Cyclophosphamide (NSC-26271) Monohydrate

Catalog No.S2057 Synonyms: Cytoxan Monohydrate

For research use only.

Cyclophosphamide (NSC-26271, Cytoxan) Monohydrate is a nitrogen mustard alkylating agent, it attaches the alkyl group to the guanine base of DNA, shown to crosslink DNA, causing strand breakage and inducing mutations.

Cyclophosphamide (NSC-26271) Monohydrate Chemical Structure

CAS No. 6055-19-2

Selleck's Cyclophosphamide (NSC-26271) Monohydrate has been cited by 27 publications

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Biological Activity

Description Cyclophosphamide (NSC-26271, Cytoxan) Monohydrate is a nitrogen mustard alkylating agent, it attaches the alkyl group to the guanine base of DNA, shown to crosslink DNA, causing strand breakage and inducing mutations.
In vitro

Cyclophosphamide (CY) is a chemotherapeutic agent with a dose-dependent, bimodal effect on the immune system. Cyclophosphamide treatment enhances apoptosis and decreases homeostatic proliferation of regulatory T cells. Cyclophosphamide downregulates the expression of GITR and FoxP3, which are involved in the suppressive activity of T(REGs).[1] Cyclophosphamide increases CYP3A4, CYP2C8, and CYP2C9 protein levels in primary human hepatocyte cultures, which thereby enhances their own rates of 4-hydroxylation in the cultured hepatocytes. [2] Cyclophosphamide has produced mutations in base-pair substituting strains of Salmonella tryphimurium in the presence of metabolic activation, but it has been shown to be negative in the E. coli chromotest. Cyclophosphamide has been shown to produce gene mutations, chromosome aberrations, micronuclei and sister chromatid exchanges in a variety of cultured cells in the presence of metabolic activation as well as sister chromatid exchanges without metabolic activation. [3]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
BALB/c 3T3 cells MWrDfZRwfG:6aXPpeJkh[XO|YYm= MlvnTY4hfmm2cn:gZ5l1d3SxeHnjbZR6KHejczDleoFtfWG2ZXSgbY4hdW:3c3Wg[Y1jenmxIFLBUGIw[yB|VEOgZ4VtdHNuIFnDOVA:OzdwNjFOwG0> NHi3Z4s9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi97OEezOFEzLz57OEezOFEzRC:jPh?=
HL60 cells M3;ye2N6fG:2b4jpZ4l1gSCjc4PhfS=> M3K4ZWN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGhNPjBiY3XscJMh[nliTWTUJIF{e2G7LDDJR|UxRThwN{mg{txO Ml7NQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjB6NUCzNFMoRjJyOEWwN|A{RC:jPh?=
BALB/c 3T3 NEDnepBEgXSxdH;4bYNqfHliYYPzZZk> NYHmbJlyUW5idnn0do8h[3m2b4TvfIlkcXS7IHHnZYlve3RiQlHMRk9kKDOWMzDj[YxteyxiSVO1NEA:KDN5Lk[g{txONg>? NWXGXlNqRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxN{i3O|E2OCd-N{i3O|E2ODxxYU6=
T-cells MVvJcY12dm:|dYDwdoV{e2m4ZTDhd5NigQ>? MXOxNFAhdWdxa3e= MYi4JIRigXN? MkX6TY1ufW6xc4XwdJJme3OrdnWgZYN1cX[rdImgZYdicW6|dDDNRXYuOSCrbn\lZ5Rm\CCEQVzCM4MhdW:3c3WgZZN{\XO|ZXSgZZMhXCClZXzsd{B{fXCycnXzd4lwdiCjdDCxNFAhdWdxa3esJIlxKHS{ZXH0[YQhQCCmYYnzJIJm\m:{ZTDpcoZm[3Srb36g[o9zKDRid3Xlb5MhdWWjc4Xy[YQhOTRiZHH5d{Bxd3O2IHnu[oVkfGmxbjDifUBndG:5IHP5eI9u\XS{eR?= MYO8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQDJ4OEC4OUc,OTh{NkiwPFU9N2F-
B-cells M{DVWWludXWwb4P1dJBz\XO|aY\lJIF{e2G7 Ml34NVAxKG2pL3vn M{HuOFgh\GG7cx?= M3P4O2ludXWwb4P1dJBz\XO|aY\lJIFkfGm4aYT5JIFo[Wmwc4SgUWFXNTFiaX7m[YN1\WRiQlHMRk9kKG2xdYPlJIF{e2W|c3XkJIF{KEJiY3XscJMhe3WycILld5Nqd25iYYSgNVAxKG2pL3vnMEBqeCC2cnXheIVlKDhiZHH5d{Bj\W[xcnWgbY5n\WO2aX;uJIZweiB2IIfl[Yt{KG2nYYP1doVlKDF2IHThfZMheG:|dDDpcoZm[3Srb36gZpkh\myxdzDjfZRwdWW2com= MXy8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQDJ4OEC4OUc,OTh{NkiwPFU9N2F-
U87 MG MoDwRY51cXS3bX;yJIF{e2G7 MYq4NEBu\y:tZx?= MYHBcpRqfHWvb4KgZYN1cX[rdImgbY4hcHWvYX6gWVg4KE2JIHPlcIx{KHinbn;ndoFnfGWmIH3veZNmKGG2IEiwJI1oN2upLDDpekBi\G2rbnnzeIVz\WRiaX6gVVJFKHhiNTDzZ4hm\HWuZR?= MlXxQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOTh2NUC0OVYoRjF6NEWwOFU3RC:jPh?=
MX1 Mm\aRY51cXS3bX;yJIF{e2G7 MVOxNlAhdWdxa3e= MUP1dEB1dyB|IIfl[Yt{ MU\BcpRqfHWvb4KgZYN1cX[rdImgZYdicW6|dDDoeY1idiCPWEGgZ4VtdHNieHXuc4dz[W[2ZXSgbY4hdnWmZTDtc5V{\SCjZHr1eoFvfCCvb3TlcEBie3Onc4Pl[EBieyCrbnPy[YF{\SCrbjDtc5V{\SC|dYL2bZZidCC2aX3lJIF1KDF{MDDt[{9s\yxicH:gRmlFKG2nYYP1doVlKHWyIITvJFMhf2Wna4O= NYOzSFlzRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkC3NlY2OTJpPkKwO|I3PTF{PD;hQi=>
U87MG MWfBcpRq[2GwY3XyJIF{e2G7 Mny5PFAhdWdxa3e= NFTKXoo3KGSjeYO= MmfYRY51cWOjbnPldkBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIGW4O21IKGOnbHzzJJhmdm:pcnHmeIVlKGmwIHH0bJlucWNibX;1d4Uh[XO|ZYPz[YQh[XNidIXtc5Ihe3WycILld5Nqd25iYYSgPFAhdWdxa3esJIl3KFF{RDDmc5IhPiCmYYnz NUDOZZpiRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkGxNFY{PzdpPkKxNVA3Ozd5PD;hQi=>
NCI-H522 MU\BcpRqfHWvb4KgZZN{[Xl? Mn3LOVAhdWdxa3e= MVSyPEBl[Xm| NIHMeY1CdnSrdIXtc5Ih[WO2aY\peJkh[WejaX7zeEBpfW2jbjDOR2kuUDV{MjDj[YxteyC6ZX7v[5Ji\nSnZDDpckBD[WykL3OgcpVl\SCvb4Xz[UBie3Onc4Pl[EBieyC2dX3vdkBoem:5dHigbY5pcWKrdHnvckBifCB3MDDt[{9s\yxiaXegZYRucW6rc4TldoVlKG:wY3Wg[IFqdHliZn;yJFI5KGSjeYOgdoVt[XSrdnWgeI8h[2:wdILvcC=> MV:8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zQDB7Mki2NEc,OjhyOUK4OlA9N2F-
U2932 MoXJRY51cXS3bX;yJIF{e2G7 M{LFbVUxKG2pL3vn MoHlOUBkd26|ZXP1eIl3\SCmYYnz NYDmS49lSW62aYT1cY9zKGGldHn2bZR6KGGpYXnud5QhcHWvYX6gWVI6OzJiY3XscJMhgGWwb3fyZYZ1\WRiaX6gV2NKTCCvb4Xz[UBie3Onc4Pl[EBieyC{ZXT1Z5Rqd25iaX6geJVud3JiYoXy[IVvKGG2IEWwJI1oN2upLDDpdEBi\G2rbnnzeIVz\WRiZn;yJFUh[2:wc3XjeZRqfmViZHH5d{Bu\WG|dYLl[EB2eCC2bzDkZZkhPDBicH;zeEBk\WyuIHnuboVkfGmxbh?= MnXaQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjh4MEW1PVMoRjJ6NkC1OVk{RC:jPh?=
MDA-MB-231 MmnaR5l1d3SxeHnjbZR6KGG|c3H5 NF\BU2E1QCCqch?= MVfDfZRwfG:6aXPpeJkh[WejaX7zeEBJd22xIIPhdIlmdnNiKHj1cYFvMSCPRFGtUWIuOjNzIHPlcIx{KGGodHXyJFQ5KGi{IHL5JG1VXCCjc4PhfUwhUUN3MDC9JFAvODlizszNMi=> NWLYb3FERGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:ve5d4NmWkaT7hZ{52cy:laHXtZoww[2:vcH;1coRgemWyb4L0Y4NiemRxQ1jFUWJNQDhxJ{7DbGVOSkx:L3G+
K562 NH7OSlhEgXSxdH;4bYNqfHliYYPzZZk> NXTldnA{PDhiaIK= M{npVGN6fG:2b4jpZ4l1gSCjZ3HpcpN1KEixbX:gd4FxcWWwczCobJVu[W5rIFu1OlIh[2WubIOgZYZ1\XJiNEigbJIh[nliTWTUJIF{e2G7LDDJR|UxKD1iMD6xOUDPxE1w MoDWQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFgwLz6FaFXNRmw9N2F-
K562 Mk\0RY51cXC{b3zp[oVz[XSrdnWgZZN{[Xl? MWi0PEBpeg>? M1P3SWFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgTI9udyC|YYDp[Y5{KCiqdX3hckkhUzV4MjDj[YxteyCjZoTldkA1QCCqcjDifUBOXFRiYYPzZZktKEmFNUCgQUAxNjF3MzFOwG0v MkTQQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFgwLz6FaFXNRmw9N2F-
MCF7 NEC3[3dEgXSxdH;4bYNqfHliYYPzZZk> NWfEWJBRPDhiaIK= NEXYTItEgXSxdH;4bYNqfHliYXfhbY5{fCCKb33vJJNieGmnboOgLIh2dWGwKTDNR2Y4KGOnbHzzJIFnfGW{IES4JIhzKGK7IITyfZBidiCkbIXlJIF{e2G7LDDJR|UxKD1iMD6xOkDPxE1w MkTWQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFgwLz6FaFXNRmw9N2F-
HepG2 MmDJR5l1d3SxeHnjbZR6KGG|c3H5 NYewTpR3PDhiaIK= NYXvcIQ3S3m2b4TvfIlkcXS7IHHnZYlve3RiSH;tc{B{[XCrZX7zJEhpfW2jbjmgTIVxTzJiY3XscJMh[W[2ZYKgOFghcHJiYomgUXRVKGG|c3H5MEBKSzVyIE2gNE4zPCEQvF2u Mn;ZQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xd4f3MoVjcS6jYz71b{9kcGWvYnyvZ49ueG:3bnTfdoVxd3K2X3PhdoQwS0iHTVLMPFgwLz6FaFXNRmw9N2F-
Assay
Methods Test Index PMID
Western blot PTEN / pAkt / Caspase 3 / GAPDH ; Caspase 3 / Cleaved-Caspase 3 / Cleaved-PARP / Tubulin ; Nuclear AIF / Cytosolic AIF / TBP / GAPDH ; LC3B I / LC3B II / GAPDH 23874108 31429028
Growth inhibition assay Cell Viability ; Tumor Volume ; Tumor Volume 31429028 24681847 21069336
IHC tumor cell invasion ; TUNEL / Caspase 3 ; PTEN / pAkt / PCNA ; ovary of mice ; Caspase-3 23874108 32308430
Immunofluorescence pAKT / pERK ; Ki-67 / UPK3 / KRT5 / pERK ; Ki-67 / KRT14 / KRT5 ; autophagy levels 31654636 31429028
In vivo Cyclophosphamide has also produced chromosome damage and micronuclei in rats, mice and Chinese hamsters, and gene mutations in the mouse spot test and in the transgenic lacZ construct of Muta Mouse. [3] Cyclophosphamide, when given in a defined sequence with a GM-CSF-secreting, neu-expressing whole-cell vaccine, enhances the vaccine's potential to delay tumor growth in neu transgenic mice. Cyclophosphamide mediates its effects by enhancing the efficacy of the vaccine rather than via a direct cytolytic effect on cancer cells. [4]

Protocol (from reference)

Solubility (25°C)

In vitro

DMSO 55 mg/mL
(197.06 mM)
Water 7 mg/mL
(25.08 mM)
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 279.1
Formula

C7H15Cl2N2O2P.H2O

CAS No. 6055-19-2
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles C1CNP(=O)(OC1)N(CCCl)CCCl.O

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Molarity Calculator

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05128617 Recruiting Drug: Epirubicin-cyclophosphamide|Drug: Paclitaxel Breast Cancer Institut de cancérologie Strasbourg Europe|Université de Strasbourg - Unité de Recherche 3072 - Mitochondries Stress oxydant Protection musculaire November 4 2021 --
NCT04757337 Recruiting Drug: Doxorubicin|Drug: Cyclophosphamide Advanced Soft-tissue Sarcoma|Metastatic Soft-tissue Sarcoma UNICANCER June 18 2021 Phase 3

(data from https://clinicaltrials.gov, updated on 2022-01-17)

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Frequently Asked Questions

Question 1:
Why S2057 Cyclophosphamide Monohydrate shows no activity in vitro assays?

Answer:
Cyclophoshamide is a prodrug and needs Pytochrome P450 to convert it to the active form: 4-hydroxy cyclophosphamide. It is widely used in vivo, if you are going to use it in vitro, you'll have to supplement Pytochrome P450 exogenously.

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