Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H22O8 |
| Molecular Weight | 414.4053 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC(OC)=C1OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](O)C4=CC5=C(OCO5)C=C24
InChI
InChIKey=YJGVMLPVUAXIQN-XVVDYKMHSA-N
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
| Molecular Formula | C22H22O8 |
| Molecular Weight | 414.4053 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=affc1058-7355-4486-8b65-378fea6f9454Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=9562603
http://products.sanofi.ca/en/condyline.pdf
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=affc1058-7355-4486-8b65-378fea6f9454
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=9562603
http://products.sanofi.ca/en/condyline.pdf
Podofilox ((abbreviated as PPT), otherwise known as podofilox) is an antimitotic drug which can be chemically synthesized or purified from the plant families Coniferae and Berberidaceae (e.g. species of Juniperus and Podophyllum). Podofilox 0.5% solution is indicated for the topical treatment of external genital warts (Condyloma acuminatum). This product is not indicated in the treatment of perianal or mucous membrane warts. Treatment of genital warts with podofilox results in necrosis of visible wart tissue. The exact mechanism of action is unknown, but is believed to exert its antimitotic effect by binding to tubulin, at a site close to but not identical to the binding site of colchicine; it is thought that this antimitotic effect causes necrosis of wart tissue, the observed clinical effect. In addition, podofilox is known to interfere with nucleoside transport, which may also contribute to its action. Adverse effects reported in less than 5% of the patients included pain with intercourse, insomnia, tingling, bleeding, tenderness, chafing, malodor, dizziness, scarring, vesicle formation, crusting edema, dryness/peeling, foreskin irretraction, hematuria, vomiting and ulceration.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2011590 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CONDYLOX Approved UsePodofilox Topical Solution 0.5% is indicated for the topical treatment of external genital warts (Condyloma acuminatum). This product is not indicated in the treatment of perianal or mucous membrane warts (see PRECAUTIONS ). Diagnosis Although genital warts have a characteristic appearance, histopathologic confirmation should be obtained if there is any doubt of the diagnosis. Differentiating warts from squamous cell carcinoma (so-called Bowenoid papulosis) is of particular concern. Squamous cell carcinoma may also be associated with human papillomavirus but should not be treated with Podofilox Topical Solution 0.5%. Launch Date1990 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17 ng/mL |
1.5 mL single, topical dose: 1.5 mL route of administration: Topical experiment type: SINGLE co-administered: |
PODOFILOX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.5 h |
1.5 mL single, topical dose: 1.5 mL route of administration: Topical experiment type: SINGLE co-administered: |
PODOFILOX plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (49.4%) Sources: Pain (54.3%) Itching (59.3%) Bleeding (29.6%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (79.2%) Sources: Pain (79.2%) Itching (83.3%) Bleeding (45.8%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (52.3%) Sources: Pain (55.8%) Itching (60.5%) Bleeding (32.6%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (83.2%) Sources: Pain (49.6%) Itching (52.9%) Bleeding (28.6%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (71.4%) Sources: Pain (71.4%) Itching (57.1%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (81.9%) Sources: Pain (50.4%) Itching (52.8%) Bleeding (26.8%) |
0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Inflammation, Pain... Other AEs: Inflammation (mild, 32.2%) Sources: Pain (mild, 23.7%) Itching (mild, 32.2%) Bleeding (mild, 19.2%) Inflammation (moderate, 30.4%) Pain (moderate, 20.4%) Itching (moderate, 16%) Bleeding (moderate, 3%) Inflammation (severe, 9.3%) Pain (severe, 11.5%) Itching (severe, 7.8%) Bleeding (severe, 0.7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Bleeding | 29.6% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 49.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 54.3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 59.3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Bleeding | 45.8% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 79.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 79.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 83.3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Bleeding | 32.6% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 52.3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 55.8% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 60.5% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Bleeding | 28.6% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 49.6% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 52.9% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 83.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 57.1% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 71.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 71.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Bleeding | 26.8% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Pain | 50.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Itching | 52.8% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Inflammation | 81.9% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult |
| Bleeding | mild, 19.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Pain | mild, 23.7% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Inflammation | mild, 32.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Itching | mild, 32.2% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Itching | moderate, 16% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Pain | moderate, 20.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Bleeding | moderate, 3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Inflammation | moderate, 30.4% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Bleeding | severe, 0.7% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Pain | severe, 11.5% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Itching | severe, 7.8% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Inflammation | severe, 9.3% | 0.5 % 2 times / day multiple, topical Recommended Dose: 0.5 %, 2 times / day Route: topical Route: multiple Dose: 0.5 %, 2 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Transcription factor IID recruitment and Sp1 activation. Dual function of TAF1 in cyclin D1 transcription. | 2003-04-11 |
|
| [Bacteremia due to Capnocytophaga spp.: two cases]. | 2003-03 |
|
| Naphthalene analogues of lignans. | 2003-02-07 |
|
| Effect of a novel somatostatin analogue combined with cytotoxic drugs on human tumour xenografts and metastasis of B16 melanoma. | 2003-01-13 |
|
| Synthesis and cytotoxicity of podophyllotoxin analogues modified in the A ring. | 2003-01 |
|
| Effect of major nutrients on podophyllotoxin production in Podophyllum hexandrum suspension cultures. | 2003-01 |
|
| High-dose therapy in diffuse large cell lymphoma: results and prognostic factors in 452 patients from the GEL-TAMO Spanish Cooperative Group. | 2003-01 |
|
| An epiisopicropodophyllin aza analogue via palladium-catalyzed pseudo-domino cyclization. | 2002-12-27 |
|
| Chemoresistant or aggressive lymphoma predicts for a poor outcome following reduced-intensity allogeneic progenitor cell transplantation: an analysis from the Lymphoma Working Party of the European Group for Blood and Bone Marrow Transplantation. | 2002-12-15 |
|
| Prodrugs of 4'-demethyl-4-deoxypodophyllotoxin: synthesis and evaluation of the antitumor activity. | 2002-12-02 |
|
| [External anogenital condylomas]. | 2002-11-21 |
|
| [Management of external genital warts by dermatologists: a French survey]. | 2002-11-21 |
|
| [Incidence and management of condylomata acuminata by French general physicians]. | 2002-11-21 |
|
| Hemi-synthesis and biological activity of new analogues of podophyllotoxin. | 2002-11 |
|
| Optimization of culture parameters for production of podophyllotoxin in suspension culture of Podophyllum hexandrum. | 2002-10-25 |
|
| External genital warts: diagnosis, treatment, and prevention. | 2002-10-15 |
|
| Methamphetamine activates DNA binding of specific redox-responsive transcription factors in mouse brain. | 2002-10-01 |
|
| Meiotic telomere clustering is inhibited by colchicine but does not require cytoplasmic microtubules. | 2002-10-01 |
|
| Zinc enhances the expression of interleukin-2 and interleukin-2 receptors in HUT-78 cells by way of NF-kappaB activation. | 2002-10 |
|
| Experimental study of podophyllotoxin dipalmitoylphosphatidylcholine liposome for topical skin application. | 2002-10 |
|
| Biosynthesis of podophyllotoxin in Linum album cell cultures. | 2002-10 |
|
| A multicomponent reaction for the one-pot synthesis of 4-aza-2,3-didehydropodophyllotoxin and derivatives. | 2002-09-19 |
|
| Four lignans from Commiphora erlangeriana. | 2002-09 |
|
| [Changes in serum concentration of podophyllotoxin after its topical application with liposome on rat skin]. | 2002-09 |
|
| Cytogenetic analysis of giant oocytes and zygotes to assess their relevance for the development of digynic triploidy. | 2002-09 |
|
| Differential modulation by estradiol of P-glycoprotein drug resistance protein expression in cultured MCF7 and T47D breast cancer cells. | 2002-08-15 |
|
| Biological activity of 4-acetyltropolone, the minor component of Thujopsis dolabrata SIeb. et Zucc. hondai Mak. | 2002-08 |
|
| Antioxidative activity of spin labeled derivatives of podophyllic acid hydrazide. | 2002-08 |
|
| [Poisoning with a podophyllin-containing wart-treating tincture]. | 2002-07-12 |
|
| Unusual implantation site of a port-a-cath system via the right femoral vein. | 2002-07 |
|
| A unique type II topoisomerase mutant that is hypersensitive to a broad range of cleavage-inducing antitumor agents. | 2002-06-25 |
|
| Microtubule damaging agents induce apoptosis in HL 60 cells and G2/M cell cycle arrest in HT 29 cells. | 2002-06-14 |
|
| Flow cytometric estimation on cytotoxic activity of leaf extracts from seashore plants in subtropical Japan: isolation, quantification and cytotoxic action of (-)-deoxypodophyllotoxin. | 2002-06 |
|
| Effect of the DNA topoisomerase II inhibitor VP-16 on illegitimate recombination in yeast chromosomes. | 2002-05-29 |
|
| Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method. | 2002-05-23 |
|
| A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs. | 2002-05-20 |
|
| Treatment of non-Hodgkin's lymphoma in the elderly. The Italian studies. | 2002-05-07 |
|
| The treatment of anogenital warts at home. | 2002-04-17 |
|
| Antitumor and antioxidant activity of spin labeled derivatives of podophyllotoxin (GP-1) and congeners. | 2002-04-05 |
|
| Evaluation of Podophyllum peltatum accessions for podophyllotoxin production. | 2002-04 |
|
| Clinical inquiries. What is the most effective treatment for external genital warts? | 2002-04 |
|
| Facial molluscum: treatment with cryotherapy and podophyllotoxin. | 2002-04 |
|
| Deoxypodophyllotoxin; the cytotoxic and antiangiogenic component from Pulsatilla koreana. | 2002-03 |
|
| Synthesis and insecticidal activity of novel 4beta-halogenated benzoylamino podophyllotoxins against Pieris rapae Linnaeus. | 2002-03 |
|
| Identification of a novel variant of the human NR2B gene promoter region and its possible association with schizophrenia. | 2002 |
|
| [High-dose chemotherapy with autologous bone marrow transplantation in children with high-risk malignant neoformations]. | 2002 |
|
| Minimising the long-term adverse effects of childhood leukaemia therapy. | 2002 |
|
| Linker length in podophyllotoxin-acridine conjugates determines potency in vivo and in vitro as well as specificity against MDR cell lines. | 2001-12 |
|
| Consolidation therapy for childhood acute lymphoblastic leukaemia: clinical and cellular pharmacology of cytosine arabinoside, epipodophyllotoxins and cyclophosphamide. | 2001-12 |
|
| [Synthesis and activities of 4-deoxy-4 beta-arylmehtylene sulfonylamido-4'-demethylpodophyllotoxins]. | 2001-02 |
Sample Use Guides
Apply twice daily morning and evening (every 12 hours), for 3 consecutive days, then withhold use for 4 consecutive days. This 1 week cycle of treatment may be repeated up to four times until there is no visible wart tissue. Podofilox 0.5% solution is applied to the warts with a cotton-tipped applicator supplied with the drug. The drug-dampened applicator should be touched to the wart to be treated, applying the minimum amount of solution necessary to cover the lesion. Treatment should be limited to less than 10 cm2 of wart tissue and to no more than 0.5 mL of the solution per day.
Route of Administration:
Vaginal
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:53:19 GMT 2025
by
admin
on
Mon Mar 31 17:53:19 GMT 2025
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| Record UNII |
L36H50F353
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008732
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NCI_THESAURUS |
C67421
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WHO-ATC |
D06BB04
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WHO-VATC |
QD06BB04
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10607
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7238
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8463
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m8933
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CHEMBL61
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24818
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C29368
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PODOPHYLLOTOXIN
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DTXSID3045645
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |