InterPAD - DETAILS

vincristine, 22-Oxovincaleukoblastine, Vinkristin, Leurocristine, Vincrystine, 57-22-7, leucristine, vincristin, Vincristinum [INN-Latin], Tecnocris, Oncovine, Vincristina [DCIT], Oncotcs, rel-Vincristine, Vincristina, Vincristinum, oncovin (brand name), DTXSID1032278, CHEBI:28445, NSC-67574, 22-oxo-vincaleukoblastine, Farmistin, DTXCID9012278, Vincristine (INN), CCRIS 5763, VIN, HSDB 3199, NCGC00163700-01, NCI-C04864, Vincrstine, EINECS 200-318-1, Leurocristine sulfate, Vincristinum (INN-Latin), UNII-5J49Q6B70F, (+)-Vincristine, LCR, VCR, CAS-57-22-7, Tecnocris (TN), 22-Oxovincaleukoblastin, 1217704-92-1, Vincasar (1:1 sulfate salt), Oncovin (1:1 sulfate salt), Vincrex (1:1 sulfate salt), Leurocristine;NSC-67574;22-Oxovincaleukoblastine, Vincristine (Leurocristine), SCHEMBL3709, CHEMBL90555, GTPL6785, L01CA02, HMS2090E19, Tox21_112067, BDBM50139772, Lilly 37231 (1:1 sulfate salt), Tox21_112067_1, NCGC00163700-02, NCGC00163700-04, NCGC00263543-01, NCI60_026703, SRI-10749-04, SRI-10749-05, FT-0698619, NS00009299, C07204, D08679, Q408977, Vincaleukoblastine, 22-oxo- 22-Oxovincaleukoblastine, methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate, methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

No.	Title	Href
1	Patchouli alcohol induces G0 /G1 cell cycle arrest and apoptosis in vincristine-resistant non-small cell lung cancer through ROS-mediated DNA damage. Thorac Cancer. 2023 Jul;14(21):2007-2017. doi: 10.1111/1759-7714.14982.	`Click`
2	Britannin a Sesquiterpene Lactone from Inula aucheriana Exerted an Anti-leukemic Effect in Acute Lymphoblastic Leukemia (ALL) Cells and Enhanced the Sensitivity of the Cells to Vincristine. Nutr Cancer. 2022;74(3):965-977. doi: 10.1080/01635581.2021.1931700.	`Click`
3	Britannin, a sesquiterpene lactone induces ROS-dependent apoptosis in NALM-6, REH, and JURKAT cell lines and produces a synergistic effect with vincristine. Mol Biol Rep. 2021 Sep;48(9):6249-6258. doi: 10.1007/s11033-021-06572-x.	`Click`

No.

Title

Href

Patchouli alcohol induces G0 /G1 cell cycle arrest and apoptosis in vincristine-resistant non-small cell lung cancer through ROS-mediated DNA damage. Thorac Cancer. 2023 Jul;14(21):2007-2017. doi: 10.1111/1759-7714.14982.

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Britannin a Sesquiterpene Lactone from Inula aucheriana Exerted an Anti-leukemic Effect in Acute Lymphoblastic Leukemia (ALL) Cells and Enhanced the Sensitivity of the Cells to Vincristine. Nutr Cancer. 2022;74(3):965-977. doi: 10.1080/01635581.2021.1931700.

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Britannin, a sesquiterpene lactone induces ROS-dependent apoptosis in NALM-6, REH, and JURKAT cell lines and produces a synergistic effect with vincristine. Mol Biol Rep. 2021 Sep;48(9):6249-6258. doi: 10.1007/s11033-021-06572-x.

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Name	Vincristine
PubChem CID	5978
Molecular Weight	825.0g/mol
Synonyms	vincristine, 22-Oxovincaleukoblastine, Vinkristin, Leurocristine, Vincrystine, 57-22-7, leucristine, vincristin, Vincristinum [INN-Latin], Tecnocris, Oncovine, Vincristina [DCIT], Oncotcs, rel-Vincristine, Vincristina, Vincristinum, oncovin (brand name), DTXSID1032278, CHEBI:28445, NSC-67574, 22-oxo-vincaleukoblastine, Farmistin, DTXCID9012278, Vincristine (INN), CCRIS 5763, VIN, HSDB 3199, NCGC00163700-01, NCI-C04864, Vincrstine, EINECS 200-318-1, Leurocristine sulfate, Vincristinum (INN-Latin), UNII-5J49Q6B70F, (+)-Vincristine, LCR, VCR, CAS-57-22-7, Tecnocris (TN), 22-Oxovincaleukoblastin, 1217704-92-1, Vincasar (1:1 sulfate salt), Oncovin (1:1 sulfate salt), Vincrex (1:1 sulfate salt), Leurocristine;NSC-67574;22-Oxovincaleukoblastine, Vincristine (Leurocristine), SCHEMBL3709, CHEMBL90555, GTPL6785, L01CA02, HMS2090E19, Tox21_112067, BDBM50139772, Lilly 37231 (1:1 sulfate salt), Tox21_112067_1, NCGC00163700-02, NCGC00163700-04, NCGC00263543-01, NCI60_026703, SRI-10749-04, SRI-10749-05, FT-0698619, NS00009299, C07204, D08679, Q408977, Vincaleukoblastine, 22-oxo- 22-Oxovincaleukoblastine, methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate, methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Drug Type	Small molecule
Formula	C₄₆H₅₆N₄O₁₀
SMILES	CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
InChI	1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
InChIKey	OGWKCGZFUXNPDA-XQKSVPLYSA-N
CAS Number	57-22-7
ChEMBL ID	CHEMBL90555
ChEBI ID	CHEBI:28445
TTD ID	D09QVV
Drug Bank ID	DB00541
KEGG ID	C07204
Toxicity	Organism	Test Type	Route(Dose)
	rat	LD50	intraperitoneal(165 mg/kg)
	mouse	LD50	intraperitoneal(254 mg/kg)
	rat	LD50	oral(322 mg/kg)
Structure			Download 2D MOL 3D MOL

Pair Name	Patchouli alcohol, Vincristine
Partner Name	Patchouli alcohol
Disease Info	[ICD-11: 2C25]	Lung cancer		Investigative
Biological Phenomena	Induction-->Blockade of cell cycle in G0/G1 phase
Gene Regulation	Down-regulation	Expression	ABCB1	hsa5243
	Down-regulation	Phosphorylation	AKT1	hsa207
	Up-regulation	Expression	BAX	hsa581
	Down-regulation	Expression	BCL2	hsa596
	Up-regulation	Expression	CASP3	hsa836
	Up-regulation	Expression	CASP9	hsa842
	Down-regulation	Expression	CCNE1	hsa898
	Down-regulation	Expression	CD44	hsa960
	Down-regulation	Expression	CDK2	hsa1017
	Up-regulation	Expression	CDKN1A	hsa1026
	Up-regulation	Phosphorylation	CHEK1	hsa1111
	Up-regulation	Phosphorylation	CHEK2	hsa11200
	Up-regulation	Phosphorylation	H2AX	hsa3014
	Down-regulation	Expression	PROM1	hsa8842
	Up-regulation	Expression	TP53	hsa7157
In Vitro Model	A-549	Lung adenocarcinoma	Homo sapiens (Human)	CVCL_0023
Result	Patchouli alcohol induces G0 /G1 cell cycle arrest and apoptosis in vincristine-resistant non-small cell lung cancer through ROS-mediated DNA damage

Pair Name	Britannin, Vincristine
Partner Name	Britannin
Disease Info	[ICD-11: 2B33.3]	Acute lymphoblastic leukemia		Investigative
Biological Phenomena	Induction-->ROS-mediated apoptosis
Gene Regulation	Up-regulation	Expression	BAX	hsa581
	Down-regulation	Expression	BCL2	hsa596
	Up-regulation	Expression	BIM	hsa10018
	Up-regulation	Expression	CASP3	hsa836
	Up-regulation	Expression	CDKN1A	hsa1026
	Up-regulation	Expression	PSMD9	hsa5715
	Down-regulation	Expression	XIAP	hsa331
In Vitro Model	MOLT-4	Adult T acute lymphoblastic leukemia	Homo sapiens (Human)	CVCL_0013
Result	The results of this study showed for the first time that Britannin, as a natural Sesquiterpene Lactone, has cytotoxic effects that could be considered as an anti-leukemic agent in the treatment of ALL. However, there is still a demand for further studies that examine the efficacy and the safety of this purified compound.

Pair Name	Britannin, Vincristine
Partner Name	Britannin
Disease Info	[ICD-11: 2B33.3]	Acute lymphoblastic leukemia		Investigative
Biological Phenomena	Induction-->ROS-mediated apoptosis
Gene Regulation	Up-regulation	Expression	BAX	hsa581
	Up-regulation	Expression	CDKN1A	hsa1026
	Up-regulation	Expression	PSMD9	hsa5715
	Up-regulation	Expression	ROS1	hsa6098
	Down-regulation	Expression	XIAP	hsa331
In Vitro Model	NALM-6	Adult B acute lymphoblastic leukemia	Homo sapiens (Human)	CVCL_0092
	Reh	Childhood B acute lymphoblastic leukemia	Homo sapiens (Human)	CVCL_1650
	Jurkat	Childhood T acute lymphoblastic leukemia	Homo sapiens (Human)	CVCL_0065
Result	Our results proposed a mechanism for the cytotoxic effect of Britannin, either as a single agent or in combination with Vincristine, in NALM-6 cells.