cyclophosphamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
alkylating agents of the cyclophosphamide group	758	50-18-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cyclophosphamide cyclophosphamid cyclophosphamidum cyclophosphan cyclophosphane cytophosphan mitoxan cyclophosphamide hydrate endoxan	Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the LIVER to form the active aldophosphamide. It has been used in the treatment of LYMPHOMA and LEUKEMIA. Its side effect, ALOPECIA, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer. Molecular weight: 261.08 Formula: C7H15Cl2N2O2P CLOGP: 0.80 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 41.57 ALOGS: -1.24 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cyclophosphamide
cyclophosphamid
cyclophosphamidum
cyclophosphan
cyclophosphane
cytophosphan
mitoxan
cyclophosphamide hydrate
endoxan

Precursor of an alkylating nitrogen mustard antineoplastic and immunosuppressive agent that must be activated in the LIVER to form the active aldophosphamide. It has been used in the treatment of LYMPHOMA and LEUKEMIA. Its side effect, ALOPECIA, has been used for defleecing sheep. Cyclophosphamide may also cause sterility, birth defects, mutations, and cancer.

Molecular weight: 261.08
Formula: C7H15Cl2N2O2P
CLOGP: 0.80
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 41.57
ALOGS: -1.24
ROTB: 5

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

Show entries

Search:

Property	Value	Reference
t_half (Half-life)	8 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	74 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	6.50 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	40 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	19.15 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
CL (Clearance)	1.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.87 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.73 L/kg	Lombardo F, Berellini G, Obach RS

Showing 1 to 9 of 9 entries

Previous1Next

Approvals:

Date	Agency	Company	Orphan
March 26, 2019	PMDA	SHIONOGI & Co., Ltd.
Nov. 16, 1959	FDA	BAXTER HLTHCARE

FDA Adverse Event Reporting System (Female)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	7103.21	11.47	4498	196097	113951	63174476
Neutropenia	3383.53	11.47	3419	197176	171586	63116841
Myelosuppression	2137.69	11.47	1175	199420	22528	63265899
Disease progression	1604.49	11.47	1957	198638	120801	63167626
Bone marrow failure	1477.07	11.47	1001	199594	28289	63260138
Acute myeloid leukaemia	1353.12	11.47	779	199816	16368	63272059
Agranulocytosis	1303.22	11.47	874	199721	24260	63264167
Cytokine release syndrome	1212.04	11.47	681	199914	13633	63274794
Pancytopenia	1090.78	11.47	1435	199160	95498	63192929
Mucosal inflammation	1064.55	11.47	1003	199592	45925	63242502

Showing 1 to 10 of 1,353 entries

Previous1 2 3 4 5…136Next

FDA Adverse Event Reporting System (Male)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	4447.80	12.77	4287	163668	132562	34656414
Cytokine release syndrome	1599.88	12.77	1123	166832	21754	34767222
Neutropenia	1571.11	12.77	2746	165209	154032	34634944
Myelosuppression	1216.57	12.77	889	167066	18376	34770600
Product use in unapproved indication	1192.18	12.77	2071	165884	115428	34673548
Disease progression	1184.99	12.77	1972	165983	106105	34682871
Mucosal inflammation	895.65	12.77	1014	166941	37608	34751368
Off label use	895.62	12.77	4176	163779	415348	34373628
Hypogammaglobulinaemia	871.13	12.77	513	167442	7227	34781749
Acute graft versus host disease	800.84	12.77	457	167498	6046	34782930

Showing 1 to 10 of 984 entries

Previous1 2 3 4 5…99Next

FDA Adverse Event Reporting System (Geriatric)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	9588.83	11.09	7748	317613	223251	79195776
Neutropenia	3840.91	11.09	5268	320093	282442	79136585
Myelosuppression	3032.20	11.09	1946	323415	38350	79380677
Cytokine release syndrome	2625.84	11.09	1705	323656	34293	79384734
Product use in unapproved indication	2109.04	11.09	3711	321650	246648	79172379
Bone marrow failure	2037.21	11.09	1680	323681	49427	79369600
Disease progression	1914.25	11.09	3003	322358	181359	79237668
Acute myeloid leukaemia	1778.36	11.09	1264	324097	29621	79389406
Cytomegalovirus infection	1752.29	11.09	1427	323934	41217	79377810
Mucosal inflammation	1655.68	11.09	1782	323579	73798	79345229

Showing 1 to 10 of 1,665 entries

Previous1 2 3 4 5…167Next

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Show entries

Search:

Source	Code	Description
ATC	L01AA01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ALKYLATING AGENTS Nitrogen mustard analogues
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35705	immunosuppressive agents
CHEBI has role	CHEBI:50903	carcinogen
MeSH PA	D000477	Alkylating Agents
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D018906	Antineoplastic Agents, Alkylating
MeSH PA	D018501	Antirheumatic Agents
MeSH PA	D007155	Immunologic Factors
MeSH PA	D007166	Immunosuppressive Agents

Showing 1 to 10 of 13 entries

Previous1 2Next

Drug Use | Suggest Off label Use Form| |View source of the data|

Show entries

Search:

Disease	Relation	SNOMED_ID	DOID
Systemic AL amyloidosis	indication	23132008
Acute lymphoid leukemia, disease	indication	91857003	DOID:9952
Chronic lymphoid leukemia, disease	indication	92814006
Chronic myeloid leukemia	indication	92818009	DOID:8552
Histiocytic lymphoma	indication	109988003
Multiple myeloma	indication	109989006	DOID:9538
Hodgkin's disease	indication	118599009
Malignant lymphoma	indication	118600007	DOID:0060058
Burkitt's lymphoma	indication	118617000
Mycosis fungoides	indication	118618005

Showing 1 to 10 of 19 entries

Previous1 2Next

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	2.39	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Show entries

Search:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	5.68		WOMBAT-PK

Showing 1 to 1 of 1 entries

Previous1Next

External reference:

Show entries

Search:

ID	Source
002631	NDDF
2907	PUBCHEM_CID
3002	RXNORM
31952	MMSL
387420009	SNOMEDCT_US
4018114	VUID
4018114	VANDF
4519	MMSL
6055-19-2	SECONDARY_CAS_RN
7154	IUPHAR_LIGAND_ID

Showing 1 to 10 of 21 entries

Previous1 2 3Next

Pharmaceutical products:

Show entries

Search:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Cyclophosphamide	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0382	CAPSULE	25 mg	ORAL	NDA	27 sections
Cyclophosphamide	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0383	CAPSULE	50 mg	ORAL	NDA	27 sections
Cyclophosphamide	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3233	INJECTION, POWDER, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	25 sections
Cyclophosphamide	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3244	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
Cyclophosphamide	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3255	INJECTION, POWDER, FOR SOLUTION	2 g	ORAL	ANDA	25 sections
CYCLOPHOSPHAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10019-935	INJECTION, POWDER, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	25 sections
CYCLOPHOSPHAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10019-935	INJECTION, POWDER, FOR SOLUTION	500 mg	INTRAVENOUS	ANDA	25 sections
CYCLOPHOSPHAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10019-936	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
CYCLOPHOSPHAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10019-936	INJECTION, POWDER, FOR SOLUTION	1 g	INTRAVENOUS	ANDA	25 sections
CYCLOPHOSPHAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10019-937	INJECTION, POWDER, FOR SOLUTION	2 g	INTRAVENOUS	ANDA	25 sections

Showing 1 to 10 of 30 entries

Previous1 2 3Next