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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL88
CHEMBL88
Compound Name CYCLOPHOSPHAMIDE
ChEMBL Synonyms CYTOXAN (LYOPHILIZED) | Neosar | Cyclophosphamide hydrate | CYTOXAN | ENDOXANA | NEOSAR | CYCLOPHOSPHAMIDE | LYOPHILIZED CYTOXAN | Cytoxan
Max Phase 4 (Approved)
Trade Names ENDOXANA | LYOPHILIZED CYTOXAN | CYCLOPHOSPHAMIDE | NEOSAR | CYTOXAN | CYTOXAN (LYOPHILIZED)
Molecular Formula C7H15Cl2N2O2P

Additional synonyms for CHEMBL88 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES ClCCN(CCCl)P1(=O)NCCCO1
Standard InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/ ...
Download InChI
Standard InChI Key CMSMOCZEIVJLDB-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • HeCaToS Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL88

Molecule Features

CHEMBL88 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:Y Oral:Y Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma3ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm1ClinicalTrials
Epidermolysis BullosaD004820EFO:1000690epidermolysis bullosa2ClinicalTrials
Genital Neoplasms, FemaleD005833EFO:1001331Genital neoplasm, female2ClinicalTrials
Glomerulonephritis, MembranousD015433EFO:0004254membranous glomerulonephritis3ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease2ClinicalTrials
Granulomatosis with PolyangiitisD014890EFO:0005297Wegener's granulomatosis3ClinicalTrials
Kidney NeoplasmsD007680EFO:0003865kidney neoplasm1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
LiposarcomaD008080EFO:0000569liposarcoma1ClinicalTrials
Multiple Sclerosis, Chronic ProgressiveD020528EFO:0003840chronic progressive multiple sclerosis3ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor3ClinicalTrials
NeutropeniaD0095033ClinicalTrials
OsteopetrosisD010022Orphanet:2781Osteopetrosis2ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
Primary MyelofibrosisD055728EFO:0002430primary myelofibrosis2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma3ClinicalTrials
AmyloidosisD000686Orphanet:314701Primary systemic amyloidosis3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm2ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease2ClinicalTrials
InfertilityD007246EFO:0000545infertility3ClinicalTrials
Inflammatory Breast NeoplasmsD058922EFO:1000984inflammatory breast carcinoma3ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease3ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Microscopic PolyangiitisD055953EFO:1000784microscopic polyangiitis3ClinicalTrials
Myeloproliferative DisordersD009196EFO:0004251myeloproliferative disorder3ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm1ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma2ClinicalTrials
Polyradiculoneuropathy, Chronic Inflammatory DemyelinatingD020277EFO:1000868chronic inflammatory demyelinating polyradiculoneuropathy2ClinicalTrials
Rhabdomyosarcoma, EmbryonalD018233EFO:0000437embryonal rhabdomyosarcoma3ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma3ClinicalTrials
Sezary SyndromeD012751EFO:1000785Sezary's disease1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000349clear cell renal carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
Condylomata AcuminataD003218EFO:0007147anogenital venereal wart3ClinicalTrials
Fanconi AnemiaD005199Orphanet:84Fanconi anemia2ClinicalTrials
Glomerulosclerosis, Focal SegmentalD005923EFO:0004236focal segmental glomerulosclerosis1ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia1ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma3ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm3ClinicalTrials
PemphigusD010392EFO:0004719pemphigus vulgaris3ClinicalTrials
Purpura, Schoenlein-HenochD011695EFO:1000965Henoch-Schoenlein purpura2ClinicalTrials
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease3ClinicalTrials
Scleroderma, LocalizedD012594EFO:1001993scleroderma3ClinicalTrials
Waldenstrom MacroglobulinemiaD008258EFO:0002616macroglobulinemia3ClinicalTrials
Amyloidosis, FamilialD028226Orphanet:85443AL amyloidosis3ClinicalTrials
Anemia, AplasticD000741HP:0001915aplastic anemia3ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
Castleman DiseaseD005871EFO:1001332Giant Lymph Node Hyperplasia2ClinicalTrials
Gestational Trophoblastic DiseaseD031901Orphanet:59305Gestational trophoblastic neoplasm3ClinicalTrials
HistiocytomaD051642EFO:0005561histiocytoma3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000094B-cell acute lymphoblastic leukemia3ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma3ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis2ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis3ClinicalTrials
NauseaD009325EFO:0006911Chemotherapy-induced nausea and vomiting1ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000196metastatic prostate cancer2ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma3ClinicalTrials
Choroid Plexus NeoplasmsD016545EFO:0007206choroid plexus cancer3ClinicalTrials
DiseaseD004194EFO:0000408disease1ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia1ClinicalTrials
Hematologic DiseasesD006402HP:0001871abnormality of blood and blood-forming tissues2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia3ClinicalTrials
Leukemia, Myelomonocytic, ChronicD015477EFO:1001779chronic myelomonocytic leukemia3ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Nephrotic SyndromeD009404EFO:0004255nephrotic syndrome3ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Purpura, Thrombocytopenic, IdiopathicD016553EFO:0007160autoimmune thrombocytopenic purpura2ClinicalTrials
ThalassemiaD013789EFO:1001996Thalassemia2ClinicalTrials
Triple Negative Breast NeoplasmsD064726EFO:0005537triple-negative breast cancer3ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma1ClinicalTrials
VasculitisD014657EFO:0006803vasculitis2ClinicalTrials
AmyloidosisD000686EFO:1001875amyloidosis3ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer3ClinicalTrials
Granulomatous Disease, ChronicD006105Orphanet:379Chronic granulomatous disease2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
Hemophilia AD006467Orphanet:98878Hemophilia A3ClinicalTrials
Immunoblastic LymphadenopathyD007119EFO:0000255angioimmunoblastic T-cell lymphoma3ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma3ClinicalTrials
Lymphoproliferative DisordersD0082322ClinicalTrials
MelanomaD008545EFO:0000756melanoma3ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm1ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma2ClinicalTrials
RhabdomyosarcomaD012208EFO:0002918rhabdomyosarcoma3ClinicalTrials
SarcoidosisD012507Orphanet:797Sarcoidosis2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated VasculitisD056648EFO:0004826anti-neutrophil antibody associated vasculitis3ClinicalTrials
Behcet SyndromeD001528EFO:0003780Behcet's syndrome2ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma3ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Hereditary Breast and Ovarian Cancer SyndromeD061325Orphanet:145Hereditary breast and ovarian cancer syndrome2ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia3ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia2ClinicalTrials
Lupus NephritisD008181EFO:0005761lupus nephritis3ClinicalTrials
MenopauseD008593EFO:0003922menopause3ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma1ClinicalTrials
MesotheliomaD008654EFO:0000770malignant pleural mesothelioma1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer3ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials
Sarcoma, SynovialD013584EFO:0001376synovial sarcoma1ClinicalTrials
ScleritisD0154232ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma2ClinicalTrials
AnemiaD000740EFO:0004272anemia1ClinicalTrials
Anemia, AplasticD000741EFO:0006927severe aplastic anemia3ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
Glomerulonephritis, IGAD005922EFO:0004194IGA glomerulonephritis3ClinicalTrials
Lymphohistiocytosis, HemophagocyticD051359Orphanet:158038Primary hemophagocytic lymphohistiocytosis2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma3ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm3ClinicalTrials
Osteogenesis ImperfectaD010013Orphanet:666Osteogenesis imperfecta1ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer2ClinicalTrials
RetinoblastomaD012175Orphanet:790Retinoblastoma3ClinicalTrials
Rhabdomyosarcoma, AlveolarD018232EFO:0000248alveolar rhabdomyosarcoma3ClinicalTrials
ThrombocytopeniaD013921HP:0001873thrombocytopenia3ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov CYCLOPHOSPHAMIDE
The Cochrane Collaboration CYCLOPHOSPHAMIDE

Metabolites for CHEMBL88

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL88. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL4730 Melanin-concentrating hormone receptor 1 Mus musculus 0.992
CHEMBL4306 Voltage-gated potassium channel subunit Kv1.5 Homo sapiens 0.300
CHEMBL266 Alpha-2b adrenergic receptor Rattus norvegicus 0.265
CHEMBL2203 Motilin receptor Homo sapiens 0.229

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4730 Melanin-concentrating hormone receptor 1 Mus musculus 0.981

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
261.1 260.0248 1.88 5 41.57 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 4 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 2.84 .73 .73 0 14 0.61

Structural Alerts

There are 14 structural alerts for CHEMBL88. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01A - ALKYLATING AGENTS
L01AA - Nitrogen mustard analogues
L01AA01 - cyclophosphamide

ChemSpider ChemSpider:CMSMOCZEIVJLDB-UHFFFAOYSA-N
DailyMed cyclophosphamide
PubChem SID: 174007432 SID: 50105634 SID: 85230959 SID: 87150 SID: 90341534
Wikipedia Cyclophosphamide

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL88



ACToR 60007-95-6 50-18-0
Atlas cyclophosphamide
Brenda 13807
ChEBI 4027
ChemicalBook CB8547532
DrugBank DB00531
DrugCentral 758
eMolecules 730751
EPA CompTox Dashboard DTXSID5020364
Guide to Pharmacology 7154
Human Metabolome Database HMDB0014672
IBM Patent System 40DAF4E7ADD52811028C5B282178E4FE
KEGG Ligand C07888
LINCS LSM-4961
Mcule MCULE-5327530727
MolPort MolPort-001-783-420
Nikkaji J2.793F J3.385.421H
NMRShiftDB 20208437
PharmGKB PA449165
PubChem 2907
PubChem: Thomson Pharma 14848034
Selleck Clafen
SureChEMBL SCHEMBL4346

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/CMSMOCZEIVJLDB-UHFFFAOYSA-N spacer
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