Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00690)
Name
Topotecan
Synonyms    Click to Show/Hide the Synonyms of This API
topotecan; 123948-87-8; Hycamtin; Topotecan lactone; Hycamptamine; Topotecane; Topotecanum; Topotecane [INN-French]; Topotecanum [INN-Latin]; (S)-Topotecan; 9-Dimethylaminomethyl-10-hydroxycamptothecin; UNII-7M7YKX2N15; Topocecan free base; CHEMBL84; NSC609699; Hycamtin (TN); 7M7YKX2N15; Hycamtamine; CHEBI:63632; 123948-87-8 (free base); SK-S-104864-A; 9-[(dimethylamino)methyl]-10-hydroxy-(4S)-camptothecin; Hycamptin; Nogitecan; Topotecan [INN:BAN]; SKF-104864-A; SK&F-104864-A; TOPOTECANHYDROCHLORIDE; CHEMBL1607; Topophore C; Topotecan Actavis; TopoCED; Topotecan (BAN); SK&F-S-104864A; SR-01000763672; SK&F 104864 A; 9-Dimethylaminomethyl-10-hydroxycamptothecin.; CCRIS 8163; MFCD00870670; HSDB 8213; SKF-S 104864; SKF 104864; SCHEMBL3836; NCIStruc1_001659; NCIStruc2_001796; BSPBio_002348; cid_60699; GTPL7101; DTXSID3042685; EX-A834; HMS2090B20; HMS3715L03; ZINC1611274; BDBM50008935; BDBM50034026; HSCI1_000228; NSC641007; AKOS015966792; AT-2921; CCG-221171; DB01030; NSC-641007; SKF-104864; SMP2_000312; SMP2_000327; NCGC00014925-02; NCGC00014925-03; NCGC00014925-04; NCGC00014925-07; NCGC00014925-10; NCGC00014925-24; NCGC00178695-01; AC-11592; AK-72818; AS-75098; HY-13768; NCI60_004771; AB0015476; dimethylaminomethyl-ethyl-dihydroxy-[?]dione; A16815; C11158; D08618; W-1887; AB00641837-09; AB00641837-11; AB00641837-12; AB00641837-13; AB00641837-14; AB00641837_15; AB00641837_16; 948T878; Q419953; SR-01000763672-3; SR-01000763672-4; BRD-K55696337-001-03-2; BRD-K55696337-003-08-7; 123948-87-8 (net), 119413-54-6 (hydrochloride); Topotecan hydrochloride hydrate, >=98% (HPLC and enzymatic)
Clinical Status
Approved
Disease Indication Ovarian cancer ICD-11: 2C73 [1]
PubChem CID
60700
Formula
C23H23N3O5
Canonical SMILES
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC(=C5CN(C)C)O)N=C4C3=C2)O
InChI
1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
InChIKey
UCFGDBYHRUNTLO-QHCPKHFHSA-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=60700"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 421.4 Topological Polar Surface Area 103
XlogP 0.5 Complexity 867
Heavy Atom Count 31 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Topotecan 0.25 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 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
Glyceryl monostearate; Ferric oxide red; Titanium dioxide; Gelatin
                   Dosage Form Oral Capsule
                   Company Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
             Drug Formulation 2 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
Glyceryl monostearate; Titanium dioxide; Gelatin, unspecified
                   Dosage Form Oral Capsule
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
          Topotecan 1 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 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
Glyceryl monostearate; Ferric oxide red; Titanium dioxide; Gelatin
                   Dosage Form Oral Capsule
                   Company Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
             Drug Formulation 2 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
Glyceryl monostearate; Ferric oxide red; Titanium dioxide; Gelatin, unspecified
                   Dosage Form Oral Capsule
                   Company GlaxoSmithKline
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
          Topotecan Hydrochloride eq 4mg base/vial injectable Click to Show/Hide the Full List of Formulation(s):          2 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
Mannito; Tartaric Acid; Hydrochloric Acid; Sodium Hydroxide
                   Dosage Form Injectable
                   Company Fresenius Kabi Usa
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [4]
             Drug Formulation 2 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
Mannito; Tartaric Acid; Hydrochloric Acid
                   Dosage Form Injectable
                   Company Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [4]
          Topotecan Hydrochloride eq 0.25mg base 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
Gelatin; Glyceryl Monostearate; Hydrogenated Vegetable Oil; Titanium Dioxide; Red Iron Oxide
                   Dosage Form Capsule
                   Company Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Glyceryl monostearate DIG Info Prostate cancer LNCaP cells (IC50 > 100000 nM) [2]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [5]
References
1 FDA label for approved topotecan from the official website of the U.S. Food and Drug Administration.
2 Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds. J Nat Prod. 2002 Feb; 65(2):206-9.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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