Details of the Drug

General Information of Drug (ID: DMK1CZJ)

Drug Name

Ingenol mebutate

Synonyms

Picato; Ingenol 3-angelate; 75567-37-2; PEP-005; PEP005; 3-Angeloylingenol; UNII-7686S50JAH; PEP 005; 3-Ingenyl angelate; Ingenol-3-angelate; 7686S50JAH; Picato (TN); Euphorbia factor H1; Euphorbia factor An1; Ingenol mebutate [USAN:INN]; [dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[ ]yl] (Z)-2-methylbut-2-enoate; I3A; Ingenol-3- angelate; Ingenol mebutate (USAN); (Z)-2-methylbut-2-enoate; SCHEMBL2526605; GTPL7443; CHEMBL1863513; HSDB 8308; VDJHFHXMUKFKET-WDUFCVPESA-N; MolPort-003-941-761; AN-262; POL-103A

Indication

Disease Entry	ICD 11	Status	REF
Actinic keratosis	EK90.0	Approved	[1], [2], [3]
Melanoma	2C30	Phase 3	[4]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

430.5

Topological Polar Surface Area (xlogp)

2

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C25H34O6
IUPAC Name: [(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
Canonical SMILES: C/C=C(/C)\\C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@H](C2=O)[C@H]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)C
InChI: InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
InChIKey: VDJHFHXMUKFKET-WDUFCVPESA-N

Cross-matching ID

PubChem CID: 6918670
ChEBI ID: CHEBI:66913
CAS Number: 75567-37-2
DrugBank ID: DB05013
TTD ID: D0E9KA
VARIDT ID: DR01483
ACDINA ID: D01160

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Sodium citrate anhydrous	E00102	6224	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Water	E00035	962	Solvent
Hydroxyethyl cellulose	E00700	Not Available	Coating agent; Suspending agent; Binding agent; Viscosity-controlling agent
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⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ingenol Mebutate 0.015% gel	0.02%	Gel	Topical
Ingenol Mebutate 0.05% gel	0.05%	Gel	Topical

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7443).
2	Nat Rev Drug Discov. 2013 Feb;12(2):87-90.
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4	ClinicalTrials.gov (NCT01546571) Study of a Melanoma Vaccine in Stage IIb, IIc, and III Melanoma Patients. U.S. National Institutes of Health.
5	The skin cancer chemotherapeutic agent ingenol-3-angelate (PEP005) is a substrate for the epidermal multidrug transporter (ABCB1) and targets tumor vasculature. Cancer Res. 2010 Jun 1;70(11):4509-19.
6	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
7	MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
8	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
9	Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
10	Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
11	Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
12	Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.