Cyclophosphamide
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1959
- First approval year
- 1959
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Cyclophosphamide
- Molecular weight
- 279.1
- Structure (SMILES)
- O.O=P1(N(CCCl)CCCl)NCCCO1
- cyclophosphamide
- Cyclophosphamide
- cytoxan
- Cytoxan
- Cytoxan (lyophilized)
- cytoxan lyophilized
- endoxana
- Endoxana
- lyophilized cytoxan
- Lyophilized cytoxan
- neosar
- Neosar
- 2h 1 3 2 oxazaphosphorin 2 amine n n bis 2 chloroethyl tetrahydro 2 oxide monohydrate
- 2H-1,3,2-OXAZAPHOSPHORIN-2-AMINE, N,N-BIS(2-CHLOROETHYL)TETRAHYDRO-, 2-OXIDE, MONOHYDRATE, (±)-
- adriamycin and cytoxan ac
- b 518
- B-518
- ciclofosfamide
- Ciclofosfamide
- cycloblastin
- Cycloblastin
- cyclophosphamide
- Cyclophosphamide
- CYCLOPHOSPHAMIDE [EP MONOGRAPH]
- CYCLOPHOSPHAMIDE [IARC]
- CYCLOPHOSPHAMIDE [MI]
- CYCLOPHOSPHAMIDE [ORANGE BOOK]
- CYCLOPHOSPHAMIDE [USP MONOGRAPH]
- CYCLOPHOSPHAMIDE [USP-RS]
- CYCLOPHOSPHAMIDE [VANDF]
- CYCLOPHOSPHAMIDE [WHO-IP]
- cyclophosphamide ep monograph
- cyclophosphamide hydrate
- Cyclophosphamide hydrate
- CYCLOPHOSPHAMIDE HYDRATE [JAN]
- cyclophosphamide hydrate jan
- cyclophosphamide iarc
And 43 more, listed on the interactive page.
- ATC classification codes
- L01AA01
Sources for recorded values
- ChEMBL ID
- CHEMBL1200796
- InChIKey
- PWOQRKCAHTVFLB-UHFFFAOYSA-N
- PubChem compound IDs
- 22420
- FDA ingredient codes (UNII)
- 8N3DW7272P
- 50-18-0
- 6055-19-2
- 3002
- 2679071
- Applicant
- BAXTER HLTHCARE
- Approval date
- 16 Nov 1959
- Application number
- NDA012141
- Patents
- 5
- Designations
- 2
- Earliest recorded loss of exclusivity
- 15 Feb 2036
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Pharmacology name
- cyclophosphamide
- Type
- Synthetic organic
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Parenteral
Mechanisms of action
- Mechanism
- DNA inhibitor
- Action type
- Inhibitor
- Target
- DNA
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000094
- Subject identifier
- D015456
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Sarcoma, Ewing
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000174
- Subject identifier
- D012512
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000181
- Subject identifier
- D002294
- Condition
- Carcinoma, Hepatocellular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000182
- Subject identifier
- D006528
- Condition
- Hodgkin Disease
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Lymphoma, B-Cell, Marginal Zone
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000191
- Subject identifier
- D018442
- Condition
- Prostatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000196
- Subject identifier
- D011471
- Condition
- Myelodysplastic Syndromes
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000198
- Subject identifier
- D009190
- Condition
- Squamous Cell Carcinoma of Head and Neck
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000199
- Subject identifier
- D000077195
- Condition
- Neoplasms, Plasma Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000200
- Subject identifier
- D054219
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000209
- Subject identifier
- D015456
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Leukemia, Erythroblastic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000218
- Subject identifier
- D004915
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Leukemia, Monocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000221
- Subject identifier
- D007948
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Leukemia, Myelomonocytic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000223
- Subject identifier
- D015479
- Condition
- Adenocarcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000228
- Subject identifier
- D000230
- Condition
- Rhabdomyosarcoma, Alveolar
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000248
- Subject identifier
- D018232
- Condition
- Immunoblastic Lymphadenopathy
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000255
- Subject identifier
- D007119
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Burkitt Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000309
- Subject identifier
- D002051
- Condition
- Carcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000313
- Subject identifier
- D002277
And 237 more, listed on the interactive page.
- Condition identifier
- EFO_0000094
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000095
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000096
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000174
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000181
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000182
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000183
- Condition identifier
- EFO_0000196
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000198
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000200
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000211
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000220
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000221
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000222
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000305
- Condition identifier
- EFO_0000313
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000339
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000349
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000384
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000389
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000409
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000519
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000540
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000544
- Highest recorded phase
- 2
And 530 more, listed on the interactive page.
- Event
- acute myeloid leukaemia
- Reports
- 726
- Reporting signal score
- 1,358.33
- Event
- bone marrow failure
- Reports
- 1,152
- Reporting signal score
- 1,571.63
- Event
- cystitis haemorrhagic
- Reports
- 408
- Reporting signal score
- 883.339
- Event
- cytokine release syndrome
- Reports
- 580
- Reporting signal score
- 994.325
- Event
- cytomegalovirus infection
- Reports
- 778
- Reporting signal score
- 1,113.94
- Event
- diffuse large b-cell lymphoma recurrent
- Reports
- 343
- Reporting signal score
- 943.068
- Event
- disease progression
- Reports
- 1,420
- Reporting signal score
- 823.352
- Event
- febrile bone marrow aplasia
- Reports
- 494
- Reporting signal score
- 1,004.73
- Event
- febrile neutropenia
- Reports
- 5,946
- Reporting signal score
- 12,268
- Event
- haematotoxicity
- Reports
- 642
- Reporting signal score
- 1,090.42
- Event
- injection site pain
- Reports
- 8
- Reporting signal score
- 748.814
- Event
- leukopenia
- Reports
- 1,438
- Reporting signal score
- 1,262.29
- Event
- mucosal inflammation
- Reports
- 1,342
- Reporting signal score
- 1,863.14
- Event
- myelodysplastic syndrome
- Reports
- 977
- Reporting signal score
- 1,818.25
- Event
- myelosuppression
- Reports
- 714
- Reporting signal score
- 1,179.69
- Event
- neutropenia
- Reports
- 4,008
- Reporting signal score
- 3,965.23
- Event
- neutropenic sepsis
- Reports
- 502
- Reporting signal score
- 922.28
- Event
- pancytopenia
- Reports
- 1,469
- Reporting signal score
- 1,367.11
- Event
- pneumocystis jirovecii pneumonia
- Reports
- 521
- Reporting signal score
- 839.335
- Event
- pyrexia
- Reports
- 3,594
- Reporting signal score
- 1,327.04
- Event
- second primary malignancy
- Reports
- 474
- Reporting signal score
- 785.02
- Event
- sepsis
- Reports
- 1,260
- Reporting signal score
- 824.903
- Event
- thrombocytopenia
- Reports
- 2,156
- Reporting signal score
- 1,240.18
- Event
- venoocclusive liver disease
- Reports
- 414
- Reporting signal score
- 809.802
- NCT00000596
- NCT00004563
- NCT00000658
- NCT00088530
- NCT00133302
- NCT00184002
- NCT00192764
- NCT00193440
- NCT00193479
- NCT00201318
- NCT00262210
- NCT00323323
- NCT00324467
- NCT00333008
- NCT00361621
- NCT00413959
- NCT00455897
- NCT00481832
- NCT00597519
- NCT00610883
- NCT00712582
- NCT00719472
- NCT00740805
- NCT00807196
- NCT00809341
And 2,176 more, listed on the interactive page.
- Dose
- 40 mg per kg to 50 mg per kg
- Route
- Intravenous
- How often
- Divided doses over 2 to 5 days
- Hydrogen bond acceptors
- 2
- Hydrogen bond donors
- 1
- Polar surface area
- 41.57
- Calculated partition coefficient (ALogP)
- 1.88
- Prodrug
- Yes
- Chirality
- Racemic
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 5
- Heavy atoms
- 15
- Molecular formula
- C7H17Cl2N2O3P
- Monoisotopic mass
- 278.0353848
- Natural product
- No
- 0054-0382
- 0054-0383
- 0338-9777
- 0338-9779
- 0781-3233
- 0781-3244
- 0781-3255
- 0781-3528
- 0781-3529
- 0781-3530
- 10019-935
- 10019-936
- 10019-937
- 10019-938
- 10019-939
- 10019-942
- 10019-943
- 10019-944
- 10019-945
- 10019-955
- 10019-956
- 10019-957
- 10019-982
- 10019-984
- 14335-470
And 57 more, listed on the interactive page.
- Recorded assays
- 2,159
- Active assays
- 22
- Confirmatory
- Other
- Screening
- Immunosuppressive Agents
- Mutagens
- Antirheumatic Agents
- Antineoplastic Agents, Alkylating
- Myeloablative Agonists
Related records
Trials (3,572)
- ......SMARTEST Trial......
- 'ADVANCE' (A Pilot Trial)
- "Cocktail" Therapy for Hepatitis B Related Hepatocellular Carcinoma
- "Phase II Study of PET Guided Neoadjuvant Chemotherapy (NAC) and Oncotype Guided Hormonal Therapy of Breast Cancer"
- "Re-Stimulated" TILs And IL-2 Therapy for Platinum Resistant Ovarian, Fallopian Tube, or Primary Peritoneal Cancer
- 05-001: Treatment of Acute Lymphoblastic Leukemia in Children
- 2-Step Approach to Stem Cell Transplant in Treating Participants With Hematological Malignancies
- 2015-12: A Study Exploring the Use of Early and Late Consolidation/Maintenance Therapy
- 211At-BC8-B10 Followed by Donor Stem Cell Transplant in Treating Patients With Relapsed or Refractory High-Risk Acute Leukemia or Myelodysplastic Syndrome
- ²¹¹At-OKT10-B10 and Fludarabine Alone or in Combination With Cyclophosphamide and Low-Dose TBI Before Donor Stem Cell Transplant for the Treatment of Newly Diagnosed, Recurrent, or Refractory High-Risk Multiple Myeloma
- 3rd Generation GD-2 Chimeric Antigen Receptor and iCaspase Suicide Safety Switch, Neuroblastoma, GRAIN
- 3RD GENERATION GD2 SPECIFIC CHIMERIC ANTIGEN RECEPTOR TRANSDUCED AUTOLOGOUS NATURAL KILLER T-CELLS FOR NEUROBLASTOMA
- 4 x Epirubicin, Cyclophosphamide, Followed by 4 x Docetaxel Versus 6 x CMF / 6 x CEF
- 6 vs 3 Cycles of Neoadjuvant Chemotherapy for Potentially Resectable Locally Advanced Thymic Epithelial Tumors
- 6xFU/Epirubicin/Cyclophosphamide (FEC) Compared to 3xFEC-3xDocetaxel in High-risk Node-negative Breast Cancer Patients
- 9-ING-41 in Pediatric Patients With Refractory Malignancies.
- A 3 Arm Randomized Study on Health-related QoL of Elderly Patients With Advanced Soft Tissue Sarcoma
- A 5 Day Course of Fludarabine and Cytarabine Followed by Full Intensity Allogeneic Stem Cell Transplantation (FA5-Bucy) in Treating Patients With High-risk, Recurrent or Refractory Acute Leukemia and Advanced Myelodysplastic Syndrome
- A Blind, Randomized and Controlled Study of Live Attenuated Varicella Vaccines
- A Blood Stem Cell Transplant for Sickle Cell Disease
Approved for (11)
- Breast cancer
- Breast carcinoma
- Breast neoplasm
- Cancer
- Classic Hodgkin lymphoma
- HER2 positive breast carcinoma
- Hodgkins lymphoma
- Lymphoma
- Neoplasm
- Nephrotic syndrome
- Plasma cell myeloma
In development for (246)
- Acute erythroid leukemia Phase 3
- Acute lymphoblastic leukemia Phase 3
- Acute megakaryoblastic leukemia Phase 3
- Acute monocytic leukemia Phase 3
- Acute myeloblastic leukemia without maturation Phase 3
- Acute myeloid leukemia Phase 3
- Acute myelomonocytic leukemia M4 Phase 3
- Adenocarcinoma Phase 3
- Adrenoleukodystrophy Phase 2
- Adult acute lymphoblastic leukemia Phase 2
- Adult liposarcoma Phase 1
- Adult T-cell leukemia/lymphoma Phase 3
- AIDS Phase 2
- AL amyloidosis Phase 3
- Alveolar rhabdomyosarcoma Phase 3
- Amyloidosis Phase 3
- Anaplastic ependymoma Phase 3
- Anaplastic large cell lymphoma Phase 2
- Anemia Phase 1
- Angioimmunoblastic T-cell lymphoma Phase 3
Other linked conditions (2)
- Idiopathic membranous glomerulonephritis
- Rapid-onset childhood obesity-hypothalamic dysfunction-hypoventilation-autonomic dysregulation syndrome