KEGG   DRUG: Cyclophosphamide
Entry
D00287                      Drug                                   
Name
Cyclophosphamide (USP);
Cyclophosphamide hydrate (JP18);
Cytoxan (TN);
Neosar (TN)
Product
  Generic
Formula
C7H15Cl2N2O2P. H2O
Exact mass
278.0354
Mol weight
279.10
Structure
Simcomp
Class
Antineoplastic
 DG01677  Alkylating agent
  DG01678  Nitrogen mustard analog
   DG01720  Isophosphoramide mustard analog
Metabolizing enzyme substrate
 DG01638  CYP2A6 substrate
 DG02919  CYP2B6 substrate
 DG02918  CYP2C8 substrate
 DG01642  CYP2C9 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Same as: C06933
Therapeutic category: 4211
ATC code: L01AA01
Chemical structure group: DG00675
Product (DG00675): D00287<JP/US>
Efficacy
Antineoplastic, Alkylating agent, Immunosuppressant
  Disease
Hodgkin's disease [DS:H00007]
Burkitt lymphoma [DS:H00008]
Multiple myeloma [DS:H00010]
Chronic lymphocytic leukemia [DS:H00005]
Acute myelogenous leukemia [DS:H00003]
Acute lymphoblastic (stem-cell) leukemia [DS:H00001 H00002]
Mycosis fungoides [DS:H01463]
Neuroblastoma [DS:H00043]
Adenocarcinoma of the ovary [DS:H00027]
Retinoblastoma [DS:H01513]
Carcinoma of the breast [DS:H00031]
Nephrotic syndrome [DS:H01657]
Comment
Active form of prodrug: 4-Hydroxycyclophosphamide [CPD:C07643]
Target
DNA
Metabolism
Enzyme: CYP2B6 [HSA:1555]; CYP2A6 [HSA:1548], CYP2C8 [HSA:1558], CYP2C9 [HSA:1559], CYP3A4 [HSA:1576]
Interaction
Structure map
map07040  Antineoplastics - alkylating agents
map07046  Immunosuppressive agents
map07050  Antirheumatics - DMARDs and biological agents
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01A ALKYLATING AGENTS
    L01AA Nitrogen mustard analogues
     L01AA01 Cyclophosphamide
      D00287  Cyclophosphamide (USP) <JP/US>
USP drug classification [BR:br08302]
 Antineoplastics
  Alkylating Agents
   Alkylating Agents, Other
    Cyclophosphamide
     D00287  Cyclophosphamide (USP)
Therapeutic category of drugs in Japan [BR:br08301]
 4  Agents affecting cellular function
  42  Antineoplastics
   421  Alkylating agents
    4211  Chlorethylamines
     D00287  Cyclophosphamide (USP); Cyclophosphamide hydrate (JP18)
Drug groups [BR:br08330]
 Antineoplastic
  DG01677  Alkylating agent
   DG01678  Nitrogen mustard analog
    DG01720  Isophosphoramide mustard analog
     DG00675  Cyclophosphamide
      D00287  Cyclophosphamide
 Metabolizing enzyme substrate
  DG01638  CYP2A6 substrate
   DG00675  Cyclophosphamide
    D00287  Cyclophosphamide
  DG02919  CYP2B6 substrate
   DG00675  Cyclophosphamide
    D00287  Cyclophosphamide
  DG02918  CYP2C8 substrate
   DG00675  Cyclophosphamide
    D00287  Cyclophosphamide
  DG01642  CYP2C9 substrate
   DG00675  Cyclophosphamide
    D00287  Cyclophosphamide
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00675  Cyclophosphamide
     D00287  Cyclophosphamide
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00287  Cyclophosphamide hydrate
  D00287  Cyclophosphamide tablets
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00287
Drug groups [BR:br08330]
 Antineoplastic
  DG01677  Alkylating agent
   DG01678  Nitrogen mustard analog
    DG01720  Isophosphoramide mustard analog
     DG00675  Cyclophosphamide
 Metabolizing enzyme substrate
  DG01638  CYP2A6 substrate
   DG00675  Cyclophosphamide
  DG02919  CYP2B6 substrate
   DG00675  Cyclophosphamide
  DG02918  CYP2C8 substrate
   DG00675  Cyclophosphamide
  DG01642  CYP2C9 substrate
   DG00675  Cyclophosphamide
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00675  Cyclophosphamide
Prodrugs [br08324.html]
 DG00675
Other DBs
CAS: 6055-19-2
PubChem: 7847353
ChEBI: 4026
LigandBox: D00287
NIKKAJI: J237.741A
LinkDB
KCF data

ATOM        15
            1   P1a P    22.9658  -14.9801
            2   N1c N    22.9715  -13.5156
            3   N1x N    24.0976  -15.6395
            4   O2x O    21.8279  -15.6395
            5   O3b O    21.6997  -14.2450
            6   C1b C    21.6646  -12.8388
            7   C1b C    24.2027  -12.7220
            8   C1x C    24.0976  -16.9523
            9   C1x C    21.8279  -16.9523
            10  C1b C    20.4335  -13.6264
            11  C1b C    25.5096  -13.3990
            12  C1x C    22.9658  -17.5999
            13  X   Cl   19.1265  -12.9613
            14  X   Cl   26.7467  -12.6054
            15  O0  O    27.7975  -15.3471
BOND        14
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     1   5 2
            5     2   6 1
            6     2   7 1
            7     3   8 1
            8     4   9 1
            9     6  10 1
            10    7  11 1
            11    8  12 1
            12   10  13 1
            13   11  14 1
            14    9  12 1

» Japanese version   » Back

KEGG   DRUG: Cyclophosphamide
Entry
D07760                      Drug                                   
Name
Cyclophosphamide (INN);
Cyclophosphamide (TN);
Cytoxan (TN)
Formula
C7H15Cl2N2O2P
Exact mass
260.0248
Mol weight
261.08
Structure
Simcomp
Class
Antineoplastic
 DG01677  Alkylating agent
  DG01678  Nitrogen mustard analog
   DG01720  Isophosphoramide mustard analog
Metabolizing enzyme substrate
 DG01638  CYP2A6 substrate
 DG02919  CYP2B6 substrate
 DG02918  CYP2C8 substrate
 DG01642  CYP2C9 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Same as: C07888
ATC code: L01AA01
Chemical structure group: DG00675
Product (DG00675): D00287<JP/US>
Efficacy
Antineoplastic, Alkylating agent
Comment
Active form of prodrug: 4-Hydroxycyclophosphamide [CPD:C07643]
Target
DNA
Metabolism
Enzyme: CYP2B6 [HSA:1555]; CYP2A6 [HSA:1548], CYP2C8 [HSA:1558], CYP2C9 [HSA:1559], CYP3A4 [HSA:1576]
Interaction
Structure map
map07040  Antineoplastics - alkylating agents
map07046  Immunosuppressive agents
map07050  Antirheumatics - DMARDs and biological agents
Other map
map00982  Drug metabolism - cytochrome P450
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01A ALKYLATING AGENTS
    L01AA Nitrogen mustard analogues
     L01AA01 Cyclophosphamide
      D07760  Cyclophosphamide (INN)
Drug groups [BR:br08330]
 Antineoplastic
  DG01677  Alkylating agent
   DG01678  Nitrogen mustard analog
    DG01720  Isophosphoramide mustard analog
     DG00675  Cyclophosphamide
      D07760  Cyclophosphamide
 Metabolizing enzyme substrate
  DG01638  CYP2A6 substrate
   DG00675  Cyclophosphamide
    D07760  Cyclophosphamide
  DG02919  CYP2B6 substrate
   DG00675  Cyclophosphamide
    D07760  Cyclophosphamide
  DG02918  CYP2C8 substrate
   DG00675  Cyclophosphamide
    D07760  Cyclophosphamide
  DG01642  CYP2C9 substrate
   DG00675  Cyclophosphamide
    D07760  Cyclophosphamide
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00675  Cyclophosphamide
     D07760  Cyclophosphamide
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D07760
Prodrugs [br08324.html]
 D07760
Drug groups [BR:br08330]
 Antineoplastic
  DG01677  Alkylating agent
   DG01678  Nitrogen mustard analog
    DG01720  Isophosphoramide mustard analog
     DG00675  Cyclophosphamide
 Metabolizing enzyme substrate
  DG01638  CYP2A6 substrate
   DG00675  Cyclophosphamide
  DG02919  CYP2B6 substrate
   DG00675  Cyclophosphamide
  DG02918  CYP2C8 substrate
   DG00675  Cyclophosphamide
  DG01642  CYP2C9 substrate
   DG00675  Cyclophosphamide
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00675  Cyclophosphamide
Prodrugs [br08324.html]
 DG00675
Other DBs
CAS: 50-18-0
PubChem: 51092052
ChEBI: 4027
LigandBox: D07760
NIKKAJI: J2.793F
LinkDB
KCF data

ATOM        14
            1   P1a P    23.6600  -17.8500
            2   N1c N    23.6600  -16.3800
            3   N1x N    24.7800  -18.4800
            4   O2x O    22.5400  -18.4800
            5   O3b O    22.4000  -17.1500
            6   C1b C    22.4000  -15.6800
            7   C1b C    24.9200  -15.6100
            8   C1x C    24.7800  -19.8100
            9   C1x C    22.5400  -19.8100
            10  C1b C    21.1400  -16.5200
            11  C1b C    26.1800  -16.2400
            12  C1x C    23.6600  -20.4400
            13  X   Cl   19.8100  -15.8200
            14  X   Cl   27.4400  -15.4700
BOND        14
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     1   5 2
            5     2   6 1
            6     2   7 1
            7     3   8 1
            8     4   9 1
            9     6  10 1
            10    7  11 1
            11    8  12 1
            12   10  13 1
            13   11  14 1
            14    9  12 1

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