Identification

Generic Name
Apatorsen
DrugBank Accession Number
DB06094
Background

Apatorsen is a second generation antisense drug which in preclinical experiments, inhibits production of Heat Shock Protein 27 (Hsp27) a cell survival protein found at elevated levels in many human cancers including prostate, lung, breast, ovarian, bladder, renal, pancreatic, multiple myeloma and liver cancer.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 7156.97
Monoisotopic: 7152.002582293
Chemical Formula
C224H304N79O116P19S19
Synonyms
  • Apatorsen

Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified).

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

OGX-427 significantly decreases levels of Hsp27, induces apoptosis in several human cancer cell lines, has single agent anti-tumor activity, and acts as a chemosensitizer in combination with several cytotoxic drugs including docetaxel.

Mechanism of action
TargetActionsOrganism
UHeat shock protein beta-1Not 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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Apatorsen sodium3N4G7RE66Y915443-09-3Not applicable

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
IFJ6X26JW6
CAS number
1002331-21-6
InChI Key
RMTMMKNSPRRFHW-UHFFFAOYSA-N
InChI
InChI=1S/C224H304N79O116P19S19/c1-88-46-284(216(318)257-168(88)225)129-34-97(401-420(327,439)363-60-114-102(39-134(386-114)289-52-94(7)187(306)281-222(289)324)406-421(328,440)362-56-110-98(35-130(381-110)285-47-89(2)169(226)258-217(285)319)402-422(329,441)368-63-119-107(44-139(390-119)297-81-252-147-182(297)267-211(237)276-194(147)313)411-430(337,449)372-66-121-108(45-140(392-121)298-82-253-148-183(298)268-212(238)277-195(148)314)412-431(338,450)375-69-123-154(163(357-29-21-349-13)201(396-123)292-54-96(9)189(308)283-224(292)326)414-435(342,454)377-70-124-155(162(356-28-20-348-12)200(395-124)290-51-93(6)173(230)262-221(290)323)415-436(343,455)378-72-126-157(165(359-31-23-351-15)203(398-126)300-84-247-142-175(232)243-76-245-177(142)300)417-433(340,452)374-68-122-152(305)160(354-26-18-346-10)199(394-122)291-53-95(8)188(307)282-223(291)325)111(382-129)57-364-426(333,445)407-103-40-135(293-77-248-143-178(293)263-207(233)272-190(143)309)387-116(103)61-367-423(330,442)403-99-36-131(286-48-90(3)170(227)259-218(286)320)384-113(99)59-366-428(335,447)409-105-42-137(295-79-250-145-180(295)265-209(235)274-192(145)311)391-120(105)65-371-429(336,448)410-106-43-138(296-80-251-146-181(296)266-210(236)275-193(146)312)389-118(106)62-369-424(331,443)404-100-37-132(287-49-91(4)171(228)260-219(287)321)383-112(100)58-365-427(334,446)408-104-41-136(294-78-249-144-179(294)264-208(234)273-191(144)310)388-117(104)64-370-425(332,444)405-101-38-133(288-50-92(5)172(229)261-220(288)322)385-115(101)67-373-432(339,451)416-156-125(397-202(164(156)358-30-22-350-14)299-83-246-141-174(231)242-75-244-176(141)299)71-379-437(344,456)419-159-128(400-206(167(159)361-33-25-353-17)303-87-256-151-186(303)271-215(241)280-198(151)317)74-380-438(345,457)418-158-127(399-205(166(158)360-32-24-352-16)302-86-255-150-185(302)270-214(240)279-197(150)316)73-376-434(341,453)413-153-109(55-304)393-204(161(153)355-27-19-347-11)301-85-254-149-184(301)269-213(239)278-196(149)315/h46-54,75-87,97-140,152-167,199-206,304-305H,18-45,55-74H2,1-17H3,(H,327,439)(H,328,440)(H,329,441)(H,330,442)(H,331,443)(H,332,444)(H,333,445)(H,334,446)(H,335,447)(H,336,448)(H,337,449)(H,338,450)(H,339,451)(H,340,452)(H,341,453)(H,342,454)(H,343,455)(H,344,456)(H,345,457)(H2,225,257,318)(H2,226,258,319)(H2,227,259,320)(H2,228,260,321)(H2,229,261,322)(H2,230,262,323)(H2,231,242,244)(H2,232,243,245)(H,281,306,324)(H,282,307,325)(H,283,308,326)(H3,233,263,272,309)(H3,234,264,273,310)(H3,235,265,274,311)(H3,236,266,275,312)(H3,237,267,276,313)(H3,238,268,277,314)(H3,239,269,278,315)(H3,240,270,279,316)(H3,241,271,280,317)
IUPAC Name
({2-[({[(2-{[({[2-({[({2-[({[(2-{[({[2-({[({2-[({[(2-{[({[5-(6-amino-9H-purin-9-yl)-2-({[hydroxy({[2-({[hydroxy({[2-({[hydroxy({[5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-yl]oxy})sulfanylidene-lambda5-phosphanyl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-4-(2-methoxyethoxy)oxolan-3-yl]oxy})sulfanylidene-lambda5-phosphanyl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-4-(2-methoxyethoxy)oxolan-3-yl]oxy})sulfanylidene-lambda5-phosphanyl]oxy}methyl)-4-(2-methoxyethoxy)oxolan-3-yl]oxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]methyl}-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-3-yl)oxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)methyl]-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl}oxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}methyl)-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-3-yl]oxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]methyl}-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl)oxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)methyl]-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl}oxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}methyl)-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-3-yl]oxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]methyl}-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl)oxy](hydroxy)sulfanylidene-lambda5-phosphanyl}oxy)methyl]-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-3-yl}oxy)({[3-({[(3-{[({3-[({[3-({[(3-{[({3-[({[5-(6-amino-9H-purin-9-yl)-3-{[hydroxy({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)-4-(2-methoxyethoxy)oxolan-2-yl]methoxy})sulfanylidene-lambda5-phosphanyl]oxy}-4-(2-methoxyethoxy)oxolan-2-yl]methoxy}(hydroxy)sulfanylidene-lambda5-phosphanyl)oxy]-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)-4-(2-methoxyethoxy)oxolan-2-yl}methoxy)(hydroxy)sulfanylidene-lambda5-phosphanyl]oxy}-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)-4-(2-methoxyethoxy)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-(2-hydroxy-4-imino-5-methyl-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})sulfanylidenephosphinous acid
SMILES
COCCOC1C(O)C(COP(O)(=S)OC2C(COP(O)(=S)OC3C(COP(O)(=S)OC4C(COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5CC(OC5COP(O)(=S)OC5C(COP(O)(=S)OC6C(COP(O)(=S)OC7C(COP(O)(=S)OC8C(CO)OC(C8OCCOC)N8C=NC9=C8NC(=N)N=C9O)OC(C7OCCOC)N7C=NC8=C7NC(=N)N=C8O)OC(C6OCCOC)N6C=NC7=C6NC(=N)N=C7O)OC(C5OCCOC)N5C=NC6=C(N)N=CN=C56)N5C=C(C)C(=N)N=C5O)N5C=NC6=C5NC(=N)N=C6O)N5C=C(C)C(=N)N=C5O)N5C=NC6=C5NC(=N)N=C6O)N5C=NC6=C5NC(=N)N=C6O)N5C=C(C)C(=N)N=C5O)N5C=NC6=C5NC(=N)N=C6O)N5C=C(C)C(=N)N=C5O)N5C=C(C)C(O)=NC5=O)N5C=C(C)C(=N)N=C5O)N5C=NC6=C5NC(=N)N=C6O)N5C=NC6=C5NC(=N)N=C6O)OC(C4OCCOC)N4C=C(C)C(O)=NC4=O)OC(C3OCCOC)N3C=C(C)C(=N)N=C3O)OC(C2OCCOC)N2C=NC3=C(N)N=CN=C23)OC1N1C=C(C)C(O)=NC1=O

References

General References
  1. Kamada M, So A, Muramaki M, Rocchi P, Beraldi E, Gleave M: Hsp27 knockdown using nucleotide-based therapies inhibit tumor growth and enhance chemotherapy in human bladder cancer cells. Mol Cancer Ther. 2007 Jan;6(1):299-308. Epub 2007 Jan 11. [Article]
  2. Rocchi P, Jugpal P, So A, Sinneman S, Ettinger S, Fazli L, Nelson C, Gleave M: Small interference RNA targeting heat-shock protein 27 inhibits the growth of prostatic cell lines and induces apoptosis via caspase-3 activation in vitro. BJU Int. 2006 Nov;98(5):1082-9. Epub 2006 Jul 28. [Article]
  3. Zoubeidi A, Zardan A, Beraldi E, Fazli L, Sowery R, Rennie P, Nelson C, Gleave M: Cooperative interactions between androgen receptor (AR) and heat-shock protein 27 facilitate AR transcriptional activity. Cancer Res. 2007 Nov 1;67(21):10455-65. [Article]
PubChem Compound
131704298
PubChem Substance
347827755

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentBladder Cancer, Cancer / Urothelial Carcinoma1
2CompletedTreatmentCastration Resistant Prostate Cancer1
2CompletedTreatmentMalignant Neoplasm of Pancreas1
2CompletedTreatmentMetastatic Bladder Cancer / Urinary Tract Neoplasms / Urologic Neoplasms1
2CompletedTreatmentNon-squamous Non-small-cell Lung Cancer (NSQ NSCLC)1
2TerminatedTreatmentMetastatic Castration Resistant Prostate Cancer (CRPC) / Prostate Cancer / Prostate Specific Antigen1
2Unknown StatusTreatmentSquamous Cell Carcinoma of Lung1
1CompletedTreatmentNeoplasms1
1Unknown StatusTreatmentBladder Cancer, Cancer1

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
logP11.4ChemAxon
pKa (Strongest Acidic)1.01ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count143ChemAxon
Hydrogen Donor Count65ChemAxon
Polar Surface Area2540.48 Å2ChemAxon
Rotatable Bond Count148ChemAxon
Refractivity1791.67 m3·mol-1ChemAxon
Polarizability662.51 Å3ChemAxon
Number of Rings51ChemAxon
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

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin binding
Specific Function
Involved in stress resistance and actin organization.
Gene Name
HSPB1
Uniprot ID
P04792
Uniprot Name
Heat shock protein beta-1
Molecular Weight
22782.3 Da

Drug created at November 18, 2007 18:29 / Updated at February 21, 2021 18:51