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Identification
NameTemsirolimus
Accession NumberDB06287
TypeSmall Molecule
GroupsApproved
Description

Temsirolimus is an intravenous drug for the treatment of renal cell carcinoma (RCC), developed by Wyeth Pharmaceuticals and approved by the FDA in late May 2007, and was also approved by the European Medicines Agency (EMEA) on November 2007. It is a derivative of sirolimus and is sold as Torisel.

Structure
Thumb
Synonyms
42-[3-Hydroxy-2-(hydroxymethyl)-2-methylpropanoate]rapamycin
Torisel
External Identifiers
  • CCI-779
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ToriselkitWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.2007-07-01Not applicableUs
Toriselliquid25 mgintravenousPfizer Canada Inc2008-01-11Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII624KN6GM2T
CAS number162635-04-3
WeightAverage: 1030.2871
Monoisotopic: 1029.602485741
Chemical FormulaC56H87NO16
InChI KeyCBPNZQVSJQDFBE-FUXHJELOSA-N
InChI
InChI=1S/C56H87NO16/c1-33-17-13-12-14-18-34(2)45(68-9)29-41-22-20-39(7)56(67,73-41)51(63)52(64)57-24-16-15-19-42(57)53(65)71-46(30-43(60)35(3)26-38(6)49(62)50(70-11)48(61)37(5)25-33)36(4)27-40-21-23-44(47(28-40)69-10)72-54(66)55(8,31-58)32-59/h12-14,17-18,26,33,35-37,39-42,44-47,49-50,58-59,62,67H,15-16,19-25,27-32H2,1-11H3/b14-12+,17-13+,34-18+,38-26+/t33-,35-,36-,37-,39-,40+,41+,42+,44-,45+,46+,47-,49-,50+,56-/m1/s1
IUPAC Name
(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-2,3,10,14,20-pentaoxo-11,36-dioxa-4-azatricyclo[30.3.1.0⁴,⁹]hexatriaconta-16,24,26,28-tetraen-12-yl]propyl]-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate
SMILES
OCC(C)(CO)C(=O)O[C@@H]1CC[C@@H](C[C@@H](C)[C@]2([H])CC(=O)[[email protected]](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[[email protected]](C)C[[email protected]](C)\C=C\C=C\C=C(C)\[C@@H](OC)C[C@]3([H])CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N3CCCC[[email protected]]3C(=O)O2)C[[email protected]]1OC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolide lactams
Sub ClassNot Available
Direct ParentMacrolide lactams
Alternative Parents
Substituents
  • Macrolide lactam
  • Macrolide
  • Alpha-amino acid ester
  • Beta-hydroxy acid
  • Piperidine
  • Oxane
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Cyclic ketone
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Lactam
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of renal cell carcinoma (RCC). Also investigated for use/treatment in breast cancer, lymphoma (unspecified), rheumatoid arthritis, and multiple myeloma.
PharmacodynamicsNot Available
Mechanism of actionTemsirolimus is an inhibitor of mTOR (mammalian target of rapamycin). Temsirolimus binds to an intracellular protein (FKBP-12), and the protein-drug complex inhibits the activity of mTOR that controls cell division. Inhibition of mTOR activity resulted in a G1 growth arrest in treated tumor cells. When mTOR was inhibited, its ability to phosphorylate p70S6k and S6 ribosomal protein, which are downstream of mTOR in the PI3 kinase/AKT pathway was blocked. In in vitro studies using renal cell carcinoma cell lines, temsirolimus inhibited the activity of mTOR and resulted in reduced levels of the hypoxia-inducible factors HIF-1 and HIF-2 alpha, and the vascular endothelial growth factor.
Related Articles
AbsorptionInfused intravenous over 30 - 60 minutes. Cmax is typically observed at the end of infusion
Volume of distribution

172 L in whole blood of cancer patients; both temsirolimus and sirolimus are extensive distributed partitioned into formed blood elements

Protein binding87% bound to plasma proteins in vitro at a concentration of 100 ng/ml
Metabolism

Primarily metabolized by cytochrome P450 3A4 in the human liver. Sirolimus, an equally potent metabolite, is the primary metabolite in humans following IV infusion. Other metabolic pathways observed in in vitro temsirolimus metabolism studies include hydroxylation, reduction and demethylation.

SubstrateEnzymesProduct
Temsirolimus
Not Available
SirolimusDetails
Route of eliminationExcreted predominantly in feces (76%), 4.6% of drug and metabolites recovered in urine. 17% of drug was not recovered by either route following a 14-day sample collection.
Half lifeTemsirolimus exhibits a bi-exponential decline in whole blood concentrations and the mean half-lives of temsirolimus and sirolimus were 17.3 hr and 54.6 hr, respectively.
Clearance

16.2 L/h (22%)

ToxicityTemsirolimus has been administered to patients with cancer in phase 1 and 2 trials with repeated intravenous doses as high as 220 mg/m2. The risk of several serious adverse events, including thrombosis, bowel perforation, interstitial lung disease (ILD), seizure, and psychosis, is increased with doses of temsirolimus greater than 25 mg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8908
Blood Brain Barrier-0.9494
Caco-2 permeable-0.664
P-glycoprotein substrateSubstrate0.8122
P-glycoprotein inhibitor IInhibitor0.8098
P-glycoprotein inhibitor IIInhibitor0.7467
Renal organic cation transporterNon-inhibitor0.7636
CYP450 2C9 substrateNon-substrate0.8699
CYP450 2D6 substrateNon-substrate0.8845
CYP450 3A4 substrateSubstrate0.7533
CYP450 1A2 substrateNon-inhibitor0.9126
CYP450 2C9 inhibitorNon-inhibitor0.8957
CYP450 2D6 inhibitorNon-inhibitor0.942
CYP450 2C19 inhibitorNon-inhibitor0.9155
CYP450 3A4 inhibitorNon-inhibitor0.9558
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9398
Ames testNon AMES toxic0.6087
CarcinogenicityNon-carcinogens0.9367
BiodegradationNot ready biodegradable0.9522
Rat acute toxicity2.8760 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9703
hERG inhibition (predictor II)Non-inhibitor0.7479
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Kit
Liquidintravenous25 mg
Prices
Unit descriptionCostUnit
Torisel 25 mg kit1467.89USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2187024 No2004-08-102015-04-14Canada
CA2429020 No2009-05-262021-11-13Canada
US5362718 Yes1999-08-152019-08-15Us
US8026276 Yes2006-07-202026-07-20Us
US8299116 Yes2004-01-252024-01-25Us
US8455539 Yes2004-01-252024-01-25Us
US8722700 Yes2004-01-252024-01-25Us
US8791097 Yes2012-11-102032-11-10Us
USRE44768 Yes1999-08-152019-08-15Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00235 mg/mLALOGPS
logP4.39ALOGPS
logP7.13ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area241.96 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity277.07 m3·mol-1ChemAxon
Polarizability112.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Kwang-Chung Lee, Ting-Huei Lee, Yen-Shih Tung, Chia-Chen Kao, Tzu-Ai Lee, “Process for preparation of temsirolimus.” U.S. Patent US20100249415, issued September 30, 2010.

US20100249415
General References
  1. Boni J, Leister C, Burns J, Cincotta M, Hug B, Moore L: Pharmacokinetic profile of temsirolimus with concomitant administration of cytochrome p450-inducing medications. J Clin Pharmacol. 2007 Nov;47(11):1430-9. Epub 2007 Oct 3. [PubMed:17913896 ]
External Links
ATC CodesL01XE09
AHFS Codes
  • 10:00
PDB EntriesNot Available
FDA labelDownload (402 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Temsirolimus.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Temsirolimus.
AprepitantThe serum concentration of Temsirolimus can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Temsirolimus.
AtazanavirThe risk or severity of adverse effects can be increased when Atazanavir is combined with Temsirolimus.
BatimastatThe risk or severity of adverse effects can be increased when Batimastat is combined with Temsirolimus.
BenazeprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Benazepril.
BexaroteneThe serum concentration of Temsirolimus can be decreased when it is combined with Bexarotene.
BosentanThe serum concentration of Temsirolimus can be decreased when it is combined with Bosentan.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Temsirolimus.
CaptoprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Captopril.
CarbamazepineThe serum concentration of Temsirolimus can be decreased when it is combined with Carbamazepine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Temsirolimus.
CilazaprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Cilazapril.
ClarithromycinThe risk or severity of adverse effects can be increased when Clarithromycin is combined with Temsirolimus.
ClozapineThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Clozapine.
ConivaptanThe serum concentration of Temsirolimus can be increased when it is combined with Conivaptan.
CyclosporineThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Cyclosporine.
DabrafenibThe serum concentration of Temsirolimus can be decreased when it is combined with Dabrafenib.
DarunavirThe risk or severity of adverse effects can be increased when Darunavir is combined with Temsirolimus.
DasatinibThe serum concentration of Temsirolimus can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Temsirolimus can be decreased when it is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Temsirolimus.
EnalaprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Enalapril.
EnalaprilatThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Enalaprilat.
ErythromycinThe risk or severity of adverse effects can be increased when Erythromycin is combined with Temsirolimus.
FluconazoleThe metabolism of Temsirolimus can be decreased when combined with Fluconazole.
FosamprenavirThe risk or severity of adverse effects can be increased when Fosamprenavir is combined with Temsirolimus.
FosaprepitantThe serum concentration of Temsirolimus can be increased when it is combined with Fosaprepitant.
FosinoprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Fosinopril.
FosphenytoinThe serum concentration of Temsirolimus can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Temsirolimus can be increased when it is combined with Fusidic Acid.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Temsirolimus.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Temsirolimus.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Temsirolimus.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Temsirolimus.
IdelalisibThe serum concentration of Temsirolimus can be increased when it is combined with Idelalisib.
IndinavirThe risk or severity of adverse effects can be increased when Indinavir is combined with Temsirolimus.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Temsirolimus.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Temsirolimus.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Temsirolimus.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Temsirolimus.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Temsirolimus.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Temsirolimus.
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Temsirolimus.
ItraconazoleThe serum concentration of the active metabolites of Temsirolimus can be increased when Temsirolimus is used in combination with Itraconazole.
IvacaftorThe serum concentration of Temsirolimus can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of the active metabolites of Temsirolimus can be increased when Temsirolimus is used in combination with Ketoconazole.
LeflunomideThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Leflunomide.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Temsirolimus.
LisinoprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Lisinopril.
LuliconazoleThe serum concentration of Temsirolimus can be increased when it is combined with Luliconazole.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Temsirolimus.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Temsirolimus.
MifepristoneThe serum concentration of Temsirolimus can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Temsirolimus can be decreased when it is combined with Mitotane.
MoexiprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Moexipril.
NatalizumabThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Natalizumab.
NelfinavirThe risk or severity of adverse effects can be increased when Nelfinavir is combined with Temsirolimus.
NetupitantThe serum concentration of Temsirolimus can be increased when it is combined with Netupitant.
PalbociclibThe serum concentration of Temsirolimus can be increased when it is combined with Palbociclib.
PerindoprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Perindopril.
PhenytoinThe serum concentration of Temsirolimus can be decreased when it is combined with Phenytoin.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Temsirolimus.
PosaconazoleThe serum concentration of the active metabolites of Temsirolimus can be increased when Temsirolimus is used in combination with Posaconazole.
QuinaprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Quinapril.
RamiprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Ramipril.
RanolazineThe serum concentration of Temsirolimus can be increased when it is combined with Ranolazine.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Temsirolimus.
RifabutinThe serum concentration of Temsirolimus can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Temsirolimus can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Temsirolimus can be decreased when it is combined with Rifapentine.
RitonavirThe risk or severity of adverse effects can be increased when Ritonavir is combined with Temsirolimus.
RoflumilastRoflumilast may increase the immunosuppressive activities of Temsirolimus.
SaquinavirThe serum concentration of Temsirolimus can be increased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Temsirolimus.
SiltuximabThe serum concentration of Temsirolimus can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Temsirolimus can be increased when it is combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Temsirolimus.
St. John's WortThe serum concentration of Temsirolimus can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Temsirolimus can be increased when it is combined with Stiripentol.
SunitinibThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Sunitinib.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Temsirolimus.
TelithromycinThe risk or severity of adverse effects can be increased when Telithromycin is combined with Temsirolimus.
TesmilifeneThe serum concentration of Temsirolimus can be decreased when it is combined with Tesmilifene.
TipranavirThe risk or severity of adverse effects can be increased when Tipranavir is combined with Temsirolimus.
TocilizumabThe serum concentration of Temsirolimus can be decreased when it is combined with Tocilizumab.
TofacitinibTemsirolimus may increase the immunosuppressive activities of Tofacitinib.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Temsirolimus.
TrandolaprilThe risk or severity of adverse effects can be increased when Temsirolimus is combined with Trandolapril.
TrastuzumabTrastuzumab may increase the neutropenic activities of Temsirolimus.
VerapamilThe serum concentration of Temsirolimus can be increased when it is combined with Verapamil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Temsirolimus.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Tfiiic-class transcription factor binding
Specific Function:
Serine/threonine protein kinase which is a central regulator of cellular metabolism, growth and survival in response to hormones, growth factors, nutrients, energy and stress signals. MTOR directly or indirectly regulates the phosphorylation of at least 800 proteins. Functions as part of 2 structurally and functionally distinct signaling complexes mTORC1 and mTORC2 (mTOR complex 1 and 2). Activ...
Gene Name:
MTOR
Uniprot ID:
P42345
Molecular Weight:
288889.05 Da
References
  1. Patard JJ, Pouessel D, Bensalah K, Culine S: Targeted therapy in renal cell carcinoma. World J Urol. 2008 Apr;26(2):135-40. doi: 10.1007/s00345-008-0237-4. Epub 2008 Feb 12. [PubMed:18265991 ]
  2. Radulovic S, Bjelogrlic SK: Sunitinib, sorafenib and mTOR inhibitors in renal cancer. J BUON. 2007 Sep;12 Suppl 1:S151-62. [PubMed:17935273 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
Comments
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Drug created on March 19, 2008 10:22 / Updated on June 29, 2016 03:04