> Trialight public data. Index of pages: https://trialight.com/llms.txt
> Web page: https://trialight.com/data/asset/cyclophosphamide-25b75968-e3cd-410a-9b24-0c349d8f7663
> Record changed: 2026-10-13

# Cyclophosphamide

Highest phase reached

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

Drug type

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

First approval year

1959

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

## Development status

**First approval year**

1959

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**Listing at source**

Listed

**Highest phase reached**

Approved

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

## Names and chemistry

**Drug type**

Small molecule

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**Drug name**

Cyclophosphamide

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**Molecular weight**

279.1

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**Structure (SMILES)**

O.O=P1(N(CCCl)CCCl)NCCCO1

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

### Brand names (12)

- cyclophosphamide
- Cyclophosphamide
- cytoxan
- Cytoxan
- Cytoxan (lyophilized)
- cytoxan lyophilized
- endoxana
- Endoxana
- lyophilized cytoxan
- Lyophilized cytoxan
- neosar
- Neosar

### Other names (68)

- 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.

## Identifiers

**ATC classification codes**

- L01AA01

Sources for recorded values

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**ChEMBL ID**

CHEMBL1200796

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**InChIKey**

PWOQRKCAHTVFLB-UHFFFAOYSA-N

Source: [www.ebi.ac.uk](https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1200796)

**PubChem compound IDs**

- 22420

**FDA ingredient codes (UNII)**

- 8N3DW7272P

### CAS registry numbers (2)

- 50-18-0
- 6055-19-2

### RxNorm IDs (RxCUI) (2)

- 3002
- 2679071

## Regulatory information

### United States

**Applicant**

BAXTER HLTHCARE

**Approval date**

16 Nov 1959

**Application number**

NDA012141

### Other regulatory facts

**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

### Drug classification

**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

### Investigated indications (262)

- **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.

### Open Targets indications (555)

- **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.

### Reported adverse events (24)

- **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

### Trial references (2,201)

- NCT00000596  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00000596)
- NCT00004563  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00004563)
- NCT00000658  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00000658)
- NCT00088530  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00088530)
- NCT00133302  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00133302)
- NCT00184002  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00184002)
- NCT00192764  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00192764)
- NCT00193440  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00193440)
- NCT00193479  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00193479)
- NCT00201318  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00201318)
- NCT00262210  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00262210)
- NCT00323323  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00323323)
- NCT00324467  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00324467)
- NCT00333008  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00333008)
- NCT00361621  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00361621)
- NCT00413959  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00413959)
- NCT00455897  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00455897)
- NCT00481832  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00481832)
- NCT00597519  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00597519)
- NCT00610883  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00610883)
- NCT00712582  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00712582)
- NCT00719472  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00719472)
- NCT00740805  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00740805)
- NCT00807196  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00807196)
- NCT00809341  
Source: [clinicaltrials.gov](https://clinicaltrials.gov/study/NCT00809341)

And 2,176 more, listed on the interactive page.

## Dosing

**Dose**

40 mg per kg to 50 mg per kg

**Route**

Intravenous

**How often**

Divided doses over 2 to 5 days

## Chemical properties

**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

## National Drug Codes

- 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.

## Evidence counts

**Recorded assays**

2,159

**Active assays**

22

### Active assay types (3)

- Confirmatory
- Other
- Screening

## Pharmacologic actions

- Immunosuppressive Agents  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D007166.html)
- Mutagens  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D009153.html)
- Antirheumatic Agents  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D018501.html)
- Antineoplastic Agents, Alkylating  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D018906.html)
- Myeloablative Agonists  
Source: [id.nlm.nih.gov](https://id.nlm.nih.gov/mesh/D019653.html)

## Related records

### Trials (3,572)

- ......SMARTEST Trial......
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- 05-001: Treatment of Acute Lymphoblastic Leukemia in Children
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- 211At-BC8-B10 Followed by Donor Stem Cell Transplant in Treating Patients With Relapsed or Refractory High-Risk Acute Leukemia or Myelodysplastic Syndrome
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- 3rd Generation GD-2 Chimeric Antigen Receptor and iCaspase Suicide Safety Switch, Neuroblastoma, GRAIN
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- 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
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### Approved for (11)

- [Breast cancer](https://trialight.com/data/condition/breast-cancer-8ac10da3-93bd-54c5-a93b-265bc6699689.md)
- Breast carcinoma
- [Breast neoplasm](https://trialight.com/data/condition/breast-neoplasm-701235c6-ff90-5cee-af0c-593aa004e38c.md)
- [Cancer](https://trialight.com/data/condition/cancer-703b1dfc-4812-50eb-83f4-d7a205d16bdb.md)
- Classic Hodgkin lymphoma
- [HER2 positive breast carcinoma](https://trialight.com/data/condition/her2-positive-breast-carcinoma-eb8493ec-908e-5435-bf56-0d20c0c9bb88.md)
- Hodgkins lymphoma
- [Lymphoma](https://trialight.com/data/condition/lymphoma-de4db685-7419-5e0e-b958-4591ffd69d43.md)
- Neoplasm
- Nephrotic syndrome
- [Plasma cell myeloma](https://trialight.com/data/condition/plasma-cell-myeloma-37186689-2591-5775-9042-2f2bf046a2b5.md)

### 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](https://trialight.com/data/condition/acute-myeloid-leukemia-b0971a7a-c18d-544e-bd7f-b1a13b9caa30.md) Phase 3
- Acute myelomonocytic leukemia M4 Phase 3
- [Adenocarcinoma](https://trialight.com/data/condition/adenocarcinoma-b5c321d1-7c49-5bf9-abd0-dfa99dbd5f29.md) 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](https://trialight.com/data/condition/amyloidosis-b8b4cb9d-0eae-5851-8654-8d69fd195e67.md) Phase 3
- Anaplastic ependymoma Phase 3
- Anaplastic large cell lymphoma Phase 2
- Anemia Phase 1
- [Angioimmunoblastic T-cell lymphoma](https://trialight.com/data/condition/angioimmunoblastic-t-cell-lymphoma-5b697108-b9cf-53e9-afde-71a36bf55d6b.md) Phase 3

### Other linked conditions (2)

- Idiopathic membranous glomerulonephritis
- Rapid-onset childhood obesity-hypothalamic dysfunction-hypoventilation-autonomic dysregulation syndrome

---

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