Cyclophosphamide chemical structure
Find information on thousands of medical conditions and prescription drugs.

Cyclophosphamide

Cyclophosphamide is a nitrogen mustard alkylating agent, used to treat various types of cancer and some autoimmune disorders. It is a "prodrug"; it is converted in the liver to active forms that have chemotherapeutic activity. more...

Home
Diseases
Medicines
A
B
C
Cabergoline
Caduet
Cafergot
Caffeine
Calan
Calciparine
Calcitonin
Calcitriol
Calcium folinate
Campath
Camptosar
Camptosar
Cancidas
Candesartan
Cannabinol
Capecitabine
Capoten
Captohexal
Captopril
Carbachol
Carbadox
Carbamazepine
Carbatrol
Carbenicillin
Carbidopa
Carbimazole
Carboplatin
Cardinorm
Cardiolite
Cardizem
Cardura
Carfentanil
Carisoprodol
Carnitine
Carvedilol
Casodex
Cataflam
Catapres
Cathine
Cathinone
Caverject
Ceclor
Cefacetrile
Cefaclor
Cefaclor
Cefadroxil
Cefazolin
Cefepime
Cefixime
Cefotan
Cefotaxime
Cefotetan
Cefpodoxime
Cefprozil
Ceftazidime
Ceftriaxone
Ceftriaxone
Cefuroxime
Cefuroxime
Cefzil
Celebrex
Celexa
Cellcept
Cephalexin
Cerebyx
Cerivastatin
Cerumenex
Cetirizine
Cetrimide
Chenodeoxycholic acid
Chloralose
Chlorambucil
Chloramphenicol
Chlordiazepoxide
Chlorhexidine
Chloropyramine
Chloroquine
Chloroxylenol
Chlorphenamine
Chlorpromazine
Chlorpropamide
Chlorprothixene
Chlortalidone
Chlortetracycline
Cholac
Cholybar
Choriogonadotropin alfa
Chorionic gonadotropin
Chymotrypsin
Cialis
Ciclopirox
Cicloral
Ciclosporin
Cidofovir
Ciglitazone
Cilastatin
Cilostazol
Cimehexal
Cimetidine
Cinchophen
Cinnarizine
Cipro
Ciprofloxacin
Cisapride
Cisplatin
Citalopram
Citicoline
Cladribine
Clamoxyquine
Clarinex
Clarithromycin
Claritin
Clavulanic acid
Clemastine
Clenbuterol
Climara
Clindamycin
Clioquinol
Clobazam
Clobetasol
Clofazimine
Clomhexal
Clomid
Clomifene
Clomipramine
Clonazepam
Clonidine
Clopidogrel
Clotrimazole
Cloxacillin
Clozapine
Clozaril
Cocarboxylase
Cogentin
Colistin
Colyte
Combivent
Commit
Compazine
Concerta
Copaxone
Cordarone
Coreg
Corgard
Corticotropin
Cortisone
Cotinine
Cotrim
Coumadin
Cozaar
Crestor
Crospovidone
Cuprimine
Cyanocobalamin
Cyclessa
Cyclizine
Cyclobenzaprine
Cyclopentolate
Cyclophosphamide
Cyclopropane
Cylert
Cyproterone
Cystagon
Cysteine
Cytarabine
Cytotec
Cytovene
Isotretinoin
D
E
F
G
H
I
J
K
L
M
N
O
P
Q
R
S
T
U
V
W
X
Y
Z

Uses

The main use of cyclophosphamide is together with other chemotherapy agents in the treatment of lymphomas, some forms of leukemia and some solid tumors.

In addition, its use is becoming more common in autoimmune diseases where disease-modifying antirheumatic drugs (DMARDs) have been ineffective. Systemic lupus erythematosus (SLE) with severe lupus nephritis, for example, may respond to pulsed cyclophosphamide.

Pharmacokinetics

Cyclophosphamide is converted by mixed function oxidase enzymes in the liver to active metabolites. The main active metabolite is 4-hydroxycyclophosphamide. 4-hydroxycyclophosphamide exists in 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 bladder epithelium and can lead to hemorrhagic cystitis. This can be prevented through the use of aggressive hydration and/or Mesna.

Mode of action

The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells which have low levels of aldehyde dehydrogenase.

Phosphoramide mustard forms DNA crosslinks between and within DNA strands. This leads to cell death.

Cyclophosphamide has relatively little typical chemotherapy toxicity, as ALDH is present in relatively large concentrations in bone marrow stem cells, liver and intestinal epithelium, protecting these tissues against phosphoramide mustard.

Side-effects

Side-effects include chemotherapy-induced nausea and vomiting (CINV), bone marrow suppression, 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.

Cyclophosphamide is itself carcinogenic, potentially causing transitional cell carcinoma of the bladder as a long-term complication.

History

Cyclophosphamide and the related nitrogen mustard-derived alkylating agent ifosfamide were developed by Norbert Brock and ASTA (now Baxter Oncology). They converted the base nitrogen mustard into a non-toxic "transport form". This transport form was a pro-drug, subsequently actively transported into the cancer cells. Once in the cells, the pro-drug was enzymatically converted into the active, toxic form. Brock and his team synthesised more than 1,000 candidate oxazophosphorine compounds, eventually finding the drug cyclophosphamide (Brock 1996).

Read more at Wikipedia.org


[List your site here Free!]


FDA clears Roxane Labs generic Cyclophosphamide tablets - Brief Article
From Drug Store News, 5/22/00 by Kim Roller

The FDA has approved Roxane Laboratories' Cyclophosphamide in 25 mg and 50 mg tablets, the first generic of Bristol-Myers Squibb's Cytoxan. For use in combination with other anti-neoplastic therapies, cyclophosphamide treats a range of malignancies, including Hodgkin's Disease, lymphoma, leukemia and breast cancer. Roxane, a wholly owned subsidiary of Boehringer Ingelheim Corp., in 1998 expanded its Columbus, Ohio, facility to specifically enhance its cyclophosphamide production. The drug requires a rigorously controlled manufacturing environment, the company said, a major reason why there has been no competition in the market in the years since Cytoxan's patent expired.

Roxane also announced the introduction of Cromolyn Sodium Inhalation Solution USP 20 mg/2mL, available in cartons of 60 and 120 unit dose vials. The product is available in color-coded five-vial ProtectaPak foil packaging to help assure the solution remains free from environmental contamination that may affect other unprotected solutions, the company said.

COPYRIGHT 2000 Lebhar-Friedman, Inc.
COPYRIGHT 2000 Gale Group

Return to Cyclophosphamide
Home Contact Resources Exchange Links ebay