Podophyllotoxin

Podophyllotoxin
Clinical data
Trade names	Condylox, Wartec, others
Other names	(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d] [1,3]dioxol-6(5aH)-one
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy; category	C;
ATC code	D07BB04 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	1.0 to 4.5 hours.
Identifiers
	IUPAC name (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one;
CAS Number	518-28-5 ;
PubChem CID	10607;
DrugBank	DB01179 ;
ChemSpider	10162 ;
UNII	L36H50F353;
KEGG	D05529 ;
ChEBI	CHEBI:50305 ;
ChEMBL	ChEMBL61 ;
CompTox Dashboard (EPA)	DTXSID3045645 ;
ECHA InfoCard	100.007.502
Chemical and physical data
Formula	C22H22O8
Molar mass	414.410 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	183.3 to 184 °C (361.9 to 363.2 °F)
	SMILES COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5[C@@H]2C(=O)OC5)O)OCO4;
	InChI 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 ; Key:YJGVMLPVUAXIQN-XVVDYKMHSA-N ;
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Podophyllotoxin (PPT) is the active ingredient in Podofilox, which is a medical cream that is used to treat genital warts and molluscum contagiosum.^[2] It is not recommended in HPV infections without external warts.^[2] It can be applied either by a healthcare provider or the person themselves.^[2]

It is a non-alkaloid toxin lignin extracted from the roots and rhizomes of Podophyllum species.^[3] A less refined form known as podophyllum resin is also available, but has greater side effects.^[4]^[5]

Podophyllotoxin was first isolated in pure form in 1880 by Valerian Podwyssotzki (1818 – 28 January 1892), a Polish-Russian privatdozent at the University of Dorpat (now: Tartu, Estonia) and assistant at the Pharmacological Institute there.^[6]^[7]^[8]

It is on the World Health Organization's List of Essential Medicines.^[9]

^ "What is Condylox?" (in German). Retrieved 2018-08-15.
^ ^a ^b ^c "Podofilox". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
^ Xu H, Lv M, Tian X (2009). "A review on hemisynthesis, biosynthesis, biological activities, mode of action, and structure-activity relationship of podophyllotoxins: 2003-2007". Current Medicinal Chemistry. 16 (3): 327–49. doi:10.2174/092986709787002682. PMID 19149581.
^ "Podophyllum Resin". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 307. hdl:10665/44053. ISBN 9789241547659.
^
See:
- Podwyssotzki V (1880). "Pharmakologische Studien über Podophyllum peltatum" [Pharmacological studies of Podophyllum peltatum]. Archiv für experimentelle Pathologie und Pharmakologie (in German). 13 (1–2): 29–52. doi:10.1007/BF01833268. S2CID 33803976. Podwyssotzki named podophyllotoxin on p. 30: " … ich nenne sie bis auf weiteres Podophyllotoxin." ( … for the time being I call it "podophyllotoxin".)
- Podwyssotzki V (10 September 1881). "The active constituents of podophyllotoxin". Pharmaceutical Journal and Transactions. 3rd series. 12: 217–219.
- Podwyssotzki V (March 1882). "On the active constituents of podophyllin". American Journal of Pharmacy. 54: 102–115.
- Podwyssotzki V (1882). "Über die wirksamen Bestandtheile des Podophyllins" [On the active components of podophyllin]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15: 377–378.
- Obituary: Kobert R (February 1893). "Valerian Podwyssotzki". Bulletin of Pharmacy. 7 (2): 49–52.
^ Cragg GM, Kingston DG, Newman DJ (2011). Anticancer Agents from Natural Products, Second Edition (2 ed.). CRC Press. p. 97. ISBN 9781439813836.
^ Shah Z, Gohar UF, Jamshed I, Mushtaq A, Mukhtar H, Zia-Ui-Haq M, et al. (April 2021). "Podophyllotoxin: History, Recent Advances and Future Prospects". Biomolecules. 11 (4): 603. doi:10.3390/biom11040603. PMC 8073934. PMID 33921719.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[1] "What is Condylox?" (in German). Retrieved 2018-08-15.

[AHFS2016-2] "Podofilox". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.

[3] Xu H, Lv M, Tian X (2009). "A review on hemisynthesis, biosynthesis, biological activities, mode of action, and structure-activity relationship of podophyllotoxins: 2003-2007". Current Medicinal Chemistry. 16 (3): 327–49. doi:10.2174/092986709787002682. PMID 19149581.

[AHFS2016R-4] "Podophyllum Resin". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.

[WHO2008-5] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 307. hdl:10665/44053. ISBN 9789241547659.

[6] See:
Podwyssotzki V (1880). "Pharmakologische Studien über Podophyllum peltatum" [Pharmacological studies of Podophyllum peltatum]. Archiv für experimentelle Pathologie und Pharmakologie (in German). 13 (1–2): 29–52. doi:10.1007/BF01833268. S2CID 33803976. Podwyssotzki named podophyllotoxin on p. 30: " … ich nenne sie bis auf weiteres Podophyllotoxin." ( … for the time being I call it "podophyllotoxin".)

Podwyssotzki V (10 September 1881). "The active constituents of podophyllotoxin". Pharmaceutical Journal and Transactions. 3rd series. 12: 217–219.

Podwyssotzki V (March 1882). "On the active constituents of podophyllin". American Journal of Pharmacy. 54: 102–115.

Podwyssotzki V (1882). "Über die wirksamen Bestandtheile des Podophyllins" [On the active components of podophyllin]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15: 377–378.

Obituary: Kobert R (February 1893). "Valerian Podwyssotzki". Bulletin of Pharmacy. 7 (2): 49–52.

[7] Podwyssotzki V (1880). "Pharmakologische Studien über Podophyllum peltatum" [Pharmacological studies of Podophyllum peltatum]. Archiv für experimentelle Pathologie und Pharmakologie (in German). 13 (1–2): 29–52. doi:10.1007/BF01833268. S2CID 33803976. Podwyssotzki named podophyllotoxin on p. 30: " … ich nenne sie bis auf weiteres Podophyllotoxin." ( … for the time being I call it "podophyllotoxin".)

[8] Podwyssotzki V (10 September 1881). "The active constituents of podophyllotoxin". Pharmaceutical Journal and Transactions. 3rd series. 12: 217–219.

[9] Podwyssotzki V (March 1882). "On the active constituents of podophyllin". American Journal of Pharmacy. 54: 102–115.

[10] Podwyssotzki V (1882). "Über die wirksamen Bestandtheile des Podophyllins" [On the active components of podophyllin]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15: 377–378.

[11] Obituary: Kobert R (February 1893). "Valerian Podwyssotzki". Bulletin of Pharmacy. 7 (2): 49–52.

[7] Cragg GM, Kingston DG, Newman DJ (2011). Anticancer Agents from Natural Products, Second Edition (2 ed.). CRC Press. p. 97. ISBN 9781439813836.

[8] Shah Z, Gohar UF, Jamshed I, Mushtaq A, Mukhtar H, Zia-Ui-Haq M, et al. (April 2021). "Podophyllotoxin: History, Recent Advances and Future Prospects". Biomolecules. 11 (4): 603. doi:10.3390/biom11040603. PMC 8073934. PMID 33921719.

[WHO22nd-9] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

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Clinical data

Trade names	Condylox,^[1] Wartec, others
Other names	(5R,5aR,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d] [1,3]dioxol-6(5aH)-one
AHFS/Drugs.com	Monograph
MedlinePlus	a684055
Pregnancy category	C
ATC code	D07BB04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	1.0 to 4.5 hours.
Identifiers
IUPAC name (10R,11R,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,7.0^11,15]hexadeca-1,3(7),8-trien-12-one
CAS Number	518-28-5^Y
PubChem CID	10607
DrugBank	DB01179^N
ChemSpider	10162^Y
UNII	L36H50F353
KEGG	D05529^Y
ChEBI	CHEBI:50305^Y
ChEMBL	ChEMBL61^Y
CompTox Dashboard (EPA)	DTXSID3045645
ECHA InfoCard	100.007.502
Chemical and physical data
Formula	C₂₂H₂₂O₈
Molar mass	414.410 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	183.3 to 184 °C (361.9 to 363.2 °F)
SMILES COc1cc(cc(c1OC)OC)[C@@H]2c3cc4c(cc3[C@@H]([C@@H]5[C@@H]2C(=O)OC5)O)OCO4
InChI 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^Y Key:YJGVMLPVUAXIQN-XVVDYKMHSA-N^Y
^NY (what is this?) (verify)