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P4405

Sigma-Aldrich

Podophyllotoxin

Empirical Formula (Hill Notation):
C22H22O8
CAS Number:
Molecular Weight:
414.41
Beilstein:
99163
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

form

powder

mp

183-184 °C (lit.)

storage temp.

2-8°C

SMILES string

COc1cc(cc(OC)c1OC)[C@H]2C3C(COC3=O)[C@@H](O)c4cc5OCOc5cc24

InChI

1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

InChI key

YJGVMLPVUAXIQN-XVVDYKMHSA-N

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Application

Podophyllotoxin has been used as a reference compound for evaluating the cytotoxicity in VERO cells. It has also been used as a reference standard in high-performance liquid chromatography (HPLC).

Packaging

100 mg in glass bottle
50 mg in poly bottle

Biochem/physiol Actions

Podophyllotoxin is a naturally occurring lignan obtained from resin podophyllin present in the genus Podophyllum. It exhibits antiviral and antimitotic properties. Podophyllotoxin may be used to treat anogenital warts in children and dermatological conditions caused by psoriasis vulgaris. It may also be used as a therapeutic agent to treat genital tumors, Wilms tumors, lung cancer, and lymphomas.
Inhibits microtubule assembly; antineoplastic.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Y Damayanthi et al.
Current medicinal chemistry, 5(3), 205-252 (1998-07-01)
Podophyllotoxin is a natural product isolated from Podophyllum peltatum and Podophyllum emodi and has long been known to possess medicinal properties. Etoposide (VP-16), a podophyllotoxin derivative, is currently in clinical use in the treatment of many cancers, particularly small cell
Svetlana M Bakunova et al.
Journal of medicinal chemistry, 52(7), 2016-2035 (2009-03-10)
Diamidine 1 (pentamidine) and 65 analogues (2-66) have been tested for in vitro antiprotozoal activities against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani, and for cytotoxicity against mammalian cells. Dications 32, 64, and 66 exhibited antitrypanosomal potencies equal or
Donald A Patrick et al.
Journal of medicinal chemistry, 50(10), 2468-2485 (2007-04-19)
3,5-bis(4-amidinophenyl)isoxazole (3)-an analogue of 2,5-bis(4-amidinophenyl)furan (furamidine) in which the central furan ring is replaced by isoxazole-and 42 novel analogues were prepared by two general synthetic pathways. The 43 isoxazole derivatives were assayed against Trypanosoma brucei rhodesiense (T. brucei rhodesiense) STIB900
Abdelhalim Babiker Mahmoud et al.
Frontiers in pharmacology, 11, 1246-1246 (2020-09-15)
In a screening of Sudanese medicinal plants for antiprotozoal activity, the chloroform fractions obtained by liquid-liquid partitioning from ethanolic extracts of fruits of Croton gratissimus var. gratissimus and stems of Cuscuta hyalina Roth ex Schult. exhibited in vitro activity against
Stanislav A Bakunov et al.
Journal of medicinal chemistry, 51(21), 6927-6944 (2008-10-10)
A series of cationically substituted 2-phenylbenzofurans 1- 49 have been synthesized, and their in vitro antiprotozoal properties against Trypanosoma brucei rhodesiense, Plasmodium falciparum, and Leishmania donovani, as well as cytotoxicity against mammalian cells, have been evaluated. Eight dications exhibited antitrypanosomal

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