Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00258)
Name
Etoposide
Synonyms    Click to Show/Hide the Synonyms of This API
etoposide; VePesid; 33419-42-0; Toposar; trans-Etoposide; Lastet; (-)-Etoposide; Zuyeyidal; Etoposido; Etoposidum; Etoposidum [INN-Latin]; Etoposide (VP16); VP 16-213; Vepesid J; VP-16-213; 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside; UNII-6PLQ3CP4P3; NSC-141540; VP 16 (pharmaceutical); 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); 6PLQ3CP4P3; Epipodophyllotoxin VP-16213; CHEMBL44657; CHEBI:4911; NK 171; Demethylepipodophyllotoxin-beta-D-ethylideneglucoside; NSC 141540; 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside); Etosid; [1,3]benzodioxol-8-one; Etoposido [INN-Spanish]; Etopophos (phosphate salt); Vepeside; Etopol; VP 16213; MFCD00869325; NSC141540; Etoposide (VP-16); SMR000112002; CCRIS 2392; HSDB 6517; VePESID (TN); EINECS 251-509-1; 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside; Etoposide,(S); 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin; Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside); Etoposide [USAN:USP:INN:BAN:JAN]; Etoposide; VP-16; CPD000112002; Epipodophyllotoxin-beta-D-ethyliden-glucoside, 4'-demethyl-; Prestwick3_000396; SCHEMBL4259; BSPBio_000611; MLS000049957; MLS001074951; MLS001424283; MLS002153463; MLS002207239; MLS002222184; Etoposide (JP17/USP/INN); BPBio1_000673; GTPL6815; DTXSID5023035; etoposide4-o-b-d-galactopyranoside; HMS2052N05; HMS2089F14; HMS2096O13; HMS2232L03; HMS3713O13; EX-A1207; ZINC3938684; BDBM50127140; Etoposide - CAS 33419-42-0; AKOS007930275; AB07572; ACN-057122; BCP9000669; CCG-101165; CS-1774; DB00773; EBD2157958; Etoposide, synthetic, >=98%, powder; NC00415; SDCCGSBI-0050405.P002; 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside (8CI); NCGC00179504-02; AS-35312; HY-13629; SBI-0051910.P002; AB00438905; A-8109; C01576; D00125; 13165-EP2269989A1; 13165-EP2270008A1; 13165-EP2270014A1; 13165-EP2270018A1; 13165-EP2272827A1; 13165-EP2272832A1; 13165-EP2275413A1; 13165-EP2275420A1; 13165-EP2277565A2; 13165-EP2277566A2; 13165-EP2277567A1; 13165-EP2277568A2; 13165-EP2277569A2; 13165-EP2277570A2; 13165-EP2277865A1; 13165-EP2277876A1; 13165-EP2280012A2; 13165-EP2281815A1; 13165-EP2287156A1; 13165-EP2289892A1; 13165-EP2292280A1; 13165-EP2292614A1; 13165-EP2292615A1; 13165-EP2292617A1; 13165-EP2295055A2; 13165-EP2295416A2; 13165-EP2295426A1; 13165-EP2295427A1; 13165-EP2298305A1; 13165-EP2298746A1; 13165-EP2298748A2; 13165-EP2298764A1; 13165-EP2298765A1; 13165-EP2298768A1; 13165-EP2298772A1; 13165-EP2298778A1; 13165-EP2298780A1; 13165-EP2301928A1; 13165-EP2301933A1; 13165-EP2305640A2; 13165-EP2305642A2; 13165-EP2305671A1; 13165-EP2305679A1; 13165-EP2305689A1; 13165-EP2308812A2; 13165-EP2308833A2; 13165-EP2308839A1; 13165-EP2308855A1; 13165-EP2308861A1; 13165-EP2311453A1; 13165-EP2311807A1; 13165-EP2311808A1; 13165-EP2311825A1; 13165-EP2311827A1; 13165-EP2311829A1; 13165-EP2311840A1; 13165-EP2311842A2; 13165-EP2314574A1; 13165-EP2316832A1; 13165-EP2316833A1; 13165-EP2316834A1; 13165-EP2374454A1; AB00438905-17; AB00438905-18; AB00438905_19; 419E420; Q418817; SR-01000763196; SR-01000763196-3; BRD-K37798499-001-02-5; BRD-K37798499-001-05-8; BRD-K37798499-001-10-8; BRD-K37798499-001-14-0; BRD-K37798499-001-27-2; Etoposide, British Pharmacopoeia (BP) Reference Standard; Etoposide, European Pharmacopoeia (EP) Reference Standard; Etoposide, United States Pharmacopeia (USP) Reference Standard; 4''-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); Etoposide for system suitability, European Pharmacopoeia (EP) Reference Standard; 121471-01-0
Clinical Status
Approved
Disease Indication Testicular carcinoma ICD-11: 2C80 [1]
PubChem CID
36462
Formula
C29H32O13
Canonical SMILES
C[C@@H]1OC[C@@H]2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
InChI
1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-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=36462"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 588.6 Topological Polar Surface Area 161
XlogP 0.6 Complexity 969
Heavy Atom Count 42 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 13
Full List of Drug Formulations (DFMs) Containing This API
          Etoposide 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
Anhydrous citric acid; Fd&c red no. 40; Fd&c blue no. 1; Ferric oxide red; Glycerin; Propylene glycol; Titanium dioxide; Gelatin; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   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]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
          Etoposide Phosphate eq 100mg base/vial injectable 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
Sodium Citrate; Dextran 40
                   Dosage Form Injectable
                   Company E.R. Squibb & Sons L.L.C.; H2-Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [6]
References
1 FDA label for approved etoposide 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 PubChem BioAssay data set.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.

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