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{{drugbox
{{DrugProjectFormSinglePage
| IUPAC_name = ''N'',''N''-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
|authorTag=<!--Overview-->
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| width = 96px
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| width2 = 150px
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| CAS_number = 50-18-0
|blackBoxWarningBody=<i><span style="color:#FF0000;">ConditionName: </span></i>
| ATC_prefix = L01
 
| ATC_suffix = AA01
* Content
| PubChem = 2907
 
| DrugBank = APRD00408
<!--Adult Indications and Dosage-->
| C = 7 |H = 15 |Cl = 2 |N = 2 |O = 2 |P = 1
 
| molecular_weight = 261.085 [[Gram|g]]/[[Mole (unit)|mol]]
<!--FDA-Labeled Indications and Dosage (Adult)-->
| smiles = C1CNP(=O)(OC1)N(CCCl)CCCl
|fdaLIADAdult======Condition1=====
| density =  
 
| melting_point = 2
* Dosing Information
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=====Condition2=====
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| protein_bound = >60%
* Dosing Information
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| elimination_half-life = 3-12 hours
:* Dosage
| excretion = [[Kidney|Renal]]
 
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* Strength of Evidence:
 
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: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]


==Overview==
<!--Pharmacodynamics-->
'''Cyclophosphamide''' (the generic name for Cytoxan, Neosar), also known as cytophosphane, is a [[nitrogen mustard]] [[alkylating antineoplastic agent|alkylating agent]], used to treat various types of [[cancer]] and some [[autoimmune disorder]]s. It is a "[[prodrug]]"; it is converted in the [[liver]] to active forms that have [[chemotherapy|chemotherapeutic]] activity.
|PD=There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.


==Uses==
<!--Pharmacokinetics-->
The main use of cyclophosphamide is together with other chemotherapy agents in the treatment of [[lymphoma]]s, some forms of [[leukemia]] and some solid tumors. It is a chemotherapy drug that works by slowing or stopping cell growth. It also works by decreasing the immune system's response to various diseases.
|PK=There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.


In addition, its use is becoming more common in [[autoimmune disease]]s where [[disease-modifying antirheumatic drug]]s (DMARDs) have been ineffective. [[Systemic lupus erythematosus]] (SLE) with severe [[lupus nephritis]], for example, may respond to pulsed cyclophosphamide. However in 2005, standard treatment for lupus nephritis changed to [[Mycophenolic acid|MMF]] from cyclophosphamide.
<!--Nonclinical Toxicology-->
|nonClinToxic=There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.


It is also used to treat [[Minimal Change Disease]] and rheumatoid arthritis. It is still used for [[Wegener's granulomatosis]].
<!--Clinical Studies-->
The trade name is Endoxan.
|clinicalStudies=There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.


==Pharmacokinetics/Pharmacodynamics==
<!--How Supplied-->
Cyclophosphamide is converted by mixed function [[oxidase]] [[enzyme]]s in the liver to active metabolites. The main active metabolite is 4-hydroxycyclophosphamide. 4-hydroxycyclophosphamide exists in [[chemical equilibrium|equilibrium]] with its [[tautomer]], aldophosphamide. Most of the aldophosphamide is oxidised by the enzyme [[aldehyde dehydrogenase]] (ALDH) to make carboxyphosphamide. A small proportion of aldophosphamide is converted into phosphoramide mustard and [[acrolein]]. Acrolein is toxic to the [[urinary bladder|bladder]] [[epithelium]] and can lead to [[hemorrhagic cystitis]].  This can be prevented through the use of aggressive hydration and/or [[Mesna]].
|howSupplied=*
Recent clinical studies have shown that cyclophosphamide induce beneficial [[Immunomodulator|immunomodulatory]] effects in the context of adoptive immunotherapy. Although the mechanisms underlying these effects are not fully understood, several mechanisms have been suggested based on potential modulation of the host environment, including:
# Elimination of T regulatory cells (CD4+CD25+ T cells) in naive and tumor-bearing hosts
# Induction of T cell growth factors such as type I IFNs, and/or
# Enhanced grafting of adoptively transferred tumor-reactive effector T cells by the creation of an immunologic space niche.


Thus, cyclophosphamide pre-conditioning of recipient hosts (for donor T cells) has been used to enhance immunity in naïve hosts, and to enhance adoptive T cell immunotherapy regimens as well as active vaccination strategies, inducing objective anti-tumor immunity.
<!--Patient Counseling Information-->
|fdaPatientInfo=There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.


==Mode of action==
<!--Precautions with Alcohol-->
The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells which have low levels of ALDH.
|alcohol=* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


Phosphoramide mustard forms DNA crosslinks between (interstrand crosslinkages) and within (intrastrand crosslinkages) DNA strands at guanine N-7 positions. This leads to cell death.
<!--Brand Names-->
|brandNames=* ®<ref>{{Cite web | title =  | url =  }}</ref>


Cyclophosphamide has relatively little typical chemotherapy toxicity as ALDHs are present in relatively large concentrations in [[Hematopoietic stem cell|bone marrow stem cells]], [[liver]] and [[intestine|intestinal]] [[epithelium]]. ALDHs protect these actively proliferating tissues against toxic effects phosphoramide mustard and acrolein by converting aldophosphamide to carboxyphosphamide that does not give rise to the toxic metabolites (phosphoramide mustard and acrolein).
<!--Look-Alike Drug Names-->
|lookAlike=* A® — B®<ref name="www.ismp.org">{{Cite web  | last =  | first =  | title = http://www.ismp.org | url = http://www.ismp.org | publisher =  | date =  }}</ref>


==Side-effects==
<!--Drug Shortage Status-->
Many people taking cyclophosphamide do not have serious side effects. [[Adverse drug reaction|Side-effects]] include [[chemotherapy-induced nausea and vomiting]] (CINV), [[bone marrow suppression]], stomach ache, diarrhea, darkening of the skin/nails, [[alopecia]] (hair loss) and [[lethargy]]. [[Hemorrhagic cystitis]] is a frequent complication, but this is prevented by adequate fluid intake and [[Mesna]] (sodium 2-mercaptoethane sulfonate). Mesna is a sulfhydryl donor and binds [[acrolein]].
|drugShortage=
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Cyclophosphamide is itself [[carcinogen]]ic, potentially causing transitional cell [[carcinoma]] of the bladder as a long-term complication. It can lower the body's ability to fight an infection. It can cause temporary or (rarely) permanent sterility. Although it is used to treat cancer, it may increase the risk of developing another form of cancer, sometimes months to years after treatment.


Other (serious) side effects include:
* pink/bloody urine,
* unusual decrease in the amount of urine,
* mouth sores,
* unusual tiredness or weakness,
* joint pain,
* easy bruising/bleeding,
* stopping of menstrual periods,
* existing wounds that are slow healing.


==History==
<!--Label Display Image-->
Cyclophosphamide and the related [[nitrogen mustard]]-derived alkylating agent [[ifosfamide]] were developed by Norbert Brock and ASTA (now Baxter Oncology). Brock and his team synthesised and screened more than 1,000 candidate oxazaphosphorine compounds.<ref>{{cite journal |author=Brock N |title=The history of the oxazaphosphorine cytostatics |journal=Cancer |volume=78 |issue=3 |pages=542-7 |year=1996 |pmid=8697402 }}</ref> They converted the base nitrogen mustard into a non-toxic "transport form". This transport form was a pro-drug, subsequently [[active transport|actively transported]] into the cancer cells. Once in the cells, the pro-drug was [[enzyme|enzymatically]] converted into the active, toxic form.
The first clinical trials were published at the end of the 1950s.<ref>{{cite journal|author=Wilmanns, H.|journal= Asta-Forschung und Therapie|year= 1958}}</ref><ref>{{ cite journal|author=Gross, R., and Wulf, G. |title=Klinische und experimentelle Erfahrungen mit zyk
lischen und nichtzyklischen Phosphamidestern des N-Losl in der Chemotherapie von Tumoren|journal=Strahlentherapie|volume= 41 (Sonderband III)|pages= 361-367|year= 1959}}</ref><ref>{{cite journal |author=Brock N |title=Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture |journal=Cancer Res. |volume=49 |issue=1 |pages=1-7 |year=1989 |pmid=2491747 |doi=}}</ref>


==References==
{{reflist|2}}




{{Chemotherapeutic agents}}


[[Category:Chemotherapeutic agents]]
[[Category:Organochlorides]]
[[Category:Phosphorus compounds]]
[[Category:Prodrugs]]
[[Category:IARC Group 1 carcinogens]]


[[de:Cyclophosphamid]]
<!--Category-->
[[ja:シクロホスファミド]]
[[pl:Cyklofosfamid]]
[[ru:Циклофосфамид]]


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[[Category:Drug]]
{{WikiDoc Sources}}

Revision as of 14:33, 17 December 2014

Cyclophosphamide
Black Box Warning
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1];

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Black Box Warning

ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content

Overview

Cyclophosphamide is a {{{drugClass}}} that is FDA approved for the {{{indicationType}}} of {{{indication}}}. There is a Black Box Warning for this drug as shown here. Common adverse reactions include .

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Condition1
  • Dosing Information
  • Dosage
Condition2
  • Dosing Information
  • Dosage
Condition3
  • Dosing Information
  • Dosage
Condition4
  • Dosing Information
  • Dosage

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Cyclophosphamide in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Cyclophosphamide in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding FDA-Labeled Use of Cyclophosphamide in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Cyclophosphamide in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Cyclophosphamide in pediatric patients.

Contraindications

  • Condition1

Warnings

ConditionName:
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content
  • Description

Precautions

  • Description

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Cyclophosphamide in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Cyclophosphamide in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Drug Interactions

  • Drug
  • Description

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Cyclophosphamide in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Cyclophosphamide during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Cyclophosphamide with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Cyclophosphamide with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Cyclophosphamide with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Cyclophosphamide with respect to specific gender populations.

Race

There is no FDA guidance on the use of Cyclophosphamide with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Cyclophosphamide in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Cyclophosphamide in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Cyclophosphamide in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Cyclophosphamide in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Cyclophosphamide in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Cyclophosphamide in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • Description

Management

  • Description

Chronic Overdose

There is limited information regarding Chronic Overdose of Cyclophosphamide in the drug label.

Pharmacology

There is limited information regarding Cyclophosphamide Pharmacology in the drug label.

Mechanism of Action

Structure

File:Cyclophosphamide01.png
This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Cyclophosphamide in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Cyclophosphamide in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Cyclophosphamide in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Cyclophosphamide in the drug label.

How Supplied

Storage

There is limited information regarding Cyclophosphamide Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Cyclophosphamide |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Cyclophosphamide |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Cyclophosphamide in the drug label.

Precautions with Alcohol

  • Alcohol-Cyclophosphamide interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

Look-Alike Drug Names

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. Empty citation (help)
  2. "http://www.ismp.org". External link in |title= (help)

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