Product Name

Cyclophosphamide

CAS Number

50-18-0

LGM Pharma is an API distributor. LGM Pharma can supply CGMP and/or DMF products, subject to availability and manufacturer requirements. LGM Pharma does not sell or supply APIs or finished dosage products to individual patients, doctors, pharmacies, or any pharmaceutical companies.

Questions? Call our customer API support number 1-(800)-881-8210

Product Name:
Cyclophosphamide
CAS Number:
50-18-0
Indication:
Cyclophosphamide is indicated for the treatment of malignant lymphomas, multiple myeloma, leukemias, mycosis fungoides (advanced disease), neuroblastoma (disseminated disease), adenocarcinoma of the ovary, retinoblastoma, and carcinoma of the breast. It is also indicated for the treatment of biopsy-proven minimal change nephrotic syndrome in pediatric patients.
Mode of Action:

Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations.

Pharmacodynamics:

Cyclophosphamide is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands – directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result – disruption of DNA function and cell death.

Metabolism:

Metabolism and activation occurs at the liver. 75% of the drug is activated by cytochrome P450 isoforms, CYP2A6, 2B6, 3A4, 3A5, 2C9, 2C18, and 2C19. The CYP2B6 isoform is the enzyme with the highest 4-hydroxylase activity. Cyclophosphamide undergoes activation to eventually form active metabolites, phosphoramide mustard and acrolein. Cyclophosphamide appears to induce its own metabolism which results in an overall increase in clearance, increased formation of 4-hydroxyl metabolites, and shortened t1/2 values following repeated administration.

Toxicity:

Adverse reactions reported most often include neutropenia, febrile neutropenia, fever, alopecia, nausea, vomiting, and diarrhea.

IUPAC:
N, N-bis(2-chloroethyl)-1, 3, 2-oxazaphosphinan-2-amine 2-oxide
ATC:
L01AA01
PubChem:
2907
DrugBank:
APRD00408
Formula:
C7 H15 N2 O2
Molecular Mass:
261.086
Synonyms:
(+-)-Cyclophosphamide, (RS)-Cyclophosphamide, 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin, 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide, 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide, 4-27-00-09750 (Beilstein Handbook Reference), 4-Hydroxy-cyclophosphan-mamophosphatide, AI3-26198, ASTA B518, B 518, Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester, BRN 0011744, CB 4564, CCRIS 188, Ciclofosfamida, Ciclofosfamida [INN-Spanish], Ciclophosphamide, Ciclophosphamide [INN], Clafen, Claphene, Cyclophosphamid, Cyclophosphamide, Cyclophosphamidum, Cyclophosphamidum [INN-Latin], Cyclophosphan, Cyclophosphane, Cyclophosphanum, Cyclophosphoramide, Cyclostin, Cyklofosfamid, Cyklofosfamid [Czech], Cytophosphan, Cytophosphane, Cytoxan, D,L-Cyclophosphamide, EINECS 200-015-4, Endoxan, Endoxan R, Endoxan-asta, Endoxana, Endoxanal, Genoxal, HSDB 3047, Lyophilized cytoxan, N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide, N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide, N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester diamide, N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide, N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid, N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid [German], N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide, NCI-C04900, Neosar, NSC 26271, NSC-26271, Occupation, cyclophosphamide exposure, Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-N'-(3-hydroxypropyl)-, intramol. ester, Procytox, RCRA waste number U058, Sendoxan, SK 20501, UNII-6UXW23996M, Zyklophosphamid, Zyklophosphamid [German]
SMILES:
N([P@@]1(NCCCO1)=O)(CCCl)CCCl
AHFS Code:
10:00.0
InChi:
1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
General Reference:
General Reference:
  1. Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. Pubmed
  2. Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. Pubmed
  3. FDA label

Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

LGM currently offers Monoclonal Antibodies (mAbs) for non-GMP/R&D use. Please inquire about Monoclonal Antibodies produced under GMP conditions.

Questions? Call our customer API support number 1-(800)-881-8210. 

Ask us about this product

API’s From Quality Manufacturers:

  • Streamlined API supply towards initial research stages as well as larger quantities of cGMP material for clinical trials and product commercialization
  • Premium quality GMP certified and fully accredited API manufacturing plants
  • Technical packages as well as access to filed DMF, ASMF or CEP (subject to availability)
  • Regulatory and technical assistance towards any submission type based on specific customer requirements

Find an API Product

SEARCH
Generic filters