Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00157)
Name
Cyclophosphamide
Synonyms    Click to Show/Hide the Synonyms of This API
cyclophosphamide; 50-18-0; Cyclophosphamid; Cytoxan; Cyclophosphane; Neosar; Cytophosphan; Procytox; Clafen; Endoxan; Cyclophosphan; Cyclostin; Sendoxan; Cyclophosphamidum; Cytophosphane; Claphene; Endoxana; Endoxanal; Genoxal; Endoxan-Asta; Endoxan R; Zyklophosphamid; Mitoxan; (RS)-Cyclophosphamide; Cyclophosphoramide; Cyklofosfamid; Endoxane; Enduxan; Semdoxan; Senduxan; (+-)-Cyclophosphamide; Cyclophosphamide anhydrous; Rcra waste number U058; Asta B 518; 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide; NSC 26271; Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester; CB 4564; NCI-C04900; SK 20501; CHEBI:4027; N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide; NSC-26271; (-)-Cyclophosphamide; UNII-6UXW23996M; N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide; NSC26271; Cytoxan (TN); 50-18-0 (anhydrous); 2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide; Cyclophosphanum; Ciclophosphamide; 2-(Bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorine 2-oxide; 6UXW23996M; N,N-Bis(2-chloroethyl)-N',O-propylenephosphoric acid ester diamide; N,N-Di(2-chloroethyl)-N,O-propylene-phosphoric acid ester diamide; Lyophilized Cytoxan; Ciclofosfamida; Cycloblastin; D,L-Cyclophosphamide; Cyklofosfamid [Czech]; N,N-bis(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine; N,N-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine; Ciclophosphamide [INN]; Zyklophosphamid [German]; Cyclophosphamide (anhydrous); ASTA B518; Ciclofosfamida [INN-Spanish]; Cyclophosphamidum [INN-Latin]; 2H-1,3,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-,2-oxide; Occupation, cyclophosphamide exposure; CCRIS 188; 4-Hydroxy-cyclophosphan-mamophosphatide; Cyclophosphamide (anhydrous form); Cyclophosphamide (TN); HSDB 3047; 2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; Cyclophosphamide (INN); SR-01000075737; NCGC00015209-05; EINECS 200-015-4; RCRA waste no. U058; BRN 0011744; Cyclophosphamide [USP:INN]; Ciclofosfamide; Cyclofosphamide; 2-(Bis(2-chloroethyl)amino)-2H-1,2-oxazaphosphorine 2-oxide; 2-[Bis(2-chloroethyl)amino]-2H-1,2-oxazaphosphorine 2-oxide; 1-Bis(2-chloroethyl)amino-1-oxo-2-aza-5-oxaphosphoridin; AI3-26198; CB-4564; Spectrum_000858; Anhydrous cyclophosphamide; CHEMBL88; Spectrum2_001146; Spectrum3_000370; Spectrum4_000304; Spectrum5_000795; Clafen(Cyclophosphamide)/; Lopac-C-0768; N,N-Bis(beta-chloroethyl)-N',O-propylenephosphoric acid ester diamide; N,N-Bis(beta-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide; Epitope ID:131782; 2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazophosphorine 2-oxide; C 0768; N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid [German]; SCHEMBL4346; (.+/-.)-Cyclophosphamide; Lopac0_000238; BSPBio_002099; KBioGR_000888; KBioSS_001338; ARONIS24566; DivK1c_000246; SPBio_001071; GTPL7154; SCHEMBL4345553; DTXSID5020364; SCHEMBL10262910; CMSMOCZEIVJLDB-UHFFFAOYSA-; KBio1_000246; KBio2_001338; KBio2_003906; KBio2_006474; KBio3_001319; CYCLOPHOSPAMIDE MONOHYDRATE; WLN: T6MPOTJ BO BN2G2G; NINDS_000246; 2-(bis(2-chloroethyl)amino)-1,3,2-oxazaphosphinane 2-oxide; HMS2090A12; HMS3260P17; HMS3715J05; Pharmakon1600-01500213; BCP02139; Tox21_500238; 2-CHLORO-5-METHYLBENZANILIDE; ABP000629; BBL022697; BDBM50237604; N,N-Bis-(beta-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid; NSC273033; NSC273034; NSC756711; STK177249; 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-, 2-oxide; AKOS005410738; CS-1425; DB00531; LP00238; MCULE-5327530727; NSC-273033; NSC-273034; NSC-756711; SDCCGSBI-0050226.P004; IDI1_000246; N,3,2-oxazaphosphorin-2-amine-2-oxide; N,O-propylen-phosphorsaeure-ester-diamid; NCGC00015209-01; NCGC00015209-02; NCGC00015209-03; NCGC00015209-04; NCGC00015209-06; NCGC00015209-07; NCGC00015209-08; NCGC00015209-09; NCGC00015209-12; NCGC00015209-28; NCGC00091741-02; NCGC00091741-03; NCGC00260923-01; AS-73255; BP-25411; HY-17420; NCI60_002097; N,O-propylenephosphoric acid ester diamide; SBI-0050226.P003; AB0007927; DB-082057; N,O-propylene-phosphoric acid ester diamide; EU-0100238; FT-0624276; FT-0665387; N,O-trimethylenephosphoric acid ester diamide; ST51005945; EN300-74526; 3356-EP2269989A1; 3356-EP2270001A1; 3356-EP2270008A1; 3356-EP2270014A1; 3356-EP2270018A1; 3356-EP2270505A1; 3356-EP2272822A1; 3356-EP2272825A2; 3356-EP2272827A1; 3356-EP2275102A1; 3356-EP2275412A1; 3356-EP2275413A1; 3356-EP2275420A1; 3356-EP2277865A1; 3356-EP2277876A1; 3356-EP2280012A2; 3356-EP2281815A1; 3356-EP2281818A1; 3356-EP2287156A1; 3356-EP2289892A1; 3356-EP2289894A2; 3356-EP2292233A2; 3356-EP2292595A1; 3356-EP2292614A1; 3356-EP2292615A1; 3356-EP2292617A1; 3356-EP2295055A2; 3356-EP2295412A1; 3356-EP2295413A1; 3356-EP2295416A2; 3356-EP2295426A1; 3356-EP2295427A1; 3356-EP2298743A1; 3356-EP2298746A1; 3356-EP2298748A2; 3356-EP2298764A1; 3356-EP2298765A1; 3356-EP2298767A1; 3356-EP2298768A1; 3356-EP2298772A1; 3356-EP2298778A1; 3356-EP2298780A1; 3356-EP2301928A1; 3356-EP2301933A1; 3356-EP2305250A1; 3356-EP2305640A2; 3356-EP2305642A2; 3356-EP2305671A1; 3356-EP2305677A1; 3356-EP2305689A1; 3356-EP2308812A2; 3356-EP2308833A2; 3356-EP2308839A1; 3356-EP2308855A1; 3356-EP2308861A1; 3356-EP2311453A1; 3356-EP2311807A1; 3356-EP2311808A1; 3356-EP2311825A1; 3356-EP2311827A1; 3356-EP2311829A1; 3356-EP2311837A1; 3356-EP2311840A1; 3356-EP2311842A2; 3356-EP2314587A1; 3356-EP2314590A1; 3356-EP2316831A1; 3356-EP2316832A1; 3356-EP2316833A1; 3356-EP2316834A1; 3356-EP2371811A2; 3356-EP2374454A1; C07888; D07760; W-5035; 27353-EP2269998A2; 27353-EP2272516A2; 27353-EP2275404A1; 27353-EP2275469A1; 27353-EP2284171A1; 27353-EP2287940A1; 27353-EP2292227A2; 27353-EP2295550A2; 27353-EP2298762A2; 27353-EP2298768A1; 27353-EP2308839A1; 27353-EP2314587A1; 27353-EP2371795A1; AB00053446-09; AB00053446-11; AB00053446-12; AB00053446_13; AB00053446_14; AB00053446_15; 005C978; 110841-EP2272827A1; 110841-EP2298305A1; 139301-EP2270008A1; 139301-EP2292617A1; Q408524; W-60377; N,O-propylenephosphoric acid ester amide monohydrate; SR-01000075737-1; SR-01000075737-6; W-105248; BRD-A09722536-002-02-4; UNII-6UXW23996M component CMSMOCZEIVJLDB-CQSZACIVSA-N; 2-[bis(2-chloroethyl)amino]-1,3,2??-oxazaphosphinan-2-one; 2-[bis(2-chloroethyl)amino]-1,3,2$l^{5}-oxazaphosphinan-2-one; 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphosphaperhydroin-2-one; N,N-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide #; 2-(Di(2-chloroethyl)amino)-2-phospha(V)-tetrahydro-2H-1,3-oxazine-2-one; 2-[Bis(2-chloroethyl)amino]tetrahydro-1,3,2-oxazaphosphorin-2-oxide; 2H-1,2-Oxazaphosphorine, 2-[bis(2-chloroethyl)amino]tetrahydro-, 2-oxide; 2H-1,3,2-Oxazaphosphorine, 2-(bis(2-chloroethyl)amino)tetrahydro-,2-oxide; N,N-Bis(.beta.-chloroethyl)-N',O-trimethylenephosphoric acid ester diamide; N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine-2-oxide; N,N-Bis-(.beta.-chloraethyl)-N',O-propylen-phosphorsaeure-ester-diamid; (+/-)-2-[Bis(2-chloroethyl)amino]tetrahydro-2 H-1,3,2-oxazaphosphorine 2-oxide; (R)-2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin 2-oxide; (S)-2-[Bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide; 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, (+)-; 2H-1,2-Oxazaphosphorin-2-amine, N,N-bis(2-chloroethyl)tetrahydro-, 2-oxide, (-)-; N,N-bis(2-chloroethyl)-2-oxo-1-oxa-3-aza-2$l^{5}-phosphacyclohexan-2-amine
Clinical Status
Approved
Disease Indication Multiple myeloma ICD-11: 2A83 [1]
PubChem CID
2907
Formula
C7H15Cl2N2O2P
Canonical SMILES
C1CNP(=O)(OC1)N(CCCl)CCCl
InChI
1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChIKey
CMSMOCZEIVJLDB-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=2907"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 261.079 Topological Polar Surface Area 41.6
XlogP 0.6 Complexity 212
Heavy Atom Count 14 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Cyclophosphamide 25 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c red no. 40; Sodium stearyl fumarate; Butyl alcohol; Fd&c blue no. 1; Isopropyl alcohol; Ammonia; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Gelatin; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
          Cyclophosphamide 50 mg capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Fd&c red no. 40; Sodium stearyl fumarate; Butyl alcohol; Fd&c blue no. 1; Isopropyl alcohol; Ammonia; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Gelatin; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
          Cyclophosphamide 25 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Acacia; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Physicians Total Care; Roxane Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
          Cyclophosphamide 50 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Acacia; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company Physicians Total Care; Roxane Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
References
1 FDA label for approved cyclophosphamide from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
4 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
5 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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