CYCLOPHOSPHAMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1959)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: L01AA01
UNII: 8N3DW7272P

Structure
InChI Key CMSMOCZEIVJLDB-UHFFFAOYSA-N
Smile O=P1(N(CCCl)CCCl)NCCCO1
InChI
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H17Cl2N2O3P
Molecular Weight 279.1
AlogP 1.88
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 41.57
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 14.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.63 - EXP
Henry's Law Constant 1.40E-11 atm-m3/mole EST
Atmospheric OH Rate Constant 7.03E-11 cm3/molecule-sec EST
Melting Point 51.5 deg C EXP
Water Solubility 4.00E+04 mg/L EXP
Vapor Pressure 4.45E-05 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 5

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hodgkin Disease 4 D006689 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Breast Neoplasms 4 D001943 ClinicalTrials
Breast Neoplasms 4 D001943 ClinicalTrials
Breast Neoplasms 4 D001943 ClinicalTrials
Waldenstrom Macroglobulinemia 3 D008258 ClinicalTrials
Pulmonary Fibrosis 3 D011658 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 3 D015451 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Scleritis 3 D015423 ClinicalTrials
Red-Cell Aplasia, Pure 3 D012010 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Leukemia, Erythroblastic, Acute 3 D004915 ClinicalTrials
Leukemia, Monocytic, Acute 3 D007948 ClinicalTrials
Leukemia, Myelomonocytic, Acute 3 D015479 ClinicalTrials
Ganglioneuroblastoma 3 D018305 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Neutropenia 3 D009503 ClinicalTrials
Leukemia, Megakaryoblastic, Acute 3 D007947 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Anemia, Refractory 3 D000753 ClinicalTrials
Anemia, Refractory, with Excess of Blasts 3 D000754 ClinicalTrials
Testicular Neoplasms 3 D013736 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Mesenchymoma 3 D008637 ClinicalTrials
Adenocarcinoma 3 D000230 ClinicalTrials
Rhabdomyosarcoma, Alveolar 3 D018232 ClinicalTrials
Immunoblastic Lymphadenopathy 3 D007119 ClinicalTrials
Burkitt Lymphoma 3 D002051 ClinicalTrials
Carcinoma 3 D002277 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 3 D015464 ClinicalTrials
Rhabdomyosarcoma, Embryonal 3 D018233 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Bone Marrow Failure Disorders 3 D000080983 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Infertility 3 D007246 ClinicalTrials
Pemphigus 3 D010392 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 3 D000077195 ClinicalTrials
Waldenstrom Macroglobulinemia 3 D008258 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Idiopathic Pulmonary Fibrosis 3 D054990 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Melanoma 3 D008545 ClinicalTrials
Rhabdomyosarcoma 3 D012208 ClinicalTrials
Medulloblastoma 3 D008527 ClinicalTrials
Kidney Diseases 3 D007674 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Menopause 3 D008593 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Glomerulonephritis, IGA 3 D005922 ClinicalTrials
Multiple Sclerosis, Chronic Progressive 3 D020528 ClinicalTrials
Granuloma, Lethal Midline 3 D006103 ClinicalTrials
Glomerulonephritis, Membranous 3 D015433 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 3 D015459 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Neuroectodermal Tumors, Primitive 3 D018242 ClinicalTrials
Granulomatosis with Polyangiitis 3 D014890 ClinicalTrials
Triple Negative Breast Neoplasms 3 D064726 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Wilms Tumor 3 D009396 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Choroid Plexus Neoplasms 3 D016545 ClinicalTrials
Anemia, Aplastic 3 D000741 ClinicalTrials
Condylomata Acuminata 3 D003218 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Pemphigus 3 D010392 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Microscopic Polyangiitis 3 D055953 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Inflammatory Breast Neoplasms 3 D058922 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Melanoma 3 D008545 ClinicalTrials
Scleroderma, Systemic 3 D012595 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 3 D015477 ClinicalTrials
Amyloidosis 3 D000686 ClinicalTrials
Behcet Syndrome 3 D001528 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Scleroderma, Localized 3 D012594 ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis 3 D056648 ClinicalTrials
Carcinoma, Renal Cell 3 D002292 ClinicalTrials
Thrombocytopenia 3 D013921 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Amyloidosis 3 D000686 ClinicalTrials
Carcinoma, Renal Cell 3 D002292 ClinicalTrials
Wilms Tumor 3 D009396 ClinicalTrials
Gestational Trophoblastic Disease 3 D031901 ClinicalTrials
Retinoblastoma 3 D012175 ClinicalTrials
Melanoma 3 D008545 ClinicalTrials
Anemia, Aplastic 3 D000741 ClinicalTrials
Amyloidosis, Familial 3 D028226 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Crohn Disease 2 D003424 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Vasculitis 2 D014657 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Immune System Diseases 2 D007154 ClinicalTrials
Osteosarcoma 2 D012516 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Leukemia, Lymphoid 2 D007945 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 2 D016553 ClinicalTrials
Leukemia, Myelomonocytic, Juvenile 2 D054429 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Epidermolysis Bullosa 2 D004820 ClinicalTrials
Purpura, Schoenlein-Henoch 2 D011695 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Carcinoma, Merkel Cell 2 D015266 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Thalassemia 2 D013789 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Hereditary Breast and Ovarian Cancer Syndrome 2 D061325 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Osteopetrosis 2 D010022 ClinicalTrials
Granulomatous Disease, Chronic 2 D006105 ClinicalTrials
Sarcoidosis 2 D012507 ClinicalTrials
Fanconi Anemia 2 D005199 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Neuromyelitis Optica 2 D009471 ClinicalTrials
Polyradiculoneuropathy, Chronic Inflammatory Demyelinating 2 D020277 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Takayasu Arteritis 2 D013625 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Mouth Neoplasms 2 D009062 ClinicalTrials
Plasmacytoma 2 D010954 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Neuroendocrine Tumors 2 D018358 ClinicalTrials
Leukemia, Prolymphocytic 2 D015463 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 2 D051359 ClinicalTrials
Castleman Disease 2 D005871 ClinicalTrials
Lymphoma, T-Cell 2 D016399 ClinicalTrials
Neuroectodermal Tumors, Primitive, Peripheral 2 D018241 ClinicalTrials
Squamous Intraepithelial Lesions 2 D000081483 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Lymphoproliferative Disorders 2 D008232 ClinicalTrials
Fucosidosis 2 D005645 ClinicalTrials
Gangliosidosis, GM1 2 D016537 ClinicalTrials
Gaucher Disease 2 D005776 ClinicalTrials
Leukodystrophy, Globoid Cell 2 D007965 ClinicalTrials
Leukodystrophy, Metachromatic 2 D007966 ClinicalTrials
Wolman Disease 2 D015223 ClinicalTrials
Neuronal Ceroid-Lipofuscinoses 2 D009472 ClinicalTrials
Sandhoff Disease 2 D012497 ClinicalTrials
Tay-Sachs Disease 2 D013661 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Tuberculosis 2 D014376 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Skin Neoplasms 2 D012878 ClinicalTrials
Immunologic Deficiency Syndromes 2 D007153 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Skin Neoplasms 2 D012878 ClinicalTrials
Niemann-Pick Diseases 2 D009542 ClinicalTrials
Nausea 1 D009325 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Head and Neck Neoplasms 1 D006258 ClinicalTrials
Hepatoblastoma 1 D018197 ClinicalTrials
Diffuse Intrinsic Pontine Glioma 1 D000080443 ClinicalTrials
Leukemia, Plasma Cell 1 D007952 ClinicalTrials
Urinary Bladder Neoplasms 1 D001749 ClinicalTrials
Carcinoma, Pancreatic Ductal 1 D021441 ClinicalTrials
Chordoma 1 D002817 ClinicalTrials
Desmoplastic Small Round Cell Tumor 1 D058405 ClinicalTrials
Thymoma 1 D013945 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Nasopharyngeal Neoplasms 1 D009303 ClinicalTrials
Carcinoma, Medullary 1 D018276 ClinicalTrials
Thymoma 1 D013945 ClinicalTrials
Sarcoma, Synovial 1 D013584 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Urinary Bladder Neoplasms 1 D001749 ClinicalTrials
Lymphoma, B-Cell 1 D016393 ClinicalTrials
Breast Carcinoma In Situ 1 D000071960 ClinicalTrials
Stiff-Person Syndrome 1 D016750 ClinicalTrials
Mesothelioma 1 D008654 ClinicalTrials
Myasthenia Gravis 1 D009157 ClinicalTrials
Glomerulosclerosis, Focal Segmental 1 D005923 ClinicalTrials
Muscular Diseases 1 D009135 ClinicalTrials
Osteogenesis Imperfecta 1 D010013 ClinicalTrials
Mesothelioma 1 D008654 ClinicalTrials
Mycosis Fungoides 1 D009182 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Liposarcoma 1 D008080 ClinicalTrials
Renal Insufficiency 1 D051437 ClinicalTrials
Sezary Syndrome 1 D012751 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 0 D018442 ClinicalTrials

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
16.71
Blood and lymphatic system disorders
10.79
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
7.83
Infections and infestations
6.97
Respiratory, thoracic and mediastinal disorders
6.23
Injury, poisoning and procedural complications
6.13
Gastrointestinal disorders
5.99
Nervous system disorders
5.12
Vascular disorders
4.72
Cardiac disorders
3.9
Skin and subcutaneous tissue disorders
3.84
Immune system disorders
2.97
Musculoskeletal and connective tissue disorders
2.89
Investigations
2.81
Metabolism and nutrition disorders
2.66

Cross References

Resources Reference
CAS NUMBER 50-18-0
ChEBI 4026
ChEMBL CHEMBL1200796
EPA CompTox DTXSID6024888
FDA SRS 8N3DW7272P
Guide to Pharmacology 7154
KEGG C06933
PubChem 22420
SureChEMBL SCHEMBL6071
CAS NUMBER 50-18-0
ChEBI 4027
ChEMBL CHEMBL88
DrugBank DB00531
DrugCentral 758
EPA CompTox DTXSID5020364
FDA SRS 6UXW23996M
Human Metabolome Database HMDB0014672
Guide to Pharmacology 7154
KEGG C07888
PharmGKB PA449165
PubChem 22420
SureChEMBL SCHEMBL4346
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