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  1. General Info
  2. Effects Info
  3. Reference
Drug Details
01. General Information
Name Cyclophosphamide
PubChem CID 2907
Molecular Weight 261.08g/mol
Synonyms

cyclophosphamide, 50-18-0, Cytoxan, Cyclophosphamid, Cyclophosphane, Endoxan, Cytophosphan, Procytox, Sendoxan, Clafen, Cyclophosphan, Cyclostin, Cyclophosphamidum, Cytophosphane, Endoxanal, Neosar, Claphene, Endoxana, Genoxal, Endoxan-Asta, Endoxan R, Zyklophosphamid, Mitoxan, Cyclophosphoramide, Cyklofosfamid, Endoxane, (RS)-Cyclophosphamide, Cyclophosphamide anhydrous, Cyclophosphanum, Enduxan, Semdoxan, Senduxan, (+-)-Cyclophosphamide, Ciclophosphamide, ASTA, Lyophilized Cytoxan, Ciclofosfamida, D,L-Cyclophosphamide, Rcra waste number U058, Asta B 518, (-)-Cyclophosphamide, Cycloblastin, NSC-26271, 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester, CB 4564, Cyclophosphamide (anhydrous), NCI-C04900, ASTA B518, SK 20501, NSC 26271, CHEBI:4027, B 518, Occupation, cyclophosphamide exposure, CCRIS 188, N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide, 4-Hydroxy-cyclophosphan-mamophosphatide, HSDB 3047, Anhydrous cyclophosphamide, EINECS 200-015-4, Ciclofosfamide, N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide, UNII-6UXW23996M, BRN 0011744, Cyclophosphamide-d4, AI3-26198, 6UXW23996M, Cyclophosphamide (INN), 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin, NSC26271, Cytoxan (TN), 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide, N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide, N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide, 50-18-0 (anhydrous), 2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide, 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-,2-oxide, Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester, CY, DTXSID5020364, CYCLOPHOSPHAMIDE LYOPHILIZED, CYCLOPHOSPHAMIDE, ANHYDROUS, N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester diamide, 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide, N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide, Cyklofosfamid [Czech], N,N-bis(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine, N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid, Ciclophosphamide [INN], 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide, 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide, Zyklophosphamid [German], NSC-756711, Ciclophosphamide hydrat, Cytoxan (Lyophilized), CYCLOPHOSPHAMIDE [INN], Ciclofosfamida [INN-Spanish], Cyclofosphamide, Cyclophosphamidum [INN-Latin], UNII-8N3DW7272P, CYCLOPHOSPHAMIDE (IARC), CCRIS 7469, CYCLOPHOSPHAMIDE (USP-RS), Cyclophosphamide (anhydrous form), Cyclophosphamide (TN), CYCLOPHOSPHAMIDE (EP MONOGRAPH), CYCLOPHOSPHAMIDE (USP MONOGRAPH), SR-01000075737, NCGC00015209-05, RCRA waste no. U058, Cyclophosphamide [USP:INN], Cycloblastine, Cyclophospham, Cyclostine, Fosfaseron, Syklofosfamid, Carloxan, Cicloxal, Genuxal, Ledoxina, 2-(Bis(2-chloroethyl)amino)-2H-1,2-oxazaphosphorine 2-oxide, 2-[Bis(2-chloroethyl)amino]-2H-1,2-oxazaphosphorine 2-oxide, 2-(Bis(2-chloroethylamino))-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide, (Bis(chloro-2-ethyl)amino)-2-tetrahydro-3,5,6-oxazaphosphorine-1,3,2-oxide-2 hydrate, [Bis(chloro-2-ethyl)amino]-2-tetrahydro-3,5,6-oxazaphosphorine-1,3,2-oxide-2 hydrate, 2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORINE 2-OXIDE, CYCLO-cell, N,N-Bis(beta-cloraethyl) N'-O-propylenphosphorildiamid monohydratum, 173547-45-0, bis(2-Chloroethyl)phosphamide cyclic propanolamide ester, CB-4564, Spectrum_000858, CHEMBL88, Spectrum2_001146, Spectrum3_000370, Spectrum4_000304, Spectrum5_000795, Lopac-C-0768, Epitope ID:131782, C 0768, N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid [German], SCHEMBL4346, (.+/-.)-Cyclophosphamide, Lopac0_000238, BSPBio_002099, KBioGR_000888, KBioSS_001338, DivK1c_000246, DTXCID70364, SPBio_001071, CYCLOPHOSPHAMIDE [HSDB], GTPL7154, SCHEMBL4345553, 2-H-1,3,2-Oxazaphosphorinane, SCHEMBL10262910, CMSMOCZEIVJLDB-UHFFFAOYSA-, KBio1_000246, KBio2_001338, KBio2_003906, KBio2_006474, KBio3_001319, CYCLOPHOSPAMIDE MONOHYDRATE, CYCLOPHOSPHAMIDE [WHO-DD], L01AA01, WLN: T6MPOTJ BO BN2G2G, NINDS_000246, 2-(bis(2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide, HMS2090A12, HMS3260P17, HMS3715J05, Pharmakon1600-01500213, AMY33449, BCP02139, Tox21_500238, BDBM50237604, N,N-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine, NSC273033, NSC273034, NSC756711, STK177249, AKOS005410738, tetrahydro-N,N-bis(2-chloroethyl)-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide, CS-1425, CYCLOPHOSPHAMIDE ANHYDROUS [MI], DB00531, LP00238, NSC-273033, NSC-273034, SDCCGSBI-0050226.P004, IDI1_000246, N,3,2-oxazaphosphorin-2-amine-2-oxide, N,O-propylen-phosphorsaeure-ester-diamid, NCGC00015209-01, NCGC00015209-02, NCGC00015209-03, NCGC00015209-04, NCGC00015209-06, NCGC00015209-07, NCGC00015209-08, NCGC00015209-09, NCGC00015209-12, NCGC00015209-28, NCGC00091741-02, NCGC00091741-03, NCGC00260923-01, AS-73255, BP-25411, HY-17420, NCI60_002097, N,O-propylenephosphoric acid ester diamide, SBI-0050226.P003, DB-082057, N,O-propylene-phosphoric acid ester diamide, WR-138719, C2236, EU-0100238, FT-0624276, FT-0665387, N,O-trimethylenephosphoric acid ester diamide, NS00000339, EN300-74526, C07888, D07760, AB00053446-09, AB00053446-11, AB00053446-12, AB00053446_13, AB00053446_14, AB00053446_15, Q408524, W-60377, N,O-propylenephosphoric acid ester amide monohydrate, SR-01000075737-1, SR-01000075737-6, W-105248, BRD-A09722536-002-02-4, Z276509078, 2-(bis(2-chloroethyl)amino)-1,3,2-oxazaphosphinane2-oxide, Bis(2-chloroethyl)phosphoramide-cyclic propanolamide ester, 2-[bis(2-chloroethyl)amino]-1,3,2??-oxazaphosphinan-2-one, 1-BIS(2-CHLOROETHYL)AMINO-1-OXO-2-AZA-5-OXAPHOSPHORIDINE, 2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one, 2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one, N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide #, 2-[Bis(2-chloroethyl)amino]tetrahydro-1,3,2-oxazaphosphorin-2-oxide, 2H-1,2-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(.beta.-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide, N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine-2-oxide, N,N-Bis-(.beta.-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid, N,N-DI(2-CHLOROETHYL)-N,O-PROPYLENE PHOSPHORIC ACID ESTER DIAMIDE, (+/-)-2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORINE 2-OXIDE, 2-(DI(2-CHLOROETHYLAMINO))-1-OXA-3-AZA-2-PHOSPHACYCLOHEXANE 2-OXIDE, 2-Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide, 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, (+)-, 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, (-)-, 2H-1,2-Oxazaphosphorine, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide, monohydrate, 2H-1,3,2-oxazaphosphorin-2-amine, N,N-is(2-chloroethyl)tetrahydro-,2-oxide, N,N-bis(2-chloroethyl)-2-oxo-1-oxa-3-aza-2$l^{5}-phosphacyclohexan-2-amine, N,N-BIS(2-CHLOROETHYL)-N'-(3-HYDROXYPROPYL)PHOSPHORODIAMIDIC ACID INTRAMOL., N,N-BIS(BETA-CHLOROETHYL)N',O-TRIMETHYLENEPHOSPHORIC ACID ESTER DIAMIDE, Phosphorodiamidic acid,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester, InChI=1/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)

Drug Type Small molecule
Formula C₇H₁₅Cl₂N₂O₂P
SMILES C1CNP(=O)(OC1)N(CCCl)CCCl
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
CAS Number 50-18-0
ChEMBL ID CHEMBL88
ChEBI ID CHEBI:4027
TTD ID D0CT9C
Drug Bank ID DB00531
KEGG ID C07888
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
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2D MOL 3D MOL
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Enhancing Drug Efficacy
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Combination Pair ID: 752
Pair Name Thymoquinone, Cyclophosphamide
Partner Name Thymoquinone
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Blockade of cell cycle in Sub-G1 phase
Gene Regulation Down-regulation Phosphorylation AKT1 hsa207
Down-regulation Expression CCND1 hsa595
Up-regulation Expression PTEN hsa5728
In Vitro Model SK-BR-3 Breast adenocarcinoma Homo sapiens (Human) CVCL_0033
MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
Result The current findings suggested that TQ can alter the cell cycle progression and induce cell death independent of FASN mediated signaling. In terms of clinical perspective, the present study clearly showed that TQ can broadly augment the effect of cyclo in breast cancer cases irrespective of Her-2+ or Her-.
Combination Pair ID: 980
Pair Name Quercetin, Cyclophosphamide
Partner Name Quercetin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Immunomodulatory
In Vitro Model 4T1 Malignant neoplasms of the mouse mammary gland Mus musculus (Mouse) CVCL_0125
In Vivo Model 4T1 cells (5×10³) in 100 µL of phosphate-buffered saline (PBS) were injected into one axillary mammary fat pad per mouse of 5–6-week-old female immunocompetent BALB/c mice.
Result Complementarity between Microbiome and Immunity May Account for the Potentiating Effect of Quercetin on the Antitumor Action of Cyclophosphamide in a Triple-Negative Breast Cancer Model
Decreasing Drug Toxicity
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Combination Pair ID: 279
Pair Name Pixinol, Cyclophosphamide
Partner Name Pixinol
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
In Vitro Model Hep-G2 Hepatoblastoma Homo sapiens (Human) CVCL_0027
Result These results suggest that compound 2e is a promising agent for anti-hepato-carcinoma, and that it also could be used in combination with CTX to increase efficiency and to reduce toxicity.
Combination Pair ID: 421
Pair Name Isoliquiritigenin, Cyclophosphamide
Partner Name Isoliquiritigenin
Disease Info [ICD-11: 2C77] Cervical cancer Investigative
Biological Phenomena Induction-->DNA damage
In Vitro Model U14 Cervical carcinoma Mus musculus (Mouse) CVCL_9U56
In Vivo Model KM mice were implanted subcutaneously with 0.2 mL (1×10⁷ mL in sodium chloride) U14 cells.
Result Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide
04. Reference
No. Title Href
1 Synthesis and Anti-Hepatocarcinoma Effect of Amino Acid Derivatives of Pyxinol and Ocotillol. Molecules. 2021 Feb 3;26(4):780. doi: 10.3390/molecules26040780. Click
2 Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide. Molecules. 2013 Jul 24;18(8):8786-98. doi: 10.3390/molecules18088786. Click
3 Thymoquinone Augments Cyclophosphamide-Mediated Inhibition of Cell Proliferation in Breast Cancer Cells. Asian Pac J Cancer Prev. 2019 Apr 29;20(4):1153-1160. doi: 10.31557/APJCP.2019.20.4.1153. Click
4 Complementarity between Microbiome and Immunity May Account for the Potentiating Effect of Quercetin on the Antitumor Action of Cyclophosphamide in a Triple-Negative Breast Cancer Model. Pharmaceuticals (Basel). 2023 Oct 6;16(10):1422. doi: 10.3390/ph16101422. Click
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