cm³
Physical Description
Cyclophosphamide is a fine white crystalline powder. Odorless with a slightly bitter taste. Melting point 41-45 °C. A 2% solution has pH of 4 to 6. Used medicinally as an antineoplastic agent. White odorless solid; Liquefies upon loss of crystallization water; Darkens on light exposure; [ICSC] White odorless crystalline solid; Solid FINE WHITE CRYSTALLINE POWDER.
Appearance
LIQUEFIES ON LOSS OF ITS WATER OF CRYSTALLIZATION Crystalline solid
State
Solid
Storage Conditions
STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992) PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Computed Properties

Structural Parameters

Heavy atom count
14
Fraction Csp3
1
Rotatable bonds
5
H-bond acceptors
2
H-bond donors
1
Molar refractivity
59.19
TPSA
41.57

LogP / Solubility

WLOGP
1.88
MLOGP
1.67
XLogP3
0.6
Consensus LogP
1.38
Log S (ESOL)
-2.32
Class (ESOL)
Moderately soluble
Log S (Ali)
-3.06
Class (Ali)
Poorly soluble
Log S (SILICOS-IT)
-3.52
Class (SILICOS-IT)
Poorly soluble

ADME

GI absorption
High
BBB permeant
Yes
P-gp substrate
No
CYP1A2 inhibitor
No
CYP2C19 inhibitor
No
CYP2C9 inhibitor
No
CYP2D6 inhibitor
Yes
CYP3A4 inhibitor
No
Log Kp (skin permeation)
-2.98

Drug-likeness / Medicinal Chemistry

Lipinski
Yes
Ghose
No
Veber
Yes
Egan
Yes
Muegge
Yes
Bioavailability score
0.55
Brenk alerts
1
Leadlikeness
Yes
Synthetic Accessibility
2

Safety & Transport

Pictogram(s)
Corrosive Acute Toxic Irritant Health Hazard
Signal
Danger
GHS Hazard Statements
H301 (63.2%): Toxic if swallowed [Danger Acute toxicity, oral] H302 (35.3%): Harmful if swallowed [Warning Acute toxicity, oral] H318 (36.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H340 (95.6%): May cause genetic defects [Danger Germ cell mutagenicity] H350 (98.5%): May cause cancer [Danger Carcinogenicity]
Precautionary Statement Codes
P203, P260, P264, P264+P265, P270, P280, P301+P316, P301+P317, P305+P354+P338, P317, P318, P319, P321, P330, P405, and P501 (click each P-code to see the statement) P203, P260, P263, P264, P270, P280, P301+P316, P308+P316, P318, P319, P321, P330, P405, and P501 (click each P-code to see the statement)
Hazard Class/Division
6.1
Packing Group
III

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