Aprinocarsen

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Aprinocarsen
DrugBank Accession Number
DB06451
Background

Aprinocarsen is a specific antisense oligonucleotide inhibitor of protein kinase C-alpha.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 6435.16
Monoisotopic: 6430.594330658
Chemical Formula
C196H249N68O105P19S19
Synonyms
  • Aprinocarsen
  • PKC-alpha
External IDs
  • ISIS 3521
  • ISIS-3521
  • LY 900003
  • LY-900003
  • LY900003

Pharmacology

Indication

Investigated for use/treatment in lung cancer.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein kinase C alpha typeNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Aprinocarsen sodium1U68ZWZ6OX331257-53-5Not applicable
International/Other Brands
Affintak

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
FMT95051CQ
CAS number
151879-73-1
InChI Key
NMYKBZSMOUFOJV-UHFFFAOYSA-N
InChI
InChI=1S/C196H249N68O105P19S19/c1-75-37-249(189(285)237-165(75)267)132-23-89(109(337-132)51-313-371(294,390)351-84-18-141(331-103(84)45-265)259-69-215-149-159(259)225-179(203)231-173(149)275)359-378(301,397)320-54-112-92(26-135(340-112)252-40-78(4)168(270)240-192(252)288)358-377(300,396)315-48-106-86(20-129(334-106)246-14-10-124(198)222-186(246)282)353-372(295,391)318-52-110-90(24-133(338-110)250-38-76(2)166(268)238-190(250)286)356-376(299,395)316-49-107-88(22-131(335-107)248-16-12-126(200)224-188(248)284)355-374(297,393)326-60-118-98(32-142(346-118)260-70-216-150-160(260)226-180(204)232-174(150)276)365-383(306,402)317-50-108-87(21-130(336-108)247-15-11-125(199)223-187(247)283)354-373(296,392)319-53-111-95(29-138(339-111)255-43-81(7)171(273)243-195(255)291)362-381(304,400)328-62-120-102(36-146(348-120)264-74-220-154-164(264)230-184(208)236-178(154)280)369-388(311,407)330-64-122-100(34-144(350-122)262-72-218-152-162(262)228-182(206)234-176(152)278)367-385(308,404)324-58-116-96(30-139(344-116)256-44-82(8)172(274)244-196(256)292)363-382(305,401)327-61-119-101(35-145(347-119)263-73-219-153-163(263)229-183(207)235-177(153)279)368-387(310,406)325-59-117-97(31-140(345-117)258-68-214-148-156(202)210-66-212-158(148)258)364-386(309,405)329-63-121-99(33-143(349-121)261-71-217-151-161(261)227-181(205)233-175(151)277)366-384(307,403)323-57-115-94(28-137(343-115)254-42-80(6)170(272)242-194(254)290)361-380(303,399)322-56-114-93(27-136(342-114)253-41-79(5)169(271)241-193(253)289)360-379(302,398)321-55-113-91(25-134(341-113)251-39-77(3)167(269)239-191(251)287)357-375(298,394)314-47-105-85(19-128(333-105)245-13-9-123(197)221-185(245)281)352-370(293,389)312-46-104-83(266)17-127(332-104)257-67-213-147-155(201)209-65-211-157(147)257/h9-16,37-44,65-74,83-122,127-146,265-266H,17-36,45-64H2,1-8H3,(H,293,389)(H,294,390)(H,295,391)(H,296,392)(H,297,393)(H,298,394)(H,299,395)(H,300,396)(H,301,397)(H,302,398)(H,303,399)(H,304,400)(H,305,401)(H,306,402)(H,307,403)(H,308,404)(H,309,405)(H,310,406)(H,311,407)(H2,197,221,281)(H2,198,222,282)(H2,199,223,283)(H2,200,224,284)(H2,201,209,211)(H2,202,210,212)(H,237,267,285)(H,238,268,286)(H,239,269,287)(H,240,270,288)(H,241,271,289)(H,242,272,290)(H,243,273,291)(H,244,274,292)(H3,203,225,231,275)(H3,204,226,232,276)(H3,205,227,233,277)(H3,206,228,234,278)(H3,207,229,235,279)(H3,208,230,236,280)
IUPAC Name
1-[4-({[(3-{[({3-[({[3-({[(3-{[({3-[({[3-({[(3-{[({3-[({[3-({[(3-{[({3-[({[5-(6-amino-9H-purin-9-yl)-3-({[(3-{[({3-[({[3-({[(3-{[({3-[({[5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl)methoxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)-5-({[hydroxy({[5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy})sulfanylidene-lambda5-phosphanyl]oxy}methyl)oxolan-2-yl]-4-hydroxy-5-methyl-1,2-dihydropyrimidin-2-one
SMILES
[H]C1(O)CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])COP(O)(=S)OC1([H])CC([H])(OC1([H])CO)N1C=NC2=C1NC(=N)N=C2O)N1C=C(C)C(O)=NC1=O)N1C=C(C)C(O)=NC1=O)N1C=CC(=N)N=C1O)N1C=C(C)C(O)=NC1=O)N1C=CC(=N)N=C1O)N1C=NC2=C1NC(=N)N=C2O)N1C=CC(=N)N=C1O)N1C=C(C)C(O)=NC1=O)N1C=NC2=C1NC(=N)N=C2O)N1C=NC2=C1NC(=N)N=C2O)N1C=C(C)C(O)=NC1=O)N1C=NC2=C1NC(=N)N=C2O)N1C=NC2=C(N)N=CN=C12)N1C=NC2=C1NC(=N)N=C2O)N1C=C(C)C(O)=NC1=O)N1C=C(C)C(O)=NC1=O)N1C=C(C)C(O)=NC1=O)N1C=CC(=N)N=C1O)N1C=NC2=C(N)N=CN=C12

References

General References
Not Available
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentLung Cancers1
3CompletedTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
2CompletedTreatmentBreast Cancer1
2CompletedTreatmentLung Cancers / Malignant Melanoma of Skin / Melanoma (Skin)1
2CompletedTreatmentNeoplasms, Lung / Non-Small Cell Lung Carcinoma (NSCLC) / Pulmonary Neoplasms1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP12.87ChemAxon
pKa (Strongest Acidic)1.03ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count119ChemAxon
Hydrogen Donor Count57ChemAxon
Polar Surface Area2279.07 Å2ChemAxon
Rotatable Bond Count116ChemAxon
Refractivity1555.79 m3·mol-1ChemAxon
Polarizability575.31 Å3ChemAxon
Number of Rings48ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...
Gene Name
PRKCA
Uniprot ID
P17252
Uniprot Name
Protein kinase C alpha type
Molecular Weight
76749.445 Da
References
  1. Lahn M, Sundell K, Kohler G: The role of protein kinase C-alpha in hematologic malignancies. Acta Haematol. 2006;115(1-2):1-8. [PubMed:16424642]
  2. Vansteenkiste J, Canon JL, Riska H, Pirker R, Peterson P, John W, Mali P, Lahn M: Randomized phase II evaluation of aprinocarsen in combination with gemcitabine and cisplatin for patients with advanced/metastatic non-small cell lung cancer. Invest New Drugs. 2005 Jun;23(3):263-9. [PubMed:15868384]

Drug created on March 19, 2008 16:33 / Updated on February 21, 2021 18:52